Compendium of Organic Synthetic Methods
Compendium of Organic Synthetic Methods Volume 8 MICHAEL 6. SMITH DEPARTMENT OF CHEMISTRY
THE UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT
A Wiley-lnterscience Publication
JOHN WILEY 81 SONS, INC. NewYork
Chichester
Brisbane
Toronto
Singapore
Cover illustration was adapted from "Disconnect By the Numbers: A Beginner's Guide to Synthesis" by M. B. Smith. Journal of Chemical Educetion, 1980, 67, 848-856.
A NOTE TO THE READER
This book has been electronically reproduced from digital information stored at John Wiley & Sons,Inc. We are pleased that the use of this new technology will enable us to keep works of enduring scholarly value in print as long as there is a reasonable demand for them. The content of this book is identical to previous printings. This text is printed on acid-free paper. Copyright
@
1995 by John Wiley & Sons, Inc.
Ail rights reserved. Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any, means, electronic, mechanical, photocopying, recording, scanning or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-601 1 , fax (201) 748-6008, E-Mail:
[email protected].
To order books or for customer service please, call 1(800)-CALL-WILEY (225-5945). Library of Congress Catalog Card Number: 71-162800 ISBN 0-471-57319-1 Printed in the United States of America 10 9 8 7 6 5 4 3 2
DEDlCAT10N This book is dedicated to Dr. Ted Hoffman, who recently retired as Senior Editor at Wiley-lnterscience after a long and distinguished career. Ted was responsible for getting the Compendium started and for keeping it going for more than twenty years. The many books and series for which Ted served as editor have contributed enormously both to chemical education and to chemical research. It would be difficult to find a bookshelf in an organic chemistry research lab anywhere in the world that does not contain one or more of the books for which Ted served as editor. On a more personal level, the publication of Volume 6 of this series in 1988 began my career as an author, and many new opportunities have been opened to me because of this. There are certainly many others who can similarly thank Ted. Iwant to use this dedication to thank Ted for his help to me, for his help to the previous authors of the Compendium, and for his contributions to the chemistry community in general (particularly the organic chemistry community). Those contributions are many and important. Thank you, and good luck in your retirement. MICHAEL 6. SMITH
V
PREFACE Since theoriginal volume in thisseries by Ian and Shuyen Harrison, thegoal of the Compendium of Organic Synthetic Methods was to facilitate the search for functional group transformations in the original literature of Organic Chemistry. In Volume 2, difunctional compounds were added and this compilation was continued by Louis Hegedus and Leroy Wade for Volume3 of theseries. Wade becametheauthor forVolume4 and continued with Volume 5. I began editing the series with Volume 6, where I introduced an author index for the first time and added a new chapter (Chapter 15, Oxides). Volume 7 introduced Section 378 (Oxides-Alkynes) through Section 390 (Oxides-Oxides). The Compendium is a handy desktop reference that will remain a valuable tool to the working organic chemist, allowing a “quick check” of the literature. It also allows one to “browse” for new reactions and transformations that may be of interest. The body of organic literature is very large and the Compendium is a focused and highly representative review of the literature and is offered in that context. Compendium of Organic Synthetic Methods, Volume 8, contains both functional group transformations and carbon-carbon bond forming reactions from the literature appearing in the years 1990, 1991, and 1992. The classification schemes used for Volumes 6 and 7 have been continued. Difunctional compounds appear in Chapter 16.Theexperienced user of the Compendium will require no special instructions for the use of Volume 8. Author citations and the Author Index have been continued as in Volumes 6 and 7. Every effort has been made to keep the manuscript error free. Where there are errors, I take full responsibility. If there are questions or comments, the reader is encouraged to contact me directly at the address, phone, fax, or E-mail addresses given below. Note that the phone and fax area code for this section of Connecticut is tentatively scheduled to change in 1996 to (860). The manuscript for Volume 8 was prepared on a Macintosh-llciTMPC using Microsoft Word” (version 5.1) for word processing. All structures were prepared using ChemDraw” (version 3.1)and the manuscript was printed with a Laserwriter” II printer. The graph presented in the introduction was prepared using Cricket-Graph.”
vii
viii
PREFACE
As I have throughout mywriting career, 1 want to thank my wife Sarah and my son Steven, who have shown unfailing patienceand devotion during this work. I also thank Ms. Carla Fjerstad, who edited this volume and was responsible for its publication. MICHAEL B. SMITH
University of Connecticut Department of Chemistry 215 Glenbrook Rd., Room 151 Storrs, CT USA 06269-3060 Voice Phone: 203-486-2881 Fax: 203-486-2981 E-mail:
[email protected]
CONTENTS ABBREVIATIONS INDEX, MONOFUNCTIONAL CO APO J IDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 PREPARATION OF ALKYNES
2 PREPARATION OF ACID DERIVATIVES AND 3 4 5 6 7 8
9 10 11 12 13 14 15 16
ANHYDRIDES PREPARATION OF ALCOHOLS PREPARATION OF ALDEHYDES PREPARATION OF ALKYLS, METHYLENES AND ARYLS PREPARATION OF AMIDES PREPARATION OF AMINES PREPARATION OF ESTERS PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS PREPARATION OF HALIDES AND SULFONATES PREPARATION OF HYDRIDES PREPARATION OF KETONES PREPARATION OF NITRILES PREPARATION OF ALKENES PREPARATION OF OXIDES PREPARAflON OF DIFUNCTIONAL COMPOUNDS AUTHOR INDEX
xi xv xvi xvii 1 6 16 54 66 117 139 166 184 200 210 220 242 247 267 276 561
IX
ABBREVIATIONS Ac
Acetyl
acac
Acetylacetonate azo-bis-Isobutyronilrile Aqueous
AIBN
9-Borabicyclo[3.3.1Jnonyl 9-BBN BINAP Bn
9-Borabicyclo[3.3.l]nonyl 2R,3S-2,2'bis-(diphenylphosphino)-111'-binapthyl Benzyl Benzoy 1
BOC
t-Butoxycarbo~~yl
BPY (BiPY) Bu CAM CAN Cat.
2,T-Bipyridyl n-Butyl Carhxamidometliyl Ceric ammonium niuate CycloCatalytic
Cbz
Carbobenzyloxy
Chirald COD COT CP CSA
2S,3R-(+)-4-Dimelhylamino1,2-diplienyl-3-me(hylbutan-2-ol
Bz
C-
CrAB
1,S-Cyclooc~xlienyl 1,3,S-Cyclooctatrieny1 Cyclopentadienyl Camphorsulfonic acid cetyltrimethylammonium bromide
Cy (c-C~H 1 1)
Cyclohexyl
"C DABCO Dba DBE DBN DBU DCC DCE
Temperature in Degrees Centigrade
1,4-Diazahicyclo[2.2.2]octa11e
Dibenzylidene acetone 1,2-Dibrornoethane 1,S-Diazabicyclo[4.3.0]non-S-ene
1,8-Diazabicyclo[S.4.0]undec-7-ene 1,3-DicycloIicxylcarbodiimide I ,2-DichIorcleUiruie
0
)(lotau
0
+OCH2Ph
C@j3NMe3+ Br-
to
BICH2CH2Br c-C@ 1~-N=C=N-C-C&I 1 3 ClCH2CH2CI
xi
xii
ABBREVIATIONS
DDQ % de DEA DEAD Dibal-H Diphos (dppe) Diphos-4 (dppb) DMAP DME
2,3-Dichloro-5,6-dicyano-l,4-benzoquinone % Diastereomeric excess Diethylamine Diethylazodicarboxylate Diisobutylaluminum hydride 1,2-6is-(Diphenylphosphino)ethane 1,4-bis-(Diphenylphosphino)butane 4-Dimethylaminopyridine Dmethoxyethane
DMF
N,N'-Dimethylformamide
DmP DPm DPPb
DDPe DpDf DPPP Dvb e'
%ee I 3
Et EDA EDTA FMN Fod FP FVP h hv 1,5-HD HMPA HMPT
iPr
LICA (LIPCA) LDA LHMDS LTMP MABR MAD mCPBA Me MEM Mes
HN(CH2CW2 Et02C-N=NC02Et (Me2CHCH2)2AlH Ph2PCH2CH2PPh2 Ph2P(CH2)4PPh2 MeOCH2CHzOMe
bis-[1,3-Di@-rnethoxyphenyl)-1,3-propanedionatoI Dipivaloylmethanato Ph2P(CH2)4PPh2 1.4 -bis-(Diphenylphosphino)butane 1,2-bis-(Diphenylphosphino)ethane Ph2PCH2CHzPPh2 bis-(Dipheny1phosphino)ferrocene 1,3-bis-(DiphenyIpliosphino)propane PhzP(CH213PPh2 Divinylbenzene Electrolysis % Enantiomeric excess 1-Ethoxyethyl EtO(Me)CHOEthyl -CH2CH3 Erhylenediamine H~NCH~CHZNH~ Erhylenediaminetetraacetic acid Flavin mononucleotide tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-oc~edio~te Cyclopentadienyl-his-carbonyl iron Flash Vacuum Pyrolysis Hour (hours) Irradiation with light 1,5-Hexadienyl Hexamethylphosphoramide (MeW2P-O Hexamethylphosphoxustriamide tMe3W3P Isopropyl -CH(CH3)2 Lithium cyclohexylisopropylamide Lithium diisopropylamide LiN(iPr)2 Lithium hexamethyldisilazide LiN(SiMe3h Lithium 2,2,6,6-tetramethylpiperidide Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide) bis-(2,6-Di-t-butyl-4-melhy1phenoxy)methylaluminum meta-Chloroperoxybenzoicacid Methyl -CH3 MeOCH2CW2OCHzP-Methoxyetiloxymethyl 2,4,6-tri-Me-C6H2 Mesityl
xiii
ABBREVIATIONS MOM Ms MS MTM NAD NADP Napth NBD NBS NCS NIS Ni(R) Oxone
@
Methoxymethyl Methanesulfony1 Molecular Sieves (3A or 4A) Methylthiomethyl Nicotinamideadenine dinucleotide Sodium triphosphopyridine nucleotide Naphthyl (CioH7) Norbomadiene N-Bromosuccinimide N-Chlorosuccinimide N-Iodosuccinimide Raney nickel 2 KHSOyKHSOq*K2S04
MeOCH2CH3S02MeSCH2-
Polymeric backbone
PCC PDC PEG
Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol
Ph
Phenyl
PhH PhMe Phth Pic
Benzene Toluene Phthaloyl 2-Pyridinecarbox y late
Pip
Piperidyl
Pr
n-Propyl
PY
Pyridine
quant. Red-Al sBu sBuLi Siamyl TASF TBAF TBDMS TBHP (1-BuOOH) t-Bu TEBA TEMPO TFA
Quantitative yield [(MeoCH2CH20)2AIH21Na sec-Butyl CH3CHaH(CH3) sec-Butyllithium CH3CH2CH(Li)CH3 Diisoam yl [(CH3)2CHGH(CH3)-12 tris-@iethylamino)sulfoniumdifluorotrimethyl silicate Tetrabutylammonium fluoride n-BuqN+ F' t-Butyldimethylsil yl f-B uMe2Si . . f-But&ydroperoxide Me3COOH tert-Butyl -C(CH3)3 Trieth ylbenzylamrnonium Bn(Et)3N+ Tetramethylpi~ridinyloxyfree radical Trifluoroacetic acid CF3COOH
-CH2CHzCH3 N
3
xiv TFAA Tf (OTf) THF THP TMEDA TMS TMP TPAP To1 Tr TRIS Tsvos)
)))I)))) x,
ABBREVIATIONS Trifluomamtic anhydride Triflate Teuahydrofuran Tetrahydwyran Tetramethy lethy lenedidiamine Trimethylsilyl 2,2,6,6-Tetrrunethylpiperidine tetra-n-Propylammoniumperruthenate Tolyl Trityl Triisopropylphenylsulfo~~ yl Tosyl = p-Toluenesulfonyl Sonication C h i d auxiliary
(CF3CO)20 -SOzCF3 (-0S02CF3) Me2NCH2CH2NMe2 -Si(CH3)3 4-CbHqCH3 -CPh3 4-MeC6H4SO2-
<
X
Miscellaneouscompounds 15 5
Alkenes
Nitriles
Ketones 12 4
Hydrtdes (RH)
27 13 28 13 29 14 30 14
39 30 40 35 41 36 42 39 43 45 44 45 45 47
24 11 25 11
Ethers, epoxides
Halldes,sulfonates.sulfates 10 3
38 29
32 16 33 18 34 18 35 28 36 29
23 10
7 3
16 6 17 6 18 7 19 8 20 9 21 9
Esters
Amines
Amides
Aldehydes 4 2 Alkyls, methybnes, aryls
Alkynes
1 1 Carboxylicacids 2 acid halides,anhydrides 2 Alcohols, phenols
54 61 55 61 56 62 57 63 58 63 59 63 60 64
47 54 48 54 49 58 50 58 51 59 52 59 53 60 69 71 70 72 71 78 72 79 73 80 74 81 75 116
67 70 68 70
61 66 62 67 63 68 64 69 65 69
85 132 86 133 87 133 88 134 89 135 90 136
96 142 97 144 98 153
81 120 82 127 83 131 99 153 100 153 101 155 102 155 103 157 104 158 105 159
91 139 92 139 93 140 94 140
76 117 77 117 78 119 79 119
114 176 115 177 116 178 117 179 118 182 119 182 120 183
111 173 112 174 113 174
106 166 107 166 108 168 109 172
134 194 135 198
132 193
129 189 130 191
127 188 128 188
123 184 124 186
121 184
149 207
145 203 146 205 147 207
142 202 143 203
138 200 139 201
165 219
162 218 163 219
157 213 158 213 159 214 160 215
152 210 153 210 154 212
166 220 167 220 168 183 222 242 169 184 225 242 170 227 171 186 227 243 172 187 228 243 173 229 174 189 230 244 175 190 231 244 176 191 233 244 177 234 178 193 237 245 179 237 180 195 238 245 209 261 210 264
225 273
196 247 197 212 251 267 198 213 251 267 199 214 252 267 200 253 201 254 202 217 254 268 203 255 204 219 255 269 205 220 256 272 206 221 258 272 207 222 259 273
30A 45A 60A 90A 105A 180A
Sect.
138 163 239
€4
Pg. 14 48
Blanks in the table correspond to sections for which no additional examples were found in the literature.
Carboxylic acids Alcohols, phenols Aldehydes Amides Amines Ketones
PROTECTION j
INDEX, MONOFUNCTIONAL COMPOUNDS
2.
290 316 291 317 292
292 319 292 320 293
322 294
279 305 279 306 280
281 308 282 309 283
311 284 378 540
368 338 369 339 370
341 371 381 543
348 332 352 380 540
365 335 366 336 367
328 329 336 330 340
318
306 326 309 327
294
414 356 414 383 544
405 353 408 354 409
380 346 382 347 383 386 349 386 382 543
350 396 351 398
375 343 376 344 377
444 362 444 3114 547
427 359 432 360 437
357 424
474 367 475 385 548
461 364 463 365 465 496 371 496 386 549
368 490 369 492 506 374 506 387 550
372 501 529 376 529 388 553
377 531 389 390 553 559
Blanks in the table correspond to sections for which no additional examples were found in the literature.
288
277
/
Sections-heavy type Pages-light type
INDEX, DIFUNCTIONAL COMPOUNDS
INTRODUCTION Relationship between Volume 8 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 8, presents about 1400 examples of published reactions for the preparation of monofunctional compounds, updating the 9250 in Volumes 1-7. Volume 8 contains about 1640examples of reactions which prepare difunctional compounds with various functional groups. Reviews have long been a feature of this series and Volume 8 adds atmost 60 pertinent reviews in the various sections. It is interesting that Volume 8 contains approximately 1200 more entries than Volume 7 for an identical three-year period. One or two important new journals appear (such asSynLett), but the most dramatic increase was in reactionsthat prepared difunctional compounds. This increase in reactions led me to “compress” the format of the Compendium somewhat, in an attempt to keep the length of the manuscript in line with previous volumes. Chapters 1-14 continue as in Volumes 1-7, as does Chapter 15, introduced in Volume 6. Difunctional compounds appear in Chapter 16, as in Volumes 6 and 7. The sectionson oxides as part of difunctional compounds, introduced in Volume7, continuein Chapter 16of Volume8withSection 378 (Oxides-Alkynes) through Section 390 (Oxides-Oxides). Following Chapter 16 is acomplete alphabetical listing of all authors (last name, initials). The authors for egch citation appear below the reaction. The principle author is indicated by underlining (Le., Kwon, T. W.; Smith, M. B.), as in Volume 7. Classification and Organization of Reactions Forming Monofunctionai Compounds. Chemical transformations are classified according to the reacting functional group of the starting material and the functional group formed. Those reactions that give products with the same functional group form a chapter. The reactions in each chapter are further classified into sections on the basis of the functional group of the starting material. Within each section, reactions are loosely arranged in ascending order of year cited (1990-1992), although an effort has been made to put similar reactions together when possible. Review articles are collected at the end of each appropriate section. The classification is unaffected by allylic, vinylic, or acetylenic unsaturation appearing in both starting material and product, or by increases or decreases in the length of carbon chains; for example, the reactionst-BuOH --* t-BuCOOH, PhCH20H -+ PhCOOH, and PhCH=CHCH20H --+ PhCH= CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Conjugate reduction and alkylation of unsaturated ketones, alxvii
xviii
INTRODUCTION
dehydes, esters, acids, and nitriles have been placed in Sections 74D and 74E (Alkyls from Alkenes), respectively. The terms hydrides, alkyls, and aryls classify compounds containing reacting hydrogens, alkyl groups, and aryl groups, respectively; for example, RCH2-H 3 RCH2COOH (carboxylic acids from hydrides), RMe --* RCOOH (carboxylic acids from alkyls), RPh -+ RCOOH (carboxylic acids from aryls). Note the distinction between R2C0--* R2CH2(methylenes from ketones) and RCOR' --* RH (hydrides from ketones). Alkylations involving additions across double bonds are found in Section 74 (Alkyls, Methylenes, and Aryls from Alkenes). The following examples illustrate the classification ofsome potentially confusing cases: RCH=CHCOOH + RCH'CH2 RCH=CH2 4 RCH"CHCO0H ArH ArCOOH ArH 3 ArOAc RCHO 3 RH RCH=CHCHO + RCH=CH2 RCHO -.* RCH3 R2CH2 4 R2CO RCH2COR + R2CHCOR RCH=CH* 4 RCH2CH3
+ HC=CH ROH + RCOOH
4
RCaX
-.*
RCOOR
RCHSHCHO
-.*
RCH2CH2CHO
RCH-CHCN
+
RCH2CH2CN
RBr
Hydrides from carboxylic acids Carboxylic acids from hydrides Carboxylic acids from hydrides Esters from hydrides Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from aldehydes Ketones from ketones Alkyls from alkenes (Hydrogenation of Alkenes) Acetylenes from halides; also acetylenes from acetylenes Esters from alcohols; also esters from carboxylic acids Alkyls from alkenes (Conjugate Reduction) Alkyls from alkenes (Conjugate Reduction)
How to Use the Book to Locate Examplesof the Preparationor Protection of MonofunctionalCompounds. Examples of the preparation of one functional group from another are found in the monofunctional index on p. xvii, which lists the corresponding section and page. Sections that contain examples of the reactions of a functional group are found in the horizontal rows of this index. Section 1 gives examples of the reactions of acetylenes that form new acetylenes; Section 16gives reactions of acetylenesthat form carboxylic acids; and Section 31 gives reactions of acetylenes that form alcohols. Examples of alkylation, dealkylation, homologation, isomerization, and transposition are found in Sections 1, 17, 33, and so on, lying close to a diagonal of the index. These sections correspond to such topics as the preparation of acetylenes from acetylenes: carboxylic acids from carbox-
INTRODUCTION
xix
ylic acids; and alcohols, thiols, and phenols from alcohols, thiols, and phenols. Alkylations that involve conjugate additions across a double bond are found in Section 74E (Alkyls, Methylenes, and Aryls from Alkenes). Examples of name reactions can be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is in Section 199 (Alkenes from Aldehydes) and Section 207 (Alkenes from Ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330 (Alcohol, Thiol-Ketone). Examples of the protection of acetylenes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and alkenes are also indexed on p. xvii. Sections (designated with an A: 15A, 30A, etc.) with “protecting group” reactions are located at the end of pertinent chapters. Some pairs of functional groups such as alcohol, ester; carboxylic acid, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should also be consulted in the text. The original literature must be used to determine the generality of reactions, although this is occasionally stated in the citation. This is only done in cases where such generality is stated clearly in the original citation. A reaction given in this book for a primary aliphatic substrate may also be applicable to tertiary or aromatic compounds. This book provides very limited experimental conditions or precautions and the reader is referred to the original literature before attempting a reaction. In n_o tnstanceshouida citation in this book be taken as a completeexperimentalprocedure. Failureto refer to the original literature prior to beginninglaboratory work could be hazardous. The original papers usually yield a further set of references to previous work. Papers that appear after those publications can usually be found by consulting Chemical Abstracts and the Science Citation Index. Classification and Organization of Reactions Forming Difunctional Compounds. This chapter considers all possible difunctional compounds formed from thegroups acetylene, carboxylic acid, alcohol, thiol, aldehyde, amide, amine, ester, ether, epoxide, thioether, halide, ketone, nitrile, and alkene. Reactionsthat form difunctional compounds are classified into sections on the basis of two functional groups in the product that are pertinent to the reaction. The relative positions of the groups do not affect the classification. Thus preparations of 1,2-aminoalcohols, 1,3-aminoalcohols, and 1,4-aminoalcohols are included in a single section (Section 326, AlcoholAmine). Difunctional compounds that have an oxide as the second group are found in the appropriate section (Sections 278-290). The nitroketone product of oxidation of a nitroalcohol is found in Section 386 (KetoneOxide). Conversion of an oxide to another functional group is generally found in the “Miscellaneous” section of the sections concerning mono-
xx
INTRODUCTION
functional compounds. Conversion of a nitroalkane to an amine, for example, is found in Section 105 (Amines from MiscellaneousCompounds). The following examples illustrate applications of this classification system: Difunctional Product
Section Title
RC=C-CSR RCH(0H)COOH RCH=CHOMe RCHFp RCH(Br)CH2F RCH(OAC)CH20H RCH(OH)C02Me RCH=CHCH2C02Me RCH=CHOAc RCH(OMe)CH2S02CH2CH20H RS02CHpCHpOH
Acetylene-Acetylene Carboxylic acid-Alcohol Ether-Alkene Halide-Halide Halide-Halide Alcohol-Ester
Alcohol-Ester Ester-Alkene Ester-Al kene
Alcohol-Ether Alcohol-Oxide
How to Usethe Book to Locate Examplesof the Preparationof Difunctional Compounds. The difunctional index on p. xviii gives the section and page corresponding to each difunctional product. Thus Section 327 (Alcohol, Thiol-Ester) contains examples of the preparation of hydroxyesters; Section 323 (Alcohol, Thiol-Alcohol, Thiol) contains examples of the preparation of diols. Some preparations of alkene and acetylenic compounds from alkene and acetylenic starting materials can, in principle, be classified in either the monofunctional or difunctional sections; for example, the transformation RCH=CHBr --* RCH=CHCOOH could be consider as preparing carboxylic acids from halides (Section25,Monofunctional Compounds)or preparing a carboxylic acid-alkene (Section 322,Difunctional Compounds). The choice usually depends on the focus of the particular paper where this reaction was found. In such cases both sections should be consulted. Reactions applicable to both aldehyde and ketone starting materials are in many cases illustrated by an example that uses only one of them. Likewise, many citations for reactions found in the Aldehyde-X sections, will include examples that can be placed in the Ketone-X section. Again, the choice is dictated by the paper where the reaction was found. Many literature preparations of difunctional compounds are extensions of the methods applicable to monofunctional compounds. As an example, the reaction RCI ROH might be used for the preparation of diols from an appropriate dichloro compound. Such methods are difficult to categorize and may be found in either the monofunctional or difunctional sections, depending on the focus of the original paper. The user should bear in mind that the pairs of functional groups alcohol, ester; carboxylic acids, ester; amine, amide; and carboxylic acid, amide --+
INTRODUCTION
xxi
can be interconverted by simple reactions. Compounds of the type RCH(OAc)CH20Ac(ester-ester) would thus be of interest to anyone preparing the diol RCH(OH)CH20H(alcohol-alcohol). Sourcesof Literature Citations. I thought it would be useful for a reader of this Compendium to see the distribution of citations used in this book (i.e., which journals have the most new synthetic methodology). As seen in the accompanying graph, Tetrahedron Letters and Journal of Organic Chemistry account for roughtly two-thirds of all the citations in Volume 8. This book was not edited to favor one category or type of article over another. Certainly, my own personal preferences undoubtedly creep into the selection of methods, but I believe that this compilation is an accurate representation of new synthetic methods that appear in the literature. Therefore, I believe the accompanying graph accurately reflects those journals where new synthetic methodology is located. I should point out that the category “23 other journals” includes: Accts. Chem. Res.; Acta Chem. Scand.; Angew. Chem. Int. Ed. Engi.; Aust. J. Chem.; Bull. Chim. SOC.Belg.; Bull. Chim. SOC.Fr.; Can. J. Chem.; Chem. Ber.; Coll. Czech. Chem. Commun.; Gazz. Chim. Ital.;Heterocycles; Ind. J. Chem.; Isr. J. Chem.; Izv. Akad. #auk. SSSR; J. Chem. SOC.;J. Her. Chem.; J. Indian Chem. SOC.;Liebigs Ann. Chem.; Org. Prep. Proceed Int.; Perkin Trans. I; Recl. Trav. Chim. Pays-Bas; Tetrahedron Asymmetry; and, Zhur. Org. Khim. In addition, six more journals were examined but no references were recorded.
Journal 23 other journals
Tetrahedron
Bull Chem Soc Jpn
Synthesis
JACS '
Synth Commun
JCS, Chem Comm
Chem Lett
SynLett
J . Org. Chem.
Tetr. Lett.'
xxii
INTRODUCTION
Citations
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
1
PREPARATION
ALKYNES
OF
&&
SECTION 1: ALKYNES FROM ALKYNES M~O&
2. I. Co2(CO)s, BF3wOEt2, CH$& CHC12 \
D
+
3.CAN.MEOH M e 0
/
/
/
\
\ I
/ (85
15)
-a
G r o v e . % ;Miskevich, F.; Smith, C.C.; Corte, J.R.TetrahedronLett., 1990, 31, 6277.
Br
PhCS-H , l o %PdC ,4% CuI
\
CK-Ph
16%PPh3, N E t 3 , MeCN CN reflux De la Rosa, M.A.; Velarde, E.; BuzrnBn, A, Synth. Cotntriun., 1990, 20, 2059.
CN
Br
59%
82%
O-CEC;;
Me3Si-C=C-H1 CuI ,PPh3 Pd(PPh3)4 , piperidine
~
Brandsrna, L.; van den Heuvel, H.G.M.; Verkruijsse, H.D. S y n A Commun., 1990, 20, 1889.
Ph-
'-
1. BuLi ,THF 2. ZIlClZ
3. Plil , Pd(PPh3)4
c
Ph - CE C- Ph
96%
Yoneda. N,; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A. Bull. Chetn. SOC.Jpn., 1990, 63, 2124.
2
Compendium of Organic Synthetic Methods, Vol8
Section 4
HCS-CHzOH, NEt3 H 2 0 , 20°C
OH 69%
PdC12[PPh2(rn-C6H4S03Na)lz Bumagin, N.A.; Bykov, V.V.;Be1etskayaJ.P. h v . Akad. Nauk. SSSR, 1990, 39, 2665 (Engl., p. 2418).
Okura, K.;Furuune, M.; mra.M,; Nomura, M.Tetrahedron Letf., 1992, 33, 5363.
SECTION 2: ALKYNES FROM ACID DERIVATIVES 0
1. Ph3P=CHC02Et ,NEt3 2. FWP (750°C)
e
Ph-CSC-H
42%
Aitken. R.A; Seth, S. SynLerf, 1990, 211, 212.
SECTION 3: ALKYNES FROM ALCOHOLS AND THIOLS NO ADDITIONAL EXAMPLES
SECTION 4: ALKYNES FROM ALDEHYDES
Me MeO-P0 CHNz
*
BocHNJ-C=C-H
Me0
67%
Hauske.;Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Terruhedron Lett., 1992, 33, 3715.
SECTION 5:
ALKYNES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 6:
ALKYNES FROM AMIDES NO ADDITIONAL EXAMPLES
Section 3
Alkynes from Alcohols
SECTION 7:
ALKYNES FROM AMINES
N”’N* Bn
t)
3
Ph
Ph
1. t-BuOK ,DMF
75°C
Ph
4-
2.3eq.t-BuOK * DMF ,75”C
N, H N“ N‘
+
PhNH2
Ph
75% Paventi, M.; Elce, E.; Jackman, R.J.; Ha! A& Telrahedron Lett., 1992, 33, 6405,
SECTION 8:
ALKYNES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 9:
ALKYNES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
SECTION 10: ALKYNES FROM HALIDES AND SULFONATES LiC=C-n-C&13 THF-DMPU
o&OTf
-20”~ , 15 min
40
n -CgH 57%
Kotsuki. H,; Kadota, I.; %hi, M. Tetrahedron Lett., 1990, 31, 4609.
MCbz
BrT
C0,Me
Bu3Sn-CS-Me ZnCI;! ,CC4, reflux
Me02Cy csC’Me NHCbz
Williams. R.M,; Aldous, D.J.; Aldous, S.C. J. Org. Chem., 1990, 55, 4657.
z E t r H .C i C
v Cu(CN)ZnI
-78°C + 0°C ,30 min
*
86% Knoess, H.P.; Furlong, M.T.;Rozema, M.J.; Knochel. P. J. Org. Chem., 1991, 56, 5974.
4
Compendium of Organic Synthetic Methods, Vol8
Section 12
I
OMe OMe Dchiai, M.; Ito, T.;Masaki, Y.J. Chem. SOC., Chem. Commun.. 1992, 15. SECTION 11: ALKYNES FROM HYDRIDES For examples of the reaction RCKH -+ RC=C-CPCR~,see section 300 (Alkyne-Alkyne).
NO ADDITIONAL EXAMPLES
mo
SECTION 12: ALKYNES FROM KETONES K@ ,18-CrOWn-6 DMF,RT,20h
Sotirious, C.; Lee, W.; S&&,
acozH COZH
56%
R.W. J. Org. Chem., 1990, 55, 2159. 1. NH2OH
Me-CrC--/
Ph
59%
Boivin, J.; Elkaim, L.; Femo, P.G.; U Tetrahedron Lett., 1992, 32, 5321.
SECTION 13: ALKYNES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 14: ALKYNES FROM ALKENES NO ADDITIONAL EXAMPLES
5
Alkynes from Miscellaneous
Section 15
SECTION 15: ALKYNES FROM MISCELLANEOUS COMPOUNDS
N - I P h
1. LDA 2. TsN=CHPh
3. t-BuOK. DMF
*
Ph-Cr C-Ph
850C
Katritzkv. A.R,; Gordeev, M.F. J. Chem. SOC., Perkin Trans. I, 1992, 1295.
SECTION 15A: PROTECTION OF ALKYNES NO ADDITIONAL EXAMPLES
70%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 2
PREPARATION OF ACID DERIVATIVES
SECTION 16:
ACID DERIVATIVES FROM ALKYNES CoCl2*6 H2O , KCN , CO 5N KOH ,PhMe ,90°C
Ph- CE C-H
Ni(CN)y4 H20, 1 am PEG - 400
Ph
Ph
- l C O , H
65% Lee, J-T.; Alper. H, Tetrahedron Lett., 1991, 32, 1769.
SECTION 17:
2%
ACID DERIVATIVES FROM ACID DERIVATIVES
Keinan.E.;Sahai, M. J. Org. Chem., 1990, 55, 3922.
Fields.;Behrend, S.J.; Meyerson, S.; Wizenburg, M.L.; Ortega, B.R.; Hall, H.K.Jr. J. Org. Chem., 1990, 55, 5165.
1. DCC , CHzClz 2. CH2=CHS02Ph Ph4C02H
Barton, D.H.R.; Chem, C-Y .;
c
Ph-CO,H
3. mCPBA ,CH2C12 4. TFAA ,22OC57% overall 5 . K2CO3 , MeCN ,22"C Tetrahedron Lett., 1991, 32, 3309.
7
Acids from Alcohols
Section 18
1.
n-Cl lH23-CO2H
>::
,DCC
2. AcOH
w
Dussault. PJ Sahli, A. J. Org. Chem., 1992, 57, 1009.
0
0 CoCl2, CH2C12,40°C , 8h
0 OMe
91%
Srivastava, R.R.; Kabalka. G.W, Tetrahedron Lett., 1992, 33, 593. BBr3, A1203 , RT , 2 0 h m
C
O
2
H
Bains, S.; Green, J.; Tan, L.C.;
SECTION 18:
m.R.M. ;&&&a.
0
* 67% G.W. Tetrahedron Lett., 1992, 33. 7475.
ACID DERIVATIVES FROM ALCOHOLS AND THIOLS
Kabalka. G.W,; Chatla, N.; Wadgaonkar, P.P.; Deshpande, S.M. Synth. Commun., 1990, 20, 1617. [(CxH17)3NMe13+{XOO"O)(02)21~)~3 PhCH2OH 4% aq. H202,9OoC
t
Ph-COOH
Venturello. C.; Cramharo, M. .I. Org. Cheni., 1991, 56, 5924.
Singh, M.; Singh, K.N.; Dwivedi, S.; Misri. R.A, S,pthesis, 1991, 291.
85%
Compendium of Organic Synthetic Methods, Volt?
8
+
-
HOOC
NaIO4, RuC13.3 HzO MeCN-CC14-HzO
Y- Y- B
*
DT
Section 19
Singh, A.K.;Varma, R.S. Tetrahedron Lett., 1992, 33, 2307.
SECTION 19: ACID DERIVATIVES FROM ALDEHYDES
Mark6.; Mekhalfia, A. Tetrahedron Lert., 1990, 31, 7237. NaC102, AcOH
E
€
eCHO
*
cnzci2
Etec 84%
w Perez, ; F.; Courtieu, J. Bull. SOC. Chim. Fr., 1990, 127, 565.
oCo2H 86%
0.8% NiCdmp)z, 3 h
Ni(dmp)z = bis-[ 1,3-di@-methoxyphenyl)-1,3-propanedionato nickel 01) Yamada, T.; Rhode, 0.;Takai,T.; M u k a i v w Chem. Lett., 1991, 5. 1. Bu3SnLi 2. Me3SiCN
PhCHO
4
3.3 eq. BuLi 4.03, CHzC12 Linderman.;Chen, K. Tetrahedron Left., 1992. 33, 6767. COCIZ.DCE ,0
PhCHo Bhatia, B.;
2
Ac20.20 h ,25"C
*
Tetrahedron Lett., 1992, 33, 7961.
PhCOOH
PhCOOH
63%
4,%
Section 21
9
Acids from Amides
ACID DERIVATIVES FROM ALKYLS, METHYLENES AND ARYLS
SECTION 20:
OAc
OAc
RuC13 , HIO4, CC4
HO2C
MeCN.If20 25-40°C
Ph
A 76%
NuRez, M.T.; Martin. V.S.J. Org. Chem., 1990, 55, 1928.
ace,,-
Br 1. Tic14 , CH2C12 , RT PhSeA COzEt
*
(Q ..),
2. NaOH , NaE3H4, EtOH RT ’ Inin
70%
. . Sllvelra.; Lenarao, E.J.; Comasseto, J.V.; Babdoub, M.J. Tetrahedron Lett., 1991. 32, 5741.
SECTION 21:
ACID DERIVATIVES FROM AMIDES 1.3 eq.
Me
.
NHn-Bu
~~n/anti=99.5/0.5
Me Me AcO+ C1
Me 0
76% 3 mt3,0.1 DOM ~ P+OH CH2C12, RT, l l h Me 2.4 LiOH RT,30h s~mti=99.uo.8
.
Tsunoda T.; Sasaki, 0.;I d , S. Tetrahedron Lett., 1990, 31, 731.
Ph
)r NH2
0
NzO4, MeCN -20°C
-
d
Ph - C02H
Kim.;Kim, K.; Park,Y.J.Tetrahedron Lett., 1990, 31, 3893.
SECTION 22: ACID DERIVATIVES FROM AMINES NO ADDITIONAL EXAMPLES
86%
Compendium of Organic Synthetic Methods, Vol8
10
Section 23
SECTION 23: ACID DERIVATIVES FROM ESTERS
60% (93% ee) Belair, N.; Deleuze, If.; Rascle, M.-C.; Maillard, B. Tefrahedron Lett., 1990, 31, 653.
D&&QJ!:.
1. A113 ,MeCN
Ph
0
OMe
82"C, 30 min
Mahajan, A.R.; Dutta, D.K.;
0
88% ;
Me
PhA0J)pJ
Ph-CO2H
w
2. H 2 0
Terrahedron Lett., 1990, 31, 3943.
DDQ ,reflux, 8 h
PhC0,H
/
90%
OMe
lb.L%L: Kim. H.R.;Yi,K.Y.Telruhedron Left., 1990, 31, 5913. Ph? Huang,
Br
0
z-z.;
ElOH
* Ph--\
CO2H
81%
- Synrhesis, 1990, 633.
OH
Ph
10% Se ,NaBH4, DMF
&C02Me A \
ih2NEt9MECN-HzO, 30°C I0 khar , 4 d
:
.r
Ph X C 0 , H
A
91%
Yamamoto.: Furuta. T.; MaIsuo, J.; Kurata, T. J. Org. Chem., 1991, 56, 5737.
n-Cl1H23CO2Bn
1. PhMe , MgI2 , reflux , 2 h 2. aq. HCI w
n-C,1H,,CO,H
70% Marlinez. A.G.; Barcina, J.O.; del Veccin, G.H.; HanackM.; S u b r m i m , L.R, Tefrakdron Lett., 1991.32, 5931.
Section 25
11
Acids from Halides
HCOOH ,H 2 0 , reflux
v 0
3h
84%
Schmid, C.R. Tetrahedron Lett.. 1992, 33, 757.
-0
--
- ~--
C0ZH
Troll.$; Wiedemann, J. Tetrahedron Leu., 1992, 33, 3847. Ph
T~BU
CuC12.2 H@ , acetone
PhC02H
96%
PhC02H
92%
RT
0
68%
Dabdoub.;Viana, L.H. Synth. Cornrnun., 1992, 22, 1619. BI3*NEtzPh, PhH , 2 h
PhC02Me
H2O,8ODC
c.
Kabalka.;Narayana, C.; Reddy, N.K. Synth. Comtnun., 1992. 22, 1793. Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids).
SECTION 24:
ACID DERIVATIVES FROM ETHERS, EPOXIDES AND THIOETHERS
44%
Fukumasa, M.; Furuhashi, K.; Umezama, J.; Takaha,phi. 0.;Hirai, T. Tetrahedron Lett.. 1991, 32, 1059.
SECTION 25:
PhCH2Cl
ACID DERIVATIVES FROM HALIDES AND SULFONATES em(Ni anode/OH-), t-BuOH/HzO
K2CO3 , 6 0 T Borsotti, G.P.; Foa', M.; Gatti. N, Synthesis, 1990, 207.
c.
PhCOOH
70%
12
Compendium of Organic Synthetic Methods, Vol8
Section 25
Schiinecker.;Walther.; Fischer, R.; Nestler, B.; Bdunlich, G.; Eibisch, H.; Droescher, P. Terrahedron Lett., 1990, 31, 1257.
PhCH2Br
20 eq. NaOCl , MeCN , RT +
PhCHO
2 h )">)
+
PhCOOH
22%
74%
Khurana. J.M,; Sahoo. P.K.; Titus, S.S.; Maikap, G.C. Synrh. Commun., 1990, 20, 1357.
0.5 Ni(CN)2*4 H 2 0 0.5 C0C12.6 H20 , 2 KCN
phk Br
3:1 CO:H2 , PhMe
5N KOH , PEG-400,3.5 d*
Br
phY7Co2H
72%
(1:l cis:trans) Grushin, V.V.;
Terrahedron Lett., 1991, 32, 3349.
\ / I .(It-
-
PdC12(PPh3)2, EtOH CO (30 a m ) , HCl , TlIF
Me0O -
H20,24h,100"C * c1 84% MS 4A . . Terrahedron Lett., 1991, 32, 4733. Urata, H.; Hu, N-X.; Maekawa, H.; 1. Pd(OAc)z(PPh3)2 DMF ,25"C
2. CO , AcOK
*
P h O C 0 , H 82%
Cacchl.;Lupi, A. Terrahedron Lett., 1992. 33, 3939.
Okano.; Harada, N.; JQjjJ,, Bull. Cherrt. SOC.Jpn., 1992, 65, 1741. PdClz(dpm)z, NaOH , CO
Br Okano.,Okabe, N.;
heptane/H~O,50°C
*
%C0,H
Bull. Chem. SOC. Jpn., 1992, 65, 2589.
63%
Acids from Nitriles
Section 28
13
SECTION 26: ACID DERIVATIVES FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 27: ACID DERIVATIVES FROM KETONES hv (Pyrex) , 5 % aq. acetone propylene oxide
Ph
*
Me
Me PhACOzH
58% Sonawane. H.R.; Kulkami, D.G.; Ayyangar, N.R. Tetrahedron Leff.,1990, 31, 7493.
Me W
N a 0 2 . W(HF),
M
e
M e b c o z H 80%
Qlah. G.pL; Ramos, M.T.; Wang, Q.; Surya Pr&&&.&,SynLelt, 1. f-BuOK ,CHCI3 hexane
0 p h y Me
2. H2, Pd-C
1991, 41.
- -r
CO,H
Ph
65%
Llama. E.F,; del C a m p , C.; Sinisterra, J.V. Org. Prep. Proceed. lnt., 1992, 24, 165.
SECTION 28: ACID DERIVATIVES FROM NITRILES
CN Cohen, M.A.; Sawden, J.;
nitrile hydralase SP 361 pH 7 ,30°C , 2 3 h
Tetrahedron Lett., 1990, 31, 1223.
-
Rhodococcus sp , strain CH5 pH 7 buffer, 435 h , RT
C I O C 0 , H
(44% conversion)
Honicke-Schmidt, P.; M
NC-COOH
r
98%
. M.P. .I. Chem. Soc., Chem. Commun., 1990, 648. enzyme fmm Rhddococcus sp.
HOOC-COOH
68%
de Raadt, A; Klempier, N.; Faber, K.; Griencl. H.J. Chem. Soc., Perkin Trans, I, 1992, 137.
14
Compendium of Organic Synthetic Methods, Vo18
OBn -
Rhodococcus bufanica ATCC 21 197
--
CEN CnN
Section 30A
f i
CIN CO2H
68%
(90% ee , S)
Kakeya, H.; Sakai, N.; Sano, A.; Yokoyama, M.; Sugai, T.; Ohm. H, Chein. Leu., 1991, 1823.
SECTION 29: ACID DERIVATIVES FROM ALKENES 1 . HBBrySMe2 ,40°C CH2Cl2.2 h
m C O 2 H
2
2. HzO ,25"C, 30 min 3. CrO3, aq. AcOH 25"C, 12 h Racherla, U.S.; Khanna, V.V.;Brown. H.C, Tetrahedron Left.,1992, 33, 1037.
SECTION 30:
97%
ACID DERIVATIVES FROM MISCELLANEOUS COMPOUNDS 1. cuc12 2. H20
PhN2' BF; * PhCOOH Olah.;Wu, A.; Bagno, A,; Surya Prakash, G.K.S.SynLett, 1990, 596. SECTION 30A:
Ph\
PROTECTION OF CARBOXYLIC ACID DERIVATIVES 1. MgBq ,ether 2. H20
COZMOM
b
Ph\
Kim.; Park,Y.H.; Kee, I.S. Tetrahedron Lett., 1991, 32, 3099.
EtCooH
42%
'*
Ph
phhoH (86-95%) OH Ph
2. LDA , TMSCl
(82-g4%)
NaOH , aq. MeOH ,reflux, 2 h Waldmiiller, D.; Braun. M,; Steigel, A. SynLett. 1991, 160.
C02H
Section 30A
OBn BnO&COzEn
15
Protection of Acids
EtOH , 10%Pd-C ,23"C
Tetrahedron Lett.. 1992, 33, 2299.
OBn BnO&C02H
90%
Other reactions useful for the protection of carboxylic acids are included in Section 107 (Esters from Carboxylic Acids and Acid Halides) and Section 23 (Carbxylic Acids from Esters).
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 3 PREPARATION OF ALCOHOLS
SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES NO ADDlTIONAL EXAMPLES
SECTION 32:
ALCOHOLS AND THIOLS FROM ACID DERIVATIVES Et3N*BH3 , 8 0 ° C , 4 h
-C02H
O -H
96%
Kfii, 0.;PlzAk, 2.; PleSek, J. Coll. Czech. Chem. Commun., 1990, 55, 2956.
co2H
1. N-methyhofpholine N-oxide
CIC02EtI THF , -10°C 2. NaBH4, MeOH , 2 0 min
CbzHNT Ph
Ph
Synthesis, 1990, 299. BnEt3N' BH4- , Me3SiCI
PhCOOH Das, J.;
CH2Clz
*
'hCH2OH
92%
b a r d Synrh. Commun.. 1990, 20,901.
PhC0,Me
1. [5% CpzTiC12/10% BuLi] ,RT THF , -78"C,2 eq. HSi(OEt)3
PhCH2OH
2. conc. HCI Berk, S.C.; Kreutzer, K.A.; Buchwald.S.L.. Am. Chem. SOC.,1991, 113, 5093.
Ph-7
NaBH4, 1 2 , RT 1nF
CO2H PhxOH Kanth, J.V.B.; Periasamv. M,.I, Org. Chem., 1991, 56, 5964.
98%
93%
Section 32
Alcohols from Acids
17
2 eq. SmI2, THF/H20 NaOH , RT
* @OH
58 sec
78%
Kamochi, Y.; Kudo. T, Chem. Lett., 1991, 893. N a B Q ,catechol
n-C8H&H,OH
F A ,4 h
n-C8H17C00H
87%
Suseela, Y .;
Tetruhedron, 1992, 48, 371.
SmI2-85%H3P04
Ph-CO,H
--
THF , 3 sec
PhCH2OH
91%
Kamochi. Y Kudo, T. Tetrahedron, 1992, 48,4301, t;
.
1. h v , 0 2 . 2 h acridine PhMe r
-
B
u
h
c
o
2
H
2. Me2S , MeOH*
t
-
B
u
h
Fe (porphyrin) , RT PhIO , CH2Cl2 ,20 h
-
'">OH
H
6070
Okada.;Okubo, K.; QhJL Tetrahedron Lett., 1992, 33, 83.
Ph
O
+
'$0
3% 46% Komuro, M.; Nagatsu, Y.;Higuchi, T.; Hirobe. M. Tetrahedron Lett., 1992, 33, 4949.
fli~
NaBH4-HzS04
89%
Abiko. A,; Masamune, S. Tetrahedron Lett., 1992, 33, 5517. 1. e- ,NaBH4
n-C7H ISCOOH Shundo, R.; Matsubara.;-;
PhCOOH -hi.
2. HzO
-
n-C7H15CH20H
70%
Hirashima, T. Bull. Chem. SOC. Jpn., 1992, 65, 530. 4 eq. SmI2,8 eq. NaOH 1-120 *
PhCH2OH
Y.; Kudo, T. Bull. Chem. SOC. Jpn., 1992, 65,3049.
92%
18
Section 34A
Compendium of Organic Synthetic Methods, Vol8
Zn(BH& , DMF , 2 4 h
n-C7H,,COOH
TFA
n-C7H15CH20H
@
90%
Ranu. B.C. ; Das, A.R. J. Chem. SOC., Perkin Trans. I, 1992, 1561.
SECTION 33:
ALCOHOLS AND THIOLS FROM ALCOHOLS AND THIOLS
OSiMe,
BuLi , THF , -78°C
TiMe3
*
A SnBu,
n-C7H15
OH 63%
n-C7H15
reverse Brook rearrangement Linderman. R.J. ; Ghannam, A. J. Am. Chem. SOC., 1990, 112, 2392. 0
FAN)
"MeYSH THF , PP ,
H?. H
PhaMe
0
2
*
2. LiAIH4, ether
Ph
>SH Me
61%
(96% ee)
Corev. EL; Cimprich, K.A. Tetrahedron Lett., 1992, 33, 4099.
SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES The following reaction types are included in this section: A. Reductions of Aldehydes to Alcohols B. Alkylation of Aldehydes, forming Alcohols. Coupling of Aldehydes to form Diols is found in Section 323 (Alcohol-Alcohol).
SECTION 34A:
G
REDUCTIONS OF ALDEHYDES TO ALCOHOLS
z
h
Zn(BH4)2, THF , -10°C
0 selective reduction of aldehydes in the presence of ketones
Ranu.; Chakraborty, R. Tetrahedron Lett., 1990, 31, 7663.
0
quant.
Section 34B
Alcohols from Aldehydes
-CHO
DMF- 1 3 2 0
19
-OH
-
98 %
also with aromatic and conjugated aldehydes
Wmg, W-B.; UL- Tetrahedron L.; Lett., 1990, 31, 1185. Zn-ZnClz 50% aq. THF
Tanaka, K.; Kishigami, S.;
+ 7%
81% of dimeric diol
Toda.F.. Org. Chem., 1990, 55, 2981.
0
hv ,cyclooctane , 4 8 h
RhCI(CO)(PMe3)2
CHO
P
Sakakura, T.; Abe, F.;
O
H
87%
Chem. Lett., 1990, 583, 585. XP4 - Zn(BH&, EtOH
PhCHO
reflux, 8 h
t
PhCH20H
80%
XP4 = crosslinked poly(4-vinylpyridine)
Flrouzabadi..H.; Tamami, B.; Goudarzian, N. Synth. Cornmun., 1991, 21, 2275. PhCHO
NiC12-6 H 2 0 , aq. DMF 30 min
c
PhCH2OH
95%
PhCH20H
98%
IbmaLR& Tetrahedron Lett., 1992, 33, 5417. PhCHO
NaBlI4 , PhH , H 2 0 , RT H-montmorillonite , 7 h
*
Subba Rao, Y.V.; (3houdarv. B.M.Synth. Commun., 1992, 22, 2711.
SECTION 34B: ALKYLATION OF ALDEHYDES, FORMING ALCOHOL ASYMMETRIC ALKYLATIONS 1.
>CHO
ether, - 1 ~ O c .30 min
2. NaOH ,H 2 0 2
*
Racherla, U S . ; Brown.H.COrg. .. Chem., 2991, 56, 401.
(96% ee)
Compendium of Organic Synthetic Methods, Vol8
20
Section 34B
Corev.:Kim, S . S . Tetrahedron Lett., 1990, 31, 3715.
M = ally1 ZnLiCl , THF , 0°C M = AIMe3Li. ether, -78OC
98
2 84
16
Overly, K.R.; Williams, J.M.; UQLYQ&L Tetrahedron Lett., 1990, 31, 4573.
(70%) (78%)
(70% dr)
Henedus.; Imwinkelried, R.; Alarid-Sargent, M. J. Am. Chem. Soc., 2990, 112, 1109.
=c
PhCHO
SiMe3
OiPr
*
20% BH3.THF/ O
OiPr
Furata, K.; Mouri, M.;
OBn CHO
>
Nehry, K.J. Jr.;
r
OH
SynLert, 1991, 561.
-
(82%ee , R)
OBn
J SnMe3 ,ether
5M LiC104, 1.7 h
phxx
m
OH
(291 dr) ; Jape, C.T. Tetrahedron Lett., 2992, 33, 1817.
82%
82%
Section 34B
Alcohols from Aldehydes
PhCHO , CH2Cl2 -780c
+OSiMe,t-Bu
OEt
OH OSiMe2t-Bu
t
Ph
+o
21
JdOEt -
77%
(45% ee)
Ts'"B H
Kivooka. S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem., 1991, 56, 2276.
5)
(1
Li
=/ ,ether ,RT (6 &~w.LB&; Carpenter, A.J. Tetrahedron Lett., 1992, 33, 1697.
1)
Reactions of EtZZn and PhCHO Et& , hexane , RT , 2 d
PhCHO A1203
Me +Ph
Fj
Me
0
PhyEt OH
(43% ee , R)
81%
Soai.;Watanabe, M.; Yamamoto, A. J. Org. Chem., 1990, 55,4832. EgZn , PhMe ,20 h
PhCHO
w
"EPh
6%
OH
HO
Rosini, C.; Franzini, L.; Pini, 0.;
CHO
Et"' H
99%
(ym
Tetrahedron Asyrnmeiry, 1990, 1 , 587.
,,,.qH
I
Y OH
(77% ee , R)
.
EtzZn, RT , 4 8 h
Me-
Ph
H
Me
* (1:l (251
40%
73%
90% Chaloner, P.A.; Langadianou, E. Tetrahedron Lett., 1990, 31, 5185. (4.51
O%ee
)
80%ee )
97.5% ee)
22
Compendium of Organic Synthetic Methods, Vol8
Ph>CHO Me
-
Et2Zn HOCH2CHzNH2
Section 34B
OH
P h y C + (83% dr, syn) Me
phy% 55% Me
Soai.;Niwa, S.; Hatanaka, T. Bull. Chem. Soc. Jpn., 1990, 63, 2129. EtzZn , hexane , -10°C ,24 h
<ELOH
CHO
67%
(95% ee ,R)
Hayashi, M.; Kaneko, T.; Qguni. N, J. Chem. SOC.,Perkin Trans. 1, 1991, 25.
PhCHO
EtzZn, 5%ephedrine
*
OH PhlEt
(66%ee , R)
60%
Chaloner. P.A,; Langadianou, E.: Peresa, S.A.R. .I. Chent. Soc., Perkin Trans. I, 1991, 2731.
Ph
Et2Zn
PhCHO
7 8 '
OH
I 3
92%
(96% ee)
3
Asami.;Inoue, S. Chem. Lett., 1991, 685.
Et2Zn , PhMe ,20 h
PhCHO
6%
*
94%
(63%ee ,S)
NMe2 NMe2
\
OH x Et H
Ph
\
(S) Rosini, C.; Franzini, L.; Iuliano, A.; Pini, D.; Salvadori. P, Tetrahedron Asymmetry, 1991, 2 , 363. EtzZn, PhMe ,20 h
PhCHO
t
OH ph
cat. Me
Nlslund, J.; Welch. C.J. Tetrahedron Asymmetry, 1991, 2, 1123.
90%
Alcohols from Aldehydes
Section 34B
?CHO OBn
EtzZn, 20 h
23
\/\/\ -
-
57%
OBn OH
20% PhkMe
(78% dr) Soai.;Hatanaka, T.; Yamashita, T. J. Chem. SOC., Chem. Commun., 1992, 927. Soai;Watanabe, M. J. Chem. SOC.,Chem. Commun., 1990, 43. HO'
- N B ~ ~
ZnEt2, PhMe , RT ,?A h
PhCHO
t
PhL
+
+
OH
Et
OH Ph-
Et
(91
2)
91%
(1
99)
80%
NMez
Kimura, K.; Sugiyama, E.; Ishizuka, T.; Kunieda. T, Tetrahedron Lell., 1992, 33, 3147.
Jq
Et2Zn , PhMe , 0°C , 3 h
PhCHO
I-Bu
+
PhqEt OH
l-BU
83%
(93%ee)
also - conjugate addition of Et2Zn Bolm.;Schlingloff, G.; Harms, K. Chem. Ber., 1992, 125, 1191. Bolm.;Ewald, M.; Felder, M. Chem. Ber., 1992, 125, 1205 [conjugate addition]. OH
HO
EgZn , -40°C
PhCHO
OH P&Et
85%C&
(91% e e , S)
78%
- N 2 N J
Mori, A.; Yu,D.;
PhCHO
Bli
SynLett, 1992, 421.
Mea
EtzZn , Ti(OiPr)4,0°C , PhMe c
TosHN
OH
PAEt OH
(81% ee , S)
Ito, K.; Kimura, Y.; Okumura, H.; Katsuki. T, SynLetL 2992, 573.
81%
24
Compendium of Organic Synthetic Methods, Vol8
Section 34B
Heaton, S.B.; Jones. GLB Tetrahedron Lett., 1992, 33, 1693.
NON-ASYMMETRIC ALKYLATIONS
(y
OH
1. Li p,p'-di-1-butylbiphenylide
THF , -78°C
SF%
-
79%
Cohen. T,;Doubleday, M.D.J. Org. Chem., 1990, 55, 4784.
,SbCl3-Fe
-I
PhCHO
2 5 T , 20 h
Wang, W-B.; Shi. L-L; Xu,R-H.; m
0 Ph,TeMe
0 BPh,
-
OH
Ph
.
&
98%
n . Y-Z, J. Chem. SOC., Perkin Trans. I, 1990, 424.
1. BuLi 2.PhCHO 3. 1 h
55%
c
Shl.; Zhou, J.L.; H!une. Y-7.. J. Chem. Soc., Perkin Trans. 1, 1990, 2847. PhCHO , MezFe.3 LiCl THF , -78"C+ RT
I
w
18 h
OH 83%
Also works with Co reagents: Kauffmann.; Laarmann, B.; Menges, D. Tetrahedron Lett., 1990, 31, 507.
SiF3
PhCHO , resorcinol
.
NEt3 CH2Ch1 RT
20h
2%
OH Ph*
Kira.;Sato, K.:Sakum-L J. Am. Chem. Soc., 1990, 112, 257. '
OH
93%
Section 34B
Alcohols from Aldehydes
e- , PhCHO , DMF B u ~ N 1C0 4
&Br
Tokuda.;Uchida, M.; Katoh, Y.;
*
Ph
25
ll"J,
80%
Chem. Lett., 1990, 461.
Bu3SnH, AIBN
L
CHO
&Ph
80%
(1: 1 trans:cis)
Yadav, V.;
Can. J. Chem., 1991, 69, 779. 1. Ba ,THF
OH 97:3
(>99:1 E:Z ;
a : y substitution)
Yanagisawa, A.; Habaue, S.; Yamamoto. H. J. Am. Chem. Soc., 1991, 213, 8955. 1. CsF , MeCN 2. ECHO
Ph
-IMe %Me3
SMe
*
Ph%Et OH
Ph--/
+
SMe
27%
26% Bonini, B.F.; Masiero, S.; Mazzanti, G.; Zani. P, Tetrahedron Lett., 1991, 32, 815.
Br
Me0,C- C: C 7 1. BuLi , -78°C
0
,OH
-
2.TiCl(OiPr)3 3. -60°C. 21 h Me02C- C3 C
3CHO
70%
0
Haannann, H.; Eberbach, W.Tetrahedron Lett., 1991, 32,903.
ClF,C
iPrCHO , Zn-CuC1
SiMe, DMA ,100"C *
& ' r
DMA = N,N-dimethylacetamide
; -
OH
SiMe,
75% Miwatashi, S.; Kuroboshi, M.; Utimoto, K. Tetrahedron Lett., 1991, 32, 1069.
26
Compendium of Organic Synthetic Methods, Vo18
"9
'
OCll F
e
oc
1.
Section 34B
d
.elher
BF-j*OEt2 2. NaI ,wet acetone
55%
Agoston, G.E.; Cabal, M.P.; Turos. E, Tetrahedron Lett., 1991, 32, 3001.
"masked"Li bis-homoenolates Ram6n, D.J.; Y u s . J . Org. Chem., 1991, 56, 3825. 1. CpzZrMe~ 2 . 5 eq. t-BuOK , THF
3. aq. KF
eg /
0
69%
Larson, A.L.; Baker, D.L.; Towne, R.W.; & a u ~ L & Tetrahedron Lett., Z991, 32, 5893.
CHO
<SiMe3
BnOTMS , C C 4 cat. Me3SiOTf Mekhalfia, A.; Mark4 I.E. Tetrahedron Leit., 1991, 32, 4119,
B(OPh), Hara, S.; SJJ&L-&.
PhCHO
0°C -) RT
Tetrahedron Leit., 1991, 32, 6749.
,3h
-Br
In, H 2 0
t
Li, C.J.; €haJX. Tetrahedron Leit., 1991, 32, 7017. Zn , AcOH
-CHO
PhMe , H 2 0
c&
--
Br
PhCHO , THF ,overnight
OH
OH
Ph
91%
7 OH c1
Qda. Y,; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 91.
99%
Section 34B
Alcohols from Aldehydes
27
1. Me3SiCi ,Nal , H 2 0 Sn
OH
2. butanal, MeCN RT.4h (98
(35:65 E:Z) J. Org. Chem., 1992, 57, 6988.
Kanagawa, Y.; Nishiyama, Y.;
t
CHO
2)
-b
76%
SiO2 (oven-dried) 15 k b a , CH2C12 25"C, 48 h
OH
58%
2%
Dauben.:Hendricks, R.T. Tetrahedron Lett., 1992, 33,603.
T
C
H
O
'%:
Bu3SnH , PhH ,8OoC
AIBN
Ph
75%
( 2 5 2 5 3 . 0 :1.0)
Enholm. E.J; Burroff, J.A. Tetrahedron Lett., 1992, 33, 1835. 1. PhCHO , THF , -78°C Li powder/CloHNb , 2h
ClJCCl
Ph m
2. H20
p
h 73%
Ram6n, D.J.; h s . M Tetrahedron Lett., 1992, 33, 2211. PhCHO , Cd , THF
+Br
b
Bu4NBr, 4 h OH Sain, B.; Prajapti, D.; Sandhu. J.S. Tetrahedron Lett., 1992, 33, 4795.
90%
1. b S n B u 3 .RT
PhCHO Marshall, R.L.;
2.F'
MeSiC13 , CH2C12, 6 d
+
Ph
Tetrahedron Lett., 1992, 33, 1365.
quant
28
Compendium of Organic Synthetic Methods, Vo18
,THF,RT
&Br
-CHO
cat. CpzTiClz , Zn , RT
Dine.;Zhao, G. Tetrahedron LRtt.,
* 3 min 1992. 33, 81 17.
Section 34B
A
80%
61% Davis. A.P, ; Jaspars, M. Angew. Chem. Int. Ed. Engl., 1992, 31, 420. PhCHO , SnC12, DMF
2% PdClZ(PhCN)z, 25°C
-OH
4
63 h
Takahara, J.P.;
P
63%
h
(3070 dr)
-Y.;
Kurusu, Y . J. Am. Chem. SOC., 1992, 114, 2577.
MeCrCIz(THF)3, THF
PhCHO
-60°C + 20”C,18 h
b
ph-(Me
OH
90%
ann. T.; Beirich, C.; Hamsen, A.; Moller, T.; Philipp, C.; Wingbermuhle, D. Chem. Ber., 1992, 125, 157. REVIEWS:
“Addition of Organochromium Compounds to Aldehydes: the Nozaki-Hiyama Reaction” Qntas. P , Synthesis, 1992, 248.
SECTION 35:
ALCOHOLS AND THIOLS FROM ALKYLS, METHYLENES AND ARYLS
No examples of the reaction RR1 + ROH (R1 = alkyl, aryl, etc.) occur in the literature. For reactions of the type RH -+ ROH (R = alkyl or aryl) see Section 41 (Alcohols and Phenols from Hydrides). 1. Brz , CHZC12 2. HF*Py , 0°C
AcO
3.30% HzOz , KF * KHC03, THF AcO’” AcO”‘ MeOH Magar, S.S.; lWu2.L. Tetrahedron Lett., 1991, 32, 7513.
Section 38
Alcohols from Esters
29
SECTION 36: ALCOHOLS AND THIOLS FROM AMIDES SmI2, LiNH2, THF MeOH , RT , 3 secn-
Ph y NH2
ph-
0 Kamochi, Y.;
OH
72%
Tetrahedron Lett., 1991, 32, 351 1.
SECTION 37: ALCOHOLS AND THIOLS FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 38: ALCOHOLS AND THIOLS FROM ESTERS HSiMe3 ,CO , PhH cat. C02(CO)8 ,25"C 1 am.
M e o w O A c
M e O ~ o s i M e 3
76% Chatani, N.; Sano, T.; Ohe, K.; Kawasaki, Y.;Murai. S. J. Org. Chem., 1990, 5.5, 5923. SmI2, LiNH2, THF MeOH , RT , I 4 min
Ph y OMe
ph7
0
OH
64%
Kamochi, Y . ; Kudo. ZTetrahedron Lett., 1991, 32, 3511.
-
Aco-0-
Pseudomoms cepacia lipase P-30
oAc
4h
H O O O A c
64%
(79% ee) Harris, K.J.; Gu, Q.M.; Shih, Y-E.; Girdaukas, G.; Sih. C.J, Tetrahedron Lett., 1991, 32, 3941. 1. Bu3Sn20, PhMe 80°C , 2 h
OAC
-2.'
2. pH 4
h
Salomon, C.J.; Mata, E.G.; Mascaretb.. O.A, Tetrahedron Lett., 1991, 32, 4239.
96%
NaBH4,ZnCIz. 2 h
Ph
Co2Et
PhNMe2, THF * 85% reflux Yamakawa. T,; Masaki, M.; Nohira, H. Bull. Chem. SOC. Jpn., 1991, 64, 2730.
30
Compendium of Organic Synthetic Methods, Vo18
Section 39
n-C5Hl lCHO , DMF ,4O"C NiC12(PPh3)-Zn , 7 h
WJ.; Konishi, H.; Matsuura, H. Chem Lett., 1991, 2023.
P h 7
5% Ti(OiPr)4,5S0C 3 eq. SiH(OEt)3 , 4 h
CO2Et
Ph7.0H
89%
Berk, S.C.; Buchww. S.L.J. Org. Chem., 1992, 57, 3751.
ALCOHOLS AND THIOLS FROM ETHERS, EPOXIDES AND THIOETHERS
SECTION 39:
-
Me
DMF ,60"C
O&
0
+ o
0
+
N3
MeTo 0 +OH
OH
N3
n-Bu3SnN3.5h 15 1 (69%) n-Bu3Sn(N3)2 , 4 h >99 1 (79%) Saito. S; Nishikawa, T.; Yokoyama, Y.;Moriwake. T, Tetrahedron Lett., 1990, 31, 221. I-Bu
I-BU
CH2C12 , -20°C , 3 h
Me
2.O"C , 12h 3. R T , l h
Maruoka, K.; Sato, J.; Banno, H.;
Me 9) 1 Tetrahedron Lelt., 1990, 31, 377.
92%
MeLi , THF , -78°C Me
OBn Arjona, 0.; 1475.
87% ; Mallo, A.; Plumet, J.; Viso, A. Tetrahedron Lett., 1990, 31,
Section 39
Alcohols from Ethers
31
BIs*PhNEt.r, PhH
Ph-OMe
*
3h
Ph-OH
85% Narayana, C.; Padmanabhan, S.; Kabalka, G.W. Tetrahedron Lett., 1990, 31,6977.
Y,Tetrahedron Lett., 1990, 31, 7467. secBuLi-CuCN
OTBDMS THF , 0°C + RT OTBDMS
90%
4)
(96
Sugita, K.; Onaka. M,; Izumi.
secBu
OTBDMS OTBDMS
73% no reaction with MeLiKuCN or n-BuLilCuCN; 78% with t-BuLi/CuCN Lautens.;Smith, A.C.; AM-El-Aziz, AS.; Huboux, A.H. Tetrahedron Lett., 1990, 31, 3253.
Me
1 eq. LDA , THF
-78°C
CS-H
I /
82%
77%
with 3 eq. LDA
Yadav. J.S,; Deshpande, P.K.; Sharma, G.V.M. Tetrahedron Lett., 1990, 31,4495. 1. LDBB , THF
0
-78OC, 2 min
n-C8H17e
. MeOH ,- 7 8 ° C
H
n-C8HI7 * + HO
LDBB = lithium 4,4'-di-t-butylbiphenylide
Cohen.;Jeong, I-H.; 1528.
Ph
n-C8H17
65%
F
H
35%
Mudryk, B.; Bhupathy, M.; Awad, M.M.A. J. Org. Chem., 1990, 55,
0~~ 1. Li , THE 2OoC * 0~~ 2. H20
4
Me
Ph-(oW70%
Azzena.;Denurra, T.; Melloni, G.; Piroddi, A.M. J. Org. Chem., 1990, 55, 5532.
32
Compendium of Organic Synthetic Methods, Vo18
S
Section 39
Bu3SnH , AIBN PhH , reflux
*
a M e 6 8 %
OH
(2.7: 1 )
Rawal. \LfL; Newton, R.C.; Krishnamurthy, V. J. Org. Chem., 1990, 55, 5181. 1. MeMgCl 2. MeMgI ,CuBr
T s A 0
3. aq. NHdCI
56%
Me
Ngiera.;Sansano, J.M. Tetrahedron, 1990, 46, 3993.
MsO
1 . BuEu(CN)Li2 ,THF -20°C
bo
2. BuzCu(CN)Li2. T H F -20°C
BuG
B OH
u
-k
&Bu Bu 1)
(1.2
Kurth. M L; Abreo, M.A. Tetrahedron, 1990, 46, 5085. MeMgI , CuBr , PBu3 O°C
*
75%
0"" 73%
Mitani. M.; Matsumoto, H.; Gouda, N.; Koyama, K. J. Am. Chem. Soc., 1990, 112, 1286.
n-
LxL OOH 78%
2. H3O'
-Bull
(90% ee , S)
Chem. SOC.Jpn., 1990, 63, 721. CpZTiC1, C6Hs
*
ZH
91%
gent, W.A.; Beattie, M.S. J. Am. Chem. SOC., 1990, 112, 6408.
Section 39
Alcohols from Ethers
Zn(BH&/Si02, THF
33
-
Ph-O RT,24h P h M O H 90% Ranu.';Das, A.R. J. Chem. SOC.,Chem. Commun., 2990, 1334. /
KFdumina, ethylene glycol 215OC. 5 h
=OH
80%
Radhakrishna, AS.; Prasad Rao, K.R.K.; Suri, S.K.; Sivaprakash, K.; Sineh, B.B,Synih. Commun., 1991, 21, 379. NaBH4, H 2 0 , RT , 4 8 h P-cyclodextrin
P h d o
*
Phr' -k OH
P h e O H
66% 17% 15% ee , S) (25% ee , S ) Hu, Y.; Uno, M.; Harada, A.; Takahashi. S, Bull. Chem. SOC. Jpn., 1991, 64, 1884.
Bu3SnH , AIBN , PhH (0.05
M)
* Me$ph
syringe pump addition
Ph
Kim.;Lee, S.; Koh, J.S. J. Am. Chem. SOC.,1991, 113, 5106.
Ph-OBn
3 AICl3 , 4 PhNMe2 CH2C12, RT 30 min
82%
H
Ph-OH
93% Akiyama. T.; Hirofuji, H.; Ozaki. S , Tetrahedron Lett., 1991, 32, 1321. Ph3SnH, hv ,70°C .-
Krosley, K.W.;
.*\
Ph-
OH
; Clapp, G.E. J. Org. Chem., 1992, 57, 840.
Dibal , CHzClz -15OC + RT
0 OTs
Chone. J.M.Tetrahedron k i t . , 1992, 33, 33.
P
h (>%
y OH
+
Ph
73%
34
Compendium of Organic Synthetic Methods, Vol8
Section 39
KI,DMF,RT * t-Bu--(>OH Mg anode, Ni foam cathode
t - B u e O4
63%
Espanet, B.; Duilach.; Phichon, J. Tetrahedron Lett.. 1992, 33, 2485.
-
hv ,MeCN-H20, Wt3
NaB H4
OH
Ph-
95%
EDline.;Wang, Q. J. Chem. Soc., Chem. Cummun., 1992, 1133. Me.,G (?H
BuLi ,ether, O°C
*
OH
Me
Lautens.;Belter, R.K. Tetrahedron Lett., 1992, 33, 2617.
Bu
HO BrQ
BuLi
93%
OSiMe2t-Bu Woo, S.;
92%
OSi Me2t-Bu
Tetrahedron Lett., 1992, 33, 2661.
OSiMe2t-Bu
Bu3SnHI AIBN
t-BuMe2Si0 &ph
c
Ph
PhH ,reflux, 3 h
OH
Kim.;Koh, J.S. Tetrahedron Lett., 1992, 33, 7391. S i 0 2 - Zn(BH& ,THF c
m"" (yo. +
(98
Ranu. B.C,; Das. A.R. J. Chem. SOC.,Perkin Trans. I, 1992, 1881.
P0
68%
MeCN , LiBr , RT
t
2)
95%
TBr
OH Amberlyst-15 resin (>99:1) Bonini. C. ; Giuliano, C.; Righi, G.; Rossi, L. Synth. Commun., 1992, 22, 1863.
Section 40
35
Alcohols from Halides
REVIEWS:
T&QLS&
"Biosynthetic, Biomimetic, and Related Epoxide Cyclizations" Org. Prep. Proceed. lnt., 1992, 24, 247.
Additional examples ofether cleavages may be found in Section 4% (Protection
of Alcohols and Thiols).
-
SECTION 40:
ALCOHOLS AND THIOLS FROM HALIDES AND SULFONATES
Br
1. (Bu$n)2O, 20°C 20 h
2. TBAF.3 H2O
-SH 71%
Gingras, M.; mp.D.N, Tetrahedron Lett., 1990, 31, 1397. 1. 1-BuLi,penmelether
-1
-78°C. 5 min 2. pentanal
*
v OH
91%
general method - preparation of 1" organolithium reagents Bailev. W.F,; Punzalan, E.R. .I. Org. Chem., 1990, 55, 5404. 1. t-BuLi , penme-ether -78°C
Bailey. W.F,; Khanolkar, A.D. J. Org. Chern., 1990, 55, 6058. 1. CICH20CH2CH2CI , ether , RT
*
BuMgCl
2. Na-K Q&-!!A; Wilson, T.E.; Stowe, J.A. Synthesis, 1990, 495.
Ph 7 Br
1. TBS-SLi ,ether 0°C - 25°C. 48 h
2. IIF, MeCN
Kraus.:Andersh, B. Tetrahedron Lett., 1991, 32, 2189.
BuCH20H
Ph 7 SH <75%
95%
36
aection 41
Compendium of Organic Synthetic Methods, Vol 8
I
1 '
BuLi , ether, -78°C cthylene oxide, CuCN -65°C -+ 25°C
I Wang, W.; DAndrea, S.V.;Freeman, J.P.; Szmuszkovicz. LJ. Org. Chem., 1991, 56, 2914. 1. n-PrSNaTol , NMP reflux (Dean-Stark) 2. HCI * 96%
GsH
NMP = N-methyl-2-pyrrolidinone
&YI LL&.
J. Org. Chern., 1991, 56, 3728. 1. BqSnH , air
PhMe ,20°C
Ph-Br
2.NaBk.EtOH
* Ph
OH
-k
Ph
80%
14%
Nakamura.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc., 1991, 113, 8980.
SECTION 41: ALCOHOLS AND THIOLS FROM HYDRIDES
3
OH
OH
90%
TFP= I,l,l-trifluoropropanone Mello, R.; Cassidei, L.; Fiorentino, M.; Fusco, C.; Curci. R. Tetrahedron Lett., 1990. 31, 3067.
0
[RU30(Pfb)6(0Et2)3+ MeCN , air (3 a m ) , 75°C 105 mol. catalyst
pfb = perlluorobutyrate
(5
15 turnovers Davis, S.; I&~QJ& J. Chem. Soc., Chem. Commun., 1990, 250.
1)
Section 41
Alcohols from Hydrides
37
I . Cuo , 0 2 ,Me3N-0 MeCN , 75°C. 6h
H CO2H
2.0.5MHCI
OH
quant.
Reinaud. 0,; Capdevielle, P.; Maurny, M. J. Chem. SOC.,Chem. Commun., 1990, 566.
0~~
CO+' - inontmorillonite
180°C. 2 h Fries rearrangement
96%
rc *-
Ts
4%
Pitchumani; Pandian, A. J. Chem. Soc., Chem. Commun., 1990, 1613.
&
OH
&
;-
(65
9)
26
66%
b a s s , N.; Wang, Q.;O l a h . S y n L e i t , 1991, 39. Rhizopus 28°C. arrkiws I8 h
0
-
0
0 ."&",I
HO& O H +
HO
42%
27%
Ouazzani,J.; Arsenivadis. S , ;Alvmz-Manzaneda, R.; Cabrera, E.; Ouvisson, G . Tetrahedron Lett., 1991, 32, 647.
0
Mucor plumbeus CBS 110-6 2d
a Me
0
+
o&,,,OH
OH
66%
/
22%
Hammoumi, A.; Revial, G.; DAngelo, J.; Girault, J.P.; Azerad, R. Tetrahedron Lett., 1991, 32, 651.
W
Oxone, TBA, 21 h 10 B U ~ N H S O ~ / C H ~ C I ~ aq. acetone , RT (dark) NaHCO3
Kumarathasan, R.; Hunter. N.R, Org. Prep. Proceed. Int., 1991, 23,651.
quant.
38
Compendium of Organic Synthetic Methods, Vo18
a
Section 41
1. HF ; S02CIF 2.90%H202, HF
-10°C -+ 0°C >98%
Olah.;Keumi, T.; Lecoq, J.C.; Fung. A.P.; Olah, J.A. J. Org. Chem., 1991, 56, 6148. 0 2 , CH2C12.3O"C
H hfacac-Zn
M
[( Fe(HBpz3)(hfacac))Ol
21 turnovers Hhfacac = hexafluoroacetyl acetone HBpz3 = hydrouis-1-pyrazolylborate Ito, M.; Fukui, H.; J. Chem. Soc., Chem. Commun., 1991, 102.
. .. m;
P. putida 02
66%
OH
34%
0
(45% ee) Sharma, N.D.; Stevenson, P.J.; Chima, J.; Gray, D.J.; LMuuJL Tetrahedron Lett., 1991, 32, 3887.
Bovd.;
6
0
N
NO, \
I MeCN , 75°C 2. H30+
80%
TMAO = Me3N-0
Reinaud.;Capdevielle, P.; Maumy, M. J. Chem. Soc., Perkin Trans. I, 1991, 2129. Ru(TPP)(CO) , HBr
= ($
%$,PhH,RT,6h
O!H
C1
Ohtake, H.; Highuchi, T.; Hirobe. & J. Am. Chem. Sac., 1992, 114, 10660.
94%
39
Alcohols from Ketones
Section 42A
SECTION 42: ALCOHOLS AND THIOLS FROM KETONES The following reaction types are included in this section: B. Alkylations of Ketones, forming Alcohols A. Reductions of Ketones to Alcohols Coupling of ketones to give diols is found in Section 323 (Alcohol
n-CSH1,
+ Alcohol).
1. M2(OAc)4
CHzClz, RT
2. Nai3H4, C e C l r
b 2
n-C3H7
n-C3H7
(70
30)
86%
Taber.;Hennessy, M.J.; Louey, J.P. J. Org. Chem., 1992, 57, 436. 1 . [Na2COyI .5 H2021 aq. THF *
))))I))
2. AcOH
-
H O G O H 86%
Kabaka. G.W.; Reddy, N.K.; Narayama, C. Tetrahedron Lett.. 1992,33,865.
SECTION 42A: REDUCTION OF KETONES TO ALCOHOLS ASYMMETRIC REDUCTION Bakers yeast
*
CICH2C02Et
OH A C 0 2 M e 51% (91%ee)
Nakamura.; Kawai, Y.; Ohno, A. Tetrahedron Lett., 1990, 31, 267.
SiMe,
(-)IPCzBCI
.
*
3h -35°C 2. HN(CHZCH~&
1.
H
OH SiMe3
67%
( 9 5 % ee)
SoderauistJ.A.;Anderson, C.L.;Miranda, E.I.; Rivera, I.; Kabalka, G.W. Tetrahedron Leff., 1990, 31, 4677.
bakers yeast t
Me
methyl vinyl ketone
OH &CO,Et Me (96
+
OH
i \ ( Co2Et Me 4)
Nakamura.; Kawai, Y.; Miyai, T.; Ohno, A. Tetrahedron Lett., 1990, 31, 3631.
96%
40
Compendium of Organic Synthetic Methods, Vol8
t
Ph
Section 42A
PhA Me
0.1
(87% ee ,R) Rama Rao. A.V,; Gujar, M.K.; Sharma, P.A.; Kaiwar, V. TefrahedronLett., 1990, 31,2341.
C7H8,-78"C, 15h
+
ph&
* Ph >9S%
u; Bakshi, R.K. Tetrahedron Lett., 1990, 31, 611. Ph
n
B ~ H ~
q : Ph
0
\
0.M.P.; Pemer. R.J.; Lijewski,
9 2 % R~ ~
Bu
n
*
Ph
OH
94% ee
Ph
L. Tetrahedron Lett., 1990, 31, 7415.
7 0
Thertrwanaerohiurrihrockii alcohol dehydrogen,zfe
*
7 OH 79% ee , S
Pseudonwnas alcohol dehydrogenase
-b 97%ee,R Shen, G-J.; Wang, Y-F.; Bradshaw, C.; Wong. C-H,J. Cherrr. Soc., Chem Cornmutt., 1990,
677.
BF3*OEt2, PhH , 0°C 3
N4 : ; .
BH3
.L
OH 81% (41% ee, R)
\
Kanth, J.V.B.; Periasamv. M. .I. Chea. Soc., Chewz. Corrzrnun., 2990, 1145.
Section 42A
Alcohols from Ketones
41
kCozH bakers yeast 28h
OH
OH
""'C02H
*
-t
T C O 2 H 30)
(70
67%
(98%ee) (>99% ee) Fuiisawa.;Mobele, B.I.; Shimizu, M. Tetrahedron Lett., 1991, 32, 7055. Zn(cra)*, THF , RT
*
Ph
P 3h
88%
-
(84% ee)
Zn(cra) = zinclsodium chiraldate
Lalloz, L.; Vanderesse, R.; Mayesky, B.; C a u h g L Chern. Lett., 1991, 1961.
Ph
L
7
Rawson, D.;
Ph
Me
L i A M 1 e$0 OMeOM@Me e o m O M . ]
OH I
Ph
THF , -78°C
84%
(94% ee) J. Chem. SOC., Chem. Commun., 1992, 494. Bu3SnH , TBAF , 0°C
*
0
OMe PhylMe OH
OMe Me
+ phLA -OH
0 ) 81% with BuZSnClH , 0°C (10 90) 72% Shibata. I,; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chern., 1992, 574049. (100
Bu
<=orev.,; Link, J.O.Tefrahedron Leu., 1992, 33, 3431.
;'
Cheng, X-M.;Cimprich, K.A.; Sarshar, S. Tetrahedron Lett,, 1991, 32, 6835.
42
Section 42A
Compendium of Organic Synthetic Methods, Vol8
Ph2SiH2, AgBF4, “HF 0°C , 6 h
Ph
OH
Phi\
c
86%
(83% ee , S )
N-. R w - N
Nishivama. H. ; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem., 1992, 57. 4306.
NON-ASYMMETRIC REDUCTION
*&
1. LDA ,THF-HMPA Cl-SiMe$I
SiMe3
2. 3. Bu3SnH. MeLiPhH ,THF AIBN 4. H20
w; Kane, R.R.; Obeyesekene, N.U. Tetrahedron Lett., 1990, 31, 1531. THF
quant.
Mittakanti, M.; Peters, J.L.; Morse. K.W, J. Org. Chem., 1990, 55, 4464.
Ph
1
Ph
A1 ,NH3 ,NHdCI, 25°C
)I))))))
-
Ph)’
OH Ph
98%
Sata.;Nagaoka, T.; Goto, T.; Saito, M. Bull. Chem. Soc. Jpn., 1990, 63, 290. NaBH4, MeOH
0
Ph
Rao,;Synth. Commun.. 1990, 20, 45.
HC02NH4, Ni(R), RT
Ph
MeOH , 3 h
+
JO”
0
10) 90%
(90
-
Ph y N H2
91%
Ph
Chen. F-E,; Zhang, H.; Yuan, W.; Zhang, W-W. Synth. Commun., 1991, 21, 107.
43
Alcohols from Ketones
Section 42A
C02Et
PhLi 2. HNTMSz , THF ,,-9OOC TMSI
PhCHO
Tph\**' Bso~co2Et
-78°C Ranu. B.C,; Das, A.R. J. Org. Chem., 1991, 56, 4796.
70%
0'"
0.1% RuC12(PPh3)3
2.4 eq. NaOH , iPlOH * 89% reflux, l h Chowdhury, R.L.; Btickval1. J-E.J. Chem. SOC., Chem. Commun., 1991, 1063. BqSnH , TBAF, THF RT.5h
OH
99%
shibah. I,; Yoshida, T.; Baba, A.; Matsuda, H. Chem. Lett., 1991, 307. NaBH4, CaC12, MeOH
0 Fujii, H.; Oshima.;
0
.
(97 Chem. Lett., 1991, 1847.
+
(ItoH 3)
92%
Fisher, G.B.; Harrison, J.; Fuller, J.C.; Goralski, C.T.; Sincaram. B. Tetrahedron Lett.. 1992, 22, 4533. REVIEWS:
"Bakers Yeast as a Reagent in Organic Synthesis" Servi. S . Synthesis, 1990, 1. "Practical and Useful Methods for the Enantioselective Reduction of Unsymmetrical Ketones" Singh. V.K, Synthesis, 1992, 605.
SECTION 42B: ALKYLATION OF KETONES, FORMING ALCOHOLS Aldol reactions are listed in Section 330 (Ketone-Alcohol)
44
Compendium of Organic Synthetic Methods, V o l 8
MeLa(OTfl2, THF -78"C.lOmin =
P h L P h
Section 42B
Me OH Ph&Ph
98% Collins. S,; Hong, Y.; Hoover, G.J.; Veit, J.R. J. Org. Chem., 1990, 55, 3565. BuLi , Yb(OTfl3
-
THF , -78OC
Me
c
(99
1)
91%
Molander.; Burkhardt, E.R.; Weining, P. J. Org. Chem., 1990, 55, 4990.
c1
[Li biphenylide , Cd2]
0-0
,TIIF
83%
-78°C + -35°C J. Org. Chem., 1990, 55, 5045.
Wu, T-C.; Xiong, H.;
1 . 2 SmCpz , THF
OH
OH
-3OOC
C l e \ v Me-
2. cyclohexanone
4)
(1
Collin, J.; Bied, C.;
BnO-CHO
57%
Tetrahedron Lett., 1991, 32, 629. $:
~
3
ether, -78°C
3
_____c
CuLi-PBu3
SiMe,
:
92%
( > 2 0 1)
Burke. S.D.; Piscopio, A.D.; Marron, B.E.; Matulenko, M.A.; Pan,G. Tetrahedron Leu., 1992, 32, 857. 2 SmI2, THF , c2 h cat. Fe@BM),
Me Me
-78°C
I
+ RT
* Me 3
DBM = dibenzoyl methide
Molander.;McKie, J.A. J.
Org. Chem., 1991, 56, 4112.
Me
e 88%
Section 44
45
Alcohols from Alkenes
1.
6Fe(C0)zCp BF3 , ether
c
2. NaI ,wet acetone
77%
Jiang, S.; TUQLL Tetrahedron Lett., 1991. 32, 4619. BuCeCIz
( y E H
77%
ultrasound used with CeC13-7 H 2 0 to prepare cerium reagent m v e s . N.;Lyford, L. Tetrahedron Lett., 1992, 33,4759.
SECTION 43: ALCOHOLS AND THIOLS FROM NITRILES 300°C. iPrOH
-CN
-OH
+
73%
hydrous zirconium oxide Takahashi, K.; Shibagaki, M.; Matsushita, H. Chem. Lett., 1990, 311.
SECTION 44: ALCOHOLS AND THIOLS FROM ALKENES Ph
+
Me
.-I300 0 0
1. [(+)-BINAPJRhCI PhMe,-5"C,72h 2. NaOH ,H2O2
Ph H,&oH M~ 73% (38%ee,S)
Sato, M.; Miyaura, N.; Suzuki. A, Tetrahedron Left., 1990, 31, 231.
PhKato, K.;
\
Co(acac)L, 0 2
iPrOH
c
OH Ph
Ph-+ 17%
46%
Ph
2 8%
Yamada.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc., Jpn., 1990, 63, 179. Ru~(CO)IZ, 180°C ( C - C ~ H I I )H~z ~0 HCOzMe , 10 h 'shaking' autoclave=
Jenner. G.Tetrahedron Lett., 1991, 32, 505.
0 9%
+
( T O H 60%
Compendium of Organic Synthetic Methods, Vol 8
46
Section 44
1.9-BBN 2. NaoOH
OSiMe,,t-Bu H0
HO with tbexylborane
HO
(1 3
1
-)
93%
(1
15
1)
91%
Harada.;Matsuda, Y.; Wada, I.; Uchimura, J. J. Chem. SOC.,Chem. Commun., 1990, 21. [RhH(PEt3)3] , 120°C ,EtOH
-OH
L
94% (n:iso = 2.22) D.L J. Chem. SOC.,Chem. Commun.. 1990, 165.
MacDougall, J.K.; -ikon.
fi
hv (Vycor) , H202 MeCN,15h
*
66% 34% Sonawane.;Bellur, N.S.; Shah, V.G. J. Chem. Soc., Chem. Commun., 1990, 1603. 1.
a". d
H
L i B b , THF 2. H 2 0 2 , NaOH
94%
OH
+
-OH 6%
w; Nunokawa, Y.; Masuda, Y.; Hoshi, M. J. Chem. SOC.,Chem. Commun., 1991, 205. 4
ph
NaBH4, iPrOH ,100"C CH2C12 , co (500 psi)
Q
Pph3 , 2 2 h
@Rh (COD)
"-( (95
p
h
b
H
5)
83%
OH
Zhou, J-Q.; Alper. H. J. Chem. Soc., Chem. Commun., 199Z, 233.
(>99
-a.
A&;
1)
15%
Xu,Z.; Morken, J.P.; Houri, A.F. J. Am. Chem. SOC.,1991, 113, 8950.
Section 44
Alcohols from Alkenes
47
1. 0.01% [PdCl(l~-C3H5)12
HSiCl3 ,0.02% R-MOP
-
2. KF , KHC03 , H202
R-MOP = (R)-2-methoxy-2-diphenylphosphino-1.1'-binaphthyl Uozumi, Y.; Lee,S-Y.; Jlavashi. T. Tetrahedron Lett., 1992, 33,7185.
2% Rh(PPh3)CI , THF *
2. NaOH , aq. H202 EtOH , THF
H
O
W
(99
+ ? OH 1)
Evans. D.A,; Fu, G.C.; Hoveyda, A.H. J. Am. Chem Soc., 1992, 114, 6671. 1. (J":B-H
Harrison, K.N.;Ma&$. 1.
%Ph
-
,250c
R o
CnLaCH(SiMe& 2. H202, NaOH T.J.J. Am. Chem. Soc., 1992, 114, 9220.
0
:B-
, PPh3
*
2% RhCI(PPh&
2. H 2 0 2 , NaOH
OH
Ph
, J
O -H 78%
+
P h X O H
(199 1) Burgess.; van der Donk, W.A.; Westcott, S.A.; Marder.; Baker, R.T.; Calabrese, J.C. J. Am. Chem. Soc., 1992, 114, 9350. 5% LiBEt3H, THF, 5 h 20°C , (Bu0)zBH
(95
5)
OH
12%
Arase. A,; Nunokawa, Y.; Masuda, Y.; Hoshi, M. .I Chem. . Soc., Chem. Commun., 1992, 51
SECTION 45:
ALCOHOLS AND THIOLS FROM MISCELLANEOUS COMPOUNDS NO ADDITIONAL EXAMPLES
48
Compendium of Organic Synthetic Methods, Vol8
Section 45A
SECTION 45A: PROTECTION OF ALCOHOLS AND THIOLS AgB
. PhH
87%
w 0 O BH r H 2 C O NO2
* w 0 O NO,
Z ( 1 0 F/mol) , aq. r-BuOH , TFA
Fukase, K.; Hata, N.; Oishi, T.;
TetrahedronLett., 1990, 31, 381.
0
0
Me 1 . 3 eq. Me3SiOTf, 5 min CHzClz , 0°C 2. neutral A1203 (grade I)
N3 Bou, V.; Vilarrasa, J. Terrahedron Lett., 1990, 31, 567.
t-BuPh20
NaH , HMPA
H 0’”
0°C. 5 min
OSiMe,t-Bu
OSiMeg-Bu
80% Shekhani.;Khan, K.M.; Mahmood, K.; Shah, P.M.; Malik, S. TetrahedronLett., 1990, 31, 1669.
0,0,
SiMeZPh
Cl,,O,,
NEt3
&>OM% KBr ,AcOH
* &nhMe
SiMe2Ph 91%
OBn
92%
Boons, G.J.P.H.;Elie, C.J.J.; van der Marel, G.A.; van Boom, J.H. TefrahedronLett., 1990, 31, 2197. 1. TfOSiOMezt-Bu CHzClz ~
2. Me$
Kim.;Kee, I S . Tetrahedron Lett., 1990, 31, 2899.
n-C8H17
OSiMe,t-Bu 95%
Section 45A
Protection of Alcohols
49
I
93%
in dioxane, Bn cleaved but not OSiR3 Tosbima, K.; Yanagawa. K.; Mukaiyama, S.; BnOH DEAD , PPh3
H
O
>Bnoh Tetrahedron Lett., 2990, 31, 6697.
h
o o
o o
74%
Baiwa. JS,; Anderson, R.C. Tetrahedron Lett., 1990, 31, 6973. FeCI, ,MeCN , RT
n-C 1OH2 1OTMS
-
1 min
n -C1OH2 1 0 H
other Lewis acids were also used
C o r t . S y n r h . Commun., 1990, 20. 757.
1. (MeO)$H2 ,pTsOH CH2C12, 10 h
n-C& 170H 2. PhSH ,pTsOH * n-C8H170- SPh
CH2C12,7 h Dieter. R.K,; Dam, R. Org. Prep. Proceed. Int., 1990, 22, 63.
56%
hv ,NBS ,CaCO3 aq. CC14
OMe
86%
OMe
ev. R . K ; Hehemann, D.G. J. Org. Chem., 1990. 55, 378. DMAP , NEt3
t-BuMe2Si0
OHOH
OHOH
Naif. V.; Buenger, G.S. Org. Prep. Proceed. Int., 1990, 22, 3. 1.0.9 MezSn(SMe)z BF3*OEt2,O0C, 16 h
Ph-
OTHP 2. H 3 0 +
)r
Ph-OH
Sato, T.; Otera.; Nozaki, H. J. Org. Chem., 1990, 55, 4770.
90%
Compendium of Organic Synthetic Methods, Vo18
50
(PPh3)4RhH, TFA
Section 45A
17
&c8H b
EtOH ,reflux
HO
98%
m; Brown, E.G.; Sobolov, S.B. .I. Org. Chem.. 1990, 55, 3691. EtsSiH, CH2C12 1% Rhztpfih , 2 h
Y OH
* -
OSiEt,
pfb = perfluorobutyrate
88% ;High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem., 1990, 55, 6082.
OTHP
bentonite earth (TONSIL) acetone, RT , 3 0 min
Me
Me
Cruz-Almanza. R.; Pkrez-Flores, F.J.; Avila. M. Synrh. Cotntnun., 1990, 20, 1125.
0
-
Oh- CF3 0
ether, 2OoC, 30 min
c
Keumi. T,; Shimada, M.; Morita, T.; Kitajima, €1. Bull. Chern. SOC..lpn., 1990, 63, 2252.
HoLo HO
HO
1. BuzSnO , PhMe reflux , 4 h
2. Pd(PPh3)4, THF RT, 1h OAc OAc
HO
HO
2)
(8
89%
Holzanfel. C.W.; Huyser, J.J.; van der Merwe, T.L.; van Heerden. F.R, Heferocycles,1991, 32, 1445.
3 eq. MgBr2, ether, RT 2.5 eq. BUSH
~z-C~H~~OMOM
t
~z-C~H~~O 97% H
Kim. &; Kee, I.S.; Park, Y.H.; Park, J.H. SynLRil, 1991, 183.
Section 45A
Protection of Alcohols
OSiMe2t-Bu
51
q~
OSiMe2t-Bu
KF-A1203, MeCN
RT
78%
OSiMe2t-Bu
ultrasound used in cases when deprotection is slow Schmittling, E.A.;
Tetrahedron Lett., 1991, 32, 7207. dihydropyran ,CH2C12 sulfonatedcharcoal MS3A.Sh
O H -
-OTHP 97%
Synth. Commun., 1991, 21, 2329.
htmyJ&
N3 ,NaH ,DMF
Br*
Ph-
*
*
O-OH
Ph-0-O
1. H2, Pd-C
92%
3. DDQ ,- 5 0 ~ Fukase. K.; Hashida, M.; Kusumoto. S , Tetrahedron Lett., 1991. 32, 3557.
4
NHBoc
MPMol OH BrBa(0H)yOBu , DMF ~ M o ~ Q + N H B n r 32 h
58%
DDQ
Fukase, K.; Yoshimura, T.; Hashida, M.; Kusumoto. S. Tetrahedron Lett., 1991,32, 4019.
OSiMepBu aq. NEt3, H2SiF6, 1 h MeCN
TIPSO
P
TIPSO
O 75%
H
+
P
O
OH
17%
Pilcher, A S . ; Hill, D.K.; Shimshock, S.J.; Waltermire, R.E.; DeShone. P.J. Org. Chem., 1992, 57, 2492.
0°"
Ph3CC1, DBU
Colin--;
0"'82
Girard, J-P.; Ross, J-C. Tetrahedron Lett., 1992, 33, 2689.
H
Compendium of Organic Synthetic Methods, Vo18
52
Section 45A
1. SiF4(gas), MeCN
~,,,OSiMej-Bu t-Bu
23"C, 20 min
i
t-Bu
2. H20
m e v . E J.; Yi, K.Y. Tetrahedron Lett., 1992, 33, 2289.
Yoshida. J.; Ishichi, Y.; Nishiwaki, K.; Shiozawa, S.; boe. S, Tetrahedron Letr., 1992. 33, 2599. BHpTHF, 20°C. 24 h
Cossv. JJ Bellosta, V.; Muller, M.C. Tetrahedron Left., 1992, 33, 5045. TiC13-Li-THF, reflux 14 h
* n-Cl6H33-OH
~-CI~H,~-O-CH~P~
Kadam, S.M.; Nayak, S.K.; Banerii.A.Tefrahedron Lett., 1992, 33, 5129.
85%
-
AIC13 PhNMe2
Ph-oBn
anisole, CH2C12
=-
Ph-OH
93%
Akivama.; Hirofuji, H.; QzakiLi Bull. Chem. S O ~Jpn., . 1992, 65, 1932. dihydropyran ,CH2CI2
Ph-
OH
H2SO4 , silica gel 10 min ChBvez.; Godinez, R. Synth. Commun., 1992, 22, 159.
Ph-OTHP
96%
AI(PO4)3 , dihydropyran
reflux , 15 min = Q,WP 97% G~&LL&J.M.;Garcia, A.; Lafont, F.; Luna, D.; Marinas, J.M. Synth. Commun., 1992, 22, 2335.
Section 45A
Protection of Alcohols
-
53
Zandbergen, P.; Willems, H.M.G.; van der Marel, G.A.; Brussee. J. ; van der Gen, A. Synth. Commun., 1992, 22, 2781. L a c & , dihydropyran H2C12,RT,4h
OH
OTHP
Bhuma, V.; IGmam&L Synth. Commun., 1992, 22, 2941.
OMe
3 eq. TMSCl , RT 1.5 eq. anisole
Ph-O
Ph A OH
90%
30 min
Akivama.;Shima, H.; Qzaki. S, SynLetf, 1992,415.
0
7;,acetone
2.5%
20°C ,45 h
BnO
90%
&
= HO
MXI~&AB.A.; Muxworthy, J.P.; Baggaley, K.H. SynLett, 1992, 646.
69%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 4 PREPARATION OF ALDEHYDES
SECTION 46: ALDEHYDES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 47: ALDEHYDES FROM ACID DERIVATIVES 6.5% (Cy3P)2RhCHC12 PhH/NEt3, H2,SO"C w
1abn.65h Grushin, V.V.;
65%
J. Org. Chem., 1991, 56, 5159.
n-CgHzlCOOH
1.2 eq. Pv 2. LiAlH&Et2)3
3. H 3 0 +
*
n-CgH21-CHO
90%
Cha.,Lee, J.C.; Lee, H.S.; Lee. S.E. Org. Prep. Proceed. &., 1992, 24, 327. '
PhCHo Yu, H.K.B.; S&m#zJ
1. Bu3SnLi 2. Me3SiCN
3 . 3 eq. BuLi 4 . 0 3 ,CH2C12
>
PhCOOH
63%
Tetrahedron Lett., 1992, 33, 6787, 6791.
SECTION 48: ALDEHYDES FROM ALCOHOLS AND THIOLS
diglyme , 120OC 12 h
Kulkami.;Mathew, T.S. TetrahedronLett., 1990, 31, 4497.
55
Aldehydes from Alcohols
Section 48
0
also with 2" alcohols to give ketones Campestrini, S.; DiFmiaJ,; Modena.fi, Bortolini, 0. J. Org. Chem., 2990, 55, 3658.
'electrolytic' MnO2 hexane , RT , 13 h
-OH
*
-CHo 78% Tsuboi. S.; Ishii, N.; Sakai, T.; Tari. I,; Utaka, M. Bull. Chem. SOC. Jpn, 1990, 63, 1888. Cr03 - "wet alumina"
-
PhCH2OH
PhCHO
90%
also for the preparation of aryl kelone from aryl alcohols Hirano, M.; Kuroda, H.;
Bull. Chem. SOC. Jpn., 1990, 63, 2433. NBS , AIBN , CC4
PhCH20SiMe3
9 5 0 8~min ~
m
PhCHO
87%
Mark6 I.E.; Mekhalfia, A.; Ollis. W.D, SynLett, 1990, 345. Me3NHCI-CrO3 ,MS 4A
-OH
CH2C12,20 h Acharva. S . P,; Rane, R.A. Synthesis, 1990, 127.
-OH
c
e- ,Pt electrodes ,pH 6.8 Ru(Upy )(~PY)OI'~
e C H O
n
C
H
75 95
O 41%
trpy = 2,2'.6',2"-terpyridine
Navarro, M.; Pe Giovani. W.F.; Romero. J.R, Synrh. Commun., 2990, 20, 399.
(13: 1 retention:isomerization) Xiao, X.;
Synth. Commun., 1990, 20, 3125.
Compendium of Organic Synthetic Methods, Vol8
56
PhCH,OH
Akamanchi.:Iyer, L.G.;
Section 48
CH2C12, RT ,30 min
PhCHo
94%
Meenakshi, R. Synth. Commun., 1991. 21, 419. hydrous zirconium oxide benzophenone, xylene
* PhCHO 81% Enux Kuno. H,; Shibagaki, M.; Takahashi, K.; Matsushita, 11. Bull. Chem. SOC. Jpn., 1991, 64, 312. PhCH2OH
RuC13 , CC4, aq. NaOCl
c-
O -H
-CHO
65°C 90% Ogibin, Yu.N.; Ilovaiskii, A.I.; Nikishin, G.I. Izv. Akud. Nauk. SSSR,1991, 40, 115 (Engl., p.99).
-
PhI . Pd(OAch Bu~NCI',D I 6 Ph
-OH
CHO 82%
Lefferv. T,Tetrahedron Lea., 1991, 32, 2121. e (3.5 F/mol) , Pt electrodes 5% Na2CO3-25% NaBr , 0°C
Go*
* n-CgH,g,CHO
PhC02
'CH2C12 H20
89%
oxidation of 1" alcohols much faster than 2" alcohols Inokuchi, T.; Matsumoto, S.; Torii. S. J. Org. Chem., 1991, 56,2416. Inokuchi, T.; Matsumoto, S.; Fukushima, M.; Toni. S,Bull. Chem. SOC. Jpn. 1991, 64, 796. Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; J. Org. Chem., 1990, 55, 462. Inokuchi, T.; Matsumoto, S.; Nisiyama, T.; Torii. S . SynLeft, 1990, 57. 1. [C13C0]20, DMSO CH2C12, -78°C
(iPr),SiQ. H Me
OH
2. mt3 , -78°C -+ 20°C
(iPr)$iQ H MeXc~o
84% Palomo. C.; Cossio, F.P.; Ontoria, J.M.; Odriozola, J.M. J. Org. Chem, 2991, 56, 5948.
Section 48
Ma, Z.; Bobbitt.
Aldehydes from Alcohols
57
J.M.J. Org. Chem., 199Z, 56, 6x10. , RT , overnight
Ph+OH
c
RuTMP(0)z
p h f i CHO
81%
TMP = tetramethylpyrazole
Higuchi, T.; Ohtake, H.; Hirobe. M. Tetrahedron Lett., 1991, 32, 7435. 1. DMSO , -78°C triphosgene
-OH
c
2. NEt3 , -78°C -+ RT
-CHO
82% Rivero, I.A.; Somanathan.;Hellberg, L.H. Org. Prep. Proceed. Int, 1992, 24, 363.
2 CuBr2 , 2 LiBr , 13 h
Ph
OSnBu3 Bu3SnOt-Bu Yamaguchi, J.; E&&J, Chem. Len., 1992, 423. CrO3, DMSO, RT.4 h
-OH
ph&CHo
78%
-CHO
68%
Lou, W-X.; Lou. J-D, Synth. Commun., 1992, 22, 767.
n-C,H,,CH,OH
'I'PCD , DMF , 80°C lh
*
n-C,Hl,CHO
80%
TPCD = tetrakis-pyridino-cobaltdichromate = [Py4Co(HCrQ)21 Hu. Y,; Hu, H. Synch. Commun., 1992, 22, 1491. SeOz , SiOz, RT
H
OH
-
r-BuOOH , CHzC12 15 h
O H C Y 7 - O H
Kalsi, P.S.; Chhabra. B.R. ; Singh,. J.; Vig, R. SynLett, 1992, 425.
90%
58
Compendium of Organic Synhetic Methods, Vol8
Section 50
REVIEWS:
"Oxidation of Alcohols by Activated DMSO and Related Reactions: An Updale: Edwell. 'CIC Synthesis, 1990, 857.
SECTION 49: ALDEHYDES FROM ALDEHYDES Conjugate reductions and Michael Alkylations of conjugated aldehydes are listed in Section 74 (Alkyls from Alkenes). ISiC13 , RT ,20 min w
OEt
PhCHO
958
Elmorsv.;Bhatt, M.V.; Pelter, A. Tetrahedron Lett,, 1992, 33, 1657. OAc
CAN, Si02 CH2CI2
c
OMe
OMe
Cotelle.; Catteau, J-P. Tetrahedron Lett., 1992, 33, 3855. Related Methods:
SECTION 50:
Aldehydes from Ketones (Section 57) Ketones from Ketones (Section 177) Also via: Alkenyl aldehydes (Section 341)
ALDEHYDES FROM ALKYLS, METHYLENES AND ARYLS
Manmez.;Alvarez, R.M.;
Barcina, J.O.; de la Moya Cerero, S.; Vilar, E.T.; Fraile, A.G.; Hanack, M.; Subramanian, L.R. J. Chem. Soc., Chem. Commun., 1990, 1571.
also, EtPh converted to acetophenone Chem. Lett., 1990, 1445.
Imamoto.;Koide, Y.;
Section 52
59
Aldehydes from Amines
DCA-MV” ,FeC12 hv (visible light) ,
Me
02*3h
DCA = 9,10-dicyanoanthracene; M V + =~ methyl viologen ketones are fromed form ACH2R a t a m a r i d ; Jroundi, R. Tetrahedron Lerr., 1991, 32, 4291.
SECTION 51: ALDEHYDES FROM AMIDES LiAIH(NEt& , THF +
RT
-CHO
59%
Cha.;Lee, J.C.; Lee, H.S.; Lee, S.E.; Kim, J.M.; Kwon, 0.0.;Min, S.J. Tetrahedron Lerr., 1991, 32, 6903.
SECTION 52: ALDEHYDES FROM AMINES
Ph
[2 Cu(N03)z/Hz02/2 HzOl
LNH,
.L
Ph-CHO
aq. MeCN Capdevielle, P.; Maumy, M. Tetrahedron Lert., 1990, 31, 3891. hv , cat. I2 ,air NMe2 ‘
Gangloff, A.R.; Judge, T.M.;
Ph,N-
95%EtOH
*
60%
-CHO
n-C6H13
66% J. Org. Chem., 1990, 5.5, 3619.
1. BuLi , THF 2. BnCl 3. H30’
* Ph-CHO
85%
Shah, J.H. J. Org. Chem., 1991, 56, 2955.
PhCH=N-OH
bakers yeast
*
PhCHO
68% (with ultrasound 96%) Kamal. A,; Rao, M.V.; Meshram, H.M. J. Chem. SOC.,Perkin Trans. I, 1991, 2056.
60
Compendium of Organic Synthetic Methods, Vol 8
1. [TiC14, NaI , MeCN] MeCN ,20 min 2. aq. NaOH
Section 53
3
*
63%
H
n-C7H15
Balicki. R,; Kaczmarek, L. Synth. Commun., 1991. 21, 1777.
PhCH2NH2
1. PhS02CI 2. KO2 ,-TIIF, 24 h
park. K.H,; Lee, J.B.Synth. Commun.,
PhCHO
e
%%
1992, 22, 1061.
Ketones from Amines (Section 172)
Related Methods:
SECTION 53: ALDEHYDES FROM ESTERS 1. & e O k
-
Pd(PPh3)4, THF RT,45h
PPh2
Ph Me-CHO
v
2. aq. HCI
80% (48% ee)
Hiroi. K,; Abe, J. Tetrahedron Lett., 1990, 31, 3623. Et3SiH, Pd-C acetone
t
D o d H
Me0
94%
Furuvama.;Lin, S-C.; Li, L. J. Ani. Chem. SOC.,1990, 112, 7050. n-C3H7C02Et
1. Li(EtZN)$ilH THF , -78°C
Cha.;Min, S.J.; Lee, H.S. Org. Prep. Proceed.
0
Ph
A SPh
n-C3H7.CHO
. t
2. H30'
82% lnf., 1992, 24, 335.
1 . Li , THF, -78°C 2. MeOH
-
PhCHO
Penn.; Owens, W.H. Terruhedron Lert., 1992, 33, 3737.
98%
Section 54
Aldehydes from Ethers
s-;.
SECTION 54:
61
ALDEHYDES FROM ETHERS, EPOXIDES AND THIOETHERS
Ph3Si
2 eq.MABR , PhMe
*
r-Bu 1-Bu
88%
(1: 100 erythro:threo)
MABR = B r c ) 0 , $ 0 3 r r-Bu Me
eCH
Ph3Si0
f-311
Maruoka, K.; Sato, J.; Yamamoto.J.Am. Chem. Soc., 1991, 113. 5449.
MABR , CH&l,, -2OT SbFS , PhMe , -78°C
loo)
(0 (83
17)
99%
47%
MABR = methyl aluminum bis-(4-bromo-2,6-di-t-butylphenoxide) Maruoka, K.;Bureau, R.; Ooi, T.; Yamamoto. H. SynLett, 1991, 491. OBn 1.
=dSiMe3
TMSOTf , MeCN
OMe
0°C , 3 0 h 2 . 0 3 , CHzClz
B;:oqoBn 24 h
BnO
CHO
10%NEt3 Bno=oBn BnO iPrOWCH2C12 BnO
CHO
-78°C
49% (10:l
@a)
Kobertz, W.R.; Bertozzi, C.R.; Bednarski. M.D, Tetrahedron Lett., 1992, 33, 737.
(77% ee)
Malacria.;Cilloir, F. Tetrahedron Left., Z992, 33. 3859. Related Methods:
SECTION 55:
Ketones from Ethers and Epoxides (Section 174)
ALDEHYDES FROM HALIDES AND SULFONATES e- , Fe(CO)5 ,MeCN
-Br
Et4NBr
-
-CHO
Yoshida.; Kobayashi, M.;Amano, S. J. Chem. Soc., Perkin Trans. I, 1992, 1127.
71%
Compendium of Organic Synthetic Methods, Vol8
62
CO (80 am), Bu3SnH
Br
Ph&
*
Section 56
ph/\/CHo
AIBN , PhH ,80°C 65% Kusano, K.;Ogawa, A.; Kambe, N.; Sonoda.N.. Am. Chem. SOC., 1990, 112, 1295. ByLLL;Kusano, K.; Masumi, N.; Yamazaki,H.; Ogawa, A.; Tetrahedron Lett., 1990, 31, 6887.
m;
1.
n-C,H 17-1
MeO-@eNa
POT EFrther
n-C8HI7CH2CHO
*
77%
2. NBS , H 2 0 Ynevama. K,; Kitagawa, K. Tetrahedron Lett., 1991, 32, 3385. TPCD , DMF , 100°C
PhCH2Cl
U
t
PhCHO
lh TPCD = tetrakis-pyridino-cobaltdichromate = [Py4Co(HCrO&l ; Hu, H. Synth. Commun., 1992, 22, 1491.
54%
SECTION 56: ALDEHYDES FROM HYDRIDES
0
iPrONO . HCI
0
w
Me-
Gordeeva, G.N.; Kalashnikov, S.M.; Gordeev, A.N.; Popov, Yu.N.; Kruglov, E.A.; Imashev, U.B. Zhur. Org. Khim.,1990, 26, 2199 (Engl., p. 1896). HF-SbFS , CO (20 a m )
*
O
H
C
~
C
NH2 DMSO - HCI , CuCI2
Br
Ir
OHC
Liedholm. B,J. Chem. SOC., Perkin Trans. I, 1992, 2235,
O
81%
(93:7 4,4':2,4') Tanaka, M.; Souma, Y. J. Chetn. Soc.. Chem. Cotnmun., 1991, 1551.
0:
H
aNH2 98%
Br
Section 59
63
Aldehydes from Alkenes
0 Boese, W.T.;
ocHo
hv (A. = 366 nm) CO (1200 psi)
91%
Q
Tetrahedron Letf., 1992, 33, 2119.
SbF5-HS03F1CO 168 min
+
CHO
1
CHO
(76
24) 90%
CHO
2%
Souma, Y.J. Org. Chem, 1992, 57, 2671.
Tanaka.;Iyoda, J.;
SECTION 57: ALDEHYDES FROM KETONES
,/.,
PhMe2Si
OBn
O.lM,launH2 PdC , RT , EtOH
20 h
80%
0
0 Cirillo, P.F.; Panek. J.S. Tetrahedron Lert., 1991, 32, 451. SECTION 58: ALDEHYDES FROM NITRILES 1. Li(hexylzN)3AIH
PhCN
THF , 0°C
2. H 3 0 +
c
Ph-CHO
u; Lee, S.E.; Lee, H.S. Org. Prep. Proceed. Int., 1992, 24, 331.
“f,””
99%
SECTION 59: ALDEHYDES FROM ALKENES
0 L O
Steckhan.
e‘ , H20 2% (Bu4N)s(HzO)RuSiW ,1039
EL: Kandzia, C. SynLerr, 1992, 139.
Related Methods:
c
0QCHO L O
Ketones from Alkenes (Section 179)
68%
64
Compendium of Organic Synthetic Methods, Vol8
SECTION 60:
Section 60A
ALDEHYDES FROM MISCELLANEOUS COMPOUNDS
-
YO NMO , DMSO , N v C l n-C9H19€H0 n-C9H19 50% 0 Nikolaides, N.; Godfrey, A.G.; QmmJ. Tetrahedron Lett., 1990, 31,6009.
n-C 1lH23
1. Sn(SPh), , EtOH
--
n-CliH23- CHO
2. SnC12-2 H20,3 h L-tartaric acid ,40"C NaHCO3, NaHSO3 3.2M HCI Urpi, F.; Vilarrasa, J. Tetrahedron Lett., 1990, 31, 7499. LN02
81%
1. BuLi ,THF , -78°C 2. n-C5HllI, 4 eq. HMPA b n-C5HllCH0 t-BuOSO2Ph -78°C - RT 83% 3. LiBr , K2CO3 ,48h H2O/ether, reflux Chemla, F.; lulia.;Uguen, D.; Zhang, D. SynLett, 1991, 501. Julia.;Uguen, D.; Zhang. D. SynLett, 1991. 503.
SECTION 60A: PROTECTION OF ALDEHYDES ethanedithiol ,Lac13 CH2C12, RT , 4 h
-CHO
Garlaschelli, L.; Vidari.G.Tetrahedron Lett., 1990, 31, 5815.
Liao, Y.;
-
; Zhu, F-H. J, Chem. SOC., Chem Commun., 1990, 493.
PhCHO , R T , 3 0 min
Me
66%
NrC
=
Lee, S-B.; Takata, T.; Endo. T, Chem. Lett., 1990, 2019.
Mey--Ph
quant.
Section 60A
65
Protection of Aldehydes
Amberlyst 15, acetone/HCHO H 2 0 , 80°C, 15 h
*
80%
a 2
U l i n i . R.; P e t h i , M. Synthesis, 1990, 336.
A C H O
PhCHo
ethane dithiol ,hexane
H-Y zeolite, reflux 90% l h Kumar. P,; Reddy, R.S.; Singh, A.P.; Pandey, B. Tetrahedron Lett., 1992, 33, 825.
DDQ , MeCN ,H 2 0 , RT
w
PhioMe OMe
Tanemura.;Suzuki, T.; Horaguchi, T. J.
PhCHO
75%
Chem. Soc., Chem. Commun., 1992, 979.
HM-zeolite , H20, PhMe
P h q oOEt Et
reflux, 9 h
Ic
PhCHO
89%
Rao. M.N.; Kumar, P.; Singh, A.P.; Reddy, R.S. Synth. Commun., 1992, 22, 1299.
wCHO
HOCH2CH20H, PhH catalyst, reflux, 30 min quant.
Otera J,; Dan-oh, N.; Nozaki, H. Tetrahedron, 1992, 48, 1449.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 5 PREPARATION OF ALKYLS, METHYLENES AND ARYLS This chapter lists the conversion of functional groups into methyl, ethyl, propyl, etc. as well as methylene (CH2), phenyl, etc.
SECTION 61: ALKYLS, METHYLENES AND ARYLS FROM ALKYNES (iPr)3SiO- C i C (CH2h /-7BU
0
N2
Me0
W E , hv
OMe
-
OSi(iPrI3
54%
Danheiser.;Cha, D.D. TetrahedronLett., 1990, 31, 1527. 1.5 eq. KOH ,37”C
DMSO , EtOH , 2 4 h 58%
Toshima, K.;Ohm, K.;Ohtake, T.;
OMe Tetrahedron Lett., 1992, 32, 391.
Ph
Bdwa. A; Austin, D.J.; Chiacchio, U.; Kassir, J.M.;Rescifina, A.; Xu,S.L. Tetrahedron Lett., 1991, 32, 5923.
-hi. E,; Harring, L.S.; Owczarczyk, 2.;Mohamud. M.M.; Ay, M. Tetrahedron Lett., 1992, 33, 3253.
Section 62
AIkyls from Acids
67
(R = TMS:R = OH = 5.2)
Bao, J.; Draagisich, V.; Wenglowsky, S.; y u l f f . W.D. J. Am. Chem. SOC., 1991, 113, 9873.
.
C02Me
1. SmIz-THF Pd(PPh314
, -78°C + 0°C
OH
57%
OH C02Me
2. =/
Inanaea.,Sugimoto, Y.;Hanamoto, I. Tetrahedron Lett., 1992, 33. 7035.
&
Me02C 210°C. 24 h
72%
Grissam.;Calkins, T.L. Tefrahedron Left.,1992, 33, 2315.
SECTION 62:
ALKYLS, METHYLENES AND ARYLS FROM ACID DERIVATIVES SiMe, 0 0 mesitylene , 165°C nitrobenzene, 125°C
+o
0 72% 0%
Kraffi.;Rich.; McDemott, P.J. J. Org. Chem., 1990, 55, 5430.
21% 100%
Compendium of Organic Synthetic Methods, Vol8
68
SECTION 63:
Section 63
ALKYLS, METHYLENES AND ARYLS FROM ALCOHOLS AND THIOLS SiMq
6
*
BF3oOEt2, CHzClz -78°C + RT
Schmitt, A.: &issin. H IJ, SynLett, 1990, 40.
Me
p
95%
(98:2 trans:cis)
1. N B S , hv ,ccl4 2. BuzCuLi , ether
OH
3. TMSI ,MeCN , heat
Me 74%
&mkiA& Tetrahedron Lett., 1991, 32, 3411. BR3, TfOH
*
Ph-CH20H
+
Ph-CH2-R
Ph-CH3
R = Me 57% R = Et 11% R = iPr 0.1% Mah.;Wu,A.; Farooq, 0.J. Org. Chem., 1991, 56, 2759.
43% 89% 99%
Nation-H , PhH
+OH
95"C'1hb
81%
Yamamoto. T.; Hideshima, C.; Surya Prakash, G.K.; Olah, G.A. J. Org. Chern., 1991, 56, 2089.
c.j$'F s n-C1 3H27
F
PhMe,Smin 2. Bu3SnH, PhMe 5 min Barton, D.H.R.; Blundell, P.; Dorchak, J.; Jang. D.O.; 47, 8969.
OH
*
13H27
CH3
95% Tetrahedron, 1991,
Section 65
Alkyls from Alkyls
69
OMe 1.5.7 eq. SnC4
-78°C + 25°C
2. ph-
OH
Me
,1h
77%
Me
Anele. S.R,; Amaiz, D.O. J. Org. Chem., 1992, 57, 5937.
SECTION 64:
ALKYLS, METHYLENES AND ARYLS FROM ALDEHYDES
*& acHo
1. NbCIs ,Zn ,DMWPhH
n-CSH 1 1 - (3C- n-C,H
11
n - w11
2. 2.6-lutidine 25"C, 10h
/
3.
CHO
/
93%
n-C#
11
25OC ,30 min Kataoka, Y.; Miyai, J.; Tezuka, M.; Takai.; Oshima, K.; Tetrahedron Lett., 1990, 31. 369.
MeMgl, NiC12(dppe)
c
Ph
Ph
93%
Tzeng, Y-L.; Yang, P-F.; Mei, N-W.; Yuan, T-M.; Yu, C-C.; h h . T-Y. J. Org. Chem., 1991, 56, 5289. REVIEWS:
"Chiral Acetals in Asymmetric Synthesis"
Alexakis.;Mangeney, P. Tetrahedron Asymmetry,
1990, I , 471.
Related Methods: Alkyls, Methylenes and Aryls from Ketones (Section 72)
SECTION 65:
ALKYLS, METHYLENES AND ARYLS FROM ALKYLS, METHYLENES AND ARYLS 1. BuLi , THF , -78°C
*
3. BuLi , THF , -78°C 84% 4. Et-I Rabideau. P.W,; Dhar, R.K.;Clawson, D.K.; Zhan, 2. Tetrahedron Letf., 1991, 32, 3969.
70
Compendium of Organic Synthetic Methods, Vol8
0 N
1. NaH 2. NMP , ZnCl2, RT 3. PdC12(PPh3)2 , PhBr
H
b
RT , PPh3,2 h 4. 140°C, 2 h
p
p
h +
Section 48
Oph+ Ph-Ph
N
H
H
40%
50%
10% .. . . m ; Gusmerol, M.; Riva, R. Tetrahedron Left., 1992, 33, 1755.
2.4 eq. Fe(C104)3 "FA, CH2C.12, RT
Me0
0
Me0
Me0
Me0
0
Tanaka, M.; Mitsuhashi, H.;
74%
Tetrahedron Left.,1992, 33, 4161.
SECTION 66: ALKYLS, METHYLENES AND ARYLS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 67: ALKYLS, METHYLENES AND ARYLS FROM AMINES 1.2.2 eq. Li naphthalenide THF , -78°C 2. Me2S04 Kawase, T.; Fujino, S.; Oda.M. TetrahedronLeft.,1990, 31, 545.
60%
SECTION 68: ALKYLS, METHYLENES AND ARYLS FROM ESTERS NaBPh4, THF Pd(dba)z , PPh3
80% 60°C Legros, J-Y.; Fiaud, J-C. Teirahedron Lett., 1990, 31, 7453.
71
Alkyls from Esters
Section 68
PhSnMe3, 5% Pd(dba)2
Ph-oAc
Ph
Ph-
Dh4F , LiCl ,23"C 69 h
57%
DeI Valle, L.; Stille. J.K.;b d u s . L S , J. Org. Chem., 1990, 55, 3019. X eq. LifLClOo
PhSe
OAc
2 min addition of BuMgBr
* P h S e B u i-
X = 2; 2 = 2 min X = 5 ; 2 = 40rnin
75% 13%
Btickvall. J-EL;Sellkn, M.; Grant, B. J. Am. Chem. Soc., 1990, 112, 6615.
0 II
tC02Me
NaWBuLi , O°C
CO,Me
2. CA(OAC)T€I~O, reflux
-
3. 2N HC1
BU
phs&
25% 87%
OH I
WMe C02Me
17%
-chi. M,; Hasebe, K.; Higashi, H.; Uchida, M.; Irie, A.; Minami, T. J. Org. Chem., 1990, 55, 1611.
heat
H
H
0
via benzyne cycloaddition-retroDick- Alder
0
43%
Meirk, D.P.; Guitih, E.; Castedo. L. Tetrahedron Lett., 1990, 31, 143.
-
cat. Pd(dba)2 , PhZnCl
J-L p
60%
Ph
Ph
Ph 0
(9.4%ee)
Fiaud, J-C.; Legros, J-Y. Tetrahedron Lett., 1991, 32, 5089. (PhMqSi)*Cu(CN)LiZ
L O ' P h ;.I-
333 1.
THF -ether
* L S i M e 2 P h 83% Higgins, D.; Lawrence, N.J.; Thomas, A.P. J. Chem. Soc., Perkin Trans. I, 1992,
72
Compendium of Organic Synthetic Methods, Vol8
pSiM
TMSCHzMgCl 5% Ni(acac)2, ether*
@ y e 2 Ph
Ph
Sengupta, S.; Leite, M.; Raslan, D.S.; Quesnelle, C.;
SECTION 69:
Section 69
J. Org. Chem., 1992, 57, 4066.
ALKYLS, METHYLENES AND ARYLS FROM ETHERS, EPOXIDES AND THIOETHERS
The conversion ROR + R R ( R = alkyl, aryl) is included in this section.
Me0
-
BuCu*BF3
i Me
0
0 0 N
BU
4Me
65%
0
Ludwig, C.; Wistrand, L-G. Acta Chem. S c a d . , 1990, 44, 707.
h,fe
2. Me1 , O°C
Me ;-
I.K,mF 4h
*Meo+
Me OMe 72%
Denurra, T.; Melloni, G.; Piroddi, A.M. J. Org. Chem., 1990, 55, 5386.
K 0
N*H
BuCu(CN)Li. LiCl
BF3,THF
Ishibuchi, S.; Ikematsu, Y.;Ishizuka. T.;
Et02C
co+k
fi
K 0
N-H
%
Tetrahedron Lett., 1991, 32, 3523.
BujSnH, AIBN
N-N l
PhSe
0
+
Ph
Kim.; Kee, IS.; Lee, S. J. Am. Chem. Soc., 1991, 113, 9882. Me0,C”
N
OMe
kO,Me
SiMe,
TiCl4, CH2Cl2 -78T
* Me@C
‘“h k02Me
(73:27 cktrans)
Shono. T.; Fujita, T.; Matsumura, Y. Chem. Lett., 1991, 81.
80%
Alkyls from Halides
Section 70
SECTION 70:
73
ALKYLS, METHYLENES AND ARYLS FROM HALIDES AND SULFONATES
The replacement of halogen by alkyl or aryl groups is included in this section. For the conversion of Rx + RH (X = halogen) see Section 160 (Hydrides from Halides and Sulfonates).
Bz'
AIC13, 10°C
C02H -
Bz'
91% 9% Kronenthal. D.R,; Mueller, R.H.; Kuester, P.L.; Kissick, T.P.; Johnson, E.J. Tetrahedron Lett., 1990, 31, 1241. BuzCuMgBr, -40°C THFlerher , I h
\IC0,Et
C0,Et
t
OTf
Bu
53% Petit, Y.; Sanner, C.; LarchevEque, M. Tetrahedron Lett., 1990, 31, 2149.
OMe
PhB(OH)2, Pd(PPh3)4 DMF , aq. Na2CO3
OMe
OTf Fu, J-M.;
Ph
Tetrahedron Lett., 1990, 31, 166.5.
Sph
c1
BuCu(CN)ZnI TIIF, 18 h -78°C -+ 25°C
Chen, H.G.; Gage, J.L.; Barrett, S.D.;
'fSph
88%
Bu (21/79 WZ)
Tetrahedron Lett., 1990, 31, 1829.
1. Z ~ u s c DMF
CO2t-BU 80%
also undergoes conjugate addition reactions Majid, T.N.; Knochel. P, Tetrahedron Lett., 1990, 31, 4413.
Compendium of Organic Synthetic Methods, Vol8
74
0
1. Pd(PPh3)d , NaOH THF , reflux, 6 h
Ph
*
2. NaOH ,H202
Section 70
Ph
Soderouist.;Santiago, B. Tetrahedron Lett.. 1990, 31, 5541. Soderouist.;Santiago, B.; Rivera, I. Tetrahedron Lett., 1990, 31, 4981.
WOT~ 0
OH
Bu4Sn DMF, ,3PdC12(PPh3)2 q.Licl 95°C. 2.5 h
74%
0 OH 0 OH Tamayo, N.; Echavarren.;Paredes, M.C.; Farifla, F.; Noheda, P. Tetrahedron Lett., 1990, 31. 5189.
n -
@fB.O
c1
)
1. BuLi , THF, -78°C 2. PhMe ,reflux, 36 h
3. H+ , AcOH
* Bu-
55%
Brown. H.C,; Rangaishenvi, M.V. Tetrahedron Lett., 1990, 31, 7113, 7115. Bu3SnH, AIBN PhH , 80°C
OMOM
OMOM
OMOM
(80
64%
20)
Nagai, M.; Lazor, J.; Wilcox. C .S, J. Org. Chem., 1990, SS, 3440.
PhBr
10%NiBr2(PPh3)2, Zn , THF 10% EtdI
-
Ph-Ph
99%
luoda.;Otsuka, H.; Salo, K.; Nisato, N.; Oda, M. Bull. Chem. SOC.Jpn., 1990, 63, 80. 1. SnzMe, LiCl , THF
Pd(PPh34 ,reflux 2. PhBr , iPrzNEt , PhMe
OTf
cat. 2,6-di-t-butyl-4-
4
methylphenol Pd(PPh3)d. reflux
Ph
(9 1
Stork. G,; Isaacs, R.C.A. J. Am. Chem. SOC., 1990, 112, 7399.
+&Ph 9)
58%
Section 70
Alkyls from Halides
M
Zncl Arcadi, A.; Burini, A,;
e
O
75
V OTf
Pd(PPhd4, THF
/
OMe
41%
u; Delmastro, M.; Marinclli, F.; Pieuoni, 8 . SynLen, 1990, 47.
Br
-
Takahashi, S.; Jvfori. N, J. Cheni. SOC., Perkin Trans. I, 1991, 2029.
Br
Li[Bu4In] , R T , 3 h
+
Bu
80%
Araki, S.; Shimizu, T.; Jin, S-J.; Butsugan...I.Chem. SOC.,Chew Cornmun., 1991, 824. PhMgBr , ether, 20 h 10% NiClz(dppf) reflux * o Yuan, K.; Scott. WJ, Tetrahedron Lett., 1991, 31, 189.
c , h
77%
1)
(2.59
Burke. S.D,; Piscopio, AD.; Kort, M.E. Tetrahedron Let(., 1991, 32, 855. Br
1. B u q n L i , THF 2. aq. AcOH
n-CsH17-( Br
n-C8H17-/
Bu
77%
Harada. T.; Kotani, Y.; Katsuhira, T.; Oku. A. Terrahedron Lett., 1991, 32, 1573
Ph,C-CI
PhzTIBr, PhLi , ether
t
Ph3C-Ph
Mark6 LE,; Kantam, M.L. Tetrahedron Lett., 1991, 32, 2255. Mark6. ISEL;Southern, J.M.; Kantam, M.L.SynLerr, 1991, 235.
74%
89%
Compendium of Organic Synthetic Methods, Vol8
76
Section 70
Mitchell. M.B.; Wallbank, P.J.TetrahedronLett., 1991, 32, 2273. 1. BuLi, t-BuOK
"[-
A S i M e 3
=Hi;,"
'
A \
SiMe3
* Bu
Bu
(3.3 Li, L-H.;
SiMe3
+
:
1)
95%
Wane., Chan, T.H. TetrahedronLett., 1991, 32, 2879.
83% Yamato. T,;Sakaue, N.; Suehiro, K.; T ~ s ~ K M.o Org. , Prep. Proceed. h t . , 1991, 23, 617.
PhH , AICl3 , 6 h
80°C
t
* (9 97% ee ( S ) Piccolo. 0,;Azzena IL; Melloni, G.; Delogu, G.; Valoti, E. J. Org. Chem., 1991, 56, 183.
0
1. (FS02)20 , EtN(iPr)2,2 h
CH2C12, -78T
OH
2. PhZnCl , THF , LiCl 5% Pd(PPh3)4 , 50°C
90%
m a ;Fuller, C.E. J. Org. Chem.. 1991, 56, 3493. P
h
w C1
BuTi(OiPr), ,THF ,-70°C 7.5% Cub2 LiCl , 6 h
Ph
Arai, M.:IUauuJ. J. Org. Chem, 1991,56, 5490.
PhICI2
b
BuLi , THF , -80°C
-
>99.8% SN2'
B U-Bu
85% Barton, D.H.R.; Jaszberenyi, J.Cs.; LeBmann, K.; Tim& T. Tetrahedron, 1992, 48, 8881.
Section 70
Alkyls from Halides
77
48%
Beueelmans.;Chastanet, J. Tetrahedron Lett., 1991, 32, 3487.
1. M e 0
0
C
0
71% 3.10 eq. Cu powder DMF , reflux Takahashi, M.; Kuroda, T.; Orgiku, T.; Ohmi7.11,H.; Kondo, K.;bm&,L . Tetrahedron Lett., 1991, 32, 6919.
SnBu3, DMF
Me0
Me0 F
OMe PdC12(PPh3)2 , LiCl PPh3, 120°C
OTf
O
M -
e 84%
Saii. J.M.; Martorell, G.; Garcia-Raw, A. J. Org. Chem., 1992, 57, 678. Martorell, G.; Garcia-Raso, A.; SaB, J.M. Tetrahedron Leu., 1990, 31, 2357.
6 I
Br
pQMe
1. Pd(PPh3)4 , DME 2. aq. Na2C03 ,reflux 24 h M
e
Ph
0 B(OH);!
77% 3. Ph-B(OH)z, reflux Unrau, C.M.; Campbell, M.G.; m s . V. Tetrahedron Lett., 1992, 33, 2773.
1 . BuLi 2. LiCloH8, -78°C
0 Phy
Lc1
N'
3. PhI ,-78°C + RT
0 e
lcPh
P&NH
Barluenea.;Montserrat, J.M.; Flbrez, J. Tetrahedron Lett., 1992, 33, 6183.
75%
Compendium of Organic Synthetic Methods, Vol8
78
o\ N
1. Zn* ,THF, RT
2. PhI , Pd(PPh3)d ,THF
Br
Sakamoto, T.; Kondo, Y.; Murata, N.;
HO-Si-
' \
Section 70
*
N
76%
Tetrahedron Lett., 1992, 33, 5373.
I. BuLi 2. BnBr , HMPA
Ph
Ph
D.
Ph-Ph
63%
Hudrlik.;Abdallah, Y.M.; Hudrlik, A.M. Tetrahedron Len, 1992, 33, 6747, 6743.
4
1. t-BuLi ,pentane-ether , -78°C 2. TMEDA 4. MeOH
89%
W.F.; Khanolkar, A.D.; Gavaskar, K.V. J. Am. Chem. Soc., 1992, 114, 8053. Bailev. W.F.; Khanolkar, A.D. Tetrahedron Lett., 1990, 31, 5993. 2e
. 10% PdC12(PPh3)2 t
PhOTf
Ph-Ph 76% DMF , 9 0 T lutand.;NCgri, S.; Mosleh, A. J. Chem. SOC., Chem. Commun., 1992, 1729. 2
-1
B- n-CaH17
vK3p04 Pd(PPhd4
Ishiyama, T.; Abe, S.; Miyaura, N.;
n-C 1qH 30
64%
Chem. Lett., 1992, 691.
-+B(OHh
OMe
2% Pd(PPh3)4, DME-HzO Ba(OH)2 ,8O"C Watanabe, T.; Miyaura, N.;
SECTION 71:
t
'
80%
SynLett, 1992, 207.
ALKYLS, METHYLENES AND ARYLS FROM HY DRIDES
This section lists examples of the reaction of RH + RR' (R.R = alkyl or aryl). For the reaction C=CH + C=C-R (R = alkyl or aryl), see Section 209 (Alkenes from Alkenes). For alkylations of ketones and esters, see Section 177 (Ketones from Ketones) and Section 113 (Esters from Esters).
Section 71
Alkyls from Hydrides
79
0.6 SnC14 , RT , 2 4 h Ph-
M e 0 w p : 8 %
SnBu3
(9:91 o:p) Chem. Lett., 1991, 133.
Yamaguchi, J.; Takagi, Y.; Nakayama, A,; Fujiwara, T.;
0
Ph
A ph
1. I-BuLi , THF -100°C + -78°C
2. soc12 , -78°C
d
-F
t-Bu
1.
h
t-BU
(9 Olah.;Wu, A.; Farooq, 0.Synthesis, 1991, 1179.
CHO
P 1)
52%
NHMe
( NHMd EtOH. reflux
2. BuLi , TMEDA ,ether
3. Etl
RT
4.2M HCl , HzO
Gray, M.; Parsons, P.J. SynLett, 1991, 729.
0
1. MeLi 58%
Quesnelle, C.; Iihama, T.; Aubert, T.; Pemer, H.; 2625.
Tetrahedron LRtt., 1992, 33,
SECTION 72: ALKYLS, METHYLENES AND ARYLS FROM KETONES
6
The conversions R2C=O -+ R-R, R2CH2, RzCHR, etc. are listed in this section.
MeVO(OEtlCI , 0 2 EtOH , 3 0 min
6
Hirao.,Mori, M.;Qh&'ro. Y.J. 018. Chem., 1990, 55, 358.
Me
90%
Compendium of Organic Synthetic Methods, Vol8
80
Section 72
Blmorsv. S.S, ;pelter, A.; Smith, K. Tetrahedron Len, 1991, 32, 4175. dioxane , 5 h 2. aq. NH4CI 12%
58%
Ind. J. Chem., 1991, 30B, 286.
Nayak, S.K.;
n
s s
MeMgI , NiClz(dppe)
* Ph
Ph-Me Yuan, T-M.; J&.
6'
T-Y. J. Org. Chem., 1992, 57, 4550. 1.
c) csz
AJ;:
84%
0 ,
2% GazC14, reflux 2.2N NaOH ,RT
(29
71)
72%
Hashimoto, Y.;Hirata, K.; Kihara, N.; Hasegawa, M.; &&&.Tetrahedron Leu., 1992, 33, 6351.
SECTION 73: ALKYLS, METHYLENES AND ARYLS FROM NITRILES Bu4Sn. MeCN hv (>300 nm)
46%
Kyushin, S.; Masuda, Y.; Matsushita, K.; Nakadaira Y.; QhsLM. ' Tetrahedron Lett., 1990, 31, 6395.
Teng, T-F.; Lin, J-13.;-Heterocycles,
1990, 31, 1201.
Section 74A
Hydrogenation of Alkenes
x
81
PhCHO , PhMe 8 0 T . 11 h
0
84%
Ph
Rvchnovskv.; Zeller, S.; Skalitzky, D.J.; Griesgraber, G. J. Org. Chem., 1990, 55, 5550. SECTION 74: ALKYLS, METHYLENES A N D ARYLS FROM ALKENES The following reaction types are included in this section: A. Hydrogenation of Alkenes (and Aryls); B. Formation of Aryls; C. Alkylations and Arylations of Alkenes; D. Conjugate Reduction of Conjugated Carbonyl Compounds and Nitriles; E. Conjugate Alkylations; F. Cyclopropanations, including halocyclopropanations
SECTION 74A: Hydrogenation of Alkenes (and Aryls)
-
Reduction of aryls to dienes are listed in Section 377 (Akene-Alkene).
d
Ph
NaTeH ,EtOH ,reflux 2.5 h
-
Ph
Barton, D.W.R.; Bohe.;Lusinchi, X . Tetrahedron, 1990, 46, 5273.
quant.
Batczewski, P.; Joule. J.A. SynM Commun., 1990, 20, 2815.
ON0*
Pd-C ,HCOOH MeOH ,70h
/
AIDer.
0””’. 0””’” +
53%
34%
Ar also reduced with other Ar-X groups
K; Vasapollo, G. Tetrahedron Left., 1992, 33,7477.
REVIEWS : “ElectrocatalyticHydrogenation Hydrogen-Activity Electrodes” Moutet. J-C. Org. Prep. Proceed. In?., 1992, 24, 309.
0 2 N - H 12%
Compendium of Organic Synthetic Methods, Vol8
82
Section 74B
"Design Concepts for Developing Highly Efficient Chiral Bisphosphine Ligands in Rhodium-Catalyzed Asymmetric Hydrogenations" SynLen, 1992, 169. Inoguchi, K.; Sakuraba, S.; &WE&.
dN2 me
SECTION 74B: Formation of Aryls
1. Et-CK-OMe ,DCE hv (253.7 nm) * 2. DCE , reflux, 4 h
50%
OH
Danheiser.;Brisbois, R.G.; Kowalczyk, J.J.; Miller, R.F. J. Am. Chem. SOC.,2990, 112, 3093.
ci
'-
11-CS-CHZOH NiClz(PPh3)~
CE C- C02Me
2 eq. PPh3 2 eq. BuLi
C02Me Bhararah, P.; Smith. E.H, J. Chem SOC.,Chem. Commun., 1991, 277. PhH , hv (Hg vapor)
Ph Olsen.;Minniear, J.C.; Overton, W.M.; Sherrick, J.M. J. Org. Chem., 1991, 56, 989.
%
hv (Hglamp/pyrex) ,I2 propylene oxide , PhH
*@@ \ /
/
Liu, L.; Yang, B.; Katz.;Poindexter, M.K. J. Org. Chem., 1991, 56, 3769.
Et
H-CECf
95%
Me Me
OH
5% Pd(OAc), ,MeCN .t 20% PPh3,5% CUI NET3,reflux, 14 h
M ~ &Me~ Me02C
~
'I'orii. S,; Okumoto, H.; Nishimura, A. Tetrahedron Lett., 1991, 32, 4167.
c OHM"
79%
Aryls from Alkenes
Section 74B
3 Et-GC-Et
NiI2 , Py ,60"C ,24 h
-
83
*tE
39%
Et
~t
6
Kong, K-C.; Chmg,L& - J. Chem. SOC., Chem. Commun., 1991, 423.
Q
VO(OEt)C12 ,Me3SiOTf EtOH , 0°C --t RT
*
Hirao.;Mori, M.; -0.
Y. Chem. Lett., 1991, 183.
OMe
82%
)$,
12, CAN ,MeOHMeCN
reflux, 8.5 h
82%
. . Honuchl.; Fukunishi, H.; Kajita, M.; Yamaguchi, A.; Kiyomiya, H.; Kiji, S. Chem. Lett., 1991, 1921.
C1 Me2HN K-;.
. .
EtOH , NEt3, heat, 2 h
Nussbaumer, P. Synthesis, 1991, 663.
0
Me
Se02-PPSE. CC4 reflux ,26 h
&ph
eMe
PPSE = trimethylsilyl polyphosphate = P205Ne3SiOSiMe3
Lee. J.G.; Kim, K.C. Tetrahedron Lett., 1992, 33, 6363.
Ce-H
83%
Me3SnSnMe3 PhNC , hv
Br Curran.;Liu, H. J. Am. Chem. SOC.,1992, 114, 5863.
96%
Compendium of Organic Synthetic Methods, VoI 8
84
Section 74C
1. [Rh(COD)C112 Bu-CC-H 2. H+ ,40"C
Padwa.;Xu, S.L. J. Am. Chem. SOC., 1992, 114,
OH 5881.
Merlic. C.A.; Bums, E.E.; Xu,D.; Chen, S.Y. J. Am. Chem. Soc., 1992, 114, 8722.
SECTION 74C: Alkylations and Arylations of Alkenes
Fotiadu, F.; Cros, P.; Faure, B.; Buono. G , Tetrahedron Lett., 1990, 31, 77.
Ph I
%-OH
Ph
1. t-BuMe2SiOTf
2 . 2 1-BuLi , THF 't-BuMe,si* -78°C + +23OC
Kim, K.D.; Magriotis. P.A. Tetrahedron Lett., 1990, 31, 6137.
Ph. 0 N= N- S02Ph /
00
=/
C02Et
,PhH ,80°c
Pd(PPh3)4, sealed t u g
Ph
OH
84%
CO2Et
Kamlgata.: Satoh, M.; Fukushima, T. Bull. Chem. SOC.Jpn., 1990, 63, 2118.
89%
Section 74C
Alkylation of Alkenes
Bp
1.Mg.THF 2. Cp.LTiCI2, CHS12
3. AIC12Et. PhMe , -78°F 4.HCI
Rigollier, P.; Young, J.R.;Fowley, L.A.;
Mea 78%
a J. Am. Chem. Soc., 1990, 112, 9441.
3 eq. PhCl , MeCN , Py Zn , NiCh(PPh3)Z *
d Ph
85
+
Ph+ph
Ph
54%
7%
Lebedev, S.A.; Pedchenko, V.V.; Lopatina, V.S.; Berestova, S.S.; Petrov, &S. Zhur. Org. Khim., 1990, 26, 1520 (Engl., p. 1312). Si(SiMe3)3+ Meb.-
-
hv ,MesSilI , 20°C
Kulicke, K.J.;Biese. B. SynLett, 1990, 91.
32)
(68
Bu3SnC1, AIBN NaBH3CN.3d *
65%
, \p +
1-BuOH ,reflux
OH
Si(SiMe3)3
OH
HO
20%
43%
Bothwick, A.D.; Caddick. S.; Parsons. P.J, Tetrahedron Lett., 1990, 31, 6911 ph
*I
J-
Me
1 . sec-BuLi, THF.-70°C
ph
Me
)AMe79%
7-
2. Me1
Barluenga.; Rodn'guez, M.A.; Campos, P.J. SynLett, 1990, 270.
PhCHO
=/ SiMeC'z,
NEt3 , 120°C
w
Ph
*
cat. PdC12(PPh3)2 Yamashita, H.; Roan, B.L.; Tanaka. M,Chem. Lett., 1990, 2175.
SiMeCl,
77%
86
Section 74C
Compendium of Organic Synthetic Methods, Vol8
Br
==/Ph , Pd(OAc)z, DMF . t
cph
TBAB , K2CO3,10O0C Br 2h L-ansky, A.; Reiser, 0.;Be Meiiere. A. SynLett, 1990, 405.
J -
HSiC13, RT
Ph
=-
/
/
92%
Ph
PhYSiC13 57% Me (64.8% ee , S)
Okada, T.; Morimoto, T.; Achiwa. K. Chetn. Lett., 1990, 999.
-
P h a F H *TiCl2(OiPr)z %FOH Ph Ph
Me
rnesirylene , MS 4A 0°C . 4 d
-
41% (84% ee)
Narasaka. K.; Hayashi, Y.; Shimada, S.; Yamada, J. lsr. J. Chetn.,1991, 31, 261. C12MeSiH. Ni* , THF ,25"C
40%
+98% ee)
SiC1,Me
1424.
92% Ni* = activated Ni, from Li reduction of NiI in THF uk. P,; Han, B-H.; Jacobsen, J.R.; Hauck, B.J. J. Chetn. Soc., Chem. Conitnun., 1991, 1. BuMgCl ,2.5% Cp2ZrClz 2. €I+
+
x>
94%
( 8 2 18 cis:trans) Knight, K.S.; Wavmouh. R. M,.I. Am. Cheni. SOC., 1991, 113, 6268.
Hatanaka, Y.; Ebina, Y.;
.I. Am. Chem, Soc., 1991, 113, 7075.
Section 74C
Alkylation of Alkenes
=?OZBn NHBoc
Carlswom, A-S.;
C02Bn
P
w
Pd(OAc)z, Bu~NCL NaHCO3, DMF
Br
87
H
B
o
c
63%
Br
J. Org. Chem, 1991, 56, 1289.
Satoh, S.; Sodeoka, M.; Sasai, H.;
& EtO2C
'
.I. Org. Chem., 1991, 56, 2278.
BusSnSiMe3, PhMe 0.1 M , Bu4NBr 3% PdC12(PPh&
Br
Li2CO3, 110°C
CO2Et
*
70%
Mori. M,; Kaneta, N.; Shihasaki, M..I. Org. Chern., 1991, 56, 3486. 5% Pdz(dba)s, PhI 2 eq. CH2(C02Et)2
PhI , DMSO , S O T Bu4NCI, NaHCO3
-
Ph
CO,Et CO2Et
82%
Larock. R.C,; Lu, Y.; Bain, A.C.; Russell, C.E. .I. Org. Chent., 1991, 56, 4589. 1.2 eq. Mg ,MeOH 2.3N HCI , 0°C
0 Dominguez, C.; Csfdcy, A.G.; IYuw,J, Tetrahedron Lett., 1991, 32, 4183.
tailors catlyst to substrate
Farina, V.;Roth, G.P. Tetrahedron Left., 1991. 32, 4243.
0
98%
88
Section 74C
Compendium of Organic Synthetic Methods, Vo18
1. MeC12SiH , CuCl Pan microwave bomb
&
TMEDA , (750 W)* microwave oven 2. HC(OEt),
N
SiMe(0EtI3
75%
Abramovitch. R.A.; Abramovitch, D.A.; Iyanar, K.; Tamareselvy, K. Tetrahedron LRtt., 1991, 32, 5251. (PhMezSi)Cu*LiCN THF , 3 0 min
0
0
quant.
Lautens. M.; Belter, R.K.; Lough, A.J. J. Org. Chern., 1992, 57. 422. SiH (SiMe&
*IDN
*
-
.Phhk
Si(SiMe3)3 81%
Kopping, B.; Chateilialoelu. C,; Zehnder, M.; Giese. B.J. Org. Chern., 1992, 57, 3994. CpzY [CH(TMS)d 14 h
-SiH,Ph
Molander. G A L ;Julius, M. J. Org. Chern., 1992, 57, 6347.
95 %
1. h v , 0 2 , DCA
H
60% DCA = 9,lO-dicyanoanlhracene
Santamaria. J,; Kaddachi, M.T.; Ferround, C. Tetrahedron Lett., 1992, 33, 781. 1. ~ - C & ~ I ~ C H ~ C H ~ M ~ C I
d n-C6H13
3% CmZrC12, THF 2.H3O+ *
G n - C , H , , (4:l
Rousset, C.J.; ,-
E:Z)
92%
Suzuki, N.; l&&&uX . Tetrahedron Lett., 1992, 33, 1965.
Section 74C
Alkylation of Alkenes
=/Bu
ICHFCOzEt
, Zn , PY , THF
*
89
Bu C H ~ C H ~ C H F C O ~ E ~
NiC12.6 HzO ,60°C Wang, Y.; Yang. Z-Y.; Burton. D.JATetrahedron Lett., 2992, 33, 2137.
TfO '
Bernocchi, E.; 3073.
73%
Pd(0Ac)z , NEt3 P(o-t0lyl)3 , DMF HO 60°C, 3 h ;Ciattini, P.G.; Morera, E.; Q&K& Tetrahedron Lett., 1992, 33,
Ph
hq,,
1 . BuLi ,-78°C 2. M q S 0 4 , -78°C -+ RT
Ph
BuTe
kq..
t
Me
93%
"Ph csPh Dabdoub. M.J. ; Dabdoub, V.B.; Comasseto, J.V. Tetrahedron Lett., 1992, 33, 2261. 1 . Pd(PPh3)d , THF PhZnCl
n-C5H1 1
2. aq. NH&l
Rossi. R.; Catpita, A.; Cossi, P. Tetrahedron Lett., 1992, 33, 4495.
Ph
TfO
NaBPh4, Pd(PPh3k
*
DMF, R T , 2 h
Ph
JrJ
Ph
73%
Ciattini, P.G.; Morena, E.; Ortar, G. Tetrahedron LRtt., 1992, 33, 4815.
cy
82% Bhatt, R.K.; Shin, D-S.; Falck, J.R.; Mioskowski. C. Tetrahedron Lett., 1992, 33, 4885.
0 0
Sakamoto, T.; Kondo, Y.;
PhI , Ag2C03, DMF c
Ph
(43% ee)
Tetrahedron Lett., 1992, 33, 6845.
62%
Compendium of Organic Synthetic Methods, Vol8
90
CJ".,,
BuMgCl , 1% Cp2ZrC12
*
Id
Section 74C
95%
(86: 14 trans:cis) Wischrneyer, U.; Knight, K.S.; Wavrnouth, R.M. Tetrahedron Lett., 1992, 33, 1135.
Ph
>-?Br Me0
B-n-C8H17
t
Ph
1
M e d 'n-CsH17 Pd(PPh3)4, dioxane 60°C, 3 q.K2CO3,16 h Abe, S.; Miyaura, N.; SUzuki. A.Bul1. Chem. SOC. Jpn., 1992, 65, 2863. OSiMe2t-Bu H
=
Me
M~
Pd(PPh3)4, THF Lizc03. Licl. reflux
*
Me
&) H
83%
OSiMeZt-Bu 91%
*Me
Liang, S.; Paauette. J..A. Acta Chem. S c a d , , 1992, 46, 597. Cp2YMe*THF,PhH (2 atm) , RT , 4 5 min
H2
*
c:d
+
c< 2%
97%
Molander.;Hoberg, J.O. .I. Am. Chem. Soc., 1992, 114, 3123.
Ph
5% Mo(CHCMe2Ph) (N[2,6-diisopropylphenyl]) (OCMe[CF312)2
PhH , 20°C, 15 min
*
bph 92%
R.H. J. Am. Chem. Soc., 1992, 114, 5426.
2. NaOH ,H2Q DiPPE = 1,2-bis(diisopropylphosphino)ethane Wescott, S.A.; Blom, H.P.; Mader. T.B.; Baker. R.T. J. Am. Chem. Soc., 1992, 114, 8863.
Section 74D
Alkylation of Alkenes
*
91
phx
OMe, 65°C
67%
(q3C3H~PdC1)2, THF * 48 h Rossi. R,; Carpita, A.; Messcri, T. Guu. Chirn. ltul., 1992, 122, 65.
Ph
SiMe2Ph
OMe
1. F3CCH21, AIBN , 85°C
Bu I
2. NaBH4, DMF O"C+ RT Cloux, R.; Kovhts, Ez. Synthesis. 1992, 409.
PhJ
d
c1
Ph
+
F,C-Bu
, Pd(0Ac)z
Ph&
*
N u ~ N110°C , , 15 h
40%
ph 57%
Hongwen, H. Synth. Commun.. 1992, 22, 2019.
Yi, P.; ;-
H Z N oI
2=/'OZEt,
37°C
- H2N
Pd(OAc)z, PhYPOTs 10 h Genet.;Blart, E.; Savignac, M. SynLeft. 1992, 715. /
SECTION 74D:
Ph
/
Conjugate Reduction of a,P-Unsaturated Carbonyl Compounds and Nitriles 1. aq. NaOH , 5 rnin Pd(0Ac)Z
\=\C02H
Ph
- \ 2. (Et0)3SiHI RT
CO2H 10 min Tour. J.Mj Pendalwar, S.L. Tetrahedron Lett., 1990, 31, 4719.
93%
0.24 [(Ph3PCuH]6 30 € 1 2 0 , RT , 1 h THF
OAc
6
M OAc
e 94%
Koenig, T.M.; Daeuhle, J.F.; Brestensky, D.M.; Strvker, J.M. Tetrahedron Lett., 1990, 31, 3237.
92
Section 74D
Compendium of Organic Synthetic Methods, Vo18
&::
0
b o &
Kiinzer.;Stahnke, M.; Sauer, G.; Wiechen. R. Terruhedron Lett., 1990, 31,3859.
0
O
1. MAD. -78°C
MAD = bis(2,6-di-t-butyl-4-rnethylphenoxy)methylaluminum
Doty, B.J.; Morrow. G.W, Tetrahedron Lett., 1990, 31, 6125.
A
(Et0)3SiH , Pd(OAc)z, aq. THF
L
OBu
O
add ester prior to silane Tour. J.M,; Cooper. J.P.; Pendalwar. S.L. J. Org.Chem., 1990, 55, 3452.
B
99%
u
n-C5H 1 1
OMOM
>90%
(70:30diastereomers) Linderman.;Griedel, B.D. J. Org. Chem., 1990, 55,5428.
CO~B d
RhCI(PPh3). THF catecholborane + -2O"C, 12 h
,C02Bn
Evans.;Fu, G.C. J. Org. Chem., 1990, 55, 5678. C- C02Et e- , PhC02H ,DMF OH
EtdNC104, (0.1 M)
82%
*L HO
CO2Et
87%
Arcadi, A.; Cacchi. S.; m; Curulli, A.; Inesi, A.; Marinelli, F. SynLett, 1990, 408.
Section 74D
Conjugate Reduction of Alkenes
93
e- ( 2e-/mol), ag. MeOH aq. KCl
Clmly - - PPV+*-Pdelectrodes
quant.
PPV = poly(pyrro1e-viologen)
Coche, L.; Ehui, B.; Limosin, D.;
m.J -CJ. Org. Chem., 1990, 55, 5905.
H2.lh
CHO
,CHO
h.. M q
4
quant.
&sNl'dClz cat* Fe
&s- Ar
Ar=p-Me-phenyl
Ali, H.M.; Naiini, A.A.; Brubaker, C.J. Jr. Tetrahedron Lett., 1991, 32, 5489. 1. NaSeH , 5 0 T , 3 h , EtOH 2 . 2 N HCI c
Ph
0
Ph&Me 84% Nishivama. Y. : Yoshida, M.;Ohkawa, S.;JIamanaka. S . J. Org. Chem., 1991, 56, 6720. CO,H
<'OZH
H 2 , EtOH
2% Me
p.
NBD = norbornadiene
Rh(NBD)Cl
quant.
(96% ee)
go
Chiba, T.; Mivashita. k;Nohira, H.; Takaya, H. Tetrahedron Lett., 1991, 32, 4145.
OAc
k& , P t 0 2 , EtOAc NEt,. RT, 2 d
OAc
OAc
Katsuki, J.;
JmmgaATetrahedron Lett., 1991, 32, 4963.
88%
Ph3SnH, BEt3 , PhH 25T,6h
Nozaki, K.; Oshima. K.; Utimoto, K, Bull. Chem. Soc. Jpn., 1991, 64, 2585.
Compendium of Orgaiiic Synthetic Methods, Vol8
94
bakers yeast, 64 h
%rMe
n-C,H, I
Section 74D
Me n-C5H1+fMe
*
0
24%
0
(>99%ee) Sakai.;Matsumolo, S.; Hidaka, S.; Imajo, N.; Tsuboi, S.; Bulf. Chem. SOC. Jpn., 1991, 64, 3473. SmI2, AcNMez ,THF
Ph
Me
-
Ph&C02Et
EtOH , 12 h
co2,,
96%
Inanaea.;Sakai, S.; Hmda, Y.; Yamaguchi, M.; Yokoyama, Y. Chem. Lett.. Z991, 2117. “ZEt
Zn , AcOH , 2 h
C02Et
98%
”)))
Marchand.; Reddy, G.M. Synthesis,
COZEt
1991, 198,
Pd(OAC),, HC02K DMF ,60°C
94%
Arcadi, A.; Bernocchi, E.; Cacchi.;Marinelli, F. SynLett, 1991. 27,
C02Me Cabrera, A.;
1. SmI2, THF 2. HMPA , RT , 3 0 min
*
&C02Me
67%
Tetrahedron Lett., 1992, 33, 5007.
4 am H2, MeOH ,25”C 24 h
’
* qumt.
Ph OMe
Me0
Me
(40% ee) Me
Sjenet.;Pinel, C.; Mallart, S.; Juge, S.; Cailhil, N.; Laffitte, J.A. Tetrahedron Lett., 1992,
33, 5343.
Section 74E
Conjugate Alkylation of Alkenes
95
(52%ee , R) Saburi.;Ohnuki, M.; Ogawawara, M.; Takahashi, T.; Uchida, Y. Tetrahedron Lett., 1992, 33, 5783.
Q
&
COzEt =/ ,DBU,DMEU
185°C.24 h
CO2Et
*
DMEU = 1,3-dimethyl-2-imidazolidinone
80%
Hwu.; Kakimelahi, G.H.; Chou, C-T. Tetrahedrontett., 1992, 33, 6469. SECTION 74E: Conjugate Alkylations
n-Bu Ph
Met
0
>-.
B(OiPr)2 0.1 q.BFpOEt2, PhMe
Ph 0 78% Hara, S.; Hyuga, S.; Aoyama, M.; Sato, M.; Suzuki. A. Tetrahedronktf.;1990, 31, 247. 2. 1. MezCu(CWi2 (PhMezSi)Cu(CN)Liz
4
m
3.aq.NH4CI 60%
Me
+
M?e
SiMe2Ph
M~
SiMe2Ph
major Lett., 1990, 31, 311.
Lee, S.-H.; -Tetrahedron
0
THF/&er/ptane
(CN)Li,
CO ,-1 10°C 4min
73% (12:l trans:cis)
; Elworthy, T.R. Tetrahedron Lett., 1990, 31, 477.
96
Section 74E
Compendium of Organic Synthetic Methods, Vol8
OTs EtZCuLi , THF
* &OH
-78°C 3 RT , 135 min
80%
Et
Charonnat.;Mitchell, A.L.; Keogh, B.P. TelrahedronLeli., 1990, 31, 315.
Eid, C.N. Jr.;
'
TetrahedronLett., 1990, 31, 305.
e- , (HglSCE electrodes) dimethyl d o n a t e n-BudNBr, MeCN
Me Me
Me
(89%) Sowell, C.G.; Wolin, R.L.; Little. R.D. TetrahedronLett., 1990, 31, 485.
Bno-w
ether, -78°C , 3 0 min 0
Me
0
+
2. NaOMe ,MeOH 14h , 2 5 T no yield
,!w?.M.E.; Lew, W. Tetrahedron Lett., 1990, 31, 623.
1.5 MeMgBr , [Cu] ether:THF , 1 h
%e
0
60
CO,E~ 3.0 TMSCl , -46°C
OBn
0
40
A
Sakata, H.; Aoki, Y.; Buwa iima. I, Tetrahedron Lett., 1990, 31, 1161.
0
C02Et 99%
Section 74E
97
Conjugate Alkylations of Alkenes
8
MesSnCu-SMez ,THF Li(Bu3SnCuSPh) -78°C
*
6 0
85%
SnBu3 I U Lesheski, E L.E.;. Kiely, ; J.S. Tetrahedron Lett., 1990. 31, 1837. 0
1.LDA9THF,-78"C
2. EtZAICl , -40°C
c
u
JSMe 3. Kpegba, K.; bieknaJ Tetrahedron Lett., 1990, 31, 1853.
s quant.
SMe
+ Me
b,..
MezAgMgBr THF CH~CIZ,
MesRh,THF
Me
/
61% Kauffmann, T,; Hiilsdiinker, A.; Menges, D.; Nienaber, H.; Rethmeier, L.; Robber, S.; Scherler, D.; Schrickel, J.; Wingbermiihle, D. Tetrahedron Lett., 1990, 31, 1553.
f i
SnBu3
I. MeLi 2.0.5CuCN-LiCI
also reacts with halides, epoxides, etc.
L1Dshutz.;Ung, C.; Elworthy, T.R.; Reuter, D.C. TetrahedronLett., 1990, 31, 4539. 4 eq. EgSiH , sealed tube r-BuOOt-Bu, 140°C PhH
Me3Si also cyclization with unconjugated dienes Kraus. G.A,; Vivas, S. TetrahedronLett., 1990, 31, 5265.
98
Section 74E
Compendium of Organic Synthetic Methods, Vo18
rl
benzophenone ,PhH hv (>300 nm) , 1 2 mM
n
S
20 min 57% Nishida. A,; Nishinda, M.; Yonemitsu, 0. Tetrahedron Lett., 1990, 31, 7035.
*
C02Me
CHCl3,
@0
NEt,
e- (1.8 F/mol) ,DMF EhNBr , Pt cathode
t
Y C O , M e cc1, 78%
Sbono,;Ishifune, M.; Ishige, 0.; Uyama, H.; Kashimura, S . Tetrahedron Lett., 1990, 31, 7181.
Lipshutz, B.H,; Sharma, S.; Reuter, D.C. Tetrahedron Lett., 1990, 31, 7253.
I
1 CpZZrClz, DCE ,PhMe , 0"
0
2. CuCN , B u C K L i THF 0 3. -23°C 0 Ireland. R.E; Wipf, P. J. Org. Chem., 1990, 55, 1425.
COzBHA I. BULi, THF
2. LiBEl3H ,THF 3.Me1,HMPA
4.N a B h , MeOH 5. 10% aq. HCl
* 75%
BHA = 2,6-di-t-butyl-4-(methoxyphenyl)-l -naphthalenecarboxaldehyde
Tornioka.;Shindo, M.; Koga, K. J. Org. Chem., 1990, 55, 2276. Tomioka.;Shindo, M.; Koga, A. Tetrahedron Lett., 1990, 31, 1739.
Section 74E
Conjugate Alkylations of Alkenes
*
C0,Et
BuMgBr , MnClz LiCl , THF , 0°C + 20°C CuCl , Me3SiC1
99
y C O , E t Bu 97%
Cahiez.;Alami, M. Tetrahedron Lett., 1990, 31, 7423, 7425.
8
4
PhCH( R)Cu(CN)ZnCl
THF
R - n-C3H7
n-C3H7
SPh
78%
Achyutha Rao, S.; Tucker, C.E.; UuzhdLTetrahedron Lett., 1990, 31, 7575.
Kim, &; Lee, J.M. Tetrahedron Lett., 1990, 31, 7627.
& : L 0
Bu3SnH. AlBN PhH (0.04 M)
SePh
Middleton, D.S.;
[C02Me
65%
; Terrett, N.K. Tetrahedron, 1990, 46, 545.
hv ,DMSO , 4 eq. iPrHgCl
C02Me
4 eq. KI
Russell.;Kim, B.H. SynLett, 2990, 87.
Li I , THF, Cu*Me$iCI 30min
Q% ,
82%
87%
LiDshutz. B.H ; Ellsworth, E.L.; Dimock, S.H.; Smith, R.A.J. J. Am. Chem. Soc., 1990, 112, 4404.
Compendium of Organic Synthetic Methods, Vol8
100
Section 74E
LiAIH4 - S b Q , THF 0°C
0
0 Savama.;Inamura, Y. Bull. Chem. SOC. Jpn., 1991. 64, 306. -SnMq
.
hv
MeCN , 15 h
&
84%
51%
m u w a . A,; Nishigaichi, Y.; Iwamoto, H. Chern. Lerr., 1991, 1013.
Dupuy, C.; Petrier, C.; Sarandeses. L.A.;
Synth. Commun., 1991, 21, 643.
1. SmI2, THF , DMPU
+
I Curran.;Wolin, R.L. SynLetf, 1991, 317.
H- CE C- C02Me
60%
20%
iPr-I, BujSnSnBuj
hv (sunlamp), 85OC 30 min
(1:2.4
C02Me 70%
E:Z)
Curran.;Kim, D. Tetrahedron, 1991, 47,6171.
!&ra&QE
Kim, D.; Ziegler, C. Tefrahedron, 1991, 47, 6189.
[
cat. CpzZrCl2, CH2C12,0°C HCSCH2CH20H CuCN-2 LiCl , THF-ether
(2.8:l trans:cis) U s h u t z . B.H.; Dimock, S.H. J. Org. Chem., 1992, 56, 5761.
82%
Section 74E
Conjugate Alkylations of Alkenes
101
Ph*OMOM SiMq
68%
CsF , DMF
OMOM
Ph
Linderman. R.J.; Ghannam, A.; Badejo, I. J. Org. Chem., 1991, 56, 5213.
0
+%
1. CpzZr(H)CI ,THF RT ,20 min, )))))I 2
.
~
0
3. CuBr=SMez,RT , 1 h wiof.;SmiU'ovich, J.H. J. Org. Chem., 1991, 56, 6494.
CO2Et
A
CI(CF2)411Zn , EtOH bromo(Py) cobaloxime (111)
+
Et02C
. ,
20"C, 1 h
(CF,),CI
Bu. C-M.; Qiu, Y-I>. Tetrahedron Letr., 1991, 32, 4001. 0
B uzCu(CN)Li2 THF , -78°C
n-C6H13T
O M e 90% Bu
Soderauist.;Rosado, I. Tetrahedron Lett., 1991, 32,4451.
Q
+oSiMezr-Bu ,ether OMe
2.5 M LiC104 , 1.2 h
70%
-
6
OSiMe,t-Bu 95%
C02Me
u; Cooke. R.J.; Henry, K.J.; Vander Roest, J.M.Tetrahedron Left., 1991, 32, 4665. TBAF
____c
Mefl:C)Xt
Me yamarnot0.y.;Okano, H.; Yamada, J. Tetrahedron Left., 1991, 32, 4749.
(7:3 dr)
61%
102
Compendium of Organic Synthetic Methods, Vol8
1. MezCu(CN)Li*, -78°C 3h n
2.
Me3Sn
uo
SnMe3 3. MezCu(CN)Liz
*
Section 74E
% 0
0
(91% E,E)
;-
Lee, J.I. Terrahedron Lett., 1991, 32, 7211.
C02t-Bu 1 . BuLi ,THF ,-78°C 2. H3O+
CO2t-BU b
88%
6
(translcis = 3.0)
Cmk,M.P. L J . Org. Chem., 1992, 57, 1495. 1 . MeLi 2. aq. H2SO4
OH
0
Alons0.F.; XusJd. Tetrahedron, 1992, 48, 2709. BhSn
Et3SiC1, -78°C
70%
OSiEt,
Cu(CN)Li
\-I
Me
* 96%
P; Emonds, M.V.M.; Stengel, P.1; OHveira, A.R.M.; Simonelli, F.; Ferreira, J.T.B. Tetrahedron Lett., 1992, 33, 49.
(91:9 trans:cis)
Toru.;Watanabe, Y.; Tsusaka, M.; Gautam, R.K.; Tazawa, K.; Bakouetila, M.; Yoneda, T.; Ueno, Y. Tetrahedron Len., 1992, 33, 4037.
Conjugate Alkylations of Alkenes
Section 74E
103
Me3ToaMeLi ,ether -40°C. 1 h
Me Mark6. I.E.; R e b i h , R. Tetrahedron Lett., 1992, 33, 1763. 1 . 4 eq. Sm12, THF , HMPA 2. CuI*P(OEt)3 , -78°C + -20°C
Ph-
I
3.
#o
Tottleben, M.J.; Curran, P.P.; WiDf. P.J. Org. Chem., 1992, 57, 1740. 1. BnNH2, cyclohexane reflux c
Me-
0
Me
C02Me 2. NaBH3CN, MeOH
Bn >6:1
Dumas, F.; dAngelo, J. Tetrahedron Lett., 1992, 33, 2005.
$
:B.(ZnlCu[CIV]C=CHBu
0'
&C02Me N E:Z)
,MqSiCI
-78°C -+ 25°C , 12 h
n-C,H 1 1 0
Waas, J.R.; Sidduri, A.R.;
57%
76%
Tetrahedron Lett., 1992, 33, 3711. C%CO,, MeCN
Me02C
COzMe add yn-one by syringe pump
Meo2cQc$Me
(88:12 cktrans)
Girard, S.; -Can.
Ph-
J. Chem., 1992, 70, 1265.
Te-
Ph
1. BuzCu(CN)Liz, THF RT 2. -78°C , * 0
0
UPh 77%
Tucci, F.C.; Chieffi, A.; Comasselo.J.V.Tetrahedron Letf., 1992, 33, 5721.
Compendium of Organic Synthetic Methods, Vol8
104
Section 74E
(67
33)
48%
WU. M-L; Wu, C-C.; Lee, P-C. Tetrahedron Lett., 1992, 33, 2547.
1. CUCN,-78°C + -4°C
2,
0
0
mdall.J.K;; Ayers, T.A. Tetrahedron Lett., 1992, 33, 5311. 2 eq. BnMgCl ,CuI TMSCl , TMEDA
Et0,C-
+ E t O , C y ph THF , -78°C + -40°C
73% 24 h van Heerden, P.S.; B e z u m L . . B.C.B.; Steenkamp,J.A.; Ferreira D, Tetrahedron Lett., 1992, 33, 2383.
t-Bu
Dieter.;Alexander, C.W. TetrahedronLett., 1992, 33, 5693. 1. BrCC13 , hv 2. MeOH ,H20
%Me3
3. BuCu(CN)Li , -78°C
0
*
"'9 c1 SiMe3
Cunico.;Zhang, C. Tetrahedron Lert., 1992, 33, 6751.
64%
BnCu(CN)ZnI c
c1
c1
67%
Ph
Ph
Sidduri, A.R.; Budries, N.; k n e a .;IhxhdL Tetrahedron Lett., 1992, 33, 7515.
105
Conjugate Alkylations of Alkenes
Section 74E
Cl(CF2)8I
d C O z E t , Zn , THF cat. SmC13 ,reflux
*
CI(CF&CH,CH,CO,Et 76%
w Zhao, ; G.; Huang,W. Tetrahedron Lett., 1992, 33, 81 19.
Q
PhBr , Ni(bipy)3(BF3)2 DMF ,ZnBr2, Bu4NBr e‘ (Zn anode, C cathode)
+
6,
52%
Sibille, S.; Ratovelomanana, V.; Perichon, J. J. Chem. SOC.,Chem. Commun., 1992, 283.
I
‘OzMe,
.
=tOzMe NHAc
0
EtOH RT ,)))))))I*
-
Sarandeses, L.A.; MouriAo, A.; 4eq.
Zn ,C ~ I
C02Me
”I”y”” 14%
J. Chem. SOC., Chem. Commun.. 1992, 798.
0,BF3*OEtz 0
25°C ,40h
Q--& C02Me
+
NHAc
quant.
Cativiela. C,; L6pez, M.P.; Mayoral, J.A. SynLett, 1992, 121.
0
BuzCuLi , ether
C3cL SiPh3
w
B
u
q SiPh3
0
-78°C
89%
DedInnocenti. A,; Stucchi, E.; Capperucci. A.; Mordini, A.; Reginato, G.; Ricci. A, SynLett, 1992, 329, 332.
ASYMMETRIC CONJUGATE ADDITION REACTIONS
8
DMS , LiCu(n-Bu)R
R=
[ €1Y % N ~
92%(8l%ee,S)
Rossiter.;Eguchi, M. Tetrahedron Lett., 1990, 31, 965.
106
Section 74E
Compendium of Organic Synthetic Methods, Volt?
ABu
[BuLVCuBr] ,ether
*
NH2 M e
63%
(68% de, R)
Me
Dieter. R.K,;Lagu, B.;Deo, N.; Dieter, J.W. Tetrahedron Lett., 2990, 31,4105.
* 0
Ph
catalyst =
ZnEt2, catalyst
ph
b
1% Ni(acac)t
0
Ph
JLb 55% (72% ee, R)
3 m OH
Ph
Hob'
Balm.; Ewald, M . TefrahedronLett., 2990, 31, 5011.
(94 Fang, C.; Suemune, H.; W a i . K,Tetrahedron Lett., 2990, 31, 4751.
6
iPrMgBr , 1% ZnCl2 , THF -9O"C, Me
f
&
Jansen, J.F.G.A.; Feringa, B.L. .I. Org. Chem.. 2990, 55, 4168.
H
fi."-OMe
+ 2.ZnBr2, THF 3. Me2CuLi , -78°C + 0°C
Tamura.;Watabe, K.;
61%
91%
(18% ee)
OH
1. MeCN 25°C
6)
Katayama, H.; Suzuki, H.; -to.
kMe
84%, S Y.J. Org. Chem., 1990, 55, 408.
Section 74E
Ph
107
Conjugate Alkylations of Alkenes
qCPh3 - P hEt n0f C P h 3 0 Et2Zn
Mewph
0
25%
OH
81%
(80%ee, 1S2R)
Soai.;Okudo, M.; Okamoto, M. Tetrahedron Lett., 1991, 32, 95. 1. Me(S-MAPP)CuLi , ether
-78"C,1 h
2.4N NH4CI
bMe 57%
(58% ee , S) Rossiter. B.E.; Eguchi, M.; Hernsndez, A.E.; Vickers, D.; Medich, J.; Marr, J.; Heinis, D. Tetrahedron Lett., 1991, 32, 3973.
$gMe $?:
Rawson, D.J.; M e v e r s . T e t r a h e d r o n Lett., 1991, 32, 2095. BuzCuLi TMSCl
c
0
0
85%
Mevers.~.~.; Leonard, W.R. Jr.; Romine, J.L. Tetrahedron Lett., 1991, 32, 597. 1. BuMgBr , TMSCl cat. CuBreSM9
HMPA , -3OT
2. KF
*
c : p o Bu (93
Sonoda, S.; Houchigai, H.; Asaoka, M.;
+
Bu= 7)
Tetrahedron Lett., 1992, 33, 3145.
81%
108
Section 74F
Compendium of Organic Synthetic Methods, Vo18
c1-,
Ph-@KPh 0 Kanai, M.: Koga, K.; M
Boc
PPh2
,MezCuLi
Me 0
79%
(84%ee , S)
a . K, Tetrahedron Lett., 1992, 33, 7193. EtZZn, Ni(acac)2
Ph
Ph
*
ether, -20°C. 1 h
Et.N
*
Ho
Ph (70% ee , R)
Ph- S a 0
Bolm.;Felder, M.; Miiller, J. SynLett,
0
Et
71%
1992, 439.
REVIEWS:
"The Evolution of Higher Order Cuprates" I&XWLULSynLerf, 1990, 119. "New Aspects of Organmopper Reagents: 1,2- and 1,2- Chiral Induction and Reaction Mechanism" Ibuka, T.; Yamamoto, Y. SynLeff, 1992, 769.
SECTION 74F:
Cyclopropanations, including Halocyclopropanations
Me3SiOHOC &
t
C02Me C02Me
02Me /
t
(dba)3PdyCHC13 PPh3 , THF , reflux
HH
COzMe
C02Me 64%
Trost. B.M,; Urabe, H. Tetrahedron Lett., 1990, 31, 615.
COZEt
Me-
n-C3H7MgBr, CuI
Et02C (6040
E:Z)
Kasatkin. A,N,; Kulak, A.N.; Biktimirov, R.Kh.; Tolstikov, G.A. Tetrahedron Lett., 1990, 31, 4915.
Cyclopropanations of Alkenes
Section 74F
P h d
N
109
0
2d 0-I-menthyl
t
Cu salen derivative catalyst
A-
Ph
+
i=02-l-menthyl
Ph C02-1-menthyl
72% 96% ee 14)
(86
98%ee
dPh ,CH2C12
L-L CO,Me
0
ko
CHN,
b
Tetrahedron Left., 1990, 31, 6005.
Lowenthal, R.E.; Abiko, A.;
cat.
p, y
.Rh-I ' RhI
trans (48% ee, 1S,2S)
h0
Ph
69% (67:33
cis (85%ee , lS,2R)
tramcis)
I)ovle., Brandes, B.D.; Kazala, A.P.; Pieters, R.J.; Jarstfer, M.B.; Watkins, L.M.; Eagle, C.T. Tetrahedron Lett., 1990, 31, 6613.
CH2(C02Eth , I 2 , 2 h
B"&
- P:;It
KzCO3, reflux Bu 39% tricapylMeNC1 T6ke, L.; Szab6, G.T.; Hell, Z.; T6h, G. Tetrahedron Leff.,1990, 31, 7501. 0.75 Dibal , PhH RT,lh
54% 77% ee
Dauben. W.G.; Hendricks, R.T.; Luzzio. M.J.; Ng, H.P. Tetrahedron Lett., 1990, 31, 6969. CFC13 , T i c 4 , 0°C 0.33 ;-
Php Me LiAIH4,30min Me Burkholder. C.R. J. Org. Chem., 1990, 55, 589.
F
85%
110
Compendium of Organic Synthetic Methods, Vo18
Br
Section 74F
TCNE , THF -1O"C, I h
wOMe
OMe
NCX::e NC C N
88%
Lee, J-Y.; Hall, H.K. Jr. J, Org. Chem., 1990, 55, 4963. 1. (+)-TMTA , MS 4A 2. CH212, Zn-Cu ,ether reflux, 24 h
Bu
B(oH)2 3. H202.2N KHCO3 TMTA = N,".N-tetramethyI
THF
-
B " q O H 91%ee
tartaramide
67%
h i . T,; Mineta, H.; Nishida, S . J. Org. Chem., 1990, 55, 4986.
r
I
Me
& CFCH ,PhH , 5 % KOH
M e CI
dibenm-18-crown-6
RT.Sd
Sheu.;Yen, C-F.; Chan, Y-L.; Chung, J-F. J. Org. Chem., 1990, 55, 5232.
o/
Ph
Zn , THF , CF2Br2
RT , overnight
F
96%
yields range from 496% with various alkenes
Q!JbaXLk Wojtowicz, H.; Burkholder, C.R. J. Org. Chem., 1990, 55, 5420.
d+
CH2N2 ,PdC12(PhCN)2 CHzClz - ether
OH
10°C + RT
c
74%
also used to convert allylamines to aminomethyl cyclopropanes Tornilov, Yu.V.; Kostitsyn, A.B.; Shulishov, E.V.; Hefedov. Synthesis, 1990, 246.
0.m
1. CO , THF
SiMe3 15"C, 2 h =c=( 2. ?-BuMe$iCI c. M % s i v OSiMe2t-Bu OSiMe,r-Bu Li HMPA ,-78°C 59% 15% Ryu, I.; Hayama. Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai. S , J. Am. Chem. Soc., 1990, 112, 7061.
4SiMe3
+
111
Cyclopropanations of Alkenes
Section 74F
*$ 1.
Me3P
@
APh
0-K+ Mew ,THF ,-6OT
Ph
60h
2.12, THF , -78°C
0
PF60
Tjaden, E.B.;
70%
J. Am. Chern. SOC., 1990, 112, 6420. -C1
1. Mg , THF 2. aa. NHLI
-
1OH
(3 2) 75% Akhmedov, M.A.; Akhmedov, I.M.; Mustafaeva, Z.G.; Sardarov, I.K.; Kostikov, R.R.; Musaeva, Kh.E. Zhur. Org. Khim., 1990, 26, 1257 (Engl., p. 1087).
& Me
Bu
BuQ,Me FCO),MeG'" OMe
-*'
THF, 100°C
I
71%
Me
Harvev. D.F,; Lund, K.P. J. Am. Chern. SOC.,1991, 113, 8916. Harvev. D.F,; Lund, K.P.; Neil, D.A. Tetrahedron Letr., 1991, 32, 6311. Kh2(5S-MEPY)4 , 25°C 74% (88% ee) Dovle. M.P,; Pieters, R.J.;Martin. S.F,; Austin, R.E.; Oalmann, C.J.; Muller, P. J. Am. Chern. SOC., 1991, 113, 1423.
\
90%
Kulinkovich, O.G.; Sviridov, S.V.; Vasilevskii, D.A.; Savchenko, A.I.; Pritylskaya, '1,s.Zhur. Org. Khim., 1991, 27, 294 (Engl., p. 250).
EtC0,Me
1 . 2 eq. EtMgBr , 10%Ti(OiPr)4 ether
t
hEk 76%
2 . 5 % aq. H2SO4,5"C OH Kulinkovich. O.G,; Sviridov, S.V.; Vasilevskii, D.A. Synthesis, 1991, 234.
112
Compendium of Organic Synthetic Methods, Vol8
Section 74F
2 CBrzFZ, CHZBr2,27 h 2 KOH (60%aq)
BufiHS04 Balcerzak, P.; Fedorjhski, M.;
F
F
70%
J. Chem. Soc., Chem. Commun., 1991, 826. n
1. Me N-NeLi
, 2 B,,L~
P h d , Ph Ph>cHo 2.HzO *CHO 73% Tanaka. K.; Matsuura, H.; Funaki, I.; Suzuki, H. J. Chem. SOC.,Chem. Commun., 1991, 1145. Bu
1 . 7 eq. CH2N2, cat. Pd(0Ac)z
%
2. NaBOq.4
ether
H70,
O % Fontani, P.;
.
; Vaultier, M.;
fi''~,
reflux, 50 mip
Bu
dioxane - HzO
76-82%
Maas&, Synthesis, 1991, 605.
t-BuSOzCHzLi ,THF n-C8H 17
2% Ni(acac)z ,reflux
m
Gai, Y.; Julia M,; Verpeaux, J-N. SynLett, 1991, 56, 269. PhzS=CHz , Cu(acac)z
NaH,THF
*
Cimetikre, B.; Julia. M,Synktt, 1991, 271.
crf^
Ph
SMe
1. BuLi ,THF -78°C -+ 0°C 2.MeOH
0
86%
'8
*
82%
Krief.;Batbeaux, P Tetrahedron Lett., 1991, 32, 417. 1. Me3SO+I-, NaH 2. r-BuOK, aq. ether
dMr r l ~ OMe -
BnO
65%
[rn-C8H17
Rodriaues. K.E, Tetrahedron Lett., 1991, 32, 1275.
t
Q"4CO2H
BnO
88%
Section 74F
Cyclopropanations of Alkenes
2::;’ 8 COzMe
=/
Me0
C0,Me
Me0 i- +C02Me
THF.6.5OC
+
113
54)
(46
PPh3
64% 39970
74)
(26 : Merndon. J.W,; Tumer, S.U. J. Org. Chem., 1991, 56, 286. Me
~ C - H M,ok Cr(CO)s , sioz ~ C - H decane ,63OC, 3 h
Me02C Meo2c<
Me02C&0
c
Me02C
94%
Katz.;Yang, G.X-Q. Tetrahedron Lett., 1991, 32, 5895. Me?
C02Me
Br
1. t-BuOK , THF -7OOC. 100 min 2. 1N HCI ,-70°Cd
(75:25 Z E )
Br 12%
88%
Duhamel.; Peschard, 0.; PIC, G . Tetrahedron Lett., 1991, 32, 4695.
\ro
-0
Y
+
Jy
Ph
Ph
O
Ph
(89% dr)
major
Davies.;Cantrell, W.R. Jr. Tetrahedron Lett., 1991, 32, 6509. Davies.;Hu, B. Tetrahedron Lett., 1992, 33, 453. Br
PhMgBr , 2 Sd, THF - HMPA -
-co,Et
-
pc,”,”
Fukuzawa. S.; Niimoto, Y.; Sakai, S. Tetrahedron Lett., 1991, 32, 7691.
NO2
OH
NZCHC02Et , PPh3 PhH , RT
t
A NO2
n-C4Hg
(10:l trans:cis)
Yu. J.;
Falck.;Mioskowski, C . J. Org. Chem.. 1992, 57, 3757.
90%
82%
91 %
114
Compendium of Organic Synthetic Methods, Vo18
TI1F WHs) , - 7 8CH2I2 T + RT
Me3Si
Section 74F
,,%+
Me$;%
H
OH
HO
HO
(1
1.3)
Lautens.;Delanghe, P.H.M. J. Org. Chem., 1992, 57, 798.
.
aq. NaOH heat
0.i.
84%
.N-TS
H?
HO
81%
Me
M o u l i n a ; Charpentier, P.; Bats, J-P.; Nuhrich, A.; Lamidey, A-M. Tetrahedron Lett., 1992, 33, 487. 1. Zn ,THF ,reflux 2. CISiMe$-Bu
I
OSiMezt-Bu
0
564
Yasui, K.; Fugami, K.; Tanaka, S.;~amaru.Y.; Ii, A.; Yoshida, Z.; Saidi, M.R. Tetrahedron Letf., 1992, 33, 785, 789.
Ph
0.03% C ~ ( P P ~ ~ ) ~ R U [ H ~ Cph ~B~HI~]
NzCHCOzEt , 6OoC,4 he
86% (cktrans = 0.69)
Demonceau.A.; Saive, E.; de Froidmont, Y.; Noels, A.F.; Hubert, A.J. Tetrahedron Lett., 1992, 33,2009.
Ph H
MeS
1. BuLi
2. PhSqCl
3. BuLi,-7g0C
H M e w M e ph.
79%
(88% dr) Krief.;Hobe, M.; Dumont, W.; Badaou, E.; Guittet, E.; Evrard, G. Tetrahedron Lett., 1992, 33, 3381. I(rief.;Hobe, M. SynLefl, 1992, 317.
Eto2Cv l.NaH,THF 2. 1,
CO2Et
3. THF ,reflux
E t o 2 C A I EtO2C
Beckwith, A.L.J.; Tozer, M.J. Tetrahedron Lett.. Z992, 33, 4975.
81%
Section 74F
Cyclopropanations of Alkenes
115
Et2Zn. CH212, -23°C. 5 h
CHzC12-10% hexane
0
P h A O H
Ph
*
NHS02Ph
Takahashi, H.; Yoshioka, M.; Ohno, M.; &hyj&&
OTs
%
AC S - H
c
Bu
Tetrahedron Lett., 1992, 33, 4103.
0 1. T ~ H N N A C I
, p m q
NEt3. CH2C12 2. RhZ(SS-MEPY)d ,C112CI2
--
0 %
74%
(77% ee)
MEPY = tetrakis[methyl-2-pyrrolidinone-5S-carboxylate~
Martin. S.F,; Oalmann,C.J.; Liras, S. Tetrahedron Lett., 1992, 33, 6727.
(101
E:Z)
Harvev. D.F,; Lund, K.P.;Neil, D.A. J. Am. Chem. SOC.. 1992, 114, 8424. jiarvev. D.F; Brown, M.F. Tetrahedron Lett., 1990, 31, 2529.
phmMe
4Ph , Zn(Hg) , ether c
59%
ClMe2SiCH2CHzSiMezCl
(11:l cktrans)
Motherwe 11. W.B.; Roberts, L.R. J. Chem. SOC.,Chem. Commun., 1992, 1582. 1. EtzZn , PhMe 2. diethyl tartrate
Ph-OH
3. Et2Zn ,CH&
vkaji, Y.; Nishimura, M.;
64%
(2:l E:Z)
Pyo, S.; Skowron, J.F. 111; QlaJK.
OH
75%
Tetrahedron Lett., 1992, 33,2515.
'
5 eq. LDA ,THF -78°C
OH (68% ee)
NHSqPh
,"3'
>
Ph-
OH
(39%ee)
Chem. Lett., 1992, 61.
55%
116
Compendium of Organic Synthetic Methods, Vo18
Section 75
Denmark.,Edwards, J.P. SynLerr, 1992, 229.
SECTION 75:
ALKYLS, METHYLENES AND ARYLS FROM MISCELLANEOUS COMPOUNDS
-
PdC12(PhCN)2 ,xylene Ti(OiPr)4
C
I
W
C
Miura. M,; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Let?., 1990, 449. PhMgBr , ZnBr2
l 76%
(N1Ph
kHO
6HO
Brown, D.S.; Hansson, T.; Lev. S.V. SynLett, 1990,48. Brown, D.S.; Charreau, P.; Lev. S.V. SynLert, 1990, 749 [with ZnC121.
Yanagisawa, A.; Nomura, N.; Yamamoto, H, SynLett, 1991, 513.
87%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 6 PREPARATION OF AMIDES
SECTION 76: AMIDES FROM ALKYNES
H-
ci
'-
CMe3
1. BuLi , THF , -60°C 2. Me3SiCI. -20°C + RT
3.55"C. PhZNH , 11 h*
heating after 2. leads to ketenes
M e 3 S i T 0
NPh, quant.
Valentl, E.; Pericas, M.A.; Serratosa, F. J. Org. Chem., 1990, 55, 395.
SECTION 77: AMIDES FROM ACID DERIVATIVES
Corriu. R.J.P.; Lanneau, G.F.; Perrot-Petta, M.; Mehta, V.D. Tetrahedron Lett., 1990, 31, 2585. NEt3 , MeCN
x:
H02C
*
n
LJ
n7
n-C6H, 1
CI EtO' p*'c, "
1114, I"
"L
OR N i l
Kim, C.W.; Chune, B.Y.; Nam Kung, J-Y.; Lee, J.M.; Kim.
S, Terrahedron Lett., 1990, 31, 2905.
HN(SiMe&, MeOH DMF, RT, 16 h
* Z:-H
0 Davis. P.D, ; Bit, R.A. Tetrahedron Lett., 1990, 31, 5201.
0
93%
Compendium of Organic Synthetic Methods, Vol8
118
Section 7
Manhas. M.S. ; Ghosh, M.; Bose, A.K. J. Org. Chem., 1990, 55, 575.
N’ N’ Me
0
Pandhi, S.B. J. Org. Chem., 1990, SS, 2196.
COOH
OL
’
nN 0
NEt3 , CHzC12
Me
sharma. S.D;
Me
PhO
P h O y
pyrrolidine , CBr4, NEt3 PPh3 ,RT , 15 min
ph Me
Me
good yield
&’ \
Einhorn. J.; Einhom, C.; Luche, J-L. Synth. Commun., 1990, 20, 1105.
P h d
reflux ;
(15:l &:trans)
OMe
Mashava, P.M.; Guan, X. Tetrahedron Lett., 1992, 32, 581.
CH3COOH
n-C&lsNH;!, PhH Ph3SbO , P4S 10
ACNH-~I-C~HI~
90% 40°C,5h Nomura.; Nakano, T.; Yamada, Y.; Matsuda, H. J. Org. Chem., 1991, 56,4076.
R U ~ ( C O )Ph-NOz ~~,
C02H
180°C, 8 h
-
Nahmed, E.M.; Jenner. G, Tetrahedron Lett., 1991, 32, 4917.
NHPh
51%
89%
Amides from Aldehydes
Section 79
U'ySh-PPh3 MeCN ,reflux
119
c
(CH2)6 Shi, Y . Tetrahedron Lett., 1992, 33, 943. Boc
1. H-N,
0 II
OSiMezt-Bu
c
0 PhA N- OH
DMAP , MeCN , 5 h 77% 2. TFA ,CH2Ci2,0°C H 6h Altenburger, J.M.; Mioskowski. C.;dOrchymont, H.; Schirlin, D.; Schalk, C.; Tamus, C. Tetrahedron Let(., 1992, 33, 5055.
PhAC1
SECTION 78: AMIDES FROM ALCOHOLS AND THIOLS CoC12, MeCN , Ac20 80"C, 15 h
-L NHAc
70%
Nayyar, N.K.; Reddy, M.M.; IgbaIJ, Tetrahedron Left., 1991, 32, 6965.
SECTION 79: AMIDES FROM ALDEHYDES
-
NBS , AIBN CC14, BuNH2
O C H O
p o N H B u
80%
Mark6.;Mekhalfia, A. Tetrahedron Left.,1990, 31, 7237.
.
1. BnOKNSO -25°C
-CHO
BF3;0Et2, CHzCI2
2. Et3SiH
Alexander, M.D.; Anderson, R.E.; Sisko, J.;
t
-NHCbZ 64% J. Org. Chem., 1990, 55, 2563.
120
Section 79
Compendium of Organic Synthetic Methods, Vo18
Msov +
Ms
@ cB(0H)2 HO
’ N,
H
Br
Na2CO3 Pd(PPh3)4
DME , reflux
/
L O
Siddiqui, M.A.; Snieckus. V, Tetrahedron Lett., 1990, 31, 1523.
*
0 L O
1. PhNH2 ,HC1, KCN 2.1-BuOK , 0 2 ,THF
PhCHO
76%
/
RT
-
49%
Chuang, T-H.; Yang,C-C.; Chiang, C-J.; l%agJ&L SynLRtt, 2990, 733.
Ph
CHO
2 eq. SIC13 ,MeCN 2 H 2 0 , CH2C12,lO h Ph b
I N H C O z M e 59%
Elm0rSv.s.s.; Nour, M.A.; Kandeel, E.M.;Pelter, A. Tetrahedron Lett., 1991.32, 1825. 1. N(SnMe3)j 2. t-BuPh2SiCl
0
CHO 3.
b
)=(:;
kN*
0
65%
SiPh2t-Bu
Busato, S.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. SynLett, 1991, 243.
SECTION 80:
AMIDES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 81: AMIDES FROM AMIDES Conjugate reductions of unsaturated amides are listed in Section 74D (Alkyls from Alkenes). 1. sec-BuLi 2.DMF 3. HCI
Boc Clark. R.D.; Muchowski, J.M.; Souchet, M.; Repke, D.B. SynLelt, 1990, 207.
121
Amides from Amides
Section 81
1. Na, THF
coupling occurs in some cases
Karman, R.;Fry, J.L. Tetrahedron Lett., 1990, 31,941. 10% Pd(OAc),
Me P 4 B ' Na'
0
30%
70%
&igg&; Dorrity, M.J.; Malone, J.F.; Sridharan, V.; Sukirthalingam, S. Tetrahedron Lerr., 1990, 31, 1343.
v
NHz
H
1. IIg(OAc)s,DMF
K
MeOH N OMe 2. N3S , DMF 0 12h 91% 0 new Hofmann rearrangement Jew. S ; Park, H.G.; Park,H-J.; Park,M.; Cho, Y. Tetrahedron Lett., 2990, 31, 1559.
0 EtOA NH, Wachter-Jurcsak,N.;
1. t-BUOH 2. NaOH 3. BEt3 ,65"C,6 h
*
4. aq. NaOH
0 EtOlcNHEt
8048% Tetrahedron Lett., 1990, 31, 5261.
Na2(P4SloO), THF .25"C 2h
-
S
L N H
88%
Brillon.D.ynrh. Commun., 2990, 20, 3085.
0
HJ- NMePh
w,Kojima, A:,
Se(AIMe32, PhMe-THF 40°C , 4 h
b
H
P
Nakajima, T.; Suga, S. SynLett, 1991, 105.
NMePh
91%
Section 8 1
Compendium of Organic Synthetic Methods, Vol8
122
(82 18) Polniaszek.; Belmont, S.E.; Alvarez, R. J. Org. Chem., 1990, 55, 215.
90%
SnC14, -23°C 1.5 h
80% Org. Chem.. 1990, 55, 1447. Fisher, M.J.; Overman.L.E.,
(CF3C0)20, RT CH2C12,5 h
he
Me
87%
Masuda, R.; Hoio. K;Ichi, T.; Sasano, S.;Kobayashi, T.; Kuroda, C. TetrahedronLett., 1991, 32, 1195.
Ph
Me
MezS(=O)CN- , DMSO 2% *
w N
S02Ph
SO,Ph
r- "
t-lMe
51%
Ph
Nadir.;Sharma, R.l.; Koul, V.K. J. Chem. Soc., Perkin Trans. I, 1991, 2015.
0-
:loti
Me
Bu3SpnhHH' AIBN
c
&o H Me
+
O7lo Me
73% (3aMe:3PMe 6:l) M i b s h i . H.: Nakamura, N.; Sato, T.; Takeuchi, M.; &eda. M, TetrahedronLetl., 1991, 32, 1725.
-ins.
123
Amides from Amides
Section 81
OMe R* = (-)S-phenylmenthyl
D.L; Badawi, M M .Telrahedron Lett., 1991, 32,2995.
Bn
1. LDA 2. BnBr
% 0
0
*
ph8-'*\-0
63%
h.*'L O (1.8:l trans:cis)
Baldwin. J.E,; Moloney, M.G.; Shim, S.B. Terrahedron Lerr., 1991, 32, 1379.
Ac
BuzSnCl . NaBHqCN
&
N.
1)
(4
90%
Clark,A.J.; Iones.; McCarthy, C.; Storey, J.M.D. Tetrahedron Lelt., 2991, 32, 2829.
Me NH2
0
H
PhCHO , PPA ,35"c
74%
72 h
H Marson.;Grabowska, U; Walgrove, T.; Eggleston, D.S.; Baures, P.W. J. Org. Chem., 1991, 56, 2603.
I
0
Y
0
NsPh
0 ~ 1 ~ 1 3
*
'),"*ph
0
m.A.; Seki, K.; Matsuda, H. J. Org. Chem., 1991, 56, 2684.
quant.
124
Compendium of Organic Synthetic Methods, Vo18
.
0
1. sec-BuLi TMEDA
THF , -78.C 2. B(OMe)3
N(iPr)L
Section 8 1
3. H30+ Br , Pd(PPh3)d
4.
aoMe
DME
81%
Me0
aq.Na2CQ
No, B.I.; Kandil, A.; Patil, P.A.; Sharp, M.J.; Siddiqui, M.A.; J. Org. Chem., 1991, 56, 3763.
*.
V. ; Josephy, P.D.
B y S n H , AIBN PhH , 8OoC m
81%
cisltrans)
Curran. D.P.; Abraham, A.C.; Liu, H. J. Org. Chem, 1991, 56, 4335. PdC12(PPh3)2, DMAC
H $ (
/
DBU95 , 115OC, psi CO 5.5 h
.r
h'l$-zf
/
0
DMAC = N,N-dimethyl acetamide Perm. U;Turner, S.R. J. Org. Chem., 1991, 56, 6573. H2
0 4 NH,
(300 psi)
CO (900 psi)
HRh(CO)(PPl;;h 2 eq. dppb ,80°C
Bra
+Meh
Qo
Y
H
40 h
63%
H
2)
(98
O
88%
QiimaL. Korda, A.; Shay, W.R. J. Org. Chem.. 1991, 56, 2024.
Me- N
Bu3SnH. AIBN PhH ,reflux ,0.02 M
--
Me-$.
Me0
Hart.; Wu, S.C. Tetrahedron Lett., 1991, 32,4099.
p
0 Me0 (I:]
95%
a$)
Section 81
Amides from Amides
1. 5% RuC12(PPh& , 2 h 140°C
CCl,
oA
N--(=
H
125
2. B y S n H , PhMe , 1 h reflux
Me
* On M N i e
H 47% Nagashma, H.; Wakamatsu, H.; Ozaki, N.; Ishii, T.; Wafanabe, M.; Tajima, T.; Itoh.K.. Org. Chem., 1992, 57, 1682. 1. BuLi , DABCO 2. 3 eq. Cu(0Ac)z
0
COzt-Bu
Kawabata, T.; Minami, T.;
OMe J. Org. Chem., 1992, 57, 1864. Bu3SnH, AIBN PhH , reflux
70%
Me Keusenkothen, P.F.; Smith. M.B. Tetrahedron, 1992, 48, 2971.
1 . LDA 2. BnBr
+ Bn 1)
Kimura, K.; Murata, K.; Otsuka, K.; Ishizuka, T.; Haratake, M.; 1992, 33, 4461.
MEOX = tetrakis[rnethyl 2-oxazolinone4(S)-carboxylate]
(71 % ee)
76%
Tetrahedron Lett.,
(80% ee)
h y . k M & ; Protopopova, M.N.; Winchester, W.R.; Daniel, K.L. Tetrahedron Lett., 1992, 33, 7819.
Compendium of Organic Synthetic Methods, Vo18
126
fi:
fiMe
Ph2NN0, PhH , 3 h
0
reflux
NH2
Section 81
O
51%
H
!XhkLQ.; Pem, S.T.; Toske, S.G. Tetrahedron Lett., 1992, 33, 433.
Kotsuki.; Iwaski, M.; Nishizawa, H. Tetrahedron Lett., 1992, 33, 4945. Me
-0\ 1
Pb(OAc)3
NaH , C12CH2-DMF 70°C, 7 h
0
0
86%
L@ez-Alvarado, P.; AvendaAo, C.; Menkndez, J.C. Tetrahedron Lett., 1992, 33,6875.
H
k0'
CH2CC13
1. PhI(COCF3)2, CH2C12 0°C , 2.5 h 2 . 3 eq. Zn dust, 12 h AcOWacetone ,RT
H
70%
Scartozzi, M.; Grondin, R.; Leblanc. '6, Tetrahedron Lett., 1992, 33, 5717.
.
j+
1 . PhLi , CuBr*SMQ THF
t-BuO"'ny
o
Ac
Kwt, W-J.;
Me3SiCI ,-78°C + RT
2. MqNH , DMF , RT , 2 8 h 3. 3 q . e S i M q 3 eq. BF3*OEt2, 18 h , RT CH2CI2
?Lo
47%
Tetrahedron Lett., 1992, 33, 7969.
-;
c1
0
Bu3SnH ,AIBN
PhMe ,reflux
'
Me
63%
Me
Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; I ls&. Trans. I, 1992, 2399.
8% Me
J. Chem. SOC.,Perkin
127
Amides from Amines
Section 82
BuBr , TBAB , KOH
Ph y NH2 0
P ~ ~ N H B ~
~
71%
80°C
0 Loupy, A.; Sansoulet, J.; Dfez-Barra, E.; Carrillo, J.R. Synth. Commun.,1992, 22, 1661.
Ph
p"k
3.3 eq. Bu3SnH
S P ~ P m e , MBN
Ph
c
14.5 h
0
Me
Me
Sato, T.; Machigashira, N.; Ishibashi, H.;
Heterocycles, 1992, 33, 139.
,PhMe
C1-CSC-H
* H---$
reflux ,80 h
0
90%
0
Gesson, J.P.; Jacquesy, J.C.; Rambaud, D. Bull. SOC.Chim. Fr., 1992, 129, 227. 1. PhMe , PhLi
CH20SiMe2t-Bu 2."-C5H11Br H Keusenkothen, P.F.;
O
.-
G CH,0SiMe2t-Bu
~-C5H11
Synth. Commun., 1992, 22, 2935.
75%
SECTION 82: AMIDES FROM AMINES 1. P C ~ 5 Bum2
~
Y N H B u
2.2
0
77%
C02H Cabral, J.; Laszlo.:Montaufier, M-T.; Randriamahefa, S.L. Tetrahedron Lett., 1990, 31, 1705.
Bai. D,; Bo, Y.;Zhou, Q. Tetrahedron Lett., 1990, 31, 2161.
128
Compendium of Organic Synthetic Methods, Vol8
H20, 100"C,0.3h
NH2
Ph
(Ac0)zNOMe
*
Section 82
Ph*NHAc
99% N-methoxy diacetamide - a new acetylating reagent many amines are acetylated at RT Kikunawa.;Mitsui. K.; Sakamoto, T. Tetrahedron Lett.. 1990, 31, 243.
0:
[Rh(OAc)213 , PPh3 H2/CO, EtOAc ,20 b autoclave ,400 psi 50°C
* Me
H
95%
Anastasiou, D.; k k s nn. W.R. Tetrahedron Lett., 1990, 31,4795,
ph LNH2
Cp2Ti(02CiPr)2, THF reflux. 24 h
' 82% H Recht, J.; Cohen, B.I.; m m a n . AS,; Kohn. L Tetrahedron Lett., 1990, 31, 7281.
H
OH
84%
m; Oda, T.; Sugahara, T.; Masui, Y . J. Org. Chem., Z990, 55, 1744.
*> Vn
Me Chamchaang, W.;
1. LiI
2. Ni(C0)d
3. I2 workup
Lr
'yo
Me
50%
A.R. J. Org. Chem., 1990, SS, 2943. 1. (EtqC),O,
2. Pb(OAc)i, AcOH
45%
21%
Lenz.; Costanza C.; Lessor, R.A.; Ezell, E.F. J. Org. Chem., 1990, 55, 1753.
Section 82
h i d e s from Amines
129
Cho, I-S.; Tu, C-L.; Mariano. P.S. J. Am. Chem. SOC., 1990, 112, 3594. montmorillonite , KSF PhMe ,reflux, 13 h
N-OH
59%
Me
Me
Synfh. Commun., 1990, 20, 3253.
1.LiAlH4 , ether, 0°C 2. AQO, Py , RT
* O N H A c
0
SynLett, 1990, 677.
SbCl5 , AgSbF6, MeCN reflux, 3 h
N.
H'
OTMS
Mukaiyama, T.; Harada, T. Chem. Left., 1991, 1653.
>=
OAc
Fembdez, S.; MenCndez, E.;
Me 89%
Synthesis, 1991, 713. 1. MeCkN-0
Ph.
0
Ph
NA
PhlCNHPh
2. f-BuOK , THF 3. H20 Aitken. R.A,; Raut, S.V. SynLett, 1991, 189.
NH, Naota, T.;
'
77%
0
c.-l'
piperidine, THF ,25"C 30 min *
N'
76%
RUHz(PPh,), , DME , 3 h benzalacetone , 140°C
SynLett, 1991, 693.
w
Go H
51%
59%
130
Compendium of Organic Synthetic Methods, Vol8
wTph
Section 82
0
1. M ~ O~A 1 N E, t 3 , MeOH c
2.TMSOTf
modified Pictet-Spengler
Cheung, G.K.; Earle, M.J.; Fairhurst, R.A.; M e V . H.; Shuhaibar, K.F.; Eyley, S.C.; Ince, F. SynLett. 1991, 721.
M e 0 OMe
M
e
6 OH
Y-Ph 1 1 ooc Me Bauenneister, S.; Gows, I.D.; Straws, H.F.; 1991, 561.
Mex
Me 0
-
-vC'ph
82%
Me
J. Chem. SOC.,Perkin Trans. I,
KMnO4, aq. MeCN
Ph
~
phb N. t-Bu
t-BU
73%
'
kN.H
0
Larsen, J.; Jargensen. K.4,; Christensen, D. J. Chem. SOC., Perkin Trans. I, 1991, 1187.
NH2
ethyl ,40T - bulvrate . lipase SP 382.1 h
hindered m i n e s gives lower yields
-NHAc
-
.r
quant.
Djeghaba, Z.; Deleuze, H.; Lk Jeso, B.; Messadi, D.; Maillard, B. Tetrahedron Lett., 1991, 32,761.
-"O .H
EtsSiH , RT ClCOzMe
t
overnight
C0,Me
OH
Wu. P-L,; Sun, C-J. Tetrahedron Lett., 1991, 32, 4137.
74%
PhSO&l, B u g 1 CHzClz, 25°C
S0,Ph
76%
Sheu, J.; SUWLMJL ; Oeschger, T.R.; Satchell, J. Org. Prep. Proceed. lnt., 1992, 24, 147.
Nomura. R,; Hasegawa, Y.; Ishimoto. M.; Toyosaki, T.; Matsuda, H. J. Org. Chem., 1992. 57, 7339.
131
Amides from Esters
Section 83
Ph
I
Me Wang, M.D.; m
CO~(CO)S , CO (54 a m ) PhH , 7 2 h
J
gr
*
. Am. Chem. SOC.,1992, 114, 7018.
,OH
56%
he
T E A , [Et02CCH2CI/Znl
Mulengi. J.K.; Fauni, N. Bull. SOC. Chim Belg., 1992, 101, 257
3 eq. MesSiCl, 6 eq. DMF 3 eq. imidazole , RT
84%
H
Berry, M.B.; Btagg, J.; Craig, D.; Willis, M.C. SynLett, 1992, 659.
CHO
SECTION 83: AMIDES FROM ESTERS MeHNCHO ,THF
OMe
100°C. NaOMe15 ,MeOH min
90%
d N H M e
Jandmann. G.E. J t ; Munson, H.R. Jr.; Gero, T.W. Synth. Commun., 1990, 20, 1203.
28)
(72
Cinquini, M.; C o d , F.; Cozzi, P.G.; Consolandi, E. Tetrahedron, 1991, 47, 8767.
0
(TMS)zN-SnNHBn hexane , RT , 12 h
Ph \Ic OMe Wang, W-B.;
J. Org. Chern., 1992, 57, 6101.
NHBn
99%
Compendium of Organic Synthetic Methods, Vol8
132
porcine pancreatic lipase. t-amyl alcohol, pH 7.8
H
h
Me
w
6d
NHZ
Section 85
'U-O40%
Gutman.;Meyer, E.; Yue, X . ; Abell, C. Tetrahedron Letr., 1992, 33, 3943.
r e - B a u d e t . ; Morere, A.; Dias. M. Tetrahedron Lett,, 1992, 33,6453, Ph-N=C=O, THF , 8 h Pd(PPh3)4, RT
OK0
70%
0
0
Tamaru. Y,;Bando, T.; Kawamura, Y.;Okamura, K.;Yoshida, Z.; Shiro, M. J. Chem. Soc., Chem. Commun., 1992, 1498.
SECTION 84:
AMIDES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDlTIONAL EXAMPLES
SECTION 85: AMIDES FROM HALIDES AND SULFONATES
&
1. 2 BuLi , -78°C
Ph>S02NH2 72% (13%ee)
N- S02Me 2'BnBr
Davis. F,A,; Zhou, P.; Lal, G.S. TetrahedronLett., 1990, 31, 1653.
II -
1
ID..
\
0-
L . .
2. NEt3 ,reflux
Flvnn.,Zabrowski, D.L. J. Org. Chem., 1990, 55, 3673.
59%
Section 87
133
Amides from Ketones
\r B~
Nf33, n-C6H14, NHEt2 C02(CO)8 ,50 atm CO
b3
Br
lOO"C, 48 h NEt, 87% wivashita. A,; Kawashima. T.; Kaji, S.; Nornura, K.; Nohira, H. Tetrahedron Lett., 1991, 32, 781.
SECTION 86: AMIDES FROM HYDRIDES
Q
80°C. 18 h 2.3 eq. Zn , 2 h AcOH + acetone 3. A c ~ OPy , , RT CH2C12.18 h
*
~
N
H
A
85%
Lehlanc.;Zamboni, R.; Bernstein, M.A. J. Org. Chem., 1991. 56, 1871.
with addition of CO, get a low yield of the aldehyde
Olah.;Wang, Q. Synthesis,
Z992, 1090.
SECTION 87: AMIDES FROM KETONES SS ,NH4OAc Py ,reflux
6
You.;Zhou, H-Y.; Wang, Q-2.;Lei, X-H. Org. Prep. Proceed. Int., 1991, 23,435.
Me
*'
Me
Ph
Phx N H ~
2.MPCA * 3. hv (254 nrn)
Me
MPCA = monoperoxycamphoric acid AuM. L;Hamrnond, M.; Gherardini, E.; Takusagawa, F. J. Org. Chem., 1991, 56, 499.
~
134
Compendium of Organic Synthetic Methods, Vo18
B Q
(NH4)zC03, PhH H-CH2SH El-Zohrv. M.F. Org. Prep. Proceed. Int.. 1992, 24, 81.
Section 88
65%
H
2 eq. n-Ca13N3 2.5 eq. TiC14, 16 h CH2C12,O"C + RT
-
b
80%
AuM. L;Milligan, G.L.; Mossman, C.J. J. Org. Chem, 1992, 51, 1635.
Aube.;Milligan, G.L. J. Am. 0
Chem. SOC.,J99J. 113, 8965.
NaBH4, NiC12.6 H 2 0
+
1
quant.
PhlC N3 MeOH ,lO°C, 5 min Ph NH, B o . H.S.P,; Reddy, K.S.;Turnbull.;Borchers, V. Synth. Commun., 1992, 22, 1339. 1. CHzI2 ,Zn , TIC14 2. C102SNCO
P
h
q
Ph
3.RT,12h
SO&l Black. T.H,; Olson, J.T.; Abt, D.C. Synth. Commun., 1992, 22, 2729. REVIEWS:
"Carbon-Carbon Bond Cleavage by the Haller-Bauer and Related Reactions" Gilday, J.P.; Paauette. L.A, Org. Prep. Proceed. Int., 1990, 22, 167.
SECTION 88: AMIDES FROM NITRILES SH
NH3' C1
Ph
A C=N -
HCI(g) ,-78"C 85%
0
new Pinner type reaction Lee, Y.Y.;Lee, J.K. Tetrahedron Lett.. 1990, 31, 1169. Lee, Y.B.; Goo, Y.M.;
Section 88
Amides from Nitriles
1. MeAI(CI)NH2 ,80°C
Ph-
CkN
P
/
PhMe
135
h
y NH2 NH
93%
2. H2O WniDati. R.S. Tetrahedron Lett., 1990, 31, 1969.
1. (MaSi)zSe, 2.2 BFyOEt2 CH2C12, 6OoC, 8 h
PhCN
&
2. aq. N ~ H C Q
Shimada, K.; Hikage, S.; Takeishi, Y.;-a.
66%
Y, Chem. Left., 1990, 1403.
NaB03.4 H20, H2O dioxane.89°C.65hb H 2:*rB
65%
(39% "purified') Reed, K.L.; GuDton. J.T.; Solarz, T.L. Synfh. Commun., 1990, 20, 563.
-
NazC03*3 H 2 0 2 , acetone
Ph-CkN
H20,SO"C
94%
Kabalka. G.W, ; Deshpande, S.M.; Wadgaonkar, P.P.; Chatla, N. Synth. Commun., 1990, 20, 1445.
Ph 7 CN
1. P ~ S ~Na2S O , ,THF ,20°C
2.H2O
*
73%
Ph-lfNH2
S
B r i l l o n . S y n r h . Commun., 1992, 22, 1397
Ph-CZN
(Me$i)zS , NaOMe , DMEU 30°C
w
80%
DMEU = 1,3-dimethyl-2-imididinone
Lin,
P-Y.;Ku, W-S.; W. M -J, Synthesis, 1992, 1219.
SECTION 89: AMIDES FROM ALKENES l.O=C=N-S02CI , CC4 0°C -) 25OC
g
ySiMe3 2. aq. Na2S03
c-
SiMe,
0
Colvin. E.W,; Monteith, M. J. Chem. SOC.,Chem. Commun., 1990. 1230.
60%
Compendium of Organic Synthetic Methods, Vol8
136
Me&
SMe3
Me
ClS02NC0, CH2C12 NazS03, NaHCO3 -20°C , 4 h
Section 89
2
Nativi, C.; Perrotta, E.; Ricci, A.; U&hJl, ' Tetrahedron Leu.,1991, 32, 2265. 1. C12NC02t-BuIPhMe 50"C, 6 h 2. Zn ,NHdOAc, 0°C dioxane , 1 4 h Tetrahedron Lett., 1991, 32, 4045.
Orlek, B.S.;
Dkuma. K,; Komiya, Y.; Ohta, H. Bull. Chem. SOC.Jpn., 1991, 64, 2402.
(26:l dr , S)
Whitesell., Yaser, H.K. J. Am. Chem. Soc., 1991, 113, 3526.
&nn.
D.L.; Zabrowski, D.L.; Nosai, R. Tetrahedron Lett., 1992, 33, 7281.
SECTION 90:
-Co2Me
AMIDES FROM MISCELLANEOUS COMPOUNDS Bu$nH, PhMe AIBN ,75"C
SCN
40 min
Bachi.;Denenmark, D.J. Org. Chem., 1990, 55, 3442.
H - N S F
94%
Section 90
Amides from Miscellaneous
NO,
aNHc
-
P ~ C I ~ - H ~ P V2040 ~MO~ 3 eq. CO ,MeOH ,DME
137
96%
Izllmi.;Satoh, Y.; Urabe, K. Chem. Lett., 1990. 795.
Kobs, U.; Neumann. W.P.Chem. Ber., 1990, 123, 2191.
N: N 0
BuLi , CHzClz
Bu t-BuO~C-N'
H t-BuQC- N
Nqo+
c
H
W 26)
(74
yamam0to.y.;Yumoto, M.; Yamada, J. Tetrahedron Lett., 1991, 32, 3079.
25%
Basha. A; Ratajczyk, J.D.; Brooks, D.W. Tetrahedron Lett., 1991, 32, 3783.
Et
BnOH , HCI/CH2C12
-N=C=O
Et
RT,Sh
NHCbz
92%
Benalil, A.; Roby, P.; Carboni, B.; Vaultier. M. Synthesis, 1991, 787. 1. PhSnMe3 ,20°C
ClSO,-N=C=O Arnswald, M.;
2. H 2 0 Chem. Ber., 1991, 124, 1997.
PhSO2NH2
82%
Zeolite (H-Y) , PhMe reflux, 24 h
M MeSe 5 = N a Reddy, T.I.R.; Bhawal, B.M.;
* MeS'No
H Tetrahedron Lett., 1992, 33, 2857.
70%
88%
Section 90
Compendium of Oiganic Synthetic Methods, Vol8
138
BuHN
Rh(C1)CO
1. P(OMe)3 , HCI
CHZCLZ -78°C 2. P(OMe)3 ,MeOH -78°C - RT
Ph
90%
Ph
Krafft.;Yu,X.Y.;Milczanowski, S.E.; Donnelly, K.D. J. Am. Chem. SOC., 1992. 114, 9215.
p-.
EtO' EtO
Ph
S
1. NaH ,THF
"fi
H
t
,
46%
t s 8
reflux, 4 h
Okurna.
K.; Ikari, K.;Ohta, H. Chem. Lett., 1992, 131.
REVIEWS:
"Organometallic Carboxamidation" Org. Prep. Proceed. lnf., 1990, 22, 271 w t a s . C.G.;
SECTION 90A: PROTECTION OF AMIDES n-C3H7CHO, p-TsOH , PhMe 70%
H
1. Et30' BF4
*
9
0
?
2.H20 67% 3.pH8 Smith, M.B.; Wang, C-J.; Keusenkothen, P.F.; Dembofsky, B.T.; Fay, J.G.; Zezza, C.A.; Kwon, T.W.; Sheu, J-L.; Son, Y.C.; Menezes, R.F. Chem. Lett., 1992, 247.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 7 PREPARATION OF AMINES
SECTION 91: AMINES FROM ALKYNES 5% PdC12(MeCN)2 MeCN-H20 , 5 h
n-C8H,fCr C\
NH,
reflux
*
Qn-C8H17 67%
Fukuda, Y.; Matsubara, S.; Utimoto. K. J. Org. Chem.. 1991, 56, 5812.
Fukuda, Y.; Ytimoto,
Ic.Synthesis,
1991, 975.
SECTION 92: AMINES FROM ACID DERIVATIVES
PhCOOH
1. SOC12 ,reflux 2. HOSA , PhMe , reflux 3.H+
c
67%
PhNH2
IIOSA = hydroxylamine 0-sulfonic acid Wallace. R.G,; Barker, J.M.; Wood, M.L. Synthesis, 1990, 1143.
lepidine ,hv Ph(02CCF3), 2.5 h 0°C -+ RT
Toao. H,; Aoki, M.; Yokovama. M. Tetrahedron Lett., 1991, 32, 6559.
52%
Compendium of Organic Synthetic Methods, Vol8
140
Section 94
SECTION 93: AMINES FROM ALCOHOLS AND THIOLS
Tf
MeNHTf ,THF
PhboH
Ph,
DEAD,PPh3
N.
Me
Edwards.;Stemerick. D.M.; McCad~y,J.R. Tetrahedron Lett., ZnN6.2 Py , PPh3, RT iPr02CN=NCO*iPr
OH
M
~
PhMe
70%
1990, 31, 3417.
~
+ 81%~
~
N3
Synthesis, 1990, 130.
Viaud, M.C.;
1. Tf20 , CHzClz , NEt3
-15OC
2. piperidine ,MeCN reflux, 12 h quant.
some mines required 10 kbar of pressure
Kotsuki. H.; Kibayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis, 1990, 1145, 1147. 1. MsCl ,NEt3 ,THF 2. c-C&IIlNH2 NEt3
H.
I
p h q NMez Me
*
PhH ,reflux
4)
,hqNMe2
50%
Me
Dieter. R.K,; Deo, N.; Lagu, B.; Dieter, J.W. J. Org. Chem., 1992, 57, 1663.
SECTION 94: AMINES FROM ALDEHYDES OHC-CHO
c
PhNH,
NHPh
HFe(C0)i , 1M KOHEtOH 52% CO , R T ,24h Shim.;Kwon, Y.G.;Doh, C.H.; Kim, H.S.; Kim, T.J. Tetrahedron Leu., 1990, 31, 105.
>
1. TsN=S=O, CHzCl2
CHo
Sisko, J.;
* 2. MeMgBr
J. Org. Chem., 1990, 55, 393.
HNHT:3S
Section 94
2
Amines from Aldehydes
J(NN
fi
+
N
1. BnN€12,20°C H20
CHOCHO 2. NaBH4
H
141
-0 N
Bn
Katritzkv, A.R,; Fan, W-Q. J. Org. Chem., 1990, 55, 3205. Kauitzkv. A.R,; Fan, W-Q.; Fu, C. J. Org. Chem., 1990, 55, 3209. 1. TsNSO , SnCI4, PhH O"C+ RT
EtCHO
91%
I
NHTs
2- &SiMe, El Ralbovsky, J.L.; Kinsella, M.A.; Sisko, J.; Weinreb. S.M. Synth. Cummun., 1990, 20, 573. 95%
Me*
1. PhNH2, PhH , reflux 2. NaBH3CN, MeOH
r/' N,) CHO
THF,5NHCI
Me
aJ r
Me
o
NHPh
65%
Barluenea.;Aznar, F.; Fraiz, S. Jr.; Pinto, A.C. Tetrahedron LRti., 1991. 32, 3205.
-%
CHO
Ts- N=TSN- Ts
b
PhMe , toluene, 1 h
Trost.;Marrs, C. J. Org. Chem., 1991, 56, 6468. PhNH2, NaBH4, MeOH 3M H2SO4, THF
Verardo, G.;
..
b
; Favret, G.; Strazzolini, P. Synthesis, 1991, 447.
1. I-BuNH~ 2. LDA , THF
\CHO Stevens,
3. CI(CH2)3Br, THF ,0°C 4. iPrONa ,iPrOH
c.;De Kimoe. & SynLett, 1991, 351. Related Methods: Section 102 (Amines from Ketones)
pBU 44%
142
Compendium of Organic d j ?:dietic Methods, Vol8
SECTION 95:
Section 96
AMINES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 96: AMINES FROM AMIDES
-
1. Me3SiC1, NEt3
PhMe ,40°C , 4 h
N H
2. BuLi
Q
B
U 70%
m,Miao, S.W.; Bharathi, S.N.; Katsuhira, T.; Bravo, A.A. J. Org. Chem., 1990, 55,
-
3682.
NaBH4,25"C, 50 h Br-
4bbori.
68%
EtzN-Me
Br
L,Takanohashi, Y . Chem. Lett., 1990, 251. 1. 2.2 eq. PhLi ,THF ,O°C 2. H 2 0 , O°C c
Ph
*3+
r Ph
PhSeSePh 73%
94%
Sekiguchi, M.; Qgawa. A; Fujiwara, S.; Ryu, I.; Kambe, N.;Sonoda. N. Chem. Lett., 1990, 2053.
0
NaBH4, THF ,65OC, 4 h (BrCH2CH212SeBr2
b
Me2NY Me
Me,Ne
Me
82%
Akaban.;Takanohashi, Y . J. Chem Soc.. Perkin Trans. I, 1991.479.
aCF3 1. PCl5 2. MeLi
NHAc
3.
/--
0
m
to) N
N-Li
57%
U
Me Strekowski. L,; Petterson, S.E.; Janda, L.; Wydra, R.L.; Harden, D.B.; Lipowska, M.; Cegla, M.T. J. Org. Chem., 1992, 57, 196.
143
Amines from Amides
Section 96
NaOEt ,DMF EtOH ,reflux
f
t
Bu' N
Bu'
Me C02Et 47%
Bartholomew, D.; Stocks, M.J.Tetrahedron Let?.. 1991, 32, 4795.
Ph. N-AC
NaBH4,I2,7O0C, 3 h
*
Ph. N.Et
Me Me Prasad, A.S.B.; Kanth, J.V.B.; Periasamv. M, Tetrahedron, 1992,48,4623.
74%
no N Ts
1. Dibal ,CH2C12, -78°C 2. PPTS
3. Tic14, Me$%-
Ts
87%
h m a n , J.; Somfai. P, Tetrahedron, 1992, 48, 9537.
Kuroboshi, M.; Hivama. T. Tetrahedron Lett., 1992, 33, 4177.
0
0
Ho
AIBN, xylene reflux, 2 h
OH 67% Hirao. K; Mohri, K.; m m i t s u . 0,; Tabata, M.; Sohma, J. Tetrahedron Lett., 1992, 33, 1459.
R
1. PhLi , TlIF -78°C -+ RT
H ;-
H
HCI 62%
McCarthy, K.E.; Martin, M.G. Tetrahedron Lett., 1992, 33, 5895. Related Methods: Section 105A (Protectionof Amines)
144
Section 97
Compendium of Organic Synthetic Methods, Vo18
SECTION 97: AMINES FROM AMINES
Ph-N'
,-
MeOH ,0.25 M NaOH DCN*,12h
Me
*
H
Ph-N:
Et hv (>280nm) Et 80% Sudha Rani, K.; Bhalerao, U.T. Tetrahedron Lett., 2990, 31, 1199. Bu3SnH, AIBN
p o Sherbum. M.S. Tetrahedron Left., 1990, 31, 1625, 3495. Sherbum, M.S.; Dickinson, J.M.; Goodman, C. J. Chem. SOC., Chem. Commun., 1990, 1065. ;Sherbum, M.S. Terrahedron, 1991, 47,4077.
;;-
Bu3SnHI AIBN PhH ,reflux *
H
(O& I 0
q N r 66%
Rosa, A.M.; Prabhakar. S. ; Lobo, A.M. Tetrahedron Left., 1990, 31, 1881.
M Me0
Me0
e
O
T
Me0
Br
'\ -
_____)
0
51%
OJ
\
OJ
0
Takano. S,; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett., 1990, 31, 2315.
n ( )N
x
4
1 . 4 BnMgCl ether, R T , 12h 2. KOH , aq. MeOH
L,
Qh
Gottlieb, L.; Mevers. A.1, Tetrahedron Left., 1990, 31, 4723.
H
76%
145
Amines from Amines
Section 97
hv ,MeCN
Ph 15% 65%
Lewis.; Reddy, G.D.TetrahedronLett., 1990, 31, 5293. hv (2280 nm) DCN ,MeCN
M
e
>
o
m
' NH
80%
DCN = 1.4-dicyanonaphthalene Pandey, G.;Sridhar, M.; Bhalerao, U.T. Tetrahedron Letf.,1990, 31, 5373.
"0 Me,N
O
0
Me0
Ph
OMe
Tomioka.:Inoue, I.;
MeLi , PhMe , -78; 20 min
Ph)--N'
Me
H
Q
(70% ee, R)
94%
OMe
Shindo, M.; Koga, K. TefrahedronLeft., 1990, 31, 6681.
DAO = pea seedling diamine oxidase Cragg, J.E.; ~
R
.
B Kgaphola, . ; M.M. Tetrahedron Left., 1990, 31,6907.
O2"0\ N
Me
%Me 0
NaHco3, EtOH heat, 3 h
Eulda. A.A,lnd.J. Chem, 1990, 298, 1017.
77%
Me
Section 97
Compendium of Organic Synthetic Methods, Vol8
146
RuClz(PPh3)3
>or" N,
PhMe ,reflux
H
quant.
Tsuji, Y.;Kotachi, S.; Huh, K-T.; Watanabe..!. Org. Chem., 2990, 55, 580.
1. Ti(OiPr)4, PhCHO , RT
-
2. NaBH3CN. H 2 0 , 2 0 h
70%
Mattson.; Pham, K.M.; Leuck, D.J.; Cowen, K.A. J. Org. Chem., 2990, 55, 2552. 1 . iPrMgBr 2. iPrMgBr
L @$ Ph
) N * '
87%
bh
Katritzkv. A.R,; Rachwal, S.; Wu, J. Can. .I. Chent., 1990, 68, 456. Kauitzkv, A.R,; Latif, M.; Urogdi, L. J. Chem. SOL,Perkin Trans. I, 1990, 667. Katritzkv. A.R,; Noble, G.; Pilarski, B.; Harris, P. Chem. Ber., 1990, 123, 1443.
N.OMe
Ph
A ! Me
NaBH4 - XI4, THF , RT b
KH":
Ph
Y2 Me
95%
(64% ee , S)
Itsuno.;Sakurai, Y.;Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. I, 1990, C0,Me
b
EtO
M~
,80"C 2h
*
Me
2. NaOMe 3. heat, 2 h Walizei, G.H.; Breitmaier. E, Liebigs Ann. Chem., 1990, 605.
H
1. BuLi 2. 1-BuLi 3. BuLi ,TMEDA ,20"C
(EtO)ZCO, -50°C -+ 20°C eN-4.5. HzO
1859.
35%
t
85% Foubelo, F.; GonzPez, R.; Fafianb, F.J.; Yus, M. J. Chem. Soc., Chem. Conimun., 2990, 1521.
;-
147
Amines from Amines
Section 97
Li[Ir(dppe)d. H2 (25 bar) THF , CHzCCLz, 30°C. 1 h
Bn .
N=iMe Ph
stainless steel autoclave
=- BnHN<
Me Ph
qum.
Chan, Y.N.C.; Meyer, D.; Qsborn. J.A,J. Chem. SOC., Chem. Commun., 1990, 869.
,OH
L
2% R U ~ ( C O PhH ) ~ ~ ,, 4 h 100°C, CO (20 Kg/cm2)
N.H & Ph
Ph
quant.
Akazome, M.; Tsuji, Y.;m a b e . Y. Chem. Lett., 1990, 635.
Ph,N.
l.Zn(BH& , ether 0°C -+ RT
H
98% 2.2NNaOH Ph FotsukifL; Yoshimura, N.; Kadota, I.; Ushio, Y.; Ochi, M. Synthesis, 1990, 401.
Me3Si-
Ph,N.
Ph
B-Q
1. n-C,H,-CH=NMe THF ,65"C, 72 h
Me3Si
2.3w0HzO2,lM NaOH
n-C3H7
3.2M HCI ; 2M NaOH
A NHMe
53%
Guyot, B.; Pornet, J.; Miginiac, L. Synrh. Commun., 1990, 20, 2409.
HPhPOzH , 120"C, DMSO
*
PhCH,NH,
U S y n t h . Commun., 1991, 21, 1425.
1. BuLi 2. CpzZrMeCl 3.60"C. THF , 12 h
fr
4-
Q
*
1. BuLi , THF
H
28% with BuBr Epline. G.A,; Kumar, A. SynLett, 1991, 347.
73%
% a -
5. MeOH Coles, N.; Whitbv. R.J. ; Blagg, J. SynLert, 1990, 271.
2. BuOMs
PhCH,NMe,
c
92%
Bu
75%
148
Section 97
Compendium of Organic Synthetic Methods, Vol8
N.OMe
A! Ph
BFyOEt2 , PhLi , PhMe -78°C
H Uno.;Terakawa, T.; &uukiJL
S y d e t t , 1991, 559.
t-Bu
Clostridia thermoaceticum ,0.033 M 0.1 M phosphate buffer (pH 8.5)
t-Bu I
Ph JNHoMe 59%
I
NHoH
0.3 M sodium formate, 5 h * 80% 0.001 methyl viologen ,40°C Braun, H.; Schmidtchen. F.P,; Schneider, A.; Tefrahedron, 1991, 47, 3329.
SiMe3 Ph p N A
%Me3
-
1.200"C. neat. 1 h 2. TMSCI ,MeOH 0°C , 1 h
Palorno.;Aizpurua, J.M.; Garcia, J.M.; Legido, M. J. 524.
4-
M e 0 0 Pb(OAc),
\ /
NH2
-
Cu(OAc)z, CH2C12,2 h
m
'+Ph
65%
SiMe3
Chem. Soc., Chem. Commun., 1991,
4N.k
95%
OMe
Barton, D.H.R.; Donnellv. D.M.X.; Finet, J-P.; Guiry, P.J. J. Chem. Soc., Perkin Trans. I, 1991. 2095. 1. HSiCI, , BF3*OEt2
PhH
O N H P h 2. KOH ,aq. EtOH
81%
Okamoto.;Kato, S. Bull. Chem. Soc. Jpn., 1991, 64, 3466. 1. KO11 , DMSO
'N
H
3. Pd(PPh3)d , KOAc DMA , 130"C, 10 h
Kozikawski.,Ma, D. Tetrahedron Lett., 1991, 32, 3317.
' N 77%
/
Section 97
Amines from Amines
H3BO-j. 180°C. 1 h t
COZEt Delbecq, P.; Bacos, D.; Celerier, J.P.; €&nunet.
HO
149
& N
95%
G,Can. J. Chem.. 1991, 69, 1201.
DEAD,PPh3.3 h CH2C12
P
CNHPh
M N\
e
Ph
80%
Bemotas. R.C,; Cube, R.V. Tetrahedron Lett., 1991, 32, 161.
7R%
H
Jackson, W.R.; Nilsson, Y. Tetrahedron Lett., 1992, 32, 1093.
;-
1 . 3 eq. BuLi-2 1-BuOK
86%
H
H Naruse, Y.; Ito, Y.;
Me,Si
J. Org. Chem., 1991, 56, 2256.
Nw".
Ph
1. PhMe, reflux, 5 h 2. H 2 0
*
Ph
Ph
Ohno, M.; Miyata, H.; Komatsu. M.; Ohshiro. Y,Tetrahedron Lert.. 1991, 32, 5093.
"OH
Ph
J!
TSCN, mt3, C C ~ t
0°C
/
A
Ph Ph Boeer.;Corbett, W.L.J. Org. Chem., 1992, 57, 4777.
TS
Ph
69%
hv ,MeOH , 2 . 5 h 1% H2S04
*
Q ~ L L LTetrahedron Lett., 1991, 32, 5235.
73%
53%
150
Compendium of Organic Synthetic Methods, Vol8
0: 3 I
NHz
Section 97
, 5 % PdC12
5% PPh3, HMPA 3 eq. NaHC03,l d 14OOC
h o c k . R.C.; Kuo, M-Y. Tetrahedron Lett., 1991, 32,569.
62%
Uno. H,; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki. H. J. Org. Chem., 1992, 57. 1504. /= N-t-Bu
Me0
1. sec-BuLi
2. aq. NH4CI
Me0 >99%
Sielecki, T.M.; Mevers. A.1, J. Org. Chem., 1992, 57, 3673.
Me
Pearson.;Postich, M.J.J. Org. Chem., 1992, 57, 6354.
(73%ee, S)
Kawate, T.; Nakapawa.; Kakikawa, T.;
Tetrahedron Asymmetry, 1992, 3,227.
L6pez-Alvarad0, P.; Avendafio, C.; Mentndez, J.C. Tetrahedron k i t . , 1992, 33,659.
Section 97
Amines from Amines
Me phA
F
151
Me
C S 2 , MeCN
.Me
*
OH
P h A N . M e 87% H
Schwartz. Me&; Gu,J.; Hu, X. Terrahedron Lett., 1992, 33, 1687.
@HOH
2.EtMgBr 1. acetone i
3. cs2
Me0
Me0
OMe
Schwartz.;Hu, X. Tetrahedron Lett., 1992, 33, 1689. 0.1 BuLi ,THF
Ph
NHMe
Ph
Ph
Fujita, H.; Tokuda.;Nitta, M.;
84%
OMe
A - L Ph N
99%
Me
Tetrahedron Lett., 1992, 33, 6359.
hv , iPrOH .'DCN
+ (97
3)
90%
pandev.;Reddy, G.D. Tetrahedron Lett., 1992,33,6533. 1 . 2 eq. H 2 0 2 , MeOH
Murahashi.; Naota, T.; Miyaguchi, N.; Nakato, T. Tetrahedron Lett., 1992, 33, 6991.
Izumi.;Yokota, T. J. Her. Chem., 1992, 29, Ph7 N =CHPh
1085.
0.5%R u C ~ ~ ( P P ~82°C &, 5% KzCO3, iPrOH , 1 8 h
*
Ph--\ H'
Ph NJ
Wmg, G-Z.;BBCkVall. J -E.J. Chem. SOC.,Chem. Commun., 1992, 980.
93%
152
Section 97
Compendium of Organic Synthetic Methods, Vol8
N
A
x2
1.0.2%Rh(COD)(Et-DUPHOS)+ OTf ' iPrOH, ~ H2~(4 a m ) ~ ~ b
Ph
quant.
Ph
2.SmI2
(89% ee , S)
Et-DuPHOS =
Burk. M.J.; Feaster, J.E. J. Am. Chem. SOC.,1992, 114, 6266. 5%-
- XTj-X
&NAPh
, 2 BuLi , PhSiH3
H,(2OOOpZ)
68%
(58% ee)
X = l,l'-binaphth-2.2-diolate
Willoughby, C.A.; E U & m L S L J. Am. Chem. Sac., 1992, 114, 7562.
2% NiSO4, K2S208 NaOH ,H20-CH2C12
E
N
.
m
RT, 3.5 h
N
87%
Yamazaki. S, Chem. Lett., 1992, 823.
CuBryLiOl-Bu ,THF
E
N
.H
RT , 2 0 min
*
W
N
89%
Yamaguchi, J.; u e d a . T. Chem. Leu.,1992, 1933.
TOgO.;Miyagawa, N.; %&@mud. Chem. Lett., 1992, 1677.
MeCH=N-NMe2
1. EtI 2. KOH ,MeOH
*
EtNMe,
a i t h . R.F.; Marcucci, J.L.; Tingue, P.S. Synth. Commun., 1992, 22, 381.
57%
Section 100
153
Amines from Halides
d$ 0"""' 1. t-BuOOH , PhH
RuC12(PPh&
2.TiC4,
66%
he
Murahashi.: Naota, T.; Nakato, T. SynLerr, 2992, 835.
SECTION 98: AMINES FROM ESTERS
Ph-
OAc
MesSiN3, 50°C, 2h Pdz(dba13 , 4 PPh3
*
Ph85%
Safi, M.; Fahrang, R.: Sinou, D. Tetrahedron Lett., 1990, 31, 527.
SECTION 99:
N,
AMINES FROM ETHERS, EPOXIDES AND THIOETHERS PhNH2, Ti02,25O-3OO0C
N
Ph
96% selectivity
Hareis, D.C; Shubkin, R.L. Tetrahedron Lert., 1990, 3J, 2991. AICI:, ,AcOH ,20 h NH;?OH*HCI,reflux
Jun. J-G,; Shin, H.S.Tetrahedron Lett., 1992, 33, 4593.
SECTION 100: AMINES FROM HALIDES AND SULFONATES
OTBS
+C02~e 6Ms
NaN3-CuI
HMPA.4h
OTBS
A C O 2 M e N3
(85
with NaN3 , DMSO (0 yamamot0.y.: Asao, N.J. Org. Chem., Z990, 55, 5304.
+
OTBS
b C 0 2 M e
63 15)
100)
86%
42%
154
Section 100
Compendium of Organic Synthetic Methods, Vo18 0.1 AgI ,LiN(SiMe3),
54%
N(Si'e3)2
THF ,reflux, 6 h
Murai.;Yamamoto, M.; Kato, S. J. Chem. SOC., Chem. Commun., 1990, 789.
NaN(CH0)2 Yinelin.
1. BuOTs , MeCN , 120°C 2. HCl
BuNH**HCl 88%
K; Hongwen, H. Synthesis, 1990, 122.
NEtz
51%
Matsumoto.; Hashimoto, S.; Otani, S. J. Chem. Soc., Chem. Commun., 1991, 306. EtzHNHN3, DMF Yokoyama, H.; Ishikawa, T.; Niwa, N.;
&&Q&
Tetrahedron Lett., 1991, 32, 663.
Saito.;Takahashi, N.; Ishiwawa, T.; Moriwake, T. Tetrahedron Lett.. 1991. 32, 667. I. Bn2NH ,K2CO3 diglyme , 14OOC
Br Purchase, C.F. 11.;
2. HCl(g),iPrOH 3. NHdHC02. 10% PdC MeOH .6S0C J. Org. Chem., 1991, 56, 457.
pyrrolidine ,50°C 6 kbar , THF
-NH* 72%
0 2 N O N 3
*
Ibata.;Isogami, Y.;Toyoda, J. Bull. Chem. SOC.Jpn., 1991, 64, 42. 1. NaNq ,PhH-DMF ,reflux 2. P(OEt)3
Ph-
Br
b
Ph/\/
91%
NHBn*HCl
3. PhCHO 77% 4. N a b , NaOH 5. aq. HCI Gajda, T.; Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak. A, Synth. Commun., 1992, 22, 1929.
155
Amines from Hydrides
Section 101
SECTION 101: AMINES FROM HYDRIDES 1. PhI(OZCCF3)z (CF3)zCHOH
MeoG Me
2. Me$iN,
u; Tohma, H.; Inagaki, M.; Hatanka, K.; Yakura, T. Tetrahedron Lett., 1991, 32, 4321. 1. PhNHz , Zn , AcOH
70°C
NHPh
*
2.NH40H
85%
MiCoviC, I.V.; IvanoviC, M.D.; Piatak, D.M.; BojiC, V.D. Synthesis, 1991, 1043. MeNOzCH3S03H. 16 h 75OC
*
Ph)=N.oH
Me
33% z
75%
(E+Z)
Coustard, J-M.; Jacauesv. J -CL Violeau, B. Tetrahedron Lett., 1992, 33, 8085.
Maenos.; Lacour, J. J. Am. Chem. Soc., 1992,
114, 767.
SECTION 102: AMINES FROM KETONES 0 phA M~
1. PhNHz ,CIIzCI2
TiC14, EtN(iPrh
2. NaCNB%
c
Ph
YNHPh
Me
94%
Barney, C.L.;Huber, E.W.; McCarthv. J. R, Tetrahedron Lett., 1990, 31, 5547.
0
n-C3H7NH2, DCE AcOH , N ~ B H ( O A C ) ~ 3h also works with
aldehydes
NH~z-C~H~ 88%
Abdel-Maeid.;Marvanoff.;Carson, K.G. Tetrahedron Lett., 1990, 31, 5595. A b d e f - w:Mayanoff, C.A. Syntett, 1990, 537.
Compendium of Organic Synthetic Methods, Vol. 8
156
Section 102
1. MeJ NOz , LDA, THF , -78°C
0 MeKn-C7H,5
2. A c ~ O 3. H2 M/A1203. MeOH
MeQn-C7H,,
c
H
53%
H2 with Pt02 and treatment of m i n e with pTsOH leads to a pyrroline Miyashita, M.; Awen, B.Z.E.; Yoshikoshi. A. Chern. Lett., 1990, 239.
aNHz 1.33% KOHEtOH reflux, 2 h
Ph-Me 0
+
CHO 2. AcOH
76%
LL Org. Prep. Proceed. Int., 1991, 23, 23.
Akula, M.R.; Wolowyk, M.W.; Knaus.
OH
P
h
0
1. Ph"'NH2 2. LiAIH4-AlC13 3. PCVC ,H2
y Co2H
-
BniO1
Mevers. A.I.; Burgess, L.E. J. Org. Chem., 1991, 56, 2294.
41%
&
Hz , Pd-C , EtOH
=
N02
N H
Me
Me
Janowitz, A.; Vavrecka, M.; Hesse. M, Helv. Chim. Acta, 1991, 74, 1352.
1.
,BH3
Me'
BO
THF
2. PPh3, HN3 , PhMe DEAD, 0°C + RT 3. PdC ,TFA
81%
Chen, C-P.; Prasad.; Repic, 0. Tetrahedron Letr., 1991, 32, 7155.
0 !hrh&&;
t-BuNH2, TiCl4-C
(87% ee)
N-t-Bu
Larsson, U.; Hansson, L. Acta Chem. Scand., 1992, 46, 1211.
75%
157
Amines from Nitriles
Section 103
1
~ K S 1H1
CCl,
1. 0 0 B0. H
2.
sh, PhMe
Ph
-6OOC
3. NaN3, DME ,aq. NaOH
YH2
n-C5HCC02H
4. 1130'
80%
5. H 2 , I'd-C
(95% ee)
u; Link, J.O. J. Am. Chem. SOC.,1992, 114, 1906.
Related Methods: Section 94 (Amines from Aldehydes)
SECTION 103: AMINES FROM NITRILES
%
CN
cat. Coz(CO)8 , PPh3 HSiMe3 , CO (atm)
N. %Me3
&Me3
PhMe , 1OO"C, 20 h%
quant.
Murai.T,; Sakane, T.; Kato. S . J. Org. Chem., 1990, 55, 449.
1. iBuzAlH 2. BuLi , THF
Ph-CN
Bu
3. NH4C1, NH40H*
Andreoli, P.; Billi, L.; Cainelli, G.; 1990, 55, 4199.
.
5% Rh on A1203
Ph--(
NH2
98%
;Martelli, G.; Spunta, G. J. Org. Chem.,
-
PhpNAPh
Ph-CN Hz ,AcOH H 85% G a l a , A.; de Mendoza, J.; Prados, P.; Rojo, J.; Echavarren, A.M. J, Org. Chem., 1991, 56,452.
PhCN
1. BH3 2. BuLi , hexane
-80°C. 2 h
t
95%
m;Hachisuka, C.; Ito, K. J. Chem. SOC.,Perkin Trans. I, 1991, 1767.
Itsuno.;Hachisuka, C.; Kitano, K.; Ito, K. Tetrahedron Lett., 1992, 33, 627. n-C1 iH23CN
3 eq. MeCeCl2 , -65'C
5h
J. Org. Chem., 1992, 57, 4521.
NH2 n-C 1 IH,3 Me 64%
158
Methods, Vol. 8
Compendium of Organic S;.....,yz
Section 104
1. NaBH(4-,)(02CEt),
PhCN
PhdNH2 Bu
2.2 eq. BuLi ,80°C, 1 h
59%
Itsuno.;Hachisuka, C.; Ushijirna, Y . Synrh. Commun., 1992, 22, 3229. SECTION 104: AMINES FROM ALKENES 1. BH? 2. [BuNH2-NaOCIl, 0°C -+RT
67%
3. aq. HCl (pH <1) 4. aq. NaOH
Kabalka. G.W,; Wang, Z. Synth. Commun., 1990, 20, 231.
Ph
PhI=NTs , MeCN 10%Cu(acac)2
I
/
Ph
1
N- TS
a D.A.; F a d , M.M.; Bilodeau, M.T. J. Org. Chem., 1991, 56, 6744.
a
95 %
MeNHpHOAc MeOH ,reflux
21h * W N H M e 82% Cliffe.;Ifill, A.D.; Mansell, H.L.; Todd,R.S.;White, A.C. Tetrahedron Lett., 1991, 32, 6789.
d
Ph
Mn (salen)
c
PhI=NTs
Ph
A
N
'Ts
46%
OConnor, K.J.; Wey, S-J.; Burrows. C.J. Tetrahedron Lett., 1992, 33, 1001. 1. MesSiOTf CH&12 I
-14°C 2. HN(OMe)2
N- OMe
3. IMNaOH
Vedeis.; Sano, H. Tetrahedron Lett., 1992, 33, 3261.
64%
MqSi f i N * OMe
cat. TFA ,CHICll Bn
J&ukE.
*
O z N W - B n 71%
Tetrahedron Lett., 1992, 33, 6607.
1. H! 3 CN
-m N'H2
50%
SH,MeOH
2*
25°C SH Tetrahedron Lett., 1992, 33, 3599. ~~
Cho, C-G.; REVIEWS:
;-
159
Amines from Miscellaneous
Section 105
"An Overview of the Total Synthesis of Pyrrolizidine Alkaloids via [4+1] Azide-Diene Annulation Methodology" Seoane, G.; Price, J.D.; Gadamasetti, K.G. Syntett, 2996, 433.
SECTION 105:
Boivin, J.; Fouquet, E.;
AMINES FROM MISCELLANEOUS COMPOUNDS
Tetrahedron Lett., 1990, 31, 85.
Ph b
Ph
p
h
81%
NO H Jevaraman. R Ravindran, T. Tetrahedron Lett., 1990, 31, 2787. 1. DME:, 12OoC, 17 h 2. PhH, NH&I, 4 h 18
3. H2 ,Pt02 ,ether 25°C
Me
3) (1 Heidt, P.C.; Bergmeier, S.C.; Pearson. W.H. Telrahedron Lett., 1990, 31, 5441. bakers yeast, pH 5 12 h , 22°C
Gibbs.;Barnes, D. Tetrahedron Lett., 1990, 31, 5555.
Me
28%
Compendium of Organic Synthetic Methods, Vol8
160
Section 105
1. PhH ,reflux, 12 h 2.NaBH4,MeOH 0°C , 1 h Pearson.; Lin, K-C. Tetrahedron Lett., 1990, 31, 7571.
N3
0
1 . 2 eq. AlI3 , MeCN , 3 h reflux
N.
2. Na2S203, H20
t
Ph
Ph
96%
Ph-N.
t
91%
Ph
Konwar, D.; Boruah, R.C.; S a n d h u . S y n t h e s i s , 1990, 337. MeOH , reflux
Ph-N3
Ph-NH2 BH4
CH$kle?
Kabalka.;Wadgaonkar, P.P.; Chatla, N. Synrh.
1 1'
1.
-N3
94%
Commun., 2990, 20,293.
BC12
,DCE
2. H 2 0 3. KOH
-N
+
H
(>99% ee)
65%
Brown.;Salunkhe, A.M.; Singaram, B. J. Org. Chem., 1991, 56, 1170.
PhMe ,reflux
c
OSiPh2r-Bu
00
OSiPhpBu
(93
Ito, M.; Maeda, M.;
'
Tetrahedron Lert.. 1992, 33, 3765.
7)
AMINESFROM NITRO COMPOUNDS O N 0 2
NH2NH2.y
O N H 2
EtOH ,reflux
Ban. B.H.; Jang, D.G. Tetrahedron Lett., 1990, 31, 1181.
85%
85%
Section 105
Amines from Miscellaneous
Ph.
AI-NiC12-6 H20-THF t
NO2
10 min Sarmah, P.; Barua. N.C. Tetrahedron Lett., 1990, 31, 4065.
NOp
Q
PdC12, EtOHIAcOH cat. Fe , 3 H2,45 min
*
NO2
161
Ph- NH2
6
90%
80%
NO2
.. Theodondls.; Manfredi, M.C.; Krebs, J.D. Tetrahedron Lett., 1990, 31, 6141.
H
85% Kasi Reddy, C.P.R.Org. Prep. Proceed. Int., 1990, 22, 117.
u,
NaSH4-c~S04,EtOH
*
PhNO,
RT , 10 min Yoo. S,; Lee, S. SynLett, 1990, 419. Pb , AcOH-DMF , R?'
Ph-
NO2
30 min
PhNH,
Ph
. ,
H
94%
-"-OH
94%
@+Z) Sera. A,; Yamauchi, H.; Yamada, 11.; Itoh, K. SynLett, 1990, 477. HC02NH4, Pd-C , THF MeOH , 6 h
*
58%
Kabalka, G.W.; Pace, R.D.; Wadgaonkar, P.P. Synth. Commun., 1990, 20, 2453.
P h 7 NO2
SnCl2,3 eq. PhSH 3 eq.NEt3 ,-PhH
10 min
Ph-+ N-OH
(E) Barua, M.; Komea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron, 1990, 46, 587.
98%
162
Compendium of Organic Synthetic Methods, Vol8
Section 105
1. NHflH2, 16OoC,2 h o
N
o
2
acetone, sealed ampule w 2.MeOH
Abdel-Baky, S.; Zhuang, M.;
0
0
N
H
2
95%
Synth. Commun., 1991, 21, 161. e- , Hg electroddC cathode H2S04, iPrOH ,H 2 0
cy""" 87%
Wessling, M.; Schafer. H.L Chem. Ber., 1991, 124, 2303. N02
1.4 eq. SmIz , THF
THF/MeOH , RT , 3 min
*
2. 10%Na2S203
Me0
Me0
Kende.;Mendoza, J.S. Tetrahedron Lett., 1991, 32, 1699.
oNo2 l.Zn(BH& , DME 5OoC, 1 h
2.Hs
Ranu.; Chakraborty, R. Tetrahedron Lett., 1991, 32, 3579. Ru3(CO)lz-NH(iPr)2
o
p
e c=N
CO , H 2 0 , 15OOC. 2 h H 2 N G G N 20 atm
quant.
Nornura. K. Chem. Lett., 1991, 1679.
Ph-NO2
Moo3 ,NazSeq NaBH4, H20
Ph-NH2
c
96%
Yanada. K,; Yanada, R.; Meguir, H. Tetrahedron Lett., 1992, 33, 1463. 5% PdC12(PPh3h
Ph S ~ C I2 ~eq., co
~
1OOOC
NO2 Akazome, M.; Kondo, T.; Watanabe.
PhNO,
W
P
"
Y, Chem. Lett., 1992, 769.
Fe , NH4C.l. H 2 0
w
75%
H
PhNH2
reflux, 1.5 h Ramadas. K .; Srinivasan, N. Synth. Cornrnun., 1992, 22, 3189.
h
g2%
Protection of Amines
Section 105A
163
REVIEWS:
"Electrophilic Aminations with Oxazuidines" Andreae, S.; Synthesis, 1991, 327.
SECTION 105A: PROTECTION OF AMINES
-
20% Pd(OH)*-C , EtOH Parr shaker, H2 (55 psi)
B n H N e O Bn
OBn
H2N*
19 h Bernotas.;Cube, R.V. Synth. Commun., 1990. 20, 1209.
c""S"
ether, 20°C, 30 min
Keumi. T,; Shimada, M.;Morita, T.; Kitajima, H. Bull. Chem. SOC. J'n., H,N
NH,*HCl
I
Bn
M~-CO,E~
0
A N .H *
Bn
aq. HCHO N-Me morpholine dioxane. toluene
Bn .
1990, 63, 2252.
0 N. Bn
( )
87%
N
MeA C0,Et
aq. HCI , MeOH
sHale, ; J.J.; Bastos, M.; Gibson, F.S. Tetrahedron Lett., 1990, 31, 2109.
0SiSz Me M e
Me' Me
RhCI(PPh3)3 , 14 h PhNHz ,80°C
\
also with aliphatic amines
Bonar-Law. R.P.;
Me, ..Me
OS1:N-Ph TB AF
Me'S iMe
72%
or TFAA ; Dorgan, B.J. Tetrahedron Lett., 1990, 31, 6721, 6725.
BF3aOEtZ , EtSH
C N -Cbz Subhas Bose, D.; -Tetrahedron
ether, 8 h Lett., 1990, 31, 6903.
92%
Section 105A
Compendium of Organic Synthetic Methods, Vol. 8
164
1. HCHO 2. cyclopenfadiene ,NMM
4
1. cat. CuSO4, aq. EtOH ,70°C
84%
2. NazSo3 ,aq. NH4CI co. P.A.; Clark, J.D.J. Org. Chem., 2990, 55, 2271.
0
also for protection of ply-01s
Allainmat, M.; L'Haridon, P.; Toupet, L.; -1lec.
H
PhCHNz , SnC12.2 HzO CHzClz, 5.5 d , RT
D, Synfhesis, 2990, 27.
H
Bn I
&OH 40%
8%
Liotta, L.J.; Ganem,B.sr. J. Chem., 2992, 31, 215.
Ph ' I BoczO, NaHCO3 NH2*HCl EtOH ,RT , 3 h
--
)))>>)>> Einhorn. J,; Einhorn, C.; Luche, J-L. SynLelt, 1992, 37.
C0,Me
BnO?
0 , 10%Pd-C
NHCbz BoCzO, EtOH , RT Baiwa. J.S, Tetrahedron Lett., 1992, 33, 2955.
TSO-N ' Boc
H
1. BuLi
-
Ph\
N- BOC H
BnO/\(
Bu.
99%
C02Me
NHB~C
92%
Boc
N' H
81%
2. B B u ~, -78"C, 1 h Gentt, J-P.; Hajicek, J.; Bischoff, L.; Greck, C. Tetrahedron Let?., 2992, 33, 2677.
Protection of Amines
Section 105A
-r H2N
O N3 J *(
mO'N'CO2H H
N3
2eq.NaHC03,18h aq. dioxane
C02H
165
I
85%
N3
ux. B.; Gerardin, P. Tetrahedron Lett., 1991. 32, 351. 0
Brim JI NHBn
I Z - C ~NH2 H ~ ~
.aq. HCHO *
0 ~ I - C ~ H INS
Bn
0 N
aq. HCI
+
N'
91%
Bn
KnaupA; Hale, J.J.; Bastos, M.; Molina, A.; Chen. K.Y,J. Org. Chem., 1992, 57, 6239. AcCl , NaI
*
0
Ihara, M.; Hirabayashi, A.; Taniguchi, N.;
W
N
. Ac
Heterocycles, 1992, 33, 851.
1. PhCHO 2. BWZO
NH,
3.1N KHS04, NaOH
Prueh.;Birchenough, L.A.; Egbertson, M.S. Synth. Also see Section 82 (Amides from Amines)
Bw-N>NH2 Commun., 1992, 22, 2357.
92%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
8
PREPARATION OF ESTERS
SECTION 106: ESTERS FROM ALKYNES
74%
Ni(COD)2, CO2
100°C
Tsuda.; Morikawa, S.; Hasegawa, N.; &cgu&L
%Me3 J. Org. Chem., 1990, 55, 2978.
SECTION 107: ESTERS FROM ACID DERIVATIVES The following types of reactions are found in this section: 1.
2.
3.
Esters from the reaction of alcohols with carboxylic acids, acid halides and anhydrides. Lactones from hydroxy acids Esters from carbxylic acids and halides, sulfoxides and miscellaneous compounds
n-C15H30C00H -G.;
MejNoBH3, reflux 2 xylene, 9 h
n-C,SH3oC02CH,n-ClSH,o
61%
Reho, A.; Latrofa, A.; €AQ&Synthesis, 1990, 853. t-BuOH , activated A1203
0
15 h
Ph>
Ot-Bu
0
85%
m a w a . K,; Yoshitake, S.; Amiya, T.; 110, K. Synth. Commun., 1990, 20, 2033.
n-C8Hl7Br
dry AcOK ,A1203 microwaves
n-C8H170Ac
92%
Bram, G.; J.OUDV.&; Majdoub, M.; Gutierrez, E.; Ruiz-Iiitzky, E. Tetrahedron, 2990. 46, 5167.
Section 107
Esters from Acids
167
EtOH ,cat. H2S04 , I .5 h
c Ph-l 93% Ph 7 1))1)1) CO2Et COOH Khurana. J.M,; Sahoo, P.K.;Maikap, G.C. Synth. Commun., 1990, 20, 2267.
BuBr , Aliquat 3 3 6 , reflux
EtC02Na
+
EtCO2Bu
95%
Synth. Commun., 1991, 21, 1545.
Vinczer, P.; Novak, L.;
1% aq. H~S04.85Oc 8h
Sueahara. K,;Fujita, T.;Watanabe, S.: Sakamoto, M.;Sugirnoto, K. Synthesis, 2990, 783.
hCo2. 1. Dibal , THF , -78OC
3h
2. “FA, CH2C12
Me
no ZnC12
+ Frenette.
ZnCI2
; Monette, M.: Bernsdn, M.A.; Young,
1991, 56, 3083.
40)
(60 (70
R.N.;Verhoeven, T.R.J.
-b
30) Org. Chem.,
PhSeSePh , CuOTF 2 eq. CaCq ,CH2Cl2
CO2H
30°C
quant.
PhSe
Miyachi, N.; Satoh, H.; Shibasaki. M,J.Chem. Soc., Perkin Trans. I, 1991, 2049.
0
CoC12, ether
PhK C1
c
Ph
Ji
-+-
Ph’$’
OEt
49%
Iabal. J,; Srivastava, R.R.Tetrahedron, 1991, 47,3155.
O 27%
.
EtI CsF ,DMF b PhCOOH PhCO2Et Sato, T.; Orera.; Nozaki, H. J. Org. Chem., 1992, 57, 2166.
94%
168
Compendium of Organic Synthetic Methods, Vol. 8
Me
1.2 eq. PIFA , 3 d
*
Section 108
M e h O Phi"
71%
PIFA = phenyliodonium bis-trifluoroacetate
C&3a!aJd,; Manage, A.C.; Murphy, P.J. Tetrahedron Lett., 1992, 33,965.
PhCH,CO,H
Fe(C10&*9 H2O ,EtOH b
PhCHzCO2Et 93%
;
Kumar, H.; Parmar, A. Synth. Commun., 1992. 22, 1087. BnCl ,NaHC03, TBAB NaI ,MeCN ,8OoC, 8 h
0 2 N ~ o o F 5 n Hu, Y.; Pa. W,; Cui, W.;
98%
Synth. Commun., 1992, 22, 2763. BnBr , BnByNCI, neat
L-
n-CSH,iCOOH
n-C5H11C02Bn
microwave (560W) 10 min Yunchene. Y,;Yulin, J.; Dabin, G . Synth. Commun., 1992, 22, 3109.
72%
Further examples of the reaction RCO2H + R'OH -) RC02R are included in Section 108 (Esters from Alcohols and Phenols) and in Section 30A (Protection of Carboxylic Acids).
SECTION 108: ESTERS FROM ALCOHOLS AND THIOLS
53% Baskaran, S.; Chandrasekaran. S, Tetrahedron Lett., 1990. 31,2775. 1. CO, S ,cat. Se
NEt3 , THF ,60"C
L-
x
autoclave, 1 h Me0 S B ~ 2. cat. S , BnBr 250°C 69% Mizuno. T.; Nishiguchi, I.; Hirashima, T.; Ogawa, A.; Kambe, N.; Sonoda, N. Tetrahedron Lett., 1990, 31, 4773.
Esters from Alcohols
Section 108
d
169
*d
1. EtCqNHNH2 2. Pb(OAc)4
OH
CO2Et
87%
Katritzkv.;-Tetrahedron
Lett., 1990, 31, 6781.
Kita. Y,; Sekihachi. J.; Hayashi, Y.; Da, Y-Z.; Yamamoto, M.; 55, 1108.
86%
Mi, S.
J . Org. Chem., 1990,
Ce(SO&, Si02, EtOAc n-C1 lH23
*
n-C11H23
LOAc 15 min Nishieuchi. T,; Taya, J. J. Chem. SOC.,Perkin Trans 1, 1990, 172.
OH
"x
CO , 0 2 ,PdCl2, THF CuCl2, HCl , RT , 1 am
~e*
OH
poly-L-leucine
O
A1Der. H.; Hamel, N. J. Chem. SOC.,Chem. Commun., 1990, 135
KMn04 - CuSO4*5 H20 CH2C12, H20
O
97%
49%
(61% ee , R)
Go
78% reflux (5 min) - RT (4.5 h) Baskaran, S.; Islam, I.; Vankar, P.S.; Chandrasekaran. S. J. Chem. Soc., Chem. Commun., 1990. 1670. lipase PS-30, DME , RT
AcO"'
OH
+
Berkowitz, D.B.;
=/
AcO"'
OAc
OH
47% (>97%ee) Tetrahedron Lett., 1991, 32, 5491.
OH
47% (?97%ee)
170
Compendium of Organic Synthetic Methods, Vol. 8
1. PhI , Pd(0Ac)z , KOAC, I 0 h BnEt3NBr, iBuCN , 9OoC
2. PCC
Ph
*
Section 108
t;.
66%
0
Mandai.; Hasegawa, S.; Fujimoto, T.; Kawada, M.; Nokami, J.; Tsuji, J. SynLeit, 1990, 85. H
O
TPAP - NMO ,MS
V
OH
CH2Cl2
*
0
TPAP = tetra-n-propylamniumpemthenate
A 0x / - -
76%
Bloch. R.; Brillet, C. SynLett, 1991, 829.
SiMe3 OH
Pseudomonas AK 25%conversion d
SiMe, + FSiMe3 OH OAc \
OAc
23% (80% ee)
63% (4% ee)
Sparks, M A . ; Panek. J.S. Tetrahedron Lett., 1991, 32, 4085. porcine pancretic lipase
ether, BuC02CH2CF3 25"C,48 h
Chone.
OH
t
Me-
41% (97% ee)
38% (98% ee) ; Mar, E.K. Tetrahedron Lett., 1991, 32, 5683.
general preparation of angelate esters Harmann, B.; Kanazawa. A.M.; DeprCs, I-P.; Pd(dba)2-dppbt DME CO (40 a m ) , 190T 48 h
=
El Ali, B.; Alner. H,J. Org. Chem., 1991, 56, 5357.
SnMe3
Terrahedron Lett., 1991, 32, 5077.
o
a
78%
Section 108
Esters from Alcohols
171
modified Mitsunobu - for sterically hindered 2" alcohols Martin. S.F,; Dodge, J.A. Tetrahedron Lett., 1991, 32, 3017.
OH
d
HO
NaH.THF S
c
%AS
4+
A d
u
(83
I)
96%
Yamada, S. J. Org. Chem., 1992, 57, 1591. Yamada. S, Tetrahedron Lett., 1992, 33, 2171.
0 Q l B u M e
OH porcine pancreatic lipase
BuCO~CH~CF~ ether, 16 h * F
53% ee
+ 95%ee
36% conversion
Morgan. B.; Oehlschlager,A.C.; Stokes, T.M. J. Org. Chem., 1992, 57, 3231. 1. BKHO , CHzC12, MS 2. BrZnCHzCOzEt , ether
(OH Ph''A H NHBn
3. satd. NhC1 4.112, 10% Pd-C , EtOH
9 bar
/
H2N
co2J3
A*H
50%
Bu
Andres, C.; Gonziilez, A.; Pedrosa. R,; Perez-Encabo, A. Tetrahedron Lett., 1992, 33,2895.
OH
6
COzMe
+oSiMyt-Bu OMe
86% 3M LiCIO, ,ether * 15 min Grieco. P.A.; Collins, J.L.; Henry, K.J.Jr. Tetrahedron Lett., 1992, 33, 4735. MeC03H, NaBr
40°C, 2 h
c
yo0
92%
Morimoto. T,; Hirano, M.; Hamaguchi, T.; Shimoyama, M.; Zhuang, X. Bull. Chem. SOC.Jpn., 1992, 65. 703.
172
Compendium of Organic Synthetic Methods, Vol. 8
Section 109
b
Pickett.;Van Dort, P.C. Tetrahedron Lett., 1992, 33, 1161
6 t-Bu
1.
4 .o ocr:
0 . .
, CHzC12
0°C 2. mCPBA 3. NaHCO3
98%
t-Bu
Morin-Fox, M.L.; hioton. M.A. Tetrahedron Leti., 1992, 33, 5699. Further examples of the reaction ROH -+ -RCO2R are included in Section 107 (Esters from Acid Derivatives) and in Section 45A (Protection of Alcohols and Phenols).
SECTION 109: ESTERS FROM ALDEHYDES n-C3H7CHO
1.5 BrZ , HzO/CHzC12
Me\( c H 2 h 1 - 0 ~
HMPT - NaHC53
0
Me,
(cH2)8qOy
94%
n-C4H9
A1 Neirabeyeh, M.; Pujol, M.D. Tetrahedron Left., 1990, 31, 2273. 0
)-CHO
€Po-(KF, 18-crown-6,1 dMeCN ,70°C
ii"1( yo 85 %
Olofson.;Dang, V.A.; Morrison, D.S.; DeCusati, D.F. J. Org. Chem., 1990, 55, 1.
CHO
*d
n-C12H250TMS , NBS
AIBN ,95"C, 15 min
Markd, I.E.; Mekhalfia, A.; Qllis. W.D.SynLett, 1990, 347.
On-'lzH25
72%
173
Esters from Amides
Section 111
2.6eq.KOH 1.3 eq. I2 ,MeOH , 1 h
PhCHO
c
98%
PhC02Me
Yamada.; Morizono, D.; Yamamoto, K. Tetrahedron Lett., 1992, 33, 4329.
OAc €lb,,,OEt MeO"' Gbmez, A.M.; ,-
1. NazCO2 ,MeOH 2. TBPSCl , irnidazole
t-BiPh2Si0
*
DMF , 4OoC , 2 4 h 3. rnCPBA , BF3-OEtz CH2C12, -10°C
MeO"'
Lbpez, J.C. Tetrahedron Lett., 1992, 33, 5105. 1. NHzOH-HCI , NaOAc MeOH , reflux, 4 h
PhCO2Me
PhCHo
2. H202,2-NBSeA, MeOH * reflux, 1 h 2-NBSeA = 2-nitrobenzene seleninic acid Said, S.B.; Skarzewski, J.; Mlochowski. J, Synfh. Commun., 1992, 22, 1851.
72%
Related Methods: Section 117 (Esters from Ketones)
SECTION 110:
ESTERS FROM ALKYLS, METHYLENES AND ARYLS
No examples of the reaction R-R -+ RCO2R' or R'C02R (R,R' = alkyl, aryl, etc.) occur in the literature. For the reaction R-H -+ RCO2R or RC02R, see Section 116 (Esters from Hydrides).
NO ADDITIONAL EXAMPLES
SECTION 111: ESTERS FROM AMIDES OMOM SnBu3
1. BuLi , THF , -78°C 2.
= L N 0
Me
'NMq
3. 1.5 eq. conc. HClO4 CHzClz , RT, overnight M .J-;.
Mar, E.K. Tetrahedron Left., 1990, 31, 1981.
43 % (92%ee)
Compendium of Organic SyniirbucMethods, Vol. 8
174
Section 113
SECTION 112: ESTERS FROM AMJNES Ph
Y
CO2H
NH2
VO(OEt)C12 EtOH , 1 h
Ph-COZEt
0
+
PhK C02Et
(89
11)
Hirao, T.; Ohshiro, Y. Tetrahedron Lett., 1990, 31, 3917.
74%
SECTION 113: ESTERS FROM ESTERS Conjugate reductions and conjugate alkylationsof unsaturatedesters are found in Section 74 (Alkyls from Alkenes).
Saha, G.; Bhattacharya, A.; Roy, S.S.; Ghosh. S, Tetrahedron Left., 1990, 31, 1483.
1. H2 (100a m ) , S-BINAP
2.1130+
Me
L o , ,
*
b
Me
96%
(99.5% ee)
Ohkuma, T.; Kitamura, M.; Novori. R. Tetrahedron Lett., 1990, 31, 5509.
using Tic14 gave fused > spirocycle in all cases
K=Me __R = Et
R = Pr
31)
(69 (75 (>1 \
25) 99j
-
Black. T.H,; McDennott, T.S.; Eisenbeis, S.A. Tetrahedron Letf., 1990, 31, 6617.
(C02Me
Bu~N Br(CH2)4Br, BF4, B NMP u~NI
e- ,A1 anode, 0.2 Amp -L
C0,Me O C 0 2 M e 40%
stainless steel cathode Folest, I-C.; Perichon, J. J. Org. Chem., 1990, 55,2503. Lu, Y-W.; NCdelCc. J-Y,;
72% 31% 64%
175
Esters from Esters
Section 113
6
1. LDA , Me3SiCI
2. MeCHCI, , BuLi 3. xylene , reflux, 10 h
4. H, , Pd-C, 4 atm.
11%
Fouque, E.; R o u s s e e; Seyden-Penne, J. J. Org. Chem., 1990, 55,4807. Br
10% T i C 4 , CHzClz * c02et 97% 40°C , 10 min (1:l erythro:threo) 2. 10%aq. HCI J. Chem. Soc., Chem. Commun., 1990, 767. Hayashi, M.; Sugiyama, M.; Toba, T.; 1. EtMgBr 2. EtCHO
C02Me Et (2.3
Kurasawa, Y.;Yokota, K. Chem. Lett., 1990, 719.
;K-.
0 1)
77%
e- , Pt elecuodes , MeCN Ph-OH
-hi.
t
BufiI, RT MA;Tsukamoto, Y.;Minami, T. Chem. Lelt., 1990, 1223.
Citterio. A.; Sebastiano, R.; Nicolini, M.; Santi, R. SynLett, 1990, 42.
other R3AI and R2AICI reagents used Maruoka, K.; Banno, H.; Yamamoto. H.SynLett, 1991, 253.
83%
176
Compendium of Organic Synthetic Methods, Vol. 8
-
Section 113
85% Carfagna, C.; Marian,L.; Musco.;Sallese, G.; &WJL J. Org. Chem., 1991, 56, 3924. BgSnH , AIBN , PhH (0.02 M),reflux
0
OK SePh
92%
Bachi.M.D.;Bosch, E. J. Org. Chem., 1992, 57, 4696. C0,Et
1. 2.2 eq. CH2Br2
2.2 eq. L i m p
2.2 eq. LiHMDS 3 . 4 eq. sec-BuLi 4.2 eq. n-BuLi 5. EtOH , HCI Kowalskl.; Reddy, R.E. J. Org. Chern., 1992, 57, 7194.
C O , M ~ t-BuOK ,THF ,air 24°C P h 4 OMe
-
79%
PhCOzMe
Heckmann, B.; Alayrac, C.; m w s k i . C;Chandrasekhar, S.;
73% Tetrahedron Lett.,
1992, 33, 5205.
Phq
OSiMa '
(
OSiMe3 $@-$F
nOpP
-
Sn(OTf)2, RT , CH2C12
95 %
RT,2h
Mukaiyama, T.; Shiina, I.; Miyashita, M. Chetn. Lett., 1992, 625.
SECTION 114:
n 0 X Me OEt 0
ESTERS FROM ETHERS, EPOXIDES AND THIOETHERS
4zzre!
TiC4, -78°C CH2CIz
-
n
0 Me
0
65 %
C0,Me
Collins, D.J.; Chw, G.L.P.; Ohrist, H. Ausr. J. Chern., 1990, 43, 617.
Section 115
Esters from Halides
177
CO2-02 (65 psi) ,70°C Rh(NBD)@-MezPh)3 BF4
* O Y 3
7d
150 turnovers
J. Chem. SOC.,Chem. Commun., 1992, 1334.
Fazlur-Rahman, A.K.; Tsai, J-C.;
SECTION 115: ESTERS FROM HALIDES AND SULFONATES
1)
(2.6
61%
Gno.;Duann, Y.F. Org. Prep. Proceed. Int., 1990, 22, 85. CICH2C02Me, NiBr2 e- (A1 anode, C cathode)
--
DMF , B u d B r , 2,2-bipy Conan, A.;
; dIncan, E.' Perichon, J. J. Chem.
Co(CO)4, Bu4N1, CO NaOEt , PhH
-
SOC.,Chem. Commun.. 1990, 48.
PhCH2COzEt 95% PhCH2Br Kantam. M.L,; Reddy, N.P.;Choudarv. B.M. Synth. Commun., 1990, 20, 2631.
1
PhMgBr ,THF , 10°C, 2 h .r
0 PhAOMe
OMe Satyanarayama, G.; i S h c a m A Synth. Commun., 1990, 20, 3273. Me0
10% C%(CO)a, NaI CO (50 atm) , TMU
EtOH , l00"C. 24 h
*
Ph
87%
C0,Et 61%
"MU = tetramethyl urea Urata, H.; Goto, D.; Fuchikami, T. Tetrahedron Lett., 1991, 32, 3091.
1
AcOH ,NaOMe ,40°C
autoclave, N2 (15 bar)
PdClAPPh3)Z , 4 h*
aco2M
Carpentier, J-F.; Castanet, Y.: Brocard, J.; Mortreux. A,: Petit. F. Tetrahedron Lett., 1991, 32,
4705.
Compendium of Organic Synthetic Methods, Vol. 8
178
PhOTf
-T
c
OSiMe?
Section 116
[~~-CsH7+'d(OAc)z Me C02Me LiOAc ,dppf, reflux 73% 6h dppf = 1,l'=bis(diphenylphosphino)ferrocene Fiorani, T. J. Org. Chem., 1991, 56, 261. Carfagna, C.; Musco.;Sallese, G.; Santi.;
OSO,F
W O A d z dppp mt3 DMSO , MeOH , CO I
*
60°C. 2 h
(yoZMe*8%
Roth. G.P,; Thomas, J.A. Tetrahedron Lett., 1992, 33, 1959. TBAF.3 H z 0 , Mo(CO)6, THF
I(CH2)41
t
reflux ,20 h
Imbeaux, M.; Web. H.; Moughamir, K.; 1992, 1678.
Rolando.C..Chem. Soc., Chem. Commun.,
1. Bu3SnC=COEt, PdClz(PPh3)z
PhI
EhNCI , DMF
2. H2SO.4,aq. acetone, reflux
PhCH2COZEt
c
Sakamolo, T.;Yasuhara, A.; Kondo, Y.; XamwhJL S y n k n , 1992, 502. Related Methods: Section 25 (Acid Derivatives from Halides).
SECTION 116: ESTERS FROM HYDRIDES
'
This section contains examples of the reaction R-H (R = alkyl, aryl, etc.).
-+ RC02R' or R'C02R
5% Pd(OAch, AcOH 20% benzquinone
2 eq. MnOz ,60°C 50°C Hansson, S.; Heumann. A, ; Rein, T.; hermark, B. J. Org. Chem., 1990, 55, 975.
60%
179
Esters from Ketones
Section 117
5% Pd(OAc),, AcOH 5% Cu(OAc)z, 5OoC
10%hydroquinone
935%
1 am. 0 2 , 2 2 h
Bystrom, S.E.; Larsson, E.M.; hermark, B. J. Org. Chem., 1990, 55, 5674.
Demir. A.S,; Sayrac, T.; Watt, D.S. Synthesis, 1990, 1119. Also via: Section 26 (Acid Derivatives) and Section 41 (Alcohols).
SECTION 117: ESTERS FROM KETONES Pb(OAc)4, BF3oOEtz MeOH , PhH , 12 h
=
Ph
Ph-C02Me 68%
Mathew, F.; My&&&
Tetrahedron Lett., 1990, 31, 3757.
OH Ph
1. Ce ,THF, RT
Br -CO,Et
2. acetophenone
G:e 0
i- P h H M e
70%
Me OH
20% Fukuzawa. S,; Sumimoto, N.; Fujinami, T.; Sakai, S. J. Org. Chem., 1990, 55, 1628. 0-
Ph
pc-0
Me
l.THF, 2. H 2 0
P h s o r 50%
Gong, L.; Leung-Toung, R.; Tidwell. T.T. J. Org. Chem., 1990, 55, 3634.
Bakash. 0.; Goyal, S.; Moriatrv, R.M,; Khosrowshah. J.S. Id.J. Chem., 1990, 298, 304.
Compendium of Organic Synthetic Methods, Vol. 8
180
Acinetobacter calcoaceticus NClB 9871 n-C1 lH23
tetraethyl pyrophosphate
Section 117
0
tl
11H23
25% (74% ee)
+ 65% recovered ketone (36% ee)
Alphand, V.; Archelas, A.;
J. Org. Chem, 1990, 55, 347.
0
;:y;)y
mCPBA ,CHZCIZ,~O"C
SnBu3
n-C6H 13
w
n-C& &02Bn
Me
Me Bakale, R.P.;Scialdone, M.A.; Johnson. C.R, J. Am. Chem. Soc., 1990, 112, 6729.
0 MeOJ
Me0
COZEt
TiC14, MeCN n-C3H7 -45T
2. H 2 0 3. cat. p-TsOH ,PhH (94 6) 68% reflux Saipo.; Shimada, S.; Hashimoto, Y.; Nagashima, T.; Hasegawa, M. Chem Letr., 1990, 1101. 0
"[d Sph , LDA ]
THF , -78°C -+ 0°C
2. mq. NH&I
*
9' 92%
Panheiser. R.L.; Nowick, J.S. J. Org. Chem., 1991, 56, 1176. Acineiobacier NClB 987 1
-
0
BnO+
OH
35% endo (95% ee) 8% ex0 (89% ee) Konigsberger, K.; Alphand, V.;Furstoss, R.;Griengl, H. Tetrahedron Lett., 1991, 32,499. 26% (85% ee)
Section 117
181
Esters from Ketones
oxone . "wet alumina"
/-0
Hirano, M.; Oose, M.; ~ M ~ Q Chem. uLL Lett., 1991, 331. 1% Ni(dpm)2, iRCHO
OL ,WE, RT ,overnight
0
0
67%
Ni(dpm)2 = bis-(dipivaloylmethanato)nickel (11)
Yamada. T,; Takahashi, K.; Kato, K.; Takai, T.; Inoki, S.; Mukaivama. T, Chem. Left., 1991, 641. Na2C04 ,CF3COOH O°C-+RT,2h
x
-
0
0
81%
Olah. G.A.; Wang, Q.; Trivedi, N.J.; Suwa Prakash. G.K. Synthesis, 1991, 739.
-
;iOMe
e - , Et4NOTs , RT
n-CioH21 SiMe,
MeOH
n-ClOH21
Yoshida.; Itoh, M.; Matsunaga, S.; Ime.3. J. Org. Chem., 1992, 57, 4877.
0-
1. DMF (H20) ,NaH 2. EtBr
Delgado, A.;
aTetrahedron Lett., 1992, 33, 2789. cat. Fe@3 ,02, RT PhCHO , PhH
\
*
I ,
b
c02Et
w%
76%
98%
Murahashi. S-IL;Oda,Y.; Naota, T. Tetrahedron Lett., 1992, 33, 7551. cyclohexanone oxygenase (E.C.I.14.13.-) cat. NADP+ ,pH 8 ,glycine-NaOH glucose 6-phosphatdglucose 6-phosphate dehydrogenase
'8
62%
(80%ee)
Taschner.;Peddada, L. J. Chem. Soc., Chem. Commun., 1992, 1384. Also via: Section 27 (Acid Derivatives).
Compendium of Organic Synthetic Methods, Vol8
182
Section 119
SECTION 118: ESTERS FROM NITRILES PPE-Me , MeOH , 150°C, 24 h
*
P h 7 CN
97%
P h 7 C02Me
PPE-Me = plyphosphate methyl ester - see 1. Org. Chem., 1969, 34.2665
Mills. F.D.; Brown, R.T. Synrh. Commun., 1990, 20, 3131.
SECTION 119: ESTERS FROM ALKENES
J. Org. Chem., 1990, 55. 891.
Baskaran, S.; Islam, I.;
.
18 h , O " C + 66°C 2. NaOH H202, 0°C
BzO Hara, S.; Kishimura, K.;
'
e-
BzO
A C02Me 75%
; Dhillon, R.S. J. Org. Chenz., 1990, 55, 6356.
1.2 eq. Phl(0Ts)OH C H S I , , 0°C
,,,,
SiMe3 2. 2.2 eq.imidazole H
H
"
(3
1)
87%
OTs
Schaumann. E.; Kirshning, A. J. Chem. Soc., Perkin Trans. I, 1990, 1481.
Inornata. K.; To&, S.; Kinoshita, H. Chem. Lett., 1990, 1567.
OH
1. Me2SmBH3 ,ether -78°C + 25°C 2. Na2Cr207.2 H 2 0 H2SO4, H2O , 10°C + reflux
Mandal.;Mahajan, S.W. Synthesis, 1991, 311.
40%
Section 120
Esters from Miscellaneous
7 Me
1. Thex-BH2 , THF NaCN, TFAA
Me
NaOOH
OBn 2. mCPBA , CH2C12
+
183
&OBn Me
Me
57%
Yokovama. Y,;Kawashima, H.; Kohno, M.;Ogawa, Y.; Uchida, S. Teiruhedron Len.,2991, 32,1479 2% PdC12(PPh& , TIlF
CGEt
SiMe3 90°C , CO (60 kg/cm2)
+
Bu
EtOH
-.-
Bu
LSiMe3 -I-
C0,Et B
U
(96 with C q ( C O ) *
A
(0
SiMq 70%
4)
loo)
18%
Takeuchi. R,; Ishii, N.; Sam, N. .I. Chem. Soc., Chem. Conimun., 1991, 1247. Also via: Section 44 (Alcohols).
SECTION 120:
ESTERS FROM MISCELLANEOUS COMPOUNDS
10)
(90
Trost. B.M,;Medic, C.A. .I. Org. Cheni., 2990, 55, 1127.
(CO)@=(
OEt Ph
)8 ,acetone ,20°C
611
Ph- C02Et
c
97%
3h
Lluch, A-M.; Jordes, L.; Shnchez-Baeza, F.; Ricart, S . ; Camps, F.; Messepuer. A.; Morel6 J.M, Tetrahedron Leir., 1992, 33, 3021.
Wang, S.L.B.; Su, J.; Wulff. W.D..I. Am. Chem. Soc.. 1992, 114, 10665.
Me,Si
+c=o
H
EtCHO , MABR -78°C , 2 h
Eo
Me3Si * Et
MABR = methyl aluminum bis(4- hromo-2.6-dir-hu tylphenoxide)
Maruoka, K.;Conception, A.B.;
SynLRtt, 1992, 3 1 .
82%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 9 PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS
SECTION 121:
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYNES
Takai.;Tezuka, M.; Kataoka, Y.; U ~ ~ Q & J.J LOrg. Chem., 1990, 55, 5310. SECTION 122:
ETHERS, EPOXIDES AND THIOETHERS FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 123:
ETHERS, EPOXIDES AND THIOETHERS FROM ALCOHOLS AND THIOLS M q S iCHNz 42% aq. HBF4 CH2Cl2, O°C
O -H
a
Ic
-0Me
Aovama.,Shiori, T. Tetrahedron Lett., 1990, 31, 5507. OH
OH
CDCl3 , RT , Tf20
Ph3P=O, 20 min
92%
-0
Hendrickson.;Hussoin, MdS. SynLett, 1990,423.
0
quant.
Section 123
Ethers from Alcohols
mCPBA , MeOH
n-C 13H27
SePh
185
wo
n - ~ , 3 ~ 2 7 L
25°C
97%
Et OH Et Tkmura.; Ohe, K.; Sugita, N. J. Chem. Soc., Perkin Trans. I, 1990, 1697.
H-C3 C-
n
HS n-C4H9
SH
02.
,BPQ, MeOH
* n-c4Hg[s)
PhH
49%
S
Demchuk, D.V.;Lutsenko, A.I.; Troyanskii, E.I.; Nikishin, G.I. Izv. Akud. Nauk. SSSR, 1990. 39, 2801 (Engl.. p. 2542). Ph
=/
$0.15BF3*OEt2
PhH , RT
.-
64%
Ph
0
OH
(9O:lO
ZE)
Inoue, T.; Inoue, S.; WLK, Chem. Lett., 1990, 55.
c7(
Ph4SbOMet DCE , 6 0 T sealed ampule, 24 h Fujiwara, M.; Hitomi, K.;
Synthesis, 1990, 106.
74%
1. e- ,Pt electrodes, MeCN EbB Nr
* Bu-S-BU 86% 2.BuBr Petrosvan.;Niyazymbetov, M.E.; Konyushkin, L.D.; Litvinov, V.P. Synthesis, 1990, 841
BUSH
EtI ,9% TBAB , KOH
OH
neat,6O0C,24h
*
E
t
O
O OEt 90%
Loupy, A.; Sansoulet, J.; Diez-Barra, E.; Carrillo, J.R. Synth. Commun., 1992, 21, 1465. Bu3P-PhSSPh
c-
1 a m ,16 h 90% quant. 10 kbar, 62"C, 3 h Kotsuki., Matsumoto, K.;Nishizawa. H. Tetrahedron Lett., 1991, 32,4155.
Compendium of Organic Synthetic Methods, Vol8
186
TFA , RT , 3 0 min+
OH
Section 124
H *o
OH
Ismail., Hilton. M.J.;
63%
SlefinoviC,M . Tetrahedron Lett., 1992, 33, 3795.
oJoLo9
( Y O H
57%
Synth. Commun., 1992, 22, 687.
Guy, R.K.;
6: eoH , 140°C
2q.
2eq.KzC03,2h
*
5% CUI * )"
(71% ee,R)
OMe
- Mro
Smith.;Jones, D. J. Chem. Soc., Perkin Trans. I, 1992, 407. 1.2 q.(CF3C02)2Hg CH2C12,20aC ,18h
Ph+OH Ph Me
l
80%
ETHERS, EPOXIDES AND THIOETHERS FROM ALDEHYDES B
n
O
A
0s PhCHO
6, OBn
--
Bn
p%
50% NaOH ,cat. BnEt3NHCI Ph Ph CH2C12 , 0°C 53% (60%ee) Breau, L.; Ogilvie, W.W.;Purst.&Tetrahedron Len., 1990, 31, 35. @
Ph,As
-OH
XO
Wmg, W-B.; Shi.; Li, Z-Q.;
PhCHO ,MeCN €W*AI@q
-
Ph 78%
- Tetrahedron Lett., 1991, 32, 3999.
Section 124
187
Ethers from Aldehydes
,iBu2Te
JBr
PhCHo
cs2CO3, THF/ether/H20c 5O"C, 19 h
ph& (71:29
75%
cis:trans)
- Tetrahedron Lett., 1990, 31, 7657.
Zhou, Z-L.; Shi, L-L.;
0 0 Ph2Te-CH3 BPh4
1. LiTMP ,THF , -78°C c
2. PhCHO -78°C + RT
also reacts with ketones Shi, L-L.; Zhou. Z-L.: Huang, Y-2. Tetrahedron Lett., 1990, 31, 4173.
h CHO
1. P ~ ~ ATHF s , , -78°C iPr3SiOTf
2. KNTMS2, -78°C 3. PhCHO , -78°C 4. TBAF , -78°C + RT Kim. k, Kim, Y.G.Tetrahedron Lett., 1991, 32, 2913.
PhCHO
+
ph
A OSiMe, -
P h + OSiMe,
R Ph
hv
(>95 Bach. T. Tetrahedron Lett., 1991, 32, 7037.
:
Fire3
Ph
5)
39%
1. n-C3H7CHO, PhSH ,H+
2. BuLi * 4 P h 3.MeI Ph 46% H 4. PhCHzMgX M t z k v . A.R.; Perumal, S.; Kuzmierkiewicz, W.; Lue, P.; Greenhill, J.V. Helv. Chim. Ada, 1991, 74, 1924.
Me Me+Co2Me
SiMezPh
Bn0,CHO
,- 7 8 0 ~
CFyOEt2, CHg12
15h
Panek. JS,; Yang, M. J. Am. Chem. SOC.,1991, 113, 9868.
85%
(30:l 4.5-syn:anti ; 96% dr)
188
Section 128
Compendium of Organic Synthetic Methods, Vo18
r-BuOSiMe3 , Me3SiH PhCHO
TMSI ,pentane -78°C + RT
*
PhCH,Ot-Bu
71%
Hartz, N.; Surva Prakash. G.K.;W, (3.4,SynLett, 1992, 569.
ysiMe3 ,()
PhCHO
-I
20% Me3SiOTf OSiMe3 CCl4,2O"C
Ph
85%
Mark6 I.E.; Mekhalfia, A. Tetrahedron Lett., 1992, 33, 1799.
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYLS, METHYLENES AND ARYLS
SECTION 125:
NO ADDITIONAL EXAMPLES
SECTION 126:
ETHERS, EPOXIDES AND THIOETHERS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 127:
ETHERS, EPOXIDES AND THIOETHERS FROM AMINES 1. NaN02, HCl
c1
2. H02CH2SH
35%
Org. Prep. Proceed. lnt., 1991, 23, 198.
Yildirir, Y.;
SECTION 128:
ETHERS, EPOXIDES AND THIOETHERS FROM ESTERS
0 S
1. MeLi 2. Me1
3.Ph3SnH
0 Me
85%
Nicolaou. K.C.; McGanry, D.G.; Somers, P.K.; Kim, B.H.; Ogilvie, W.W.; Yiannikouros,G.; Prasad, C.V.V.; Veale, C.A.; Hark, R.R. J. Am. Chem. SOC..1990, 112, 6263.
Section 129
Ethers from Ethers
189
qSePh
PhSeSePh ,THF , 15 h
OAC
2.5 eq. Sm12 , 5% PdCI;! c 20% PPh3,25'C
84%
Fukuzawa.: Fujinami, T.; Sakai, S. Chem. Left., 1990, 927. fO y OPh 0
5% Pd(0Ac)z. THF 20% PPh3 ,25"C, 1 h
c
=foPh
87%
Larock, R.C.; Lee, N.H. Tetrahedron Left., 1991, 32, 6315.
& !!
SEt
2 eq. NiC12.6 HzO 2 &.Zn* ,-8eq.-PPh3
DMF , 2 3 T , 2 0 h
SEt
*
73%
W~~LJL Chianelli, E . ; D. J. Chem. Soc., Chem. Commun., 1991, 627.
S
n-C ~
O
H SMe ~
3 eq. DBH , CH2Cl2 1 py
~
O
~
L-
n-C
CF3
80%
DBH = 1,3dibromo-5,5-demethylhydantoin Juroboshi, M.; Suzuki, K.; Hivama. T. Tefrahedron Lett., 1992, 33, 4173. Pdz(dba)s, dppb , PhOII THF,60T, 12h
0
O K OMe
-0Ph
75%
Goux, C.; Lhoste, P.; SiwuJL SynLetf, 1992, 725. Goux, C.; Lhoste, P.; D. Tetrahedron Left., 1992, 33, 8099 [with thiols].
mu.
SECTION 129: ETHERS, EPOXIDES AND THIOETHERS FROM ETHERS, EPOXIDES AND THIOETHERS
0
1. 5% Pd(0AC)z 3 KOAc , DMF
Bu~NCI,80°C
Meoa, Me0
m'
2.4% Pd(0Ac)z 9% PPh,, MeCN 2 A g K 0 3 , 8o°C 3. H, ,PtOz ,EtOAc , IWmin
Larock.;Gong, W.H. J. Org. Chem., 1990, 55, 407.
68% overall
190
Compendium of Organic Synthetic Methods, Vo18
Nambu, Y.;
Section 129
Tetrahedron Lett., 1990, 31, 1723.
Eisch.;Galle, J.E. J. Org. Chem., 1990, 55, 4835. e- , S, , Pt electrodes
37%
OMe Le Guillanton, G.; Do, Q.T.: Simonet, J. J. Chem. Soc., Chem. Commun., 1990, 393. t-BuOK , 18crown-6 PhH ,reflux, 4 h
Duldre, J-P.; Rodriguez, J. Synlh. Commun., 1990, 20, 1893. iBu2AlSePh , PhMe Nishivama. Y,; Nakata, S.; Mamanaka. S, Chem Lett., 1991, 1775. SmI2-MeCN ,MeCN t-BuOH, HMPA
Ph with mines as well as ethers Ujikawa, 0.; Yamaguchi, M. Tetrahedron Len., 1991, 32, 1737. Zn(BH& on Si02 THF , -lO°C, 8h b a l . V&;
Me
*
g
80%
Me
Singh, S.P.; Dufour, C.; Michoud, C. J. Org. Chem., 1991, 56, 5245.
191
Ethers from Halides
Section 130
EgSiH , TMSCl
-
Ph-SEt
4
83% InC13, CH2Cl2 , RT Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han,J.S.; Kobayashi, S. Bull. Chem. Soc. Jpn., 1991, 64, 2524.
SEt
Ph
Ph
BnOTMS , Et3SiH , O T 5% SbCIyAgSbFs, 2 h
Ph Ph*oJph
w
83%
Harada, T.; Mukaivama. T, Chem. Lett.. 1992, 1901.
SECTION 130:
ETHERS, EPOXIDES AND THIOETHERS FROM HALIDES AND SULFONATES OBn
+
*
F
MqGaCI ,MeCN
BnO
90 h
80)
,-
quant.
Koide, K.; Ohno, M. Tetrahedron Lett., 1990, 31, 2435.
Fllssph , phoph 25OoC, 8 h
Ph-I
Ph-S-Ph
quant.
Wang, Z.Y.; Hay, A.S. Tetrahedron Lett., 1990, 31, 5685.
Ph-
Br
PhqSn-Te-SnPhl ,45"C 4 CSF , CD3CNt 24 h +.
Ph,Te,,Ph quant.
Li, C.J.;
Tetrahedron Lett., 1990, 31, 6291.
BnOH ,t-BuOK , TDA-1 140°C, 2 h
98% TDA-1 = see J. Org. Chem., 1985, 50, 3717 Lgupv. A,; Philippon, N.; Pigeon, P.; Sansoulet. J.; Galons. H. Synth. Commun., 1990, 20, 2855.
Section 130
Compendium of Organic Synthetic Methods, Vol8
192
Hengchane. C. ; Zhenzhong, L.; Wei, L. Synrh. Commun., 1990, 20, 3313.
pe Kimpe. N,; Stevens, C. Tetrahedron, 1990, 46,6753.
0 0
c1 OTf Pd(OAc)2.(R)-BINAP iPr2NEt. W H , 2 2 h
Ozawa, F,; Kubo, A.; b
o....o 0
/
c1 + %
/ 17)
(83
shi. T, J. Am. Chem. SOC.,1991, 113, 1417.
c1
86%
J. Org. Chem., 1991, 56,3739.
Kitamura.; Kabashima, T.;
Se
3%
94%
1. CO (5 am), D B U , HzO MeCN ,8O"C, 1 h
*
Bu-Se-Bu
75%
2. BuCl , 80°C, 1 h pishivma. Y,; Katsuura, A.; Negoro, A,; Hamanaka S.; Miyoshi, N.; Yamana, Y.;Ogawa, A.; Sonoda. N.J. Org. Chem., 1991, 56, 3776. NaOMe ,DMF ,reflux 10% CuBr ,30min Keegstra, M.A.; Peters, T.H.A.; Brandsma. L.Tetrahedron, 1992, 48,3633. S(MgBr)z, ether
Br
U
S
-
86%
Nedugov, AN.; Pavlova, N.N. Zhur. Org. Khim., 1992, 28, 1401 (Engl., p. 1103).
193
Ethers from Ketones
Section 132
NaCN ,EtOH , HzO reflux
--
OMS Pehmlow. H, ; Muler, J.; Seilz, C.: Strecker, A.R.; Kohlmann, A. Tetrahedron Lett., 1992, 33, 3607. Al2O3, Na2S
Br(CH2),Br
5
*
1.69 x l o 3 M
79%
Tan, L.C.; Pagni, R.M.; Kabalka. G.W. ; Hillmyer, M.; Woosley, J. Tetrahedron Lett., 1992, 33, 7709. Related Methods: Section 123 (Ethers from Alcohols).
SECTION 131:
ETHERS, EPOXIDES AND THIOETHERS FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 132:
6
ETHERS, EPOXIDES AND THIOETHERS FROM KETONES
1.12, MeOH
90%
M~ 2. PhH,NaHC03
Me COZEt see Tamara Y.;Yoshimoto, Y. Chern. Id.1980,888. , CO,Et
NazSz03 , aq.NaOH
& h i s A L Tetrahedron Lett., 1990, 31, 481.
Me3S=O+ I - , t-BuOK DMSO , RT ,16 h
86%
t
Synth. Cornmun., 1990, 20, 1193.
*At
f i S n B u 3 , 80°C, 2h p-ni titrobenzene BuZSnBrZ - HMFT
Yano, K.; Hatta, Y.; Baba.;Matsuda, H. SynLett, 1991, 555.
0
quant.
Compendium of Organic Synthetic Methods, Vol8
194
0 m.
osph
1. PhSH , HzO-BF3,O"C CHzClz, 1 min
76%
2. Et3SiH , 0°C --j RT , 3 he
G.%; Wang,Q.; Trivedi, N.J.; &uyi&&&.
Section 134
G.K. Synfhesis, 1992, 465.
Relaled Methods: Section 124 (Epoxides from Aldehydes).
SECTION 133:
ETHERS, EPOXIDES AND THIOETHERS FROM NITRILES NO ADDlTIONAL EXAMPLES
SECTION 134:
ETHERS, EPOXIDES AND THIOETHERS FROM ALKENES 1 -
PhO-
excess NaTeH p
h
O
EtOH ,reflux 24h
y
T
e
y oPh
Me Me
85% + 14% of other tellurides Barton.;Bohe, L.; Lusinchi, X . Tetrahedron Lett., 1990, 31, 93.
Adam. W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett., 1990, 31, 331.
Ph
Ph\=
MnTPPCl
2
38%
TPPCl was undefined; other quinones led to higher yields
s; Ohno, M.;
Tetrahedron Lett., 1990, 31, 6039. 10% F2 in N2, H2O MeCN , 0°C , 1 min
Oo
85%
Rozen.; Kol, M. J. Org. Chem., 1990, 55, 5155.
195
Ethers from Alkenes
Section 134
PhSeSePh ,hemin-NaBH4 PhH - EtOH , 2 4 h
Ph-
Me PhA
47%
SPh
Kano. K.; Takeuchi, M.; Hashimoto, S.; Yoshida, 2. Chem. Lelt., 1990, 1381.
Jb
Lo
3% VO(acp)z, DCE 3 am 0 2 , MS 4 A ,75°C
78%
acp = 2-acetylcyclopentanone
Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Leff., 1990, 1657.
NaOCl ,0.05 M , RT
Ph\=
*
2% Ni(bpy)2C12
ph\o
74%
B; Yamazaki, Y. Bull. Chem. SOC.Jpn., 1991, 64, 3185. Ph
Me \--I
aq. NOCl , CH2CIz
wMe
Ph
b
88%
0
5% Mn (salen) derivative
(84%ee , 1R2S)
Jacobsen., Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. SOC., 1991. 113, 7063. Zhang, W.; Jacobsen. E.N. J. Org. Chem., 1991. 56., 2296. Lee, N.H.; Muci, A.R.; lacobsen. E.N, Tetrahedron Lett., 1991, 32, 5055.
Ph\=
1. MeOCH20S020Me. -20°C 2. MeOH t
Ph
OMe OMe
56%
Lebedev, M.Yu.; Balenkova, E.S. Zhur. Org. Khirn., 1991, 27, 1388 (Engl., p. 1214).
Ph 4
4.5 eq. ZnBrz , CH2Br2 33%
e' (Zn anode)
Durandetti, S.; Sibille. S;, Pkrichon, J. J. Org. Chem., 1991, 56, 3255. V2O5, 5 t-BuOOH
45°C , 3 h
*
0
0 45 90
Laszlo.;Levart, M.; Singh, G.P. Tetrahedron Len., 1991, 32, 3167.
196
Compendium of Organic Synthetic Methods, Vol8
COzMe P e P h
hv PhH(sunlamp) ,overnight c
&'OZMe+ SePh
Section 134
&C02Me
60%
'%
/
SePh20%
Bvers. J.H,; Gleason, T.G.; Knight, K.S. J. Chem. SOC., Chem Commun., 1991, 354.
-
yields are poor (16%) with 1-decene as a substrate Masaki.;Miura, T.; Mukai, I.; Itoh, A.; Oda, H. Chem. Lett., 1991, 1937. C8F171,EtOH , RT PhSeSePhhIaBH4 2h
63%
n-C8H 17
Kitagawa, K. Tetrahedron Lett., 1991. 32, 375.
30% H 2 0 2 , NaIlCO3
CH2Cl2, 18-crown-6
eN3 63%
m; Duldre, J-P. J. Org. Chem., 1991, 56, 469.
OMOM
OMOM
>: =-
acetone
Me
"#I
Me
(>13:1)
Schultz.;Harrington, R.E.; "ham, F.S. Tetrahedron Lett., 1992, 33, 6097.
SnBq
NPSP , SnC14 ,-78"C CH2C12
NPSP = N-phenylselenophthalimide
Herndon. J.W.; Harp, J.J. Terruhedron Letr., 1992, 33, 6243.
68%
Section 134
Ethers from Alkenes
197
-
Bu3SnCI. NaCNBH3
.
OSiMe,CH,B r AIBN r-BuOH
b
reflux, 8 h
(1
1)
Koreeda.;Visger, D.C. Tetrahedron Lett., 1992, 33, 6603. 25 eq. MeCHO , 0 2 40"C,6h
86%
80%
0
Kaneda. K,; Haruna, S.; Imanaka, T.; Hamamo~o,M.; Nishiyama, Y.; Jshii, Y. Tetrahedron Lett., 1992, 33, 6827. 2.5% Ni(&np)2,02 (1 atm) 2 eq. i W H O , RT
-
b 0
Ni(dmp)z = [ 1,3-bis(pmethoxyphenyl)-1.3-propanedionato]nickel 01)
quant
Yamada. T,; Takai, T.; Rhode, 0.;Mukaiyama, T. Buff. Chenr. Soc. Jpn., 1991. 64, 2109.
Takai.;Hala, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. SOC.Jpn., 2991, 64, 2513 [witli Fe(dmph1. Mukaivama. T,; Takai, T.; Yamada, T.; Rhode, 0. Chetn. Lett., 1990, 1661. Yamada, T.; Takai, T.; Rhode, 0.;Mukaivama. T, Chetn. Lett., 1991, 1. N-methylimidazole , t-BuCHO Mn (salen) derivative PhF, RT ,02
*
& /
78%
(63% ee , lS,2R) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett., 1992, 2231. Takai, T.; Hata, E.; Yorozu, K.; Mukaiyama, T. Chent. Leit., 1992, 2077.
Mn W e n ) derivative
(34%ee , RR) . SynLett. 1992, 407. Hatayama, A.; Hosoya, N.; Irie, R.; Iio, Y.; ' Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Tetrahedron Lett., 1990, 31, 1345. ' Irie, R.; Noda, K.; Ito, Y.; Tetrahedron Lert., 1991, 32, 1055. ' Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Tetrahedron Asymmetry, 1991, 2, 481.
Section 135
Compendium of Organic Synthetic Methods, Vo18
198
PhIO , Mn porphyrin
c
imidazole
Ph
10
45%
(48% ee) Konishi, K.; Oda, K.; Nishida, K.; Aida, T.; Inoue.. Am. Chem. SOC., 1992, 114, 3 3.
Ph%
2 eq. iPrCHO ,02, DCE
Ph
Ph
b
Ph 2% Ni (salen) derivative, 10 h Oda,T.; Irie, R.; YilfSuki. T,; Okawa, H. SynLet?, 1992, 641. Irie, R.; Ito, Y.;&@&J ’ Tetrahedron Lett., 1991, 32, 6891.
SECTION 135:
88%
ETHERS, EPOXIDES AND THIOETHERS FROM MISCELLANEOUS COMPOUNDS (7:2: 1) NaH:t-AmONa:Ni(OAc)z THF , 16.5 h
0
n-C,2H&” n-CI2H2;
n-C 2H25
n-C l2H;;’*
67%
Becker, S . ; Fort, Y.; Caubkre, P. J. Oig. Chem.. 1990, 55, 6194.
Ph,
QS.
BnBr , 3 eq. DMF , 155°C
*
Me
Bernard, A.M.; Caredda, M.C.;
. .
Bu-
Me
70%
Piras.;Serra, E. Synthesis, 1990. 329.
TiC14, NaI , MeOH , RT 5 min
0
S.
Ph,
Bu
t
92%
s I
Synthesis, 1991, 155.
4 eq. MesSiOMe ,60°C
PhOMe 51%
m. G.A.; Wu, A. Synthesis, 1991, 204. Q
Lawesson’sreagent THF , RT
Bartsch.;Erker, R. Tetrahedron Lett., 1992, 33, 199.
Ph’
s, ph
Ethers from Miscellaneous
Section 135
'-
0 Bu'
Bu
2 eq. TsOH , 2 eq.NaI
30 min
-
/
Bu'
199
*'
Dtabowicz. J,; Dudzinski, B.; Mokdajczk, M. SynLett, 1992, 252. REVIEWS: "Recent Developments in the Area of Annulated Furans" Padwa A,; Murphree. S.S. Org. Prep. Proceed. int., 1991, 23, 547.
Bu
quant.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 10 PREPARATION OF HALIDES AND SULFONATES
SECTION 136:
HALIDES AND SULFONATES FROM ALKYNES NO ADDlTIONAL EXAMPLES
SECTION 137:
HALIDES AND SULFONATES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 138:
HALIDES AND SULFONATES FROM ALCOHOLS AND THIOLS
1 0' 60-98%
IJgge.
G .L,; Gottardo, C. Synrh. Commun., 1990, 20, 1473.
0""
CFCI, , -78°C -+ 20°C
Olah. G.A,; Li, X-Y.SynLert, 1990, 267.
67%
Section 138
20 1
Halides from Aldehydes
Bay, E.; Bak,D.A.; Tmony, P.E.; Leone-Bav. 4 . J . Org. Chem., 1990, 55, 3415. P2I4 , l o 2 ~ O K,85"C
*
OH
-1
86%
Lame. M-Q; Cairon, P.; Villemin, D. Synth. Commun., 1990, 20, 41.
Ph
OTHP
LiBroBF3 ,ether
ph&Br
'53%
also with NabBF3 to give iodides and with 1" and 2" OTHP derivatives Vankar.;Shah, K. Tetrahedron Lett., 1991, 32, 1081. (BrCHzCH2)2SeBrz ,80"C b n-CBHl7OH 7h n-C8H17Br Bkabori.; Takanohashi, Y. Bull. Chem. SOC. Jpn., 1991. 64, 3482.
0
98%
0
3 q.M@N=CC12 C1 dioxane ,40"C , !XI min
HO-&OH OH OH
*
a&c1OH
OH
73%
Benazza, M.; Uzan, R.; Beaupere, D.; Demailly, G. Tetrahedron Lett., 1992, 33, 3129, 4901.
-OH n-CsH11
Ph3P.Brz. MeCN Py , 0°C - RT
&Br 96%
n-C5H11
Sandri, J.; Viala. J, Synth. Commun., 1992, 22, 2945.
SECTION 139:
n-C,H13CHO
HALIDES AND SULFONATES FROM ALDEHYDES "(PhO)3PBrz" , CH2C12 -15°C 3 0°C
Hoffmann. R.W.; Bovicelli, P. Synthesis, 1990, 657.
>
n-C,H,,-(
Br Br
70%
Compendium of Organic Synthetic Methods, ~ 0 1 8
202
Section 142
1.Tf20
-CHO
2. Buq' PhjSnF2-
* 4F
68% Martinez. A.G.; Barcina, J.O.; Rys, A.Z.; Subramanian, L.R. Tetrahedron Lett., 1992, 33, 7787.
SECTION 140:
HALIDES AND SULFONATES FROM ALKYLS, METHYLENES AND ARYLS
For the conversion R-H --t R-Halogen, see Section 146 (Halides from Hydrides). NO ADDITIONAL EXAMPLES
SECTION 141: HALIDES AND SULFONATES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 142: HALIDES AND SULFONATES FROM AMINES
F
quant.
Kim. Y.H,; Lee, C.H.; Chang, K.Y. Tetrahedron Left., 1990, 31, 3019.
RT + reflux 2.MeCN,
CN-H /
70%
Smith. W.B,; Ho, 0-C. J. Org. Chem., 1990, 55, 2543.
0 Bu
2. PhSH 3.6 eq. AgNO3, PhMe' HF-PV . 90°C I
,
+ Bu
Q BU
54% 39% Haroulounian, S.A.; Di Zio, J.P.; Katzenellenbogen, J.A. J. Org. Chem., 1991, 56, 4993.
Halides from Halides
Section 144
NBS , Py/(HF),
N-NH,
PhL
203
*
Ph
m; Reddy, V.P.; Li, X-Y.; Cm&& Synkrt, 1990, 594.
0
NH,
0''
Me3SiCl , NaNO2 BnEgNCI , CCI4
*
10h
86%
Lee. J.G.; Cha, H.T. Terruhedrun Letf., 1992, 33, 3167.
SECTION 143: HALIDES AND SULFONATES FROM ESTERS 4 eq. DBH B u ~ N 'H2F3-
-
63%
DBH = 1,3-dibromo-5,5-dimethyl hydantoin
Kuroboshi, M.;
SECTION 144:
Chem. Lett., 1992, 827.
HALIDES AND SULFONATES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
-
SECTION 145:
HALIDES AND SULFONATES FROM HALIDES AND SULFONATES H I , 130°C, 5 h
Br
-1
Namavari, M.; Satyamurthy, N.; Phelps, M.E.; E3g&J&
BrMg--Q-Me
+ nN
' 8F
o
90%
Tetrahedron Letr., 1990, 31, 4973.
freon ,O°C
*
8
F
G Me
Satvamurthv. N.; Bida, G.T.; Phelps, M.E.; Barrio, J.R. J. Org. Chem., 1990, 55, 3373.
30%
Compendium of Organic Synthetic Methods, Vo18
204
Q
1. Mg , ether 2. cs2
*
3. XeF2, CH2C12 0°C -+ RT (72 h)
Me
4
Section 145
+
Me
Me
73%
21%
Zupan, M.; Bregar, Z. Tetrahedron Lett., 1990, 31, 3357. 1. Mg
Me
2. cmzrc12
B
h Me B r
r
3.Br2
+
' Br+Br
Me +
Br+Br
Me
Me
(99
1)
Takahashi, T,; Fujimori, T.; Seki, T.; Saburi, M.; Uchida, Y.; Rousset, C.J.; Negishi. E, J. Chem. Soc., Chem. Commun., 1990, 182. MgI2, CS2,48"C, 5 h
75%
=-
>>>>)>>>
TfO
Martinez.;War, E.T.; L6pez, J.C.; Alonso, J.M.; Hanack.; Subramanian, L.R. Synthesis, 1991, 353.
Mcoel CF3SiEt3, KF CuI , DMF/NMP 80"C, 24 h
Urata, H.;
.
.
82%
Tetrahedron Lett., 1991, 32, 91.
0
Br
NaOCl (pH 9) , CHC13 6% Ni TPP , BnBu3NBr --
pJcl
qumt.
TPP = 5,10,15,20-telraphenyl porphyrin OConnor, K.J.; BUKOWS.C.LJ. Org. Chem., 1991, 56, 1344.
Br
CCF2C02Me, KF & I , 120"c, 8 h
c
Ph ph lcF3 84% Su, D-B.; Duan,J-X.; Chen. 0-Y,Tetrahedron Lett., 1991, 32, 7689.
Section 146
Halides from Hydrides
pG"2g f
KF , TMSO2,18O0C 5h
205
F O N O 2 83%
CH
@PPh,
Yoshida, Y.;
@
; Tomoi, M. Chem. Leu., 1990, 769.
CF3Br. Bu4NBr, RT e- , DMF , TMEDA
3bar
Me0
Me0
Paratian, J.M.; Sibille, S . ; Pkrichon, 3. J. Chem. SOC.,Chem. Commun., 1992, 53.
0
Bu4PF-(HF) , MeCN
c
c1
80°C. 12 h Uchibori, Y.; IJmeno, M.; Seto, H.; Qian, Z.;
SECTION 146:
SynLerr. 1992, 345.
(yl+ 0""
HALIDES AND SULFONATES FROM HYDRIDES
0
Ni (salen)
2h
57% Querci, C.; Suologo, S.; Picci. M, Tetrahedron Left., 1990, 31, 6577.
5%
I,,CAN.Ih MeCN
*co$o
AcO
AcO OAc
Asakura. J,; Robins, M.J. J. Org. Chem., 1990, 55, 4928.
AcO OAC
Meoa BnMe3NBr, RT CH2CI2 - MeOH 2h
Kaiirraeshi. S,; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans. I, 1990, 897.
206
Compendium of Organic Synthetic Methods, Vol8
6
Section 146
HCl-mCPBA , DMF RT ,20 min
Cl
30%
CI
68%
2%
Chung, K.H.; Kim, H.J.; Kim, H.R.; U Synih. Commun., 1990. 20, 2991 12. Ag2SO4, EtOH RT , 15 min
84%
S v . , S y n t h . Commun., 1992, 22, 3215.
m w Lodge, w -; . B.A.; By, A.W. Synth. Commun., 1990, 877.
6 0
. .
CuBr , TFA , MeCN EbNOTs , e-
0
C electrodes, 20 F h o l*
80%
Mllanl.~.; Kobayashi, T.; Koyama, K..I. Chem. SOC.,Chem. Commun., 1991, 1418.
75% Kodomari. M.; Ammokura, N.; Takeuchi, K.; Yoshitomi, S . Bull. Cfiem. SOC.Jpn., 1992, 65, 306.
eoH
Amberlyst-A26*Br3,24 h CH2C12 (dark)
=-
B
r
o
o
H
+
QOH Br
86% 7% Smilh. K,; James, D.M.; Matlhews, I.; Bye, M.R. J. Chem. Soc., Perkin Trans. I, 1992, 1877. IPy2BF4,2 HBF4 c r r 2 c i 2 , RT
+
0' 48%
Barluenga.;GonzBlez, J.M.; Garcfa-Martfn,M.A.; Campos, P.J.; Asensio, G. 1. Chem. Soc., Chem. Commun., 1992, 1016.
Section 147
Halides from Ketones
207
I
5% PhI(0H)OTs ,NIS
MeOH , RT , 2 3 h
84%conversion
Bovonsombat, P.; Angara, G.J.; McNelis. E, SynLett, 1992, 131. a-Halogenations of aldehydes, ketones and acids are found in Sections 338 (HalideAldehyde), 369 (Halide-Ketone), 359 (Halide-Esters) and 319 (Halide-Acids).
SECTION 147:
HALIDES AND SULFONATES FROM KETONES
8
MeNbCI4, ether -78"C-rRT*
67%
also with MezNbCl3
also with aldehydes
Kauffmann. T,; Abel, T.; Neiteler, G.; Schreer, M. Tetrahedron Lett., 1990, 31, 493.
Motherwell.;Wilkinson, J.A. SynLett, 1991, 191. e- , NEt3.3 €IF, DME Yoshiyama, T.;
.
.
F
Phx
Chem. Lett., 1992, 1995.
F
Ph
44%
SECTION 148: HALIDES AND SULFONATES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 149:
HALIDES AND SULFONATES FROM ALKENES
For halocyclopropanations, see Section 74E (Alkyls from Alkenes).
h a new HI surrogate
[PhNEtz*BI3], AcOH 10°C + 25°C
--
Reddy, Ch.K.; Periasamv. M. Tetrahedron Lett., 1990, 31, 1919.
82%
I
208
Compendium of Organic Synthetic Methods, Vo18
ph%$?GBr2 @
Section 149
A3,4
70% 20%
A4.'
5%
0
Collado, I.G.; Madero, J.G.; Massanet. G.M.; Luis, F.R. Tetrahedron Lett., 1990, 31, 563.
Kaiieaeshi.;Moriwaki, M.;Fujisaki, S.; Kakinami, T.; Okamoto, T. Bull. Chem. SOC.Jpn., 1990, 63, 3033.
HBr ,20 min 11% 83% HBr ,Si@, 0.7 h 96% 0% (COBrlz. A1~03,20min 99% 0% KrODD.;Daus, K.A.; Crawford, S.D.; Tubergen, M.W.; Kepler, K.D.; Craig, S.L.; Wilson, V.P. J. Am. Chem. SOC.. 1990, 112, 7433.
MnOz, Me3SiC1 , THF
\r\l\/\\
30"C, 6h 84%
Bellesia, F.; Ghelfi, F.; Pagnoni, U.M.; Pinetti, A. Synth. Cummun., 1991, 21, 489. B u ~ N B ~ *CHC13 B~~,
Ph&
P h T p h Br
Ph
700 min 78% r min 98% Berthelot. J.; Benammar, Y . ; Lange, C. Tetrahedron ten., 1991, 32, 4135.
)))>)I)
Ph
CC14 , L E E , Cu(iPrNH2)2CI 72°C. microwaves (600 W)
&
c1 Ph+CCI,
Adamek, F.; HAiek. M, Tetrahedron Lett., 1992, 33, 2039.
90% conversion
Section 150
SECTION 150:
Halides from Miscellaneous
HALIDES AND SULFONATES FROM MISCELLANEOUS COMPOUNDS NO ADDITIONAL EXAMPLES
209
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER 11 PREPARATION OF
HYDRIDES
This chapter lists hydrogenolysisand related reactions by which functional groups are replaced by hydrogen:e.g. RCH2X -+ RCH2-H or R-H.
SECTION 151: HYDRIDES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 152: HYDRIDES FROM ACID DERIVATIVES This section lists examples of decarboxylations (RC02H + R-H) and related reactions.
Delbecq, P.; Celerier, J-P.;I&m.nw&
Tetrahedron Lett., 1990, 31,4873.
(Me3Si)3SiH1AIBN PhMe ,80"C, 10 h
Ballestri, M.;
..
0
92%
; Cardi, N.; Sornmazzi, A. Tetrahedron Lett., 1992, 33, 1787.
SECTION 153: HYDRIDES FROM ALCOHOLS AND THIOLS This section lists examples of the hydrogenolysis of alcohols and phenols (ROH
-OH
5.5%P-cyclodextrin 0.4 N KOH , KCNKCI CoCI2.6 H20
Lee, J-T.; Alper. H, Tetrahedron Leu., 1990, 31, 4101.
t
91%
-+
R-H).
Section 153
211
Hydrides from Alcohols
PhyOH
6 Li", 10%DBB 48 h
c
))")
Ph
Ph
'I
72%
Ph
DBB = 4,4'-di-t-butylbiphenyl Karaman, R.; Kohlman. D.T.; Tetrahedron Lett., 1990, 31, 6155.
v
WC12(PMePh2)4 c
<1 min
OH
M
+
m
93% Jang, S.; Atagi, L.M.; W r . J.M, J. Am. Chem. SOC., 1990, 112, 6413.
Ph).- OSiMe, SEt
Et3SiHI CHzClz ~
TMSCI-InC13 , RT
Ph
SEt
7%
83%
Po
Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han,J.S.; Kobayashi, S. Chem. Letf., 1990, 2239.
$1
B(iPr)g , CF3S03H
80%
Olah, G,A,; Wu, A. Synthesis, 1991, 407.
OH
N a B h ,ether TFA ,25"C, 1 h
*
Nutaitis. C.F,; Patragnoni, R.; Goodkin,G.;Neighbour, B .; Obaza-Nutaitis, J. Org. Prep. Proceed. Int., 1991, 23,403. Nutaitis. C.F.; Bemardo, J.E. Synth. Cummun., 1990, 20,487.
o:H
5% SmI2, HMPA ethylene glycol
0'b 'O PC
RT,3h
oo
0&.' O PC
Hanessian.;Gkard, C.; Chiara. J.L. Tetrahedron Lett., 1992, 33, 573.
90%
212
Section 154
Compendium of Organic Synthetic Methods, Vo18
0
Barton.;Jang, D.O.; Jaszberenyi, J.Cs. Tetrahedron Lett., 1992, 33, 2311. PhH , TsOH hv (A = 254 nm)
0
&0
/
P
h Brq
a
Piva. 0. Tetrahedron Lett., 1992, 33, 2459.
m
o
75%
Ph
H
1. TsCI , NaH ,THF 2. NaBH4 , NiC12.6 H 2 0 MeOH
92%
J. Chem. Soc., ferkin Trans. I, 1992, 1897.
Wang, F.; Chiba, K.;
3 eq. [VCkdTHF)612 [ Z ~ Z C ~ ~ I
Ph&
Ph OH
CH2C12
*
0 Ph 0 4 " # P h
59%
using acetate as starting material led to 91% yield of ketone Inokuchi, T.; Kawafuchi, H.; Chem. Lett., 1992, 1895. Also via: Section 160 (Halides and Sulfonates).
SECTION 154: HYDRIDES FROM ALDEHYDES For the conversion RCHO
CHO
-+
0.05 q.~ ( S - B I N A Pc104 )
I)Ct-Bu Wu, X-M.; Funakoshi, K.; &ai&
4
R-Me, etc., see Section 64 (Alkyls from Aldehydes).
CH2C12,RT
t-Bu (>99% ee , R)
Tetrahedron Lett., 1992, 33,6331.
87%
213
Hydrides from Esters
Section 158
SECTION 155:
HYDRIDES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 156: HYDRIDES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 157: HYDRIDES FROM AMINES This section lists examples of the conversion RNH2 (or R2NH)
+
R-I{.
Leone, C.L.; Chamberlin. A,R, Tetrahedron Lett., 1991, 32, 1691. 1. KOH 2.2 eq. NHzCl
NHTs
*
MeO-
56%
Guziec. F.S. Jr.; Wei, D. J. Org. Chem., 1992, 57, 3772.
Ph
y Ph N.
OH
HC02NH4, Pd-C , MeOH RT,2h
Ph-Ph
c
98%
Balicki. R. Gau. Chim. Ital., 1992, 122, 133.
SECTION 158: HYDRIDES FROM ESTERS This section lists examples of the reactions RC02R'
3
R-H and R02CR'
Barton., Jang, D.O.; Jaszberenyi, J.C. Tetrahedron Lea., 1990, 31, 4681.
-+ N-I.
Compendium of Organic Synthetic Methods, Vo18
214
*kSMe
Section 158
2% I - C ~ ~ H ~ S S H 2% dicumyl peroxide Et3SiH
*/\/\/\/
S
92%
Kirwan, J.N.; Roberts. B.P.; Willis, C.R. Terrahedron Leu., 1990, 31, 5093.
A N 0 2
PK" Eo,Et OBannon, P.E.;
1.1MNaOH .EtOH RT 2.DMSOH20 reflux. 30 min
A N 0 2
Ph'" H
+ ph.*-'&*
NO2
11%
79%
J. Org. Chem.. 1990, 55, 353.
-J.&
RhCl(PPh& ,Et3SiH
p@/Me
0 PhH ,reflux Liu. H-J,; Zhu, B-Y.Synth. Conimun., 1990, 20, 557. Ph
SMe
90%
PhSiH3, AIBN , I h PhMe , reflux quant.
U
Barton.; Jang, D.O.; Jaszberenyi, J.Cs. SynLett, 1991.435. 1. MeLi ,ether
2.
xcenE 0°C --t RT
*
- 100°C -+ RT
&Ph
82%
(82%ee , R)
Matsumoto, K.; LluaJL Tetrahedron Lett., 1991, 32,4129.
SECTION 159:
HYDRIDES FROM ETHERS, EPOXIDES AND THKOETHERS
This section lists examples of the reaction R-0-R' + R-H.
MeOy
0~~ 1. Et3SiH, SnBr2-AcBr
Me
CHzCI2 , 0°C
2. Bu3SnH, AIBN PhH , reflux
Onvama.;Ichimura, Y.; Koga, G. Bull.
I
/
/
Chem. Soc. Jpn., 2991, 64, 2581.
85%
Section 160
Hydrides from Halides
215
REVIEWS:
"Transition Metal Mediated C-S Bond Cleavage Reactions" Synthesis, 1990, 89.
Lub. T-Y.; Ni, 2-J.
SECTION 160:
HYDRIDES FROM HALIDES AND SULFONATES
8"
This section lists the reductions of halides and sulfonates, R-X
6
[MeOCH2CH20(CH2)313SnH 5% aq. NaHCO3 , RT ,40 min + hv (sunlamp)
C02H
+ R-H.
88%
Br
a water soluble tin hydride reagent Light, J.; J~E&JYA Tetrahedron Lett., 1990, 31, 2957.
bp
5% Pd(OAc)z, DMF dppp $9O"C,3.5 h
o,
93%
Cabri.;De Bemardinis, S.; Francalanci, F.; Panco, S . ; $anti. R.J. Org. Chem., 1990, 55, 350.
NEt3,10% PdC H2 (65 psi) ,MeOH
Me0
OMe 0S 02CF,
6h
+
Me0
OMe
90% Sail, J.M.; Dopico. M.; Martorell, G.; Garcia-Raso, A, J. Org. Chem.. 1990, 55, 991. NaI ,H3PO4, MeCN reflux, 4.5h
Mandal. A& ; Nijasure, A.M. SynLett, 1990, 554.
Br
e- , 10%SmC13, DMF Bu~NBF~
*
6
0
Hebri, H.; Dubach, E.; Wrichon, J. Synth. Commun., 1991, 21, 2377.
87%
quant.
-
216
Compendium of Organic Synthetic Methods, Vol8
C1
Section 160
E13Si. hexane ,reflux
5% TBHN 2% r-dodecanethiol
96%
TBHN = di-1-butyl hyponitrite
Cole, S.J.; Kirwan, J.N.; 103.
RobeE!s.;Willis, C.R. J. Chetn. Soc., Perkin Truns. I,
(>25
1)
1991,
84%
no Lewis acid (1 >25) 90% .. Guindon. Y ,; Lavallk, J-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. .I. Am. Chetn. SOC., 1991, 113, 9701.
1. AII3, MeCN , 80°C, 1 h 2. H 2 0 -
-
Ph
0 A Ph
92%
Borah, H.N.; Boruah, R.C.; Sandhu, J.S. .I. Cheni. Soc., Chem. Commun., 1991, 154. (MesSi)$iMeSH , 80°C t-BUONNOt-Bu , 1 h F
Br
92%
Daroszewski, J.; Lusztvk.;Degueil, M.; Navarro, C.; Conzmun., 1991, 586.
J. Chetii. Soc., Chew
-
NiBrz(dppp) , PPh3 , Zn DMF , MeOH , KI M e 2O"C, 16 h Sasaki.; Sakai, M.; Sakaibara, Y.; Takagi, K. Cheni. Lett., 1991, 2017.
,,hq
Bu3SnH, AIBN
C02Et PhMe , -78°C
~e
Br
hv (sunlamp)
30min
-
OMe Ph k
c 0 2 E t
Me (32
+
9
97%
OMe ph0kfC02Et Me 1)
90%
Guindon.;LavalltSe. J-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett., 1991, 32, 27.
Guindon.;Yoakim, C.; Lemieux, R.; Boisvert, L.; Delorme, D.; Lett., 1990, 31, 2845.
- Tetrahedron
Section 160
Hydrides from Halides
I , 2 , PhMe, 24 h
n-C 1 1 H23
Br -/
lOO"C, 10 eq. NaBG4
I =
Ballesui, M.; 1991, 56, 678.
-
n-CloH21
Ph
64%
SnClzPh
Org. Chem., 1991, 56, 490.
(Me3Si)3SiH
6 ..
11H23
H3C
03
Ph
Blanton.,Salley, J.M.J.
217
#
ArBN 90°C ' PhMec
82%
; Clark, K.B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem.,
, ,
Bu3SnH , Pd(PPh3)4
I
25°C. 3 h Taniguchi, M.; Takeyama, Y.; Fugami, K.; Qshima. 1991, 64, 2593.
0' u;
n-C10H21
b
\=
92%
K,;Ytimoto. K, Bull. Chem. SOC..lpn.,
NiBr2, Zn ,EtOH 60°C,20h
Lee, M-S.; Yamaguchi, K.; Kawai, Y.; Sasaki, K.; Sakakibara, Y. Bull. Chem. SOC. Jpn., 1992, 65, 1739.
Ollivier, J.; Piras, P.P.; Stolle, A.; Aufranc, P.;
;
Tetrahedron Lett.,
1992, 33, 3307.
Ph3PH1, MeCN , RT
Ph
3h
4
Kamiya, N.; Tanmatu, H.; Ishii. Y, Chem. Lett., 1992, 293.
Ph
85%
Compendium of Organic Synthetic Methods, Vol8
218
Section 162
REVIEWS :
"New Mechanistic Insight into Reductions of Halides and Radicals with Samarium (11) Iodide" SynLelt, 1992, 943.
Curran.;Fevig, T.L.; Jasperse, C.P.; Totleben, M.J.
SECTION 161: HYDRIDES FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 162: HYDRIDES FROM KETONES
+ R2C-H.
This section lists examples of the reaction R2C-(C=O)R 1. TsNHNHz ,MeOH 2. LiAlH4, THF ,60°C
ph& . . Balllnl.; Petrini, M.;
- Ph-
NO2
66%
J. Org. Chem., 1990, 55, 5159.
P(OiPr)3 , reflux
*
Ph
p
h
w
51%
C)lah.;Wu, A. SynLett, 1990, 54.
1. Dibal , heptane 90°C, 6 h
P h T
Ph
2.2eq.AlBr3,9O0C 20 h Eisch.;Liu, Z-R.; Boleslawski, M.P. J. Org. Chem., 1992, 57, 2143.
Ph
x SEt
Ph
SEt
PzI4 CHzC1z725"C 2h
w
Ph Ph> (85
Saimoto, H.; Kanzaki, A.; Miyazaki, K.; Sashiwa, H.; 1992, 65, 2842.
0 PhA Ph
Et3SiH , PPHF , 0°C + RT -
PhbPh
PPHF = pyridinium poly(hydrogen fluoride)
Olah.;Wang, Q.; Surva Prakash. G.K. SynLett, 1992, 647.
+
65%
Ph Ph+o 15) 85% Bull. Chem. SOC. Jpn.,
96%
Section 165
219
Hydrides from Miscellaneous
SECTION 163: HYDRIDES FROM NITRILES This section lists examples of the reaction, R-C=N isonitriles ( R - N e ) .
-+
3 eq.Btb, THF, 3 h
(-$
R-H (includes reactions of
TN
CN Ph
cN7ph
71%
b r a . K,;Shimamura, Y.;Fujita, M. J. Org. Chem., 1991, 56, 2920. 1. Bu3SnH. AIBN PhH , reflux b
81%
2. DBU
SynLen, 1991, 107. 1. MeLi 2. H2O
P h 3 N
c
Ph?
79%
"normal" nitrile addition with RMgX
KulD.; Romanelli, A.Org. Prep. Proceed. In(., 1992, 24, 7. SECTION 164: HYDRIDES FROM ALKENES NO ADDITIONAL EXAMPLES
SECTION 165: HYDRIDES FROM MISCELLANEOUS COMPOUNDS NaHTe , DMF , RT
PhJ
SOZPh
*
0
P
h 0
p
64%
Huang, X.; Pi, J-H. Synrh. Cornniun., 1990, 20, 2297. S02Ph
S d z , THF , HMPA -2OOC. 30 min
14%
Kiinzer, H.; Stahnke, M.; Sauer, G.; Wiechert, R. Tetrahedron Lea., 2991, 32, 1949.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
12
PREPARATION OF KETONES
SECTION 166: KETONES FROM ALKYNES
0 J. Chem. SOC., Chem. Commun., 1990, 1469.
Subramanian, R.S.;
HCOzH, lOO"C, 6 h
Menashe, N.; Reshef, D.; Sbvo.
&: C-Me
0
92%
Y. J. Org. Chem., 1991, 56, 2912.
NaAuClO4, aq. MeOH
n-C,H,
* -
Sh
0
* n-C,H,%Me
0 60)
(40
Fukuda, Y.; Utimoto. K, J. Org. Chem., Z991, 56, 3729.
94%
PhSeSePh , MeOH , 1 h
Ph- Ci C-H
(NH4)2S208, reflux
P h q o M e 75% OMe Tiecco. M,; Testafem, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. J. Org. Chem., 1991, 56, 4529. *
SECTION 167: KETONES FROM ACID DERIVATIVES 0
n-C91-11$L- c1
0
Me3TI
n-cgH~$LMe
Markb, I.E.; Southern, J.M. J. Org. Chem., 1990, 55, 3368.
85%
Section 167
22 1
Ketones from Acids
Ph
[2 C~(N03)2/H202/2H201
Ph Y Co2H Ph
m
MeCN
Po
Ph
55%
Capdevielle, P.; Maumy, M. Tetrahedron LRtt., 1990, 31, 3891. 1. Me3SiC1, Li/THF 2. air
q;
3. BzCl , AIC13 4. KFDMF
Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett., 1990, 31, 6179. Nation-H reflux, 30,min PhH 90%
0
0
Yamato.; Hideshima, C.; S u v a Prakash, G.K.; Olah, G.A. J. Org. Chem., 1991, 56, 3955. /L S n B q
Ph-"
0
,EbNC1
0
Ph?
c
0
BusSbCHzPh, THF
PllJ-C,
-78°C + R T , 1 h
c
82%
0
BuzSnClz , 3 0 min Yano,K.;Baba.;Matsuda, H. Chem. Lett., 1991, 1181.
Ph
Ph
87%
Zhang,L-J.; Huang. Y-Z.;Jiang, H-X.; Duan-Mu, J.; Liao, Y. J. Org. Chem., 1992, 57, 774.
Ac1
n-C7H15
3% MnClqLi~,THF BuMgCl , 100°C
1
w
n-C7H15
BU
87%
Cahiez.;Laboue, B. Tetrahedron Lett., 1992, 33, 4439. Cahiez.;Chavant, P-Y.; Metais, E. Telrahedron Lett., 1992, 33, 5245. SnMe3
A
Me&
AIC13, CH2C12 -78°C. 1 h Karin.;Lee, J.C.; SunU, J. Tetrahedron Lett., 1992, 33, 4953. SiMe3
85%
222
Compendium of Organic Synthetic Methods, Vo18
Kc1
Boivin, J.; El Kaim,L.; ZulJ&
-
PhCOOH
1
TFAA , Py ,ether
n-C ISH3 1
1.
Section 168
n-C1SH31 CF3
2ooc ' O'
81%
Tetrahedron Lett., 1992, 33, 1285.
ph3p d C02r-B
Me;?N-
,DMAP
N=C=N-Et
CH2C12 - -
2. oxone 0 79% Yasserman. H.H,; Ennis, D.S.; Blum, C.A.; Rotello, V.M. Tetrahedron Lett., 1992, 33, 6003. 1. cu* 2. BzCl
c1
c-
d
0 p h
65%
Cu* = activated zerovalent copper Stack, D.E.; Dawson, B.T.; J. Am. Chem. SOC.,1992, 114, 5110.
SECTION 168: KETONES FROM ALCOHOLS AND THIOLS
OH
1. MsCl, CHzCI;! NEt3,O"C , 3 h
2. 2 eq. NaOEt ,EtOH 12b ,2S°C a Gmb-like reaction Pestchanker.;Giordano, O.S. Tetrahedron Lett., 1990, 31, 463. u*'
OH
Cr-PILC/I'BHP CH2Cl2, RT ,24 h
LOH 94%
Cr-PILC = chromia-pillaredmontmorillonite
0"
(Shoudarv.; Durgaprasad, A.; Valli, V.L.K. Tetrahedron Lett., 1990, 31, 5785.
WMnOd2
-
-
55%
Firouzabadi. H.; Seddighi, M.; Mottaghinejad, E.; Boloufchian, M. Tetrahedron,1990, 46,6869.
223
Ketones from Alcohols
Section 168
DAIB = (diacetoxyiodo)benzene
Rama Kri-.
30% K.VJ Sujatha, K.;&nil. R.S, Tetrahedron Let?., 1990, 31, 1351.
PhI(02CCF3)2 aq. MeCN , 2 h 0°C
Barret.;Daudon, M. Tetrahedron Left., 1990, 31,4871.
0
73%
0'
Me0
0""
Clz , CH2C12 , Na2CO3 PhCl , RT , 1 h Bull. Chem. SOC.Jpn., 1990, 63, 947. Yamaguchi, M.; Takata, T.; 5% (Ph3SiO)zCrOz, RT
OSiMe3 4 eq. 70% 1-BuOOH
;s
CHzC12
Muzart.; Ajjou, A.N. SynLert, 1991, 497.
4
OH
Me
Hirano, M.; Oose, M.;
Y OH
63%
-
97%
Q0
oxone, CHzClz "wetA1203"
80%
25"C, 2 h
Me
Bull. Chem. SOC.Jpn., 1991, 64, 1046.
CrO3 , "wetAl2O3" , 15 h
*
hexane 0 H h o , M.; Nagasawa, S.; Jvlorimoto. T, Bull. Chem. SOC.Jpn., 1991, 64, 2857.
95%
224
Compendium of Organic Synthetic Methods, Vo18
>:
4
Section 168
,TFP
CHzClz,20min * -20°C Metlo, R.; Cassidei, L.; Fiorentino, M.; Fusco, C.; Hummer, W.; JHger, V.; Chem. Soc., 1991, 113, 2205.
a J. Am.
NMO , CHzClZ MS 4A. TPAP
HO
0
P A P = tetra-n-butylammoniumpermthenate
Miranda Moreno, M.J.S.; S&M&&L;
75430%
Camps Neves, A.S. Tetrahedron Lett., 1991, 32, 3201.
also - aldehydes from R-CH20TMS Piva.0.; Amougay, A.; Pete, J-P.Tetrahedron Letf., 1991, 32, 3993. 9
io+n-C,F7
-fOH
7
n-C4F; F t CFCI,, 0°C RT , 9 h DesMarteau, D.D.; Petrov, V.A.; Montanari, V.;Pregnolato, M.;&a&&. 1992, 33, 7245. PdC12(PPhj)2, DME Ti(OiPr)4 ,Zn(acac)Z
OH
120°C. 18 h
Itoh, K.; Hamaguchi, N.;
98%
Tetrahedron Lett.,
ph51%
; Nomura, M. J. Chem. Soc., Perkin Trans. I, 1992, 2833.
Firouzabadi. K; Sharifi, A. Synthesis, 1992, 999.
Section 168
Ketones from Alcohois
03 OH
RuCI2(PPh3)3 acetone , 1 h
(IIIWO)
225
-
91%
Wang, G-Z.; Backvall, J-E. 1. Chem. SOC., Chem. Commun., 1992, 337.
@
20% SbCl5,2OoC, 3 h
83%
- -
Harada, T.; Mukaiyama, T. Chem. Lett., 1992.81.
CuBr2 - LiOt-Bu , THF , RT
-
94%
also for preparation of aldehydes from 1' alcohols
Yamaguchi, J.; Yamamoto, S.; Takeda. T, Chem. Lett.. 1992, 1185.
9NC'k0
C1-N
k Yc1
0
OH
Py ,acetone
-
0
G.A.; Nalbandy, M. Synth. Commun., 1992, 22, 1589.
REVIEWS :
"Synthetic Oxidations with Hypochlorites"
Skarzewskl.,Siedlecka, R. Org. Prep. Proceed. lnt.. 1992, 2 4 , 6 2 5 . Related Methods: Section 48 (Aldehydes from Alcohols and Phenols).
SECTION 169: KETONES FROM ALDEHYDES CHO 1. 1.5 eq. AlMez(BHT)(OEt2) PhMe , 1.Sh
BHT = 2,6-di-t-buty1-4-methylphenol Power, M.B.; Barron. Mi. Tetrahedron Lett., 1990, 31, 323.
quant.
85%
226
Compendium of Organic Synthetic Methods, Vol8
Section 169
CO~(CO)E, PY,12 h stainless steel autoclave (CO:H2 - 10 MPa)
PhLCHo
60%
Fontaine, M.; Noels. A.F.; Demonceau, A.; Hubert, A.J. Tetrahedron Lett., 1990. 31, 3117.
fi
1. BuLi , t-BuONa
THF , -78°C
MEM OBn
2. Me1 , -78°C
OBn
n
also reacts with aldehydes
97%
Lloshutz.;Garcia, E. Tetrahedron Lett., 1990, 31, 7261.
@-o
0
, c o , 200°C
PhCHO
R U ~ ( C O )48 I ~h,
Kondo, T.; Akazome, M.; Tsuji, Y.;
l!mmkJ,
50%
J. Org. Chem., 1990, 55, 1286.
1. (MejSi)zC(Li)OMe THF
n-C9HlGH0
2. HCI ,aq. THF
-
0 n-C9H19
75%
Yoshida.; Matsunaga, S.;Ishichi, Y.; Maekawa, T.; ISQLLJ. Org. Chem., 1991. 56, 1307.
Me3Si0 Ph
0
PhCHO
Me
iPro 0
C02H
20% &l O+C0,H*BH3-THF OiPr
OH
OSiMe3
P h v P h ph
86%
(955 erythro:threo) (85% ee , R)
Furuta, K.; Maruyama, T.; Yamamoto. H,J. Am. Chem. SOC.,1991. 113, 1041.
Ketones from Amides
Section 171
SECTION 170:
227
KETONES FROM ALKYLS, METHYLENES AND ARYLS
This section lists examples of the reaction, R-CH2-R'
0 --L C0,Et
2
R(C=O)-R'.
+CO,Et
CHlClz , 0°C 2. TEA, PhH , 2 5 T
0
good yield
Hoffman. R.V,; Kim, H-0.; Wilson, A.L. J. Org. Chem., 1990, 55, 2820.
SECTION 171: KETONES FROM AMIDES 0
n-C6H f N . OMe Me
Bergman, R.; Nilsson, B.;
Ms
(y
1.
ether
9
RT
2. H2O 3. wet silica 86% Tetrahedron Left.,1990, 31, 2783.
1. TFAA , DCE
2.6-di-t-butyl-4-methyl pyridine
2. 83OC
H
3. H20/CC14, reflux
88%
(98% ee)
Chen, L.; Ghosez. L, Tetrahedron Lett., 1990, 31, 4461. I-BuLi ,THF -7WC -+ -20°C
he
Souchet.;Clark, R.D. SynLeft, 1990, 151.
1
Ph
NEtz
1. sec-BuLi , TMEDA 2.
OBr
CHO
3. t-BuLi ; -78T -+ RT 4. air
Wang, X.; Snieckus. \L SynLett, 1990, 313.
*
& /
0
60%
Section 172
Compendium of Organic Synthetic Methods, V 01 8
228
.OMe
MeQNli;" Me'
1.5 eq. PhMgBr ,THF
0°C , 1 h
Me
0
4 eq. PhMgBr ,65OC, 7 h
0
* p h f l N OMe 95% 0 Me
-
+
21%
P+Ph 62%
Sibi. MP,;Sharma, R.; Paulson, K.L. Tetrahedron Letr., 1992, 33, 1941.
SECTION 172: KETONES FROM AMINES 1. H2, TFA, PtO2
2. Me1
3. Na , EtOH 4. H20 Stevens, R.V.; Canarv. J.W, J. Org. Chem., 1990, 55, 2237.
Me
#N-NMe*
MMPP-6 H 2 0 , MeOH pH 7 buffer, 0°C , 5 min
0
0
76%
MMPP = magnesium monoperoxyphthalate Bnders, D,; Plant, A. SynLert, 1990, 725.
Ph
-T
N-J Pi
1. PhCH=NPh , DMF t-BuOK, 75°C * 2. aq. H+
+
7 N-H PK
P h r P h 0
94% Paventi, M.; Hav. A S , Tetrahedron Lett., 1991, 32, 1617.
PhYPh
Fe(C104)3, MeCN
"OH
Ir
PhKPh II
0
79%
Kumar, H.; Kaur, B.; Kumar. B. Ind. J. Chem., 1991, 308,849.
Ph
PhIClz , Py , CHC13
FN-OH
1O"C, 3 h Radhakrishna, AS.; Augustine, B.; Sivaprakash, K.; 1473.
75%
Synth. Commun., 1991, 21,
Ph)= Me
229
Ketones from Esters
Section 173
6 eq. KHSO5 ,acetone
N- N H n
0 PhlMe
99%
10°C. 24 h * Synth. Commun., 1992, 22, 1583.
Jung, J.C.; Kim, K.S.;
DMSO , Me3SiCl MeCN , reflux
Ph
e
Ph
0 , , ) ,
98%
Ghelfi, F.; Grandi. R,; Pagnoni, U.M. Synth. Commun., 1992, 22, 1845.
0
2 eq. (Me$i0)2CrO2
N-OH
CH2C12
Lee., Kwak, K.H.; Hwang, J.P. Synrfi. Commun., 1992, 22, 2425. N - N H T ~ Na2C03- 2 H202 ,4OoC * DMF - H20 PhA Me Narayana, C.; Reddy, N.K.;
Ph
quant.
i
82%
Me
Synth. Commun., 1992, 22, 2587.
SECTION 173: KETONES FROM ESTERS 02CEt
Bacillus coagulans 0.2 M phosphate buffer pH 6.5, 30°C, 18 h
BnO
BnO
OBll
26% (95% ee) Matsumoto, K.; Suzuki, N.; Q&I,H,Tetrahedron Lett., 1990. 31, 7159. AI(SiMe3)3 , THF 1.1eq. CuCN , 0°C +
Ph
Me
57% (42% ee)
0 Me
SiMe3
82%
Nakada, M.; Nakamura, S.; Kobayashi, S.; Ohno. M, Tetrahedron Lett., 1991, 32,4929. OSiMel
Ph-0
K 0
C1
4
Ph
-,AgOTf
CH2C12
*
Phd P h
87% Takeda. K,; Ayabe, A.; Kawashima, H.; Harigaya, Y . Tetrahedron Lett., 1992, 33, 951.
230
Compendium of Organic Synthetic Methods, Vo18
1. 1.4 Fez(C0)g ,ether 2. BF3*OEt2,CHzC12
OAc
0 OSiMe3
h C O , E t
3. Me3N-O
Section 174
EC0& 71%
(1 :1 diastereomer ratio) Qggn. J.R;Carroll, M.K. Tetrahedron Lerf., 1991, 32, 1141.
DCA (h = 450 nm) MeCN [photoinduced electronic transfer]
ph3
Me3Si0
*
38%
DCA = 9 . 1 0 - d i c y a n o a n t e
Tetrahedron Left., 1992, 33, 1973.
Heidbreder, A.;
L
Pichia farinosa 0.2 phosphate buffer pH6.5,30min
*
b+& S
74% (55% ee) Kume, Y.;
23%
Tetrahedron Len., 1992, 33, 6367.
SECTION 174:
KETONES FROM ETHERS, EPOXIDES AND THIOETHERS
Meom AgOTf
SPhSPh
-;-
CHZC12
Ausr. J. Chem., 1990, 43, 815.
Chen, K.; Koser. G.F. J. Org. Chem., 1991, 56, 5764.
95%
0
Ketones from Halides
Section 175
23 1
t-BuMe,SiO MeCN , 0°C
+
*
1)
(>20
Snider. B.B.; Kwon,T. J. Org. Chem., 1990, 55, 4786.
87%
BnBr , THF , 2 0 T Bu4N+(Ph3SnFzJ 6h
99%
.
Ginma.. M, Tetrahedron Lett., 1991, 32, 7381.
OSiMeB
AgOzCCF3, BuI CHzC12 -78°C -+ 25°C
*
a:u 56%
Jefford, C.W.; Sledeski, A.W.; Lelandais, P.; Boukouvalas, J. Tefrahedron Lett., 1992, 33, 1855.
SECTION 175:
KETONES FROM HALIDES AND SULFONATES
&
Reid.; Reny Runge, J.M.Tetrahedron Lett., 1990, 31, 1093. Br
=/OBu ,
NEt3
91%
Me
TIOAc , DMF 100°C , dppe 91% Cabri.;Candiani, I.; Bedeschi, A.; Santi, R. Tetrahedron Lett., 1991, 32, 1753. I . Zn* ;CuCN.2 LiBr
" 2. BzCl also for conjugate addition Zn* = ZnCl2Li naphth. reaclions and reaction with ArX Zhu, L.; Wehmeyer R.M.; &&g. R.D. .I. Org. Cherii., 1991, 56, 1445.
92%
0
232
Section 175
Compendium of Organic Synthetic Methods, Vol8
n Me Kraus. G .At; Hansen, J. SynLett, 1990, 483. OBu
, Pd(0Ac)z PhxMe dppp , NEt3 , DMF * 0 90% 80"C, 3 h 2. H+ Cabn.;Candiani, I.; Bedeschi, A.; Pence, S.; Santi, R. J. Org. Chem., 1992, 57, 1481.
Ph-oTf
1.
=/
S02Tol t-BuOK ,THF , -78°C
81% 3740.
D.R; Robinson, LA.; Amato, G.S.; Osterhout, M.H. J. Org. Chern.. 1992, 57, 1. Li ,ZnCl2 , 0°C
UBr
2. C13CCOCI ))I)))) = O"C+ 23°C Core?. E J.; Link, J.O. Tetrahedron Lett., 1992, 33, 3435. /
/
1.
4
n-Ck!H17,B
mCC 82%
, I - B u - N S , K3P04
Pd(PPh3h
+
2. H3O+
0 Ph'Lc n-C*H,, 97%
Ishiyama, T.; Oh-e, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett., 1992, 33,4465. Related Methods:
Section 177 (Ketones from Ketones). Section 55 (Aldehydes from Halides).
Ketones from Hydndes
Section 176
233
SECTION 176: KETONES FROM HYDRIDES This section lists examples of the replacement of hydrogen by ketonic groups, R-H + R(C=O)-R'. For the oxidation of methylenes, R2CH2 -+ R2C=O, see section 170 (Ketones from Alkyls).
(y N
-
O'K 0 CF3
AICl3
F3C
sM Qo H
61%
Shimada, M.; Takahashi, M.; Kitajima, H. Chem. Left., 1990, 783.
;-
Asvanpar.;Lahoti, R.J.; Srinivasan, K.V.; Daniel, T. Synthesis, 1991, 322.
ArMe gives ArcHO Firouzabadi. H,; Salehi, P.; Sardarian, A.R.; Seddighi, M. Synrh. Commun., 1991, 21, 1121.
xi
n-CsH11 0
n-CsH11
10%GaC13,20% AgC104 CH2C12, RT ,20 h
Me0
n-C5H 1 1
Me0
91%
Mukaiyama, T.; Ohno, T.; Nishimura, T.; Suda, S.; Kobayashi, S. Chem. Left., 1991, 1059.
Ph-
Ph
t-BuOOH Cr-pillared montmorillonite
0
* p h A ph
90%
Choudarv. B.M.; Prasad, A.D.; Bhuma, V.; Swapna, V. J. Org. Chem., 1992, 57, 5841. A c ~ OCH2C12 , 4% SbCl5 ,30 min
1 eq. LiC104
MeOO -Me 89%
Mukaiyama, T.; Suzuki, K.; Han, J.S.; Kobayashi, S. Chem. Lett., 1992, 435
234
Section 177
Compendium of Organic Synthetic Methods, Vol8
SECTION 177: KETONES FROM KETONES This section contains alkylations of ketones and protected ketones, ketone transpositions and annulations, ring expansions and ring openings and dimerizations. Conjugate reductions and Michael alkylations of enone are listed in Section 74 (Alkyls from Alkenes).
For the preparation of enamines or imines from ketones, see Section 356 (Amine-Alkene).
Do
Me
excess Me1 ,DMSO
KOH (solid) 60°C
M e Me 90% Langhals, E.; Lanehals. H, Tetrahedron Lett., 1990, 31, 859.
<siMe3
m:u
PhMe.4; ~
~
0
74%
1
6
Bu SPh also with Cr(C0)6 Choi, Y.R.; Kim,B.J.; Jeong, J.U.; Lee, S.; Lee, J.H.; Pyun, C. Tetrahedron Lett.,
m;
1990, 31, 2713.
1. Pb(OAc)4, Hg(0Ac)z ,CHC13
PhB(0H)Z 2. py '
-
$c,,
&E02Et
774
Morgan, J.; Pinhev. J.T,J. Chem. Sac., Perkin Trans. I, 1990, 715. 1. hv ,hexane 2. 150°C
Me
-+ 45%
-M.;Arai, M.; Nishizawa, K.; Hasegawa, T. J. Chem. SOC.,Chem. Commun., 1990, 374.
1. LDA , THF , -78°C 2. BuLi , -78°C -+ 0°C
3.n-CsH11Br -78"~3 -20°C 71% A u-n Nakahira, H.; Rvu. L;Ikebe, M.; Kanbe, N.; Sonoda. N,Angew. Chem. Int. Ed. Engl., 1991, 30, 177.
SnBu3
Section 177
Ketones from Ketones
OSiMe, I
235
0
1. Meti-LiBr ,ether
II
(92% ee , R)
3. BnBr , PhMe
Murakata, M.; Nakajima, M.; %ma. & J. Chern. Soc., Chern. Conmun., 1990, 1657.
0
1.2.5 LDA , THF 10 HMPA , O°C
0
Me
2. Me1 , -78°C
Me Me
R = Li
s95 80 >95
= Bn
= Bz
5 20
(34%) (90%)
5
(79%)
Mdhrvev. G.J.; Andersen, M.W. Teirahedron Lett., 1990, 31, 4569. CDCN , KF.2 1120 (Ph3SnbTeI5 h
Li, C-J.;
m.D.N Tetrahedron Lett., 1991, 32, 1545. anhydrous FeC13 on S i 0 2 , CH2C12
mo
8
63%
Patnev. H.K. Tetrahedron Lett., 1991, 32, 2259.
+g,, 0
Rhz(OAc), , RT CHzClz, 12 h
+ +
Me
0
85%
Sonawane. H.R,; Bellur, N.S.; Ahuja, J.R.; Kulkami, D.G. .I. Org. Chern., 1991, 56, 1434.
6 0
1. "-N(h
,DMI;
NEti , 3 h , h v (sunlamp) 2.H30'
Russell. G.A.; Wang, K. J. Org. Cbent., 1991, 56, 3475.
90%
Compendium of Organic Synthetic Methods, Vol8
236
Section 177
SmI2, THF ,DMPA
DMPU = 1,3-dirnethyl-3,4,5,6-tetrahydro-2( 1H)-pyrimidinone Batey, R.A.; bbhawell. W.B. Tetrahedron Lett., 1991, 32, 6211,6649.
*Q+w
reflux
slow addition (7-10 h)
18% 0
of 3.3 eq. BusSnH with
0 74% AIBN to PhH Dowd. P.; Zhang, W. J. Am. Chem. Soc., 1991, 113, 9875. Zhang, W . ;Dowd. P. Tetrahedron Lett., 1992, 33, 3285. 0
M~
1. EtAlCh , CHzC12
RT,16h
-
2. H 2 0
H Fujiwara, T.; Tomaru, J.; Suda, A.; Se , H 2 0 , DBU CO (30 atm) , 120°C
P
h 0
b
24 h
33. 6347.
Do 77%
H
(93:7 cis:trans)
Tetrahedron Lett., 1992. 3332583.
L + PhM
Ph
10%
m; Inoue, J.; Teranishi, K.; Moriwaki, M.; . .
82%
Tetrahedron Lett., 1992, 33, 331 1.
LaumLLL;
3%
Tetrahedron k t t . , 1992,
Satoh, T.; Itoh, N.; Gengyo, K.; Yamakawa. K , Tetrahedron Letf.. 1992, 33, 7543.
Section 179
Ketones from Alkenes
aC>
237
Related Methods: Section 49 (Aldehydes from Aldehydes).
SECTION 178: KETONES FROM NITRILES
N
1. Cp2Zr-propyleneI"Cj~Zr" 2. H30'
-
-is
d
M Ts
e 54%
Mori. M.; Uesaka, N.; Shibasaki, M. .I. Chem. SOC.,Chetn. Cornmun., 1990, 1222.
SECTION 179: KETONES FROM ALKENES 2% Pd(OAc)z, aq. MeCN 90% benzoquinone
0.24M ~
*Y 1 0 ~
~
82%
Miller, D.G.; Wavner. D.D.M.J. Org. Chem., 1990, 55, 2924.
Eilbracht.;Hiittmann, G-E. Chem. Ber., 1990, 123, 1053. Ellbracht.;Hiittmann, G-E.; Deullen, R. Chem. Ber., 1990, 123, 1 0 6 3 . cat. RuO2 ,MeCHO , 3 h acetone , 0 2 ,40°C pyromellitic acid
*
0""
77%
pyromellitic acid = 1,2,4,5-benzenetetracarboxylicacid
Kaneda. K.; Haruna S.; Imanaka. T.; Kawamoto, K. J. Chem. SOC., Chem. Cornmun., 1990, 1467 CO (75 atm) , 80°C, 3 h Bu3SnH, AIBN ,PhH
0.05 M (32:68
ZE)
&LL;Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda. N, J. Chem. Soc.. Chetn. Cornmun., 1992, 1018.
238
Compendium of Organic Synthetic Methods, Vol8
1. BH-j-THF ,THF ,2"C
2. PCC, CH2C12, reflux
Parish.;Parish, S . ; Honda, H. Synth.
/\/\/\// Ishiyama, T.; Miyama, N.;
-
Section 180
0, 77%
Commun., 1990, 20, 3265.
1.9-BBN 2. CO ,n-GH13I
x
.c
Pd(PPh3)4, hv K3P04, PhH ,RT 24 h
n-C6H 1 3
n-C8H 1 7
67%
Tetrahedron Lett.. 1991, 32,6923.
[PdCl(NO-J(MeCN)2] \CyCl2;32;p,4 m \ + \
15% CHO 48% DPA = N,N-diethyl pivaloyi chloride Kiers, N.H.; Ferinm. B.L.; van Leeuwen, P.W.N.M. Tetrahedron Lett., 1992, 33, 2403.
See also: Section 134 (Ethers from Alkenes).
SECTION 180:
Section 174 (Ketones from Ethers).
KETONES FROM MISCELLANEOUS COMPOUNDS
Conjugate reductions and reductive alkylations of enones are listed in Section 74 (Alkyls from Alkenes). Ketones from oximes are listed here.
gMe
Takeda, K.; Torii, K.; Qgura. H, Tetrahedron Lett., 2990, 31, 265. TMSCl ,NaNO2 ,CC4 5% Aliquat 336 , RT , 5 h
&Me 95%
Lee. J.G,; Kwak, K.H.; Hwang, J.P. Tetrahedron Lett., 1990, 31, 6677.
Me&
bc.0 H
1. PhCeCI2, THF , -78°C 2. aq. NH4CI. -78°C -+ RT
0 * Me3SidPh
Kits.; Matsuda, S.; Kitagaki, S.; Tsuzuki, Y.;Akai, S. SynLett, 1991, 401.
79%
Section 180A
MeO.
Protection of Ketones
1
239
Li, THF
"OMe
-78"C+ 22°C 2. B u t i , -78°C 422°C
h e Me
99%
Whipple, W.L.; Reich. HJ. J. Org. Chem, 1991, 56, 2911. 1. PhCH=CFZ 2. Ni(R)
W N . @
>q H "'
0
0
29%
Ph'
Purrineton.~.~.; Sheu, K-W. Tefrahedron Lett., 1992, 33, 3289. 1. c02 2. PhLi
3.aq. NH4CI Zadel, G.;
92%
Angew. Chem. lnt. Ed. Engl., 1992,31, 1035.
SECTION 180A: PROTECTION OF KETONES e' , wet MeCN Ptanode.1.30V
sUs
70% Martre, A-M.; Mousset. G,; Be1 Rhlid, R.; Veschambre, H. Tetrahedron Lett., 1990, 31, 2599.
0;:
10% SiH212, CHCI3 -42oc, l m i n
99% Keinan. EL;Perez, D.; Sahai, M.; Shvily, R. J. Org. Chent.. 1990, 55, 2927.
0
[ZrOcl2*8 H 2 0 , aq. NaOHl ethylene glycol
74%
W a k i . M,; Takahashi, K.; Kuno, H.; Matsushita, H. Bull. Chern. Soc. Jpn., 1990, 63, 1258.
240
Compendium of Organic Synthetic Methods, Vo18
SEt
GaC13, MeOH , 0 2
SEt
CH2C12, RT , 2 4 h
*
P
h
Section 180A
o
O
71%
Hashimoto, Y.; Kihara, N.; Umehara, H.; Hasegawa, M. Chem Lett., 1990, 831.
o(3
HSCHzCHzSH, PhMe activated bentonite, 5 h
99%
Miranda, R.; Cervantes, H.; Joseph-Nathan, P. Synth. Commun., 1990, 20, 153. sulfonated charcoal PhH , reflux 98%
Patney, H.K. Tetrahedron Lett., 1991, 32, 413.
Q
2 [EtSH , TeC141 C4H4C12, RT
m,H.; Masumoto, K.; Inamasu, T.; &&i&Tefrahedron , Lett., 1991, 32, 2039. hn (>360 nm) , 0 2
6h
Klunata.;Kato, Y . ; Hasegawa, E. Tetrahedron Lett., 1991, 32, 4349.
n Ph&
Me
1. SbCl=, , CH2C12,O"C 2. aq. NaHC03,O"C w
0
Ph
4Me
Kamata. M.; Otogawa, H.; Hasegawa, E. Tetrahedron Lett., 1991, 32, 7421.
78%
24 1
Protection of Ketones
Section 180A
hydroxy apatite, 1 h (Et0)3SiH , heptane 99% hydroxy apatite = [Ca10(P04)6(OH)21 Izumi., Nanami, H.; Higuchi, K.; Onanaka, M. Tetrahedron Lett., 1991, 32, 4741. 1. TMSOTf , Me2S
CH2Cl2 , -78°C
2. TMSOTf * TMSOCH2CHzOTMS 3. aq. K2CO3
CHO
E
C
H
O 80%
Kim.; Kim, Y.G.; Kim. D. Tetrahedron Letr., 1992, 33, 2565. acetone-CH2CI2 0°C , 2 4 h
>95% 98% conversion D'Accolti, L.; Fiorentino, M.; Fusco, C.; Adam. W,;Gonzhlez-Nufiez, M.E.; Mello, R. Tetrahedron Lett., 1992, 33, 4225.
w;
Ph
s s''Me3 U
e- (P(electrodes)
t
Ph 9SiMe,
0
NaC104, aq. MeCN
95%
Suda. K,;Watanahe, J.; Takanami, T. Tetrahedron Lett., 1992, 33, 1355.
pS
hv (visible), MeCNIH20 methylene green
*
p i y Me
u; Wang, Q. Tetrahedron Lett., 1992, 33, 5909. ~
G
.
A
Ph
1
91%
Me
.Wang, ; Q. SynLert, 1992, 335.
Ph
SEt
x SEt
DMSO , 140°C.4 h
Me
Rao, Ch.S.; Chandrasekharam, M.;;&&I
t
Ph
2.0
94%
Me
m i p p a . H, Tefruhedron Lett.. 1992, 33, 8163.
See Section 362 (Ester-Alkene) for the formation of enol esters and Section 367 (Ether-Alkenes) for the formation of enol ethers. Many of !he methods in Section 60A (Protection of Aldehydes) are also applicable to ketones.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
13
PREPARATION OF NITRILES
SECTION 181: NITRILES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 182: NITRILES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 183: NITRILES FROM ALCOHOLS AND THIOLS (NiSO&S208-NaOH) NH3, HzO
Ph-OH yamazaki.;Yamazaki,Y. Chem. Lett., 1990, 571.
*
PhCN
82%
SECTION 184: NITRILES FROM ALDEHYDES P h x ' N Moore, J.S.;
NMe,
1. Me1 , 150 min 2. DBU ,25"C
-
Ph3(""
83%
J. Org. Chem., 1990, 55, 3314.
PhCHo 2.5 KZS20g
*
PhCN
+
PhCOOH 11%
82% horn, P.K.; Savre. L.M, Tetrahedron Lett., 1991, 32, 1007.
PhCHO
(NiS04/K2SzOg-NaOH) NH3. HzO
Yamazaki.; Yamazaki, Y. Chem. Left., 1990, 571.
PhCN
76%
Section 187
243
Nitriles from Amines
Mexican Bentonite
PhCHO
rn
PhCN 50% microwaves (2450 MHz) Delgado, F.; Cano, A.C.; Garcfa, 0.: Alvarado, J.; Velasco, L.; Alvarez. C,; Rudler, H. Synth. Commun.,1992, 22, 2125.
SECTION 185: NITRILES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 186: NITRILES FROM AMIDES
0 P h A N V
Ph3PBr2, NEt3, RT CH2C12,lO h
H
c
Ph
89% Walters. M.A,; McDonough, C.S.; Brown, P.S. Jr.; Hwm, A.B. Tetrahedron Lett., 1991, 32, 179. 1. CBr4, PPh3 , MeCN R T + reflux
0 Ph
. )
Ph-CN
NHOMe 2. Zn ,DMF , AcOH reflux
Sakamoto, T.; Mori, H.; Takizawa, M.;
69%
Synthesis, 1991, 750.
SECTION 187: NITRILES FROM AMINES
OH
?!
i
J! H Et
K 0
EtO
l*
2. heat
CN
,MeCN , cat. NJ33 25 "C
-
C t
PM
liL-Ll*
95%
Thomas.;Greyn, H.D. Synthesis, 1990, 129.
GN-OH 4 eq. PPh3,2 eq. CC4
MeCN , RT
c1
$C=N
97%
c1
Kim, J.N.; Chung, K.H.; Rvu. E.K. Synth. Commun.,1990, 20, 2785.
244
Section 191
Compendium of Organic Synthetic Methods, Vol8
KSF , montmorillonite ,PhMe
Phh
b
N- OH
reflux, 15 h Meshram. H.M, Synthesis, 1992, 943.
Ph-C=N
70%
SECTION 188: NITRILES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 189:
NITRILES FROM ETHERS, EPOXIDES AND THIOETHERS
M e 0 OMe Ph Ph
TMS-CM , RT , 5 h [Rh(COD)CI]z
Me0 CN 86% Ph + p h T,Bull. Chem. SOC.Jpn.,
Soga, T.; Takenoshita, H.; Yamada, M.; Han, J.S.; -a.
1991, 64, 1108.
Mukaiyama, T.; Takenoshita, H.; Yamada, M.; Soga, T. Chem. Lett., 2990,229 (Z product].
SECTION 190: NITRILES FROM HALIDES AND SULFONATES 2 eq. KCN ,dppf ,NMP 2% Pd2(dba)3*CHC13
*
0..
96%
Takaei.~.; Sasaki, K.; Sakakibara, Y. Bull. Chem. SOC.Jpn., 1991, 64, 1118. SECTION 191: NITRILES FROM HYDRIDES AICI3, CS2 -70°C + 0°C
L
CEN 51%
Bultke, K.; Reiher, T.;
-
0
Synth. Commun., 1992. 22, 2231.
SECTION 192: NITRILES FROM KETONES Preparations of nitriles from oximes and hydrazones, which are ketone derivatives, are found in Section 195. NO ADDITIONAL EXAMPLES
245
Nitriles from Miscellaneous
Section 195
SECTION 193: NITRILES FROM NITRILES Conjugate reductions and Michael alkylations of alkene nitriles are found in Section 74D (Alkyls from Alkenes). HCHO , H2 (CO) , DMF cat. R u ~ ( C O ) I Z230°C , * 16 h
Ph 7CN
86%
CN
Chem. Lett., 1990, 765.
A h , F.; Hayashi, T.;
Rhodococcus phosphate buffer butanica *
A
Ph*Me
P
C
N +
P
3OoC, 3 h
C /
0.1% substrate 56% (27% ee)
30% (95% ee)
Kakeya, H.; Sakai, N.; Sugai, T.; Q h J L Tetrahedron Lett., 1991, 32, 1343. K2C02, EtBr
Ph-CN
c
Ph
1"+
Et
PhfCN
Et
Et 16% 58% Xu. C.Z.; Mao, X.J.;Shen, H.B.; Chen, W.Q. Org. Prep. Proceed. lnt., 1991, 23, 153.
SECTION 194: NITRILES FROM ALKENES NO ADDITIONAL EXAMPLES
SECTION 195:
NITRILES FROM MISCELLANEOUS COMPOUNDS
The preparation of nitriles from oximes and other compounds are presented here.
Ph
xN.
OH
1. AII3 , MeCN 82°C , 2 h
2. H 2 0
c
Ph- C=N
92%
Konwar, D.; B o ~ a hR.C.; , Sandhu. J.S. Tetrahedron Lett., 1990, 31, 1063.
N
246
Compendium of Organic Synthetic Methods, Vol8
Section 195
Sn(SPh), , PBu3 , DEAD
n-C11H23
n-CiIH23-CN
DMAP , CHzClz ,(lo(? 10 min Urpi, F.; Vilarrasa, J. Tetrahedron Lett., 1990, 31, 7499.
0-
N.NHBz
98%
e- (0.7 V) ,2.2F/mol NaCN ,MeOH Pt electrodes
- OCN 70%
Okimoto, M.; f2hihaL J. Org. Chem., 1990, 55, 1070.
Ph-N=(
c1 c1
e- , Hg cathode, Pt anode DMELiCIO4, Na2C03 15°C
c
Ph- NEC
91%
Gulrado.;Zapata, A.; Fenor, M. Tetrahedron Lett., 1992, 33,4119. REVIEWS :
"TheIsocyanide-CyanideRearrangement;Mechanism and Preparative Applications" Meier, M.; Haaf, K.; Pakusch, J.; Wolber, E.K.A.; Miiller, B. Angew. Chem. Inf. Ed. Engl., 1991, 30, 893.
;-
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
14
OF ALKENES
PREPARATION
SECTION 196: ALKENES FROM ALKYNES n-C5H11 - CE C-n-C5H
1. M l 5 , HMPARHF PE T a c h , Zn ,DMElPhH
2. aq. NaOH
n-C5Hl n - C 5 ~ I , d
Nb 74% (>99:1 2:E) Ta 85% (>99:1 Z:E) Kataoka Y.; Takai. IL;Dshima. K.; Utimoto. K Tetrahedron Lett., 1990, 31, 365. 1. t-BuLi , hexane/ether -78°C -+ 25°C
<'c
b
2.H20
SiMe3
Wu, G.;Cederbaum, F.E.; &&hjJ.
SiMe,
95%
Tetrahedron Letf., 1990, 31,493.
Ph
l.t-BuLi, -78°C pentane/ether
/
2. -78"C, l h
+
/
&Jh
+
I
88% 6% v. W.F.; Ovaska, T.V.Tetrahedron Lett., 1990, 31, 627.
-
,OH
PhMe2SM, THF 2h
PhMe2SiwOH
Ph
6%
-k
cat. C Y ~ P - P ~ [ - C H ~ = C H ~ ] ~(5.2 82% M u m h v . P r o c t e r , G . Tetrahedron Lett., 2990, 31, 1051.
1)
SiMezPh
248
Section 196
Compendium of Organic Synthetic Methods, Vo18
/ Br--C
Bu3SnH PhH , 8OoC *
9""
-
C3 C- SiMe,
0.5 [(PPh3)c~iH]6
Ph- CE C-Ph
5 H 2 0 , PhH , reflux 1.5 h
SiMe,
16%
tandem cyclizations Kilbum.J.D. Tetrahedron Len, 1990, 31, 2193.
*
Ph
Ph
w
91%
Daeuble, J.F.; McGettigan, C.; Strvker. J.M., Tetrahedron Lett., 1990, 31, 2397.
OTMS M< Me3Si-Si-CzC7( Mi Me Me
me351
FeC13 A
MqSiCl
CMezSi
Me
kc+Me 82%
Tetrahedron Lett.. 1990, 31, 5607.
Bu3SnHt THF (MeCNhMo(C0)y
n-C3H&: C- n-C3H7
(a-al1yl)Br
-
AnBu3
n-C3H7
n-C3H7
95%
Zhang, H.X.; GuiM. F,; Balavoine, G. .I. Org. Chem., 1990, 55, 1857. [PhMgBrlLnCI,]
I
C
Me Ph Me Wang, R-T.; Chou, F-L.; J.uo.F-T.J. Org. Chem., 1990, 55, 4846.
Hooc-,ph
68%
V o c 1 3 , PhCl , reflux 70 h ,proton sponge
Meier, I.K.; Schwartz. J, J. Org. Chem., 1990, 55, 5619.
n-C,H,,-CE C-H
Zn , 1,2-dibromoethane EtOH , 1 h
Aerrsens, M.H.P.J.; van der Heiden, R.; Heus, M.: 3421.
n-C6H13\
>90%
Synth. Cornmun., 1990, 20,
Alkenes from Alkynes
Section 196
X
F Zc-( Me
~ - C ~ H I
-
n-GHis R,Sn
F
C*
H Me
249
+
n-C7Hl$flrC--(
Bu3SnLi. THF ,78"C X=Br, R=Bu (50 MqSnCuBrLi ,THF X = OTs, R=Me (100 Marshall. J.A.; Wang,X J. Org. Chem., 1990, 55, 6246.
50) 0)
SnR,
Me
67% 75%
1.2 ea. DibaJ
(8020 Z:E) Kuchin, A.V.; Markova, S.A.; Gorobets, E.V.: Tolstikov, G.A. Izv. Akad. Nauk. SSSR,1990, 39, 1151 (Engl., p. 1034). 1. Bu3SnSiMe3, THF cat. Pd(PPh3)4 , 60°C
Ph-
'%Me3
Ph-
CEC-H 2. HI , Bu4NI , PhMe 0°C Mori. M,; Watanabe, N.; Kaneta, N.;Shibasaki, M. Chem. Lett., 1991, 1615.
(>99
1)
9
90%
59%
Inanaea.,Yokoyma, Y.; Baba, Y.; Yamaguchi, M. Tetrahedron Lett., 1991, 32, 5559.
(p
Bu3SnH , LiCl , DMF 5% Pd(PPh3)4 , 60°C
OTf
C.H
8h
Bu
Luo. F-T,; Wang, R-T.Tetrahedron Left., 1991, 32, 1103. 1. HB(c-C6H11)2,THF
Ph- C: C- SiMe,
Ph
0°C 4 25°C
w
2. PhBr , THF , NaOH Pd(PPh314, reflux 3. NaOH ,H202
phr-( SiMe,
Soderauist. J.A; Le6n-C016n, G. Tetrahedron Lett., 1991,32,43.
40%
57%
250
Compendium of Organic Synthetic Methods, Vo18
P h . C : C n B r
Section 196
1.5 eq. S d z , THF,24 h
60%
reflux
Bennett.;Larouche, D. SynLett, 1991, 805. 7% Co(acac)3 , dppe 6 eq. Et2AlCl
CEC-H
78%
Lautens.;Tam, W.; Edwards, L.G. J. Org. Chem., 2992,57,8. n-C3H,-CE C- H
1. cat. Zr porphyrin Et3A1, 55 h
- n-C3H7F
2. Ht
Shibata, K.; Aida, T.; Jnoue. S , Tetrahedron Lett., 1992, 33, 1077.
26%
Et
CpzZr(H)CI , THF
u s h u t z . B.H,; Keil, R.; Barton, J.C. Tetrahedron Lett., 1992, 33, 5861. u t z . B.H.; Keil, R.; Ellsworrh, E.L. TetrahedronLett., 2990, 31, 7257.
Ph
Ph
1.4 eq. Mg ,THF 2. Cp2TiCI2,CH2CI2
(5
Ph
I.,
C (96
Harms, A.E.; &&J&
4)
42%
Tetrahedron Left.,1992, 33, 6565. 1. TMSCl ,Nal ,H20
H- CI C- Ph
MeCN
+
2. BuZnCl ,cat. Pd(PPh&
Ph
*
B~
54%
Luo.; Fwu, S-L.; Huang, W-S. TetrahedronLett., 1992, 33, 6839.
Tour. J . K ; Pendalwar, S.L.; Kafka, C.M.; Cooper, J.P. J. Org. Chem., 1992, 57, 4786.
Alkenes from Alcohols
Section 198
25 I
SECTION 197: ALKENES FROM ACID DERIVATIVES 10 eq. Tic13 , THF
PhKC1 0
5 eq. LiAlH4,ll h
w
Ph
Ph
Ph
+
+
w
18% Ph
74% Bull. SOC.Chim. Belg., 1991, 100, 375,
Dang, Y.;
SECTION 198: ALKENES FROM ALCOHOLS AND THIOLS 1. TMSCl , HMDS
2. L i t NH3 3. NH4CI
Ballester, P.; Cap4 M.;
Ph G
02s P
-
a J.M. Tetrahedron Lett., 1990, 31, 1339. h
SmI2, THF
--
’
Ph
Ph
)” Me’
Nd
82%
Kende. AS,; Mendoza, J.S.Tetrahedron Lett., 1990, 31, 7105.
phbCH0
1. Me3GeCH2C02bBuLDA THF , -78°C 2. H20, -78°C 3. BF3aOEt2, CH2C12 , 4 h
also with ketones Inoue, S . A m . L J. Org. Chem., 1991, 56, 437.
kH
n-C16H33
BF3aOEt2, CHzClz 25°C. 10 min
*
E:Z)
(8:l
P
h
’ w
C02t-Bu 80%
ny33 7” (79:21 E:Z)
+
(95
5)
90%
Posner. ; Shulman-Roskes,E.M.; Oh, C.H.; Carry, J-C.; Green, J.V.;Clark, A.B.; Dai. H.; Anjeh, T.E.N. Tetrahedron Lett., 1991, 32, 6489.
Compendium of Organic Synthetic Methods, Vol8
252
0
EtO- OEt p - c1
CbzHN C O B . NaH ,THF 0 Berti, F.; Ebert.;Gardossi, L. Tetrahedron Lett.,
* CbzHN
SECTION 199: ALKENES FROM ALDEHYDES
PhCHO
t
-
QOBn
1992, 33, 8145.
(Me$i)2CHPh , TASF C H g l z , 2OoC, 1 h
Section 199
Ph
0
75%
Ph
92% (E:Z = 1:l)
TASF = tris-(dimethylamino)-sulfonium difluorotrimethyl siliconate Palorno.;Aizpurua, J.M.; Garcia, J.M.; Ganboa, I.; Cossio, F.P.; Lecea, B.; L6pez. C. J. Org. Chem., 1990, 55, 2498.
1. BuzTe , THF, 80°C 2. PhCHO
0
Ph3P-CHZI
Y -7.;Shi, L-L. Chem. Ber.,
Li, S-W.;
0
58%
1990, 123, 1441.
0
T.Synktt, 1990, 322.
PhCHO , BuLi , PhH 5 min
ph;3
Ph-CHzCH,
Ph3PMe Br , Na t-amyl alcohol mesitylene ,reflux
4CHO Tsunoda, T.; JIudlickv.
c
1 ) ) ) ) ) ) ) )
63%
- 3 .2 Ph
3) quant. Ph
(1
Low. C.M&SynLett,
1991, 123.
SiMe,Ph
YSnBu3
1. BuLi , THF ooc
j~~
2. TFA ,THF , RT 12 h
w
5 1% (61:39 cis:trans) Barrett. A.G.M,; Hill, J.M. Tetrahedron Lett., 1991, 32, 3285.
(from hexanal)
nC5H I 1
Alkenes from Aldehydes
Section 199
PhCHO
+ M~/”
253
ZnBr2, BuLi
ZnBr
Ph
Me
Ph
i+ NMez
68%
(86% ee , S)
HO
Qp-mlzer. W.; Radinov, R.N. Tetrahedron Lett., 1991, 32, 5717.
79%
Afonso, C.A.M.; Motherwe 11. W.B,; O’Shea, D.M.; Roberts, L.R. Tetrahedron Lelt., 1992, 33, 3899.
0
1. LDA ,
P h ’ S y F
Ph
. MsCl ,NEt3 3 . 3 eq. BuLi
F
70% Satoh, T.; Itoh, N.; On&, K.; Kitoh, Y . ; Yamakawa. K, Tetrahedron Lett., 1992, 33, 1483.
CHO
BugSnCHBr2, LiI CIc12, DMF , THF 25OC
Hodpson. D.M. Tetrahedron Lett., 1992, 33, 5603.
--
NbCl5, MeLi ,DME
PhCHO
Ph-Ph
quant.
Kauffmann. T.; Kallweit, H. Chem. Ber., 1992, 125, 149. Related Methods: Section 207 (Alkenes from Ketones).
SECTION 200:
ALKENES FROM ALKYLS, METHYLENES AND ARYLS
This section contains dehydrogenations to form alkenes and unsaturated ketones, esters and amides. It also includes the conversion of aromatic rings to alkenes. Reduction of aryls to dienes is found in Section 377 (Alkene-Alkene). Hydrogenation of aryb to alkanes and dehydrogenations to form aryls are included in Section 74 (Alkyls from Alkenes).
254
Section 202
Compendium of Organic Synthetic Methods, Vol8
DCE , MeCCl3 , AIC13 5OoC,30 m h
cr
98%
Ph
SynLett, 1991, 925.
Sonawane. H.& ; Sudalai, A.; Daniel, T.;
SECTION 201: ALKENES FROM AMIDES Section 65 (Alkyls from Alkyk). Section 7 4 (Alkyls from Alkenes).
Related Methods:
Godfrey, A.G.; G a n e m . J . Am. Chem. SOC.,1990, 112, 3717.
SECTION 202: ALKENES FROM AMINES PhMe
&?
&I%
02
Davis. F,A,; Chen, B. J. Org. Chem., 1990, 55, 360.
n-CloH21
Me3Si
&
NH2
1. iAmON0, gl. AcOH %
2. BF3eOEt2
n-CtoH21, w
62%
J. Org. Chem., 1990, 55, 4474,
P
Et02C
Br
CO2Et
Bu3SnH AIBN PhH ,reflux 9
N-NH SO2ME-
ME3 = 2-mesityl
Kim. S ; Cho, J.R SynLert, 1992, 629.
60%
255
Alkenes from Esters
Section 203
SECTION 203: ALKENES FROM ESTERS
ax%
1. MeLi ,ether , 0°C 2. MeCu ,O"C, 23 h
3. O"C+ 24°C
Me
(91% ee)
Denmark. S.E,; Marble, L.K. J. Org. Chem., 1990, 55, 1984.
C0,Bn
1, B u - C S - P ~ ( O A C ) ~ CHSlz-THF 2 3 T , 30 min 2. H2, Lindlar , PhH 23°C
* ( 9 5 5 Z:E) '
Hashimoto, S.; Miyazaki, Y.; Shinoda, T.; 1loo. OPh
76%
J. Chem. SOC., Chem. Commun., 1990,
Bu3SnH. AIBN
PhH,6h
*
boMe
4
63%
Me M.T.; Dudek, C.M.; Cheung, A.W-H. Tefrahedron Lett., 1992, 33, 181.
OCHO
Pd(acac)z, PBu3, PbH 1.[HCOOH/NEt3/PhH]
RT ,30min
2. Hfl
88%
t-Bu t-Bu Mandai. T.; Suzuki, S.; Murakami, T.; Fujita, M.; Kawada, M.; Tsuii. J, Tetrahedron Leff., 2992, 33, 2987.
SECTION 204:
ALKENES FROM ETHERS, EPOXIDES AND THIOETHERS CpzNb , THF, 12 h
MeOzC o-
- 7 8 O C 4 RT
Schobert. R.; Hohlein, U. SynLeff, 2990, 465.
* (97:3 2:E)
86%
Section 205
Compendium of Organic Synthetic Methods, Vo18
256
AcO
2. 10% KF overnight
40)
( 60
(1.2: 1 a$,
40%
(1:2 a$,
Marco-Contelles, J.L.; Femhdez, C.; Ghmez, A.; Martin-Lehn, N. Tetrahedron Lett., 1990, 31, 1467.
d,,. SiMe3
Ph
BuLi ,DME
-78°C -+RT
. P h w S i M e 3 3%
Ph-
Bu
(98:Z E:Z)
Ukaji, Y.;Yoshida, A.; m a w a . T, Chem. Letf.. 1990, 157.
&\
\ Bu RS%
1. r-BuLi 2. t-BuLi
SiMq
* /JBu
SiMe3 93%
(16534
EZ)
F Tetrahedron Lett., 1991, 32, 3457. Santiago, B.; Lopez, C.; Soderaut,t.J.A. Lopez, C. Tetrahedron Lett., 1991, 32, 6305.
;-
ALKENES FROM HALIDES AND SULFONATES
SECTION 205:
2 Et-I
1. r-BuLi, ether, -78OC 2. c12zIcp2
3.
25°C
(y
4. 2N HCI
general method - preparation of lo organolithium reagents Neglshl.,swanson, D.R.; Roussel, C.J. .I. Org. Chem., 1990, 55, 5406.
Ph
Ph
Br
cysteine , NazSeO3 H20,O"C , 5 min
ph&Ph
98%
the R,R-diastereomergave 0% yield of alkene
Yanada.; Yanada, R.; Meguri, H. J. Chem. Soc., Cheni. Conlmun., 1990, 730.
Alkenes from Halides
Section 205
PhCHCl,
iron (11) oxalate ,DMF , 1 h 160°C
--
257
PhCH=CHPh
92%
Khurana.; Maikap, G.C.; Mehta, S.Synrhesis, 1990, 731.
H.N$l
d SnBu3, PdAdbah
OA N H
P ( 2 - f ~ ~ l,)NMP 3 , RT 16 h
O
AN H
w.V.; Hauck, S.I. SynLetl, 1991. 157.
n 0 0
1 . 3eq. NaNH2 2.m3,ether
89%
n
< -50°C 69% 3. aq. NH4Cl Isaka, M.; Ando, R.; Morinaka, Y.; Nakamura, E. Tetrahedron Lett., 1991, 32, 1339.
c1
c1
1.2.2 r-BuLi ,ether, -100°C 2. CuBr.SMe2, AcCl 3.BuLi
*-
SiMe, 4 . X
Bu
X = TFA/TBAF X = KH,TBAF Barrett. A.G.M,; Flygare, J.A. J. Org. Chem., 1991, 56, 638.
94:6 E:Z)
5:95 E Z )
DMF , 160°C. 210 min
Ph&Ph
Ph
66%
Khurana.;Maikap, G.C. J. Org. Chem., 1991, 56, 2582. Khurana.;Maikap, G.C.; Sahoo, P.K.Synthesis, 1991, 827.
Larock.;Berrios-PeRa, N.G.; Fried, C.A. .I.
Org. Chem.. 1991, 56, 2615.
59% 57%
258
Compendium of Organic Synthetic Methods, Vol8
n-C5H11
Y
SiMe,Ph
c1
; .M.G.A-
1. Mg* (ether) 2. CuBr*SMez 3. BuCOCl 4. MeLi 5. x
*
n-C5H11
Section 205
==(
Me
Bu
X = TsOH 60% Mg* = activatedMag x=KH 61% Hill, J.M.; Wallace, E.M. J. Org. Chem., 1992, 57, 386. Cu (powder), MeOH Cu(C104)2*(H20)6
phHph Br Br
Ph
\==\
e
9
RT,4h Vijayashree, N.; Sapuelson. A.G Tetrahedron Lett., 1992, 33,559. /
\
OMS
NaI , Zn ,HMPA heat
(5:95 E:Z) (955 E:Z)
88%
Ph
82%
OMS
Ghosh.;Karpa, A.; Saha, G.; Paua, D. Tetrahedron Lett., 1992, 33, 2363. n-C&I 1-Br
*
S 0 2 P h . Zn , DMF
0.05 Co (porphyrin) ,20°C
c
&n-C6H11
85%
Giese.;Erdmann, P.; GBbel, T.; Springer, R. Terrahedron Lett., 1992, 33, 545.
SECTION 206: ALKENES FROM HYDRIDES For conversions of methylenes to alkenes (RCH2R' 200 (Alkenes from Alkyls).
0
Sakakura, T.; Abe, F.;
+ RR'C=CH2), see Section
RhCI(CH2=CH2)(PMe3)2 0.7 mm0Vdm3, 70°C hn (I > 375 nm), CH;?=CH2
(1 am)
turnover rate = 160 Chem. Lett., 1991, 297, 359.
Section 207
Akenes from Ketones
259
SECTION 207: ALKENES FROM KETONES I
0hira.s.Ishi, ; S.; Shinohara, K.; Nozaki, H. Tefrahedron Lett., 1990, 31, 1039.
%
1. t-BuLi 2. SOClZ
0
76%
Olah.G.A.; Wu, A.; Farooq, 0.;Surya Prakash, G.K. J. Org. Chem., 1990, 55, 1792.
($
+
$.&
Ph3P=CHC02EtI 70°C 4h
P h %+* Ph' 'OH
Me
A
enantioselectiveWittig-Homer in solid state
[43%ee (-11 I
Toda. F.; Akai, H. J. Org. Chem., 1990, 55, 3446.
Ph Ph
Po
CpzTiMeZ, PhMe ,65"C
*
Ph)= Ph
90%
Petasis. N.A.; Bzowej. E.I. J. Am. Chem. SOC.,1990, 112, 6392.
Ph
TIC14 , Hg , Mg ,THF
Po Ph
0°C + reflux, 2 4h
c
Ph
w y h Ph
87%
9
90%
Carroll, A.R.; Taylor, W.C. Aust. J. Chem., Z990, 43, 1439. 1. Me3SiCHzLi. ether 2. aq. H+
Ph
3. Nafion-H , CHzC12, RT l h
51%
Me
Olah.;Reddy, V.P.; Suva Prakash, G.K. Synthesis, 1991, 29.
P
h
260
Compendium of Organic Synthetic Methods, Vol8
1. LDA ,THF ;TfZNPh
O = C
N-Boc
-78OC-t O°C
2,
CI-
C
t
I
Section 207
-W
B
o
c
83%
Pd(PPhj)4, LiCl ,NazC03 DME , H2O ,reflux
a?)-
-
B(OH)~
Wusuow. D.J.; Wise, L.D. Synthesis, 1991, 993.
N
SOzMe
I . LDA , THF , -78OC 2. acetone
-w
poor yields with saturated aldehydes
51%
Baudin, J.B.; Hareau, G.;Julia.;Ruel, 0.Tetrahedron LeU., 1991, 32, 1175.
b”
1.9-BBN
2.NaOH ;Rangaishenvi, M.V.; Brown, H.C.; (&k 1991, 56, 1543. DME , TiC13Li , 16 h reflux
70% i. C.T; Hasha, D.L J. Org. Chem.,
*
Ph Me 83% E ; 9% Z
Nayak, S.K.; B a n e r u J. Org. Chem., 1991, 56, 1940. MeMgI , 18 h
c
Ph
70%
Ni, Z-J.; Mei, N-W.; Shi, X.; Tzeng, Y-L.; Wang, M.C.; Luh. T-Y. J. Org. Chem., 1991, 56, 4035.
W i s . N.A,; Bzowej, E.I. J. Org. Chem., 1992, 57, 1327.
6
Me
-
C
6
H
#?
O + PN.h
1. BuLi ,
Me
2. H20 3. AcOH
n
t
(91% ee ,R)
t-Bu Hanessian.;Beaudoin, S . Tetrahedron Lett.,
n
'b
26 1
Alkenes from Alkenes
Section 209
t-Bu 1992, 33, 7655, 7659.
Me3SiC(Nz)Li, THF -78°C -+ 0°C
0
n-C6H 13
Ohira. S,; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun., 1992, 721. (Me-$iCH2)3TiCp
P
h
h
SiMe,
, PhMe
100°C
Akritopoulou, I. SynLett, 1992, 665. Related Methods:
Section 199 (Alkenes from Aldehydes).
SECTION 208: ALKENES FROM NITRILES NO ADDITIONAL, EXAMPLES
SECTION 209: ALKENES FROM ALKENES PhBr (sealed tube) Ph 75% OEt (E/Z 85/15)
OEt
Parrain, J-L.; Duchene, A.; Quintard. J-P. Tetrahedron Lett., 1990, 31, 1857.
Malane&;
cz:EF
1. n-CsH?MgBr, ether NiClz(dppe)
2. aq. NH4C1
-
Menicagli, R.; Lardicci, L. Gun. Chim. Itul., 1990, 120, 217
262
Compendium of Organic Synthetic Methods, Vol8
Section 209
1. 15% bpy*Fe(O)
PhH ,25"C , 3 0 min
OBn
2. cat. TsOH ethylene glycol
B ~ *
Takacs, B.E.; Takacs.& Tetrahedron Lett., 1990, 31, 2865. P-cyclodexuin , CeC13.7 H 2 0 CoC12, KCN , KCS , 24 h
-H
H2 (1 atm) , RT , 3 N NaOH
(98
85%
+>=( 2)
95%
Lee, J-T.; elper. H, J. Org. Chem., 1990, 55, 1854. 0
0
Me0
Verma, P.; Pav. S , l n d . J. Chem., 1990, 298, 652.
0
0
Me0
84%
,25"C, 14h
Me
Si02 , glass ampule
0
85%
Veselovskii, V.V.; Gybini, A S .; Lozanova, A.V.; Moiseenkov, A.M.; Smit, V.A. I n . Akad. Nauk. SSSR, 1990, 39, 107 (Engl., p. 94).
CH 2=C =CH,
1. Bu&n2/BuLi , CuCN THF , -78°C
2. Me1 , -78°C -+ 0°C *
Barbero, A.; Cuadrado, P.; Fleming, I.: Gonzdez, A.M.; Commun., 1990, 1030.
n-C6H 13 \=
C=
2 eq. C12AIH 5% PhB(OH)2
=r
M~SnBu396%
J. Chem. SOC.. Chem.
n-C6H13
\\
Nanahara. S,; Maruoka, K.; Doi, Y.; Yamamoto, H. Chem. Lett., 1990, 1595.
92%
263
Alkenes from Alkenes
Section 209
1. BuLi ,THF 2. t-BuOH, -50°C
/
Me3Si
~
Me3SiuBu
+
24 h
Me3s BU
3. BuI
(83
.. Degl’Innocenti, A.; Mordini. A; Pagliai, L.; Ricci, A. SynLett, 1991,
17)
155.
Fuchikami. T.; Ubukata, Y.; Tanaka, Y. Tetrahedron Lett., 1991, 32, 1199.
90%
IS)
(8 1 (94% ee, S )
Lamothe, S.; Chan. T.H, Tetrahedron Lett., 199
74%
92%
32, 1847.
1. Mg* , THF , RT
Ph A
P
h
-
2. -78°C + RT BrBr
Ph
Mg* = [MgC12/THF/Li naphth.]
65%
Rieke.; Xiong, H. J.
Org. Chem., 1991, 56, 3109; J. Org. Chem., 1992, 57, 6560. Xiong, H.; Rieke. R.D, Tetrahedron Lett., 1991, 32, 5269.
BuLi , THF
TsO
SnBu3
-20°C
+ 0°C
61%
Barbero, A.; Cuadrado, P.; Gonziilez, A.M.; h,!&JJ,; Rubio, R.; Fleming, I. Tetrahedron Lett., 1992, 33, 5841. 1. Cp$r(H)CI , THF
4n-C6H 13
2.Ph-O.
OEt OEt c a t . ~ u 0~ ~
y,’
Venanzi, L.M.; Lehmann, R.; Keil, R.;
?-
F%qH1’ +
(93
Phy n-C,H 7)
85%
Tetrahedron Lett., 1992, 33, 5851.
264
Compendium of Organic Synthetic Methods, Vo18
Section 210
pn-c8H 1.9-BBN 2. 3% Pd(PPb3k dioxane, THF K3P04,6o0C
Br
Miyaura, N.; Ishikawa, N.;
&"3
*
80%
6
n-C8H17
Tetrahedron Lett., 1992, 33, 2571.
MQ ,Me 1. 18O"C, 10 h 2. TBAF-DMF
Ph 68%
Me
hire ~~
(85:15
cis-4,5:trans-4,5)
Stork.; Chan, T.Y.; Breault, G.A. J. Am. Chem. SOC., 1992, 114, 7578. BusSnH , Pd(PPh3)4
45%
$Sn% (3654 E:Z)
Mivake.; Yamamura, K. Chem. Lett., 1992,473. REVIEWS: "Ketene Dithioacetals in Organic Synlhesis: Recent Developments" Synthesis, 1990, 171. "Acyclic Stereocontrol via [2,3]-Wittig Sigmatropic Rearrangement" Mikami, K.; Nakai, T. Synthesis, 1991, 594.
SECTION 210:
ALKENES FROM MISCELLANEOUS COMPOUNDS N2
Ph
,OMe P'OMe 0
FVP (350°C) 1
0
-
5
~
*~
P h 4 ~
60%
Tomioka.;Watanabe, M.; Kobayashi, N.; Hirai, K. Tetrahedron Lett., 1990, 31,5061.
Section 210
Alkenes from Miscellaneous
TyM &f) *
+
265
&,) 1111
N
R = AC
(7.3 36.4:l cis anti:cis syn
R = CH2OH
1) 98% 1.7:1 exomdo
1.9) 91% 1:1.3 exomdo
(1
13.2:1 cis antkcis syn
Masjededizadeh, M.R.; Dannecker-Doerig, I.; Little. R.D, J. Org. Chem., 1990, 55, 2742. CloHBNa, THF
76%
/
n-CRH17
n-CRH17
Beels, C.M.D.; Coleman, M.J.;
SynLetr, 1990, 479.
Crearv.;Wang, Y-X.;Gill, W. Tetrahedron Lett., 1991, 32, 729.
")-., a
1 . 2 eq. PhzCHLi , THF HMPA
-
Fe(CO),
2. TFA , -78"C, 1 h 3. aq. NaHCO3
fl:h 67%
Donaldson. W.A.; Hossain, M.A. Tetrahedron Lett., 1992, 33, 4107.
0
F iPr-Ph
OH t-Bu
Ph3COTftMeCN 2,6-lutidine 60°C
6* t-Bu
I)enmark.; Chen, C-T. J. Am. Chem. Soc., 1992, 114, 10674. BnCu(CN)ZnI
THF ,0°C
c
b 9 9 % ee , S)
)---SLPh
m. M-C.P.; Tau, S-I. J. Chem. SOC., Chem. Commun., 1992, 13.
68%
60%
266
Compendium of Organic Synthetic Methods, Vo18
n-C11H23
Pho2SY Li
ClCHzMgCl , THF -78OC --t RT
*
DeLima, C.; Iulla.;Verpeaux, J-N. SynLett, 1992, 133. REVIEWS:
"Methods for the Synthesis of Ally1 Silanes" 1101.
L a d s x J X Synthesis, 1990, 969,
Phosphonates in Organic Synthesis" . . "Vinyl Mmaml..; Motoyoshiya, J. Synlhesis, 1992, 333.
Section 210
bn-C11H23
82%
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
15
PREPARATION
OF OXIDES
This chapter contains reactions which prepare the oxides of nitrogen, sulfur and selenium. Included are N-oxides, nitroso and nitro compounds, nitrile oxides, sulfoxides, selenoxides and sulfones. Oximes are considered to be mines and appear in those sections. Preparation of sulfonic acid derivatives are found in Chapter Two and the preparation of sulfonates in Chapter Ten.
SECTION 211: OXIDES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 212: OXIDES FROM ACID DERIVATIVES 1. NazS03, NaHC03
Hz0.75OC
*
2. ClCHzCOOH , 19 h aq. NaOH , reflux
Brpwn. R.W.J. Org. Chem., 1991, 56, 4974.
SECTION 213: OXIDES FROM ALCOHOLS AND THIOLS
Park, Y.J.;Shin, H.H.; Kim, Y.H. Chern. Left., 1992, 1483.
SECTION 214: OXIDES FROM ALDEHYDES
%CHO
MeNHOH , Z " C
*
0.0 0 E N M~
good yield
Ciganek. E, J. Org. Chem., 1990, 5.5, 3007. 1. Ph2PH , NbCls ,CHzCI;!
Ph
-78°C Ph-P,' Ph 2. BF3.OEt2, -78°C + RT Suzuki.;Hashimoto, T.; Maeta, H.; Matsumoto, T. SynLett, 1992, 125.
ph/\/CHo
6
92%
268
Compendium of Organic Synthetic Methods, Vo18
SECTION 215:
Section 217
OXIDES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 216: OXIDES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 217: OXIDES FROM AMINES NH,
1. (Et0)2POCI , ether 2. isolate phosphorimidale 3. CH2C12,26 h 5 eq. isoamyl nitrite
-
0
o. b;
OEt
0^,,OEt
Nikolaides, N.; Tetrahedron Leti., 1990, 3I, 1113. Luo, J.; Ganem. B, Tetrahedron Lett., 1991, 32, 3145 [with (Bn02)POHI.
-
H z q , MeOH Na~W04QH20
NI
H
M % s I
0 0
89%
Murahashi. S-IA;Mibui, H.; Shiota, T.; Tsuda,T.; Watanabe, S. J. Org. Chetn., 1990, 55, 1736.
phn
NHMe
acetone ,0°C
-
Murrav. R.W,; Singh, M.J. Org. Chem., 1990, 55, 2954.
Me -.f N@ : rn 00
0""'(yNO'-% HOF , MeCN -10°C
Rozen., Kol, M.J. Org. Chern., 1992, 57, 1342. N- OH
1. urea-HzQ complex ,MeCN
TFAA , 0°C , 3 h
2. Na2HP04, MeCN
rNo
Ballini, R.; Marcantoni, E.; Petrini. M, Tetrahedron Lett., 1992, 33,4835.
70%
Section 2 19
Oxides from Ethers
Qlah.;Ramaiah, P.;Lee,G.K.;
269
SynLetr, 1992, 337.
SECTION 218: OXIDES FROM ESTERS NO ADDlTIONAL EXAMPLES
SECTION 219:
OXIDES FROM ETHERS, EPOXIDES AND THIOETHERS HP(=O)[OH]2, AczO
dioxane ,reflux 2h Klosinski. P, Tetrahedron Lett., 1990, 31, 2025.
Ph‘
’+
0 H
0.1 TeOz , 0.01 HCl Hz02.2 h
74%
0 Ph”V
92%
Kim.;Hwang, H.J.; Cheong, C.S.; Hahn, C.S. Tetrahedron Lett., 1990, 31, 2893.
mY.: Inazu, T. Tetrahedron Lett., 1990, 31, 5955. Ph, s/\
aq. HNO3 ,6h
t
9
0
92% GasDarrini. F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palrnieri, G. J. Org. Chem.. 1990, 55, 1323. Me3PhNBr, Py , H 2 0 , 3 h
t
10°C - RT RBbai, J.; Kapovits, I.; Tanks, B.; Tamas, J. Synthesis, 1990, 847.
270
Section 219
Compendium of Organic Synthetic Methods, Vo18
30% H202, Me
Drabowicz, J.; tyfwa, P.; Popielarczyk, M.; Mikotajczyk, M. Synthesis, 2990, 937. RUCIz(PPh&, PhH
PhS02Cl
Sph
+ , 140°C. 24 h
+P
SO2Ph
h
S
y SPh
c1
54%
71%
Kamigata. N; Ishii, K.; Ohlsuka, T.; Matsuyama, H. Bull. Chem. SOC. fpn., 1991, 64, 3479.
Ph-S-Me
oxone , “wet“ kaolin
-
PhS0,Me 97% C H 9 2 ,reflux , 4 h Hirano, M.; Tomaru, J.; Morimoio, T. Bull. Chem. SOC. Jpn., 1991, 64, 3752. Hirano, M.; Tomaru, J.; Morimoto. T. Chem. Lett., 1991, 523 [with montmorillonite]. Mortierella isabellina (ATCC 42613)
PhA
S‘ Ph
PhA;‘Ph 0
+
48%
(58%ee , R) Holland, H.L.; Rand, C.G.; Viski, P.; Brown, F.M. Can. J. Chem., 2991, 69, 1989.
Ph‘
’V
Bu(MnO&, MeCN
Ph
reflux, 4 h
c
0 Ph”VPh
88%
Firouzabadi. H.; Seddighi, M. Synth. Commun., 1991, 21, 211.
Ph‘
s’Me
Ph-1=0 , 0.1 PhSeOzH 45”C, 1 h
8:
0 Ph‘”Me
86%
Roh, K.R.; Kim, K.S.;Kim. Y . 9 Tetrahedron Left., 1991, 32, 793.
Me’
s*To1
Ti(OiPr)4, t-BuOOH
,H20,45h
Komatsu, N.; Nishibayashi, Y.;Sugita, T.;
0 Me’’.Tol
88%
(73% ee , R) Terrahedron Lett., 1992, 33, 5391.
Oxides from Ethers
Section 219
Ph-
s. Me
1% O s 0 4 , NMO
27 1
*
Katdor.;Hammond, M.Tetrahedron Left., 1991, 32, 5043.
Ph-S-Ph
H ~ I 0 6 - R u 0 4 , 3h CCI@leCN/H20
Ph-SO,-Ph
Ic
76%
Rodriguez, C.M.; Ode, J.M.; Palazbn, J.M.; Martin. V.S. Tetrahedron, 1992,48, 3571.
Ph’
s*Me
3% Mn (salen) derivative HOOH , MeOH
Ph’S-Me
90%
(47% ee , S) Tefrahedron Left., 1992, 33, 71 11.
Palucki, M.; Hanson, P.;
Ph-S-Ph
0
b
NaOBr ,hexaneEtOAc “wet”monimorillonite 15 min *
0 Ph”*ph
78%
Hirano, M.; Kudo, H.; Morimoto. T.Bull. Chem. SOC. Jpn., 1992, 65, 1744.
CC4,4h
Me
Tol’
0 0. To14 s ’ ~ e 95%
*
Me,,Me
(>95% ee , S)
Me
Davis. F.A.; Reddy, R.T.; Han, W.; Carroll, P.J. J. Am. Chem. Soc., 1992, 114, 1428.
Ph-
S-
PhIO , HC1-silica gel “pulverization“
Ph
Sohmiya, H.; Kimura, T.; Fujita, M.;
Ph’
.’
b
Chem. Leff.,1992, 891.
1 eq. oxone, A1203
Me
CH2C12,reflux
PhAS02Cl
c.
3 eq. of oxone led to the sulfone Greenhakh. R.P, SynLetf, 1992, 235.
0 Ph‘S-Me
96%
98%
Compendium of Organic Synthetic Methods, Vo18
272
Section 22 1
REVIEWS:
"Some Routes to Chiral Sulfoxides with Very High Enantiomeric Excesses" Kagan, H.B.; Reviere, F. SynLetl, 1990, 643.
"-
SECTION 220: OXIDES FROM HALIDES AND SULFONATES 1. P(OEt)3, 13OOC 2. Me3SiC1, KI
Ph-C1
OH P' OH
MeCN,6O0C n v 3. H z 0 , RT , 5 min 87% Pilarski, B.; Johnson, J.W. Org. Prep. Proceed. ht.,1990, 22, 209.
;-
TosSOzNa , aq. DMF , 3 min
PhCHzC1 Biswas. G.K.; Jash, S.S.; W PhCHzCl
. . y&runJ.;
c
)))))I)
PhCH2SO2Tol
85%
charvya. P, Id.J. Chem.. 1990, 298, 491.
PhSOzNa , A1203
*
PhCH2SOzPh
>>)))>>) Ben Alloum, A. Synrh. Commun.. 1990, 20, 925.
97%
SECTION 221: OXIDES FROM HYDRIDES
9 c1 PC13 , AICI3, 16 h CHzC12, reflux
PL
c1
-
64%
Dlah. G.A,; Farooq, 0.;Wang, Q.; Wu, A. J. Org. Chem., 1990, 55, 1224.
(0:m:p 44:3:53) Suzuki. €1.; Murashima, T.; Shimizu, K.; Tsukamoto, K. Chem. Letl., 1991, 817. Suzuki. H,; Murashima, T.; Shimizu, K.; Tsukamoto, K. J. Chem. Soc., Chem. Commun., 1991, 1049.
Section 225
213
Oxides from Miscellaneous
SECTION 222: OXIDES FROM KETONES S
1. mCPBA
Ph -(I
-50°C
S' 0
H
65%
(90%E) Barbaro, G.; Battaglia, A.; Giorgianni, P.; Bonini, B.F.; -a Chem., 1990, 55, 3744.
ni. G,; Zani, P. J. Org.
0)
(100
quant.
with MeC(=S)SBu - obtain 80:20 mixture Le Nocher, A.M.; Metzner, P. Tetrahedron Left., 1991, 32, 747.
SECTION 223: OXIDES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 224: OXIDES FROM ALKENES NO ADDITIONAL EXAMPLES
SECTION 225: OXIDES FROM MISCELLANEOUS COMPOUNDS This section includes oxides prepared from other oxides
SOZPh S02Ph
1. Br(CH2)3COzR, hv 2. Bu3SnHI AIBN
*
R = thiohydroxamic acid
Padwa;Murphree, S.S.; Yeske, P.E. Tetrahedron Lett., 0
2
H-K'OMe
Ph
Ph
OMe
,PhH
Cu(acac)z
0
SO2Ph 82%
1990, 31, 2983,
0 phyP-OMe
52%
Ph OMe
m v . A . K ; Polezhaeva, N.A.; Mustaphin, A.H.; Khotinen, A.V.; Arbuzov, B.A. Synthesis, 1990, 515.
274
Compendium of Organic Synthetic Methods, Vo18
Section 225
5) 97)
R=Me (95 R = Ph (3 J. Org. Chem.. 1990, 55, 3464.
Chang, 2-Y.;
dco2Me c
1. BuLi
3 C 0 2 M e
2. Me1
8 2
b*
Chou.; Tsai, C-Y.; Huang, L-J. J. Org. Chem., 2990, 55, 5410. 1.3 eq. UDP , PhMe 2.MeI
c) S O2
67%
‘s- 0 2
*
96% 79%
92%
UDP = ultrasonically dispersed potassium Chou. T-S; Hung, S-H.; Peng, M-L.; Lee, S-J. Tetrahedron Lett., 1991, 32, 3551.
0 .Me
i:
OOPS. Me
HO
M~
2. PhMgBr , 5 h
-70°C4 RT
Ph
0 * Me”*Ph **,
Tetrahedron Lett., 1991, 32, 5885.
Benson, S.C.;
Ph-
1. AlMe3 ,RT ,CH2C12 30 min
Bu N+S02C1
(>99%ee)
71%
AlC13, 90°C. 14 h
Katritzkv. A.R.; Wu,J.; Rachwal, S.;Rachwal, B.; Macomber, D.W.; Smith, T.P. Org. Prep. Proceed. lnt., 1992, 24, 463.
S02F Fee. L; Sullivan, E.L.;
BuLi , THF -78OC
-
G S 0 2 - B u 92%
Cusak, K.P.; Funaro, J.M. J. Org. Chem., 1992, 57, 697.
Section 225
Oxides from Miscellaneous
&-
275
0
BuMgBr , THF ,-70°C
c
Tole
Br
81%
Bu
(99% ee , S) Cardellicchio, C.; Fiandanese, V.; Naso. F,; Scilimati, A. Tetrahedron Lett., 1992, 33, 5121.
Falck.;Yu, J. Tetrahedron Lett., 1992, 33, 6723.
'C+J
N-OH
- y j
1. NaBH3CN. pH 3-4
2. PhMe ,reflux
00
94%
Fox, M.E.; Holmes.; Forbes, I.T.; Thompson, M. Tetrahedron Lett., 1992, 33. 7421. REVIEWS:
"AsymmetricCarbon-Carbon Bond Formation Using Sulfoxide-StabilizedCarbanions"
lUkAJ, Tetrahedron Asymmetry, 1992, 3,961. "Cyclic Sulfites and Cyclic Sulfates"
LQLUIY.B.B. Synthesis, 2992, 1035.
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
CHAPTER
16
PREPARATION OF DIFUNCTIONAL COMPOUNDS
SECTION 300: ALKYNE
- ALKYNE
82%
Stracker, E.C.;
Tetrahedron Lett., 1990, 31, 6815. I . CuC12.2 H2O
Ph- CE C-H
60%
Ph-CEC-CEC-Ph
2. "solidslate" , RT , 3 h
A solid-state Glaser reaction Toda. F,; Tokumaru, Y. Chern. Left., 1990, 987.
f
o'
c:C' H
cat. CuI , 2 TMEDA 0 2 , a ~ e t o n el, h
t-Bu,
0-C ~ C - CC. E 0-t-Bu
77%
Valenii, E.; Pericas. M.A.; Serratosa, F. .I. Am. Chem. Soc., 1990, 112, 7405. 2 q . Ph-CrC-Li
1. CuCN t
2. BuCd-I-Ph+ OTsTIIF, - 7 O T -+ RT
Ph-CZC-CEC-BU
+
Bu-CiC-CiC-BU
71%
8%
UT.; Tanaka, T.; Tanipuchi.;Stang, P.J. .I. Chem. Soc., Perkin Trans. I, 1991, 2892.
.
1. CuBr P v . DBU
Brandsma.;Verkruijsse, H.D.; Walda, B. Synth. Commun., 1991, 21, 137
Alkyne - Alcohol
Section 302
PhCK-H , CUI PdC12(PPh3)2
Ph- CI C-I
277
Ph- CEC- Cz C-Ph
HN(iPr)z, THF
quant.
Witvak. J,; Chan, J.B. Synth. Commun., 1991, 21, 977.
R-c:
cJ1
J3-c: c-
CO2Me
H-CGCJ
Cul ,DMF ,N&03,16 h * Bu~NCI , -20°C+>20°C
C,. 78%
Jeffery, T.; Gueugnot, S . ; Linstrumelle, G. Tetrahedron Lett., 1992, 33, 5757.
SECTION 301: ALKYNE
- ACID DERIVATIVES
NO ADDITIONAL EXAMPLES
SECTION 302: ALKYNE
- ALCOHOL, THIOL
SiMe,
BuLi ,THF
O O *"
c!
/
-78°C
Me3Si ' Tetrahedron Lett., 1990. 31, 7353.
Tomooka, K.; Watanabe, M.;
(6.6
TolO$Y
Ph
N, ,N- S02Tol
1. Ph,SnCH*C=CH, CHzCIz 2. iPrCH0, -78°C. 2.5 h
OH
P
64%
1)
Suzuki, M.; Morita, Y.; Novori. R.J. Org. Chem., 1990, 55,441.
'h%&
H
c: C-H
(94% ee , R)
i3r
92%
76%
Corev. E.J.; Yu, C-M.; Lee, D-H. J. Am. Chem. Sac., 1990, 112, 878.
PhCHO
(Ph-C=C-)zZn, 14 h hexane - THF
Ph
)- C: C- Ph
Bu2PH Me
Niwa, S.;
c
Ph
HO
J. Chem. Sac., Perkin Trans. I. 1990, 937.
(34% ee)
99%
278
Compendium of Organic Synthetic Methods, Vol8
0 +Me
n-C6H,gCZC-Li
*THF
~ z - C ~,H C ,S C
c
8%Me3Ga, R T , 1 h only 3% yield without Me3Ga
Section 302
87%
Me
Fukuda,Y.; Matsubara.; Lambert, C.; Shiragami, H.; Nanko, T.; Bull. Chem. SOC.Jpn., 1991, 64, 1810.
; Nozaki, H.
1 . PhCHO , THF 2. ICH2ZnI
Ph
95%
Tetrahedron Lett., 1991, 32, 1855.
Rozema, M.J.;
Sn(OTf)z, CH2C12
Ph-C:C-H
Ph- CE C<
,t-BuCHO M%N
t-Bu
OH
81%
NMq
m a c . i i c h i . M.; Hayashi. A.; Minami, T. J. Org. Chetn., 1991, 56, 4091.
Br
H-ci c--/
1 . B u ~ SR~T,, 12 h 2. BuMgBr , THF ,O°C
3. PhCHO , 1 h O°C + RT
OH
b
P h L C3 c.
B a n g , L.J.: HmgJL - Huang, Z-11. Tetrahedron Lett., 1991, 32, 6579.
91%
OH
Ph-Cg-U , THF
ph
OH
Ph
e-99 4) 96% Chini, M.; U F , ;Favero. L.; Macchia, F. Tetrahedron Lett., 1991, 32, 6617.
Ph-CE C-(
OBn Me
Cp+3Ciz, BuLi THF , -78°C
BR*OEtz, PhCHO* THF , overnight 0°C -) RT
P
h
c'..cq Me
(86
Ph
+
Ph?
Me
Ph OH
14)
80%
(3: 1 antixyn)
Ito, H.; Nakamura, T.; 3kguchi. T,; Hanzawa, Y. Tetrahedron Leu., 1992, 33, 3769.
Section 304
Alkyne - Amide
8%
279
cat. OsO4, O°C , 3 0 h
Ph- Ci C
d
*
Ph-CEC<
OH OH
91%
(53% ee)
OMe
N
Jeong, K-S.; Sjo, P.; &arp&s.,J€&
Tetrahedron Lett., 1992, 33, 3833.
.
1. Dihal THF -20°C. 1 h
c
2 . 4 . NH4CI
Nussbaumer. P.; Stiitz, A. Tetrahedron Lett., 1992.33. 7507.
SECTION 303: ALKYNE
- ALDEHYDE
NO ADDITIONAL EXAMPLES
SECTION 304: ALKYNE
- AMIDE n
1. h 4 e q S . N
78%
0
U
PhC0,Me
2 BuLi , THF , -78°C + 0°C
2.
ON Me
NEt3. CHzClz
0 "
RT
@ ,
o
Ph-CEC-S-N
n0
w
7%
LeClercq, M.; Briennc, M.J. Tetrahedron Lett., 1990, 31, 3875. CO ,THF , S O T 5% Pd(0Ac)z
n - C 7 H p C I c+ Me0,CO
lcool
Mandai.; Ryoden, K.; Kawada,M.;
0
Er
Ts
66%
Tetrahedron Lett., 1991, 32, 7683.
- AMINE
mBr
1. Triton-B , MeOH 40°C
Ph
'C.* c~
K~C03.6h
NHTs
SECTION 305: ALKYNE
w
2. 110°C 3. MeNHBr
Frey, H.; b p p . G, Synthesis, 1990, 931
MexCx-H Ph
NHBn
88%
280
Compendium of Organic Synthetic Methods, Vol8
dC1 , PdCW'Ph3)2 Br
Section 306
CI
Ph- CE C- H
Ph-Cr C-Cr C-NEt,
CUI, PPh3, N E t 3 , 14 h* reflux 2. EgNLi , ether, 14 h , RT
15%
Synthesis, 1990, 125.
Loffler, A.;
Bu.
1.
Bu.
Bu-Cd2-H , PdC12(PPh3)2
N
CUI, NEt3, RT
PhA C1
Lin. S-Y; Sheng, H-Y.; Huang, Y-Z. Synthesis, 1990, 235.
N
PhLC:
C- Bu
60%
BuNH2,3% CuBr MeCN ,20"C, 5 h
* -&NZiiH
92%
Gen. R.; Polizzi, C.; Lardicci, L. Tetrahedron Lett., 1991, 32. 7471.
;-
- ESTER
SECTION 306: ALKYNE
0
Pd(OAc)z, N E t 3 ,EtOH
Ph- Cg C- I- Ph OTs 614.
OSiMe3 F=( , Sn(OTf)z Me
20%
80%
H,; Stang, P.J. J. Chem. SOC.,Chem. Cotnmun., 1990,
Xitamura. T,; Mihara, I.; -chi.
BU- Cr C- CHO
Ph- CE C- CO,Et
b
CO , RT
P.8 SEt
Me
*
OSiMe3 EtSJQCS C- Bu Me
€I
67%
(93:7 syn:anti; 91% ee)
CH2C12, -78°C Mukaiyama, T.; Furuya, M,; Ohsubo, A.; Kobayashi, S. Chem. Lett., 1991, 989.
H- Ci C
JCOZH
1. t-BuOK 2. Bu-CS-Br ,THF-MeCN /
Pd(P(o-tolyl)3 ,25"C 48 h
Bu'
Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett., 1992, 33, 281 1.
C.'
c** 41%
Alkyne - Ether
Section 307
SECTION 307: ALKYNE
c1- c: c- c1
28 1
- ETHER, EPOXIDE, THIOETHER 2 E t S H , 2 KH , THF 0°C + RT , 20 h
EtS- Cr C- SEt
87% Riera, A.; CabrC, F.; Moyano, A.; Perich, M.A.; Santamarfa, J. Tetrahedron Lett., 1990, 31, 2169.
0'" 0-crc-I
Sorensen, H.;
c"
! 0'"
BICH~CH~B Zn~ , THF , Me3SiC1 CsHllBr
1. n-BuLi 2.ZnBr2 3. H20
OMe
n - C 6 7 13
C 8.1
C-Me
56%
Tetrahedron Len.,1990, 31, 7597.
C: C- %Me3
Courtemanche, G.;
"'0-CEC-n-CSHII
CuCN , THF
*
QCM:-siMe3 OMe
80%
- Tetrahedron Lett., 1991, 32, 5317. 4% Mn (salen) derivative NaOCl , CH2C12, RT
pH 11.3,5 h
n-C6H!3
-
C
'5
+
0 Me
(2:l trans:cis) trans (93% ee , SR) cis (58% ee) Lee, N.H.; lacobsen.E.N.Tetrahedron Lett., 1991, 32, 6533. Me3Si-CK-SiMe3 S n C 4 , -20°C
AcO" OAc Tsukiyama, T.; hobe. M. Tetrahedron Lett., 1992, 33, 7911.
AcO"'
85%
282
Compendium of Organic Synthetic Methods, Vol8
0
0
(iBuzTeCHzCCSiMe3) Br I LiTMP ,THF
PhCHO
Section 308
p
t
-78°C 4RT
h
q
q.-
76%
c.
SiMe,
(82: 18 cistrans)
Mukai, C.; Uchiyama, M.;
Hanaoka.M..Chem. SOC., Chem. Commun., 1992,
SECTION 308: ALKYNE
n-C,HqCE C-H
1014.
- HALIDE
FkF ,CuI ,NEt3 I
F
c
Pd(PPh3)2C12 RT 3 70°C
n-C,H,-CX
F
69%
Yang, Z-Y.; Burton. D.J. Tetrahedron Lett., 1990, 31, 1369.
93% Wagner, A.; Heitz, M.P.; Mioskowsk i. C,Tetrahedron Letl., 1990, 31, 3141.
W CO,H F
Ph
1. Br2 , CC4 ,reflux 2. NaHC03, acetone reflux
d"CPh
Ph
3. PhCSCH , PPh3 Pd(OAc)z, B u N H ~
F
49%overdl
Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Tetrahedron Lett., 1990, 31.4449.
Ph- C3 C-H
Me3SiOOSiMe3 ZnI2 , THF
Ph-CZ C-I
90%
Casarini, A.; Dembecb.; Reginato, G.; Ricci.;Seconi, G. Teirahedron Lett., 1991, 32, 2165.
0
I ( o A ~ ) ~Me3SiCII2CaC-H ,CHzCl2 BF3.0Et2 , MgSO4, -20°C lh
c &
I
C=C-H
80%
.. Ochlar.; Ito, T.; Takaoka, Y.; Masaki, Y. J. Am. Chem. Soc., 1991, 113, 1319.
Alkyne - Ketone
Section 309
SECTION 309: ALKYNE
0
283
- KETONE
n-C3H7-CeH,RT
/b 1% [RhCI(PMqE] L acetone
0 C Z C J 86%
4
Tefrahedron Left., 1990, 31, 7063.
Nikishin, (3.1.; &N&YJ
6
Me-CH=C=CHSnPh, THF , -4O"C, 30 min
6..C
M~
86%
Haruta. J,; Nishi, K.; Matsuda, S.; Akai, S.; Tamura, Y.; Kita. Y . J . Org. Chetn., 1990, 55, 4853. 1. t-BuOK, t-BUOH 2. HCS-IPh BF4 RT,2h
0
0
..
Ito, T.; Takaoka, Y.;Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y.J. Chem. Soc., Chem. Comrnun., 1990, 118.
;
0 PPh,
Ph
Br
1 . 1 2 , K 2 C 0 3 , MeOH 2.PhCHO,2K2C03
MeOH ,60°C
-
CrC-Ph
64%
Iman, M.; Bouyssou, P.: Chenauli. J. Synthesis, 1990. 631.
.
silica gel, -20°C , 1 h RT ovemighl
H-CEC
silica gel catalyzed Eschenmoser reaction
Abad.;Agullb, C.; Am6, M.; CuRat, A.C.; ZaragozA, R.J. SynLen, 0
NHiPr
1.5 eq. LiTMP , 0°C , 1 h 2 . 3 q.TMS-CI , -70°C 2h
1991, 787.
0
Ph- Cr C 4
Ph Me 3. AcOH ,AcONa ,pH 4;. Me Bartioli. G.; Cimarelli, C.; Palmieri. G. Terrahedron Lett., 1991, 32, 7091.
80%
284
Compendium of Organic Synthetic Methods, Vo18
0 E
t-BuMeZSiO,,,
EtzN
Q
Section 31 1
~ O c ~ OSiMcyc-Bu ~ ~ .
PhH, RT
t-BuMqSiO,,,
Yoshino, T.; Okamoto, S.; &&& J. Urg. Chem., Z99Z. 56, 3205.
Ciattini, P.G.; Morera, E.;
n-CgH17.Cf C-H
Tetrahedron Lert., 1991, 32, 6449. 1. HB(0iPrh 2. BF3*OEtzICHKIz Ph , reflux, 8 h
Ph rr-C8H17-CiC
Ph
Ph
Fujishima, H.; Takada, E.; Hara, S.; SuzdaA ‘ Chem. Lett., 1992, 695.
SECTION 310: ALKYNE
-
NITRILE
NO ADDITIONAL EXAMPLES
SECTION 311: ALKYNE
( c1
- ALKENE
1.6 €IC=CMgCI , THF 0.065 NaI , 0.15 CuCl 15 h c
2 . 2 BuLi ,THF , -78°C 3.THF, -78°C .6 h ClJ=Ll
5%
Gleiter. R,; Merger, R. Tetrahedron Letr., 1990. 31,1845.
OH
*
CUI, NEt3 ,60”C OH 85% Mieaani. GL;Chevalier, C.; Grass, F.; Allmang, G.; Morel, D. Terrahedron Lett., 1990, 31, 5161.
285
Alkyne - Alkene
Section 31 1
OTHP &
Pd(PPh3)4, LiCl CUI,NHEtz ,THF
n - c 6 H 1 y T ciC-Bu OC0,Me
)eB"
n-C6H13
*
Me
60%
RT , 3 0 min
q.*
cL. OTHP
Mandai, T.; Nakata, T.; Murayama, H.; Yamaoki, H.; Ogawa, M.; Kawada, M.; Tsuii. J, TefrahedronLeft.,1990. 31, 7179.
Me C.B.
c=c<
Me
Bu3SnH, AIBN , PhH 80°C
Me
Br
C.
Me
J. Org. Chem., 1990, 55, 2983.
Ph2MeSi- Cr C-H
RhCI(PPh3hYRT PhMe , 3 0 h
Ph2MeSi c
%
CE C- SiMePh2
94% Ohshita, J.; Furumori, K.; Matsuguchi, A.; j&&am&. J. Org. Chem., 1990, 55, 3271.
Me
PhOCHZCK-H
,,C02Me 4%Pd(OAc)z, TDMPP
zc-i H
~
Me
PhOJ Trost.;Kottirsch. G. J. Am. Chem. Soc., 1990, 112, 2816.
6'.c
32%
Balova, LA.; Remizova, I..; Favorskaya, LA. Zhur. Org. Khim., 1990, 26, 729.
pmdta = pentamethyldiethylenetriamine Dfxien, S.; Clinet, J-C.; Duaach.; PCrichon, J. J. Chenz. Soc., Chem. Commun., 1991, 549.
286
Section 3 11
Compendium of Organic Synthetic Methods, Vol8
Arcadi, A,; Cacchi. S,; Del Mastro, M.; Marinelli, F. SynLett, Z99Z, 409. 1 . SiamyhBH 2, B u - C d - L i
Bu-C' C-H
BuXC:C-Bu
w
60%
Neeishi. E,; Yoshida, T.; Abramovitch, A.; Lew, G.; Williams, R.M. Tetrahedron, 1991, 47, 343.
1. Br+3.
0
/
, Py-HF
Ph- CEC - H
.c
Ph
b
2. P h C S H , Pd(0Ac)z PPh3, NEt3 , 3 h reacts with alkenes to give dienes reflux
Ph
wc 83%
F
E:Z)
(92:8
Eddarir, S.; Mesldagh, H.; Rolando, C. Tetrahedron Lett., 1991, 32, 69.
bOTf
TfO
2.4 eq. Me3Si-CS-H 4% PdC12(PPh3)2
15% CuI THF-iPr2NH
Suffert.;Briickner, R. Tetrahedron Lett., 1991. 32, 1453. 1. 12, THF
M CSiMe3 ~C-H
n-C6H 13
Me&
2. Bu-CS-SnMe3 (MeCN)PdC12
n-C H
+
74%
Stracker, E.C.; Zweifel. G,Tetrahedron Lett., 1991, 32, 3329. n-CsHlI-CS-H, piperidine PdC12(PhCN)z , 3 0 min
n-C5H1 1-
Y
c1
SiMe3 CiC-H
l3%
Bu-CZC
n-C5H11 t
Alami, M.; Linstrumelle, C. Tetrahedron Lett., 1991, 32, 6109.
= i
q.\
C.
93%
n-C5H1 1
287
Alkyne - Alkene
Section 3 1 1
Bouyssi, D.; Balme, G.; Gore, J. Tetrahedron Lett., 1991, 32, 6541. Br ,Aliquat-336
H-Cg C<
H
30%aq. NaOH ,CuCl CHKlz, 20°C. 24 h J. Org. Chem., 1992, 57, 2188.
Grushin, V.V.;
60%
Pd(OAc)z, Pph3,CuI
OTBS n-C5H1 I
87%
1)
(8
Torii. S.; Okumoto, H.; Kotani, T.; Nakayasu, S.; Ozaki, H. Tetrahedron Lett., 1992, 33, 3503.
Br- CE C-(
0~~
DMF ,20°C
SnBu3,
*
OEt
\c:c-<
OEt PdC12(MeCN)z, 1h Beaudet, I.; Parrain, J-L.; Q&ard. J -P, Tetrahedron Lett., 1992, 33, 3641.
OEt
H- C: C- C02Me
1 . LiBr-AcOH , MeCN , reflux 2.Ph-Cg-H , PdCIz(PPh&
80%
* Me@C. q..
c k dPh
u; Huang, X.;Ma, S. Tetrahedron Lett., 1992, 33, 2535. 1. PhBr , PdC12.2 PPh3
H- Cr !\ SEt
PPh3, CuBr ,NEt3 reflux
2. Zn , EtOH ,reflux 3.N a H 2 NH3 (Iiq)
4. H 2 0
7
w
Ph\=/
c!'
85%
H 54% overall
Fossatelli, M.; van der Kerk, A.C.T.H.M.; Vasilevsky, S.F.; Jha&mJ. Tetrahedron Lett., 1992, 33. 4229.
288
Section 313
Compendium of Organic Synthetic Methods, Vol8
REVIEWS :
"Molecular Design, Chemical Synthesis, and Biological Action of Enediynes"
Nicolaou.;Smith, A.L. Accts. Chem. Res., 1992, 24, 497.
SECTION 312: CARBOXYLIC ACID
- CARBOXYLIC ACID
Muzart.; Ajjou, A.N. Synth. Cornmun., 1991, 21, 575. montmorillonite , 3 0 T
Choudarv. B.M.; Valli, V.L.K.; Durga Prasad, A. Synth. Cornmun., 1991, 21, 2007.
SECTION 313: CARBOXYLIC ACID
0
- ALCOHOL, THIOL
1. HCN , iPr20
CHO (S)-oxynitrilase 2.aq.HCI 70% (98% ee)
Effenbereer. F,; Hiirsch, B.; Ftirster, S.; Ziegler, T. Tetrahedron Lett., 1990, 31, 1249.
'<
0
E'O'bEt 0
1. LiNTMSz , -78°C 2.2.2 q.PhCHO ,-78°C 3.aq.NaOH
--
HO c-(Ph
OH
+
OH H02Cpph
Me
Me
4, H ~ O +
1.2) 97%
(98.8
Longmire, C.F.; Evans. S.A. Jr. .I. Chem. SOC., Chem. Commun., 1990, 922.
Bu
5 eq. immobilized Rhodococcus sp. 24 h
Bu X C O * H
62% Klempier, N.; de Raadt, A.; Faber, K.; Griengl, H. Tetrahedron Lett., 1991, 32, 341.
Acid - Alcohol
Section 3 13
1. PhCHO , Zn TMSCl , PhH 2. KOH , MeOH
289
+
OH HOOC,&H Ph (44% ee , R)
51%
Basavaiah. D,; Bharathi, T.K. Tetrahedron Lett., 1991, 32, 3417.
Me
1
Me*
COzH
B(0iPr)Z
NEt3 ,CHzClz
HO Me +CO,H
+
Me
95%
(99: 1 synmti)
Wang,2.; Meng, X-J.; Kabalka, G.W. Tetrahedron Lett., 1991, 32, 5677.
9
BSLDH ,NADH H+ , 2.8 d
COzH
OH T C O Z H
66%
(99% ee) BSLDH = Bacillus stearothermophilus lactate dehydrogenase Casv. G,; Lee, T.V.; Lovell, H. Tetrahedron Lett., 1992, 33, 817. 1. [NaOWKCVNaOCI1 , MeOH *. KI , j n n m
c
OH
/h/ OH
+ 24% mandelic acid
Ph C02H 57%
Guthrie.;Cossar, J.; h..L Can. .I. Chem., 1991. 69, 1904.
P h Y O 0-
5% R u ~ ( C O D ) ~ ( O ~ C C F ~ ) ~ 2 dppb , 10 eq. HCOOH OH + Ph dC02H 10 eq. NEt3 reflux, dioxane
Shimizu. I.; Tekawa, M.; Maruyama, Y . ; Yamamoto, A. Chew Lett., 1992, 1365.
SECTION 314: CARBOXYLIC ACID
- ALDEHYDE
NO ADDITIONAL EXAMPLES
80%
290
Compendium of Organic Synthew Methods, Vol8
SECTION 315: CARBOXYLIC ACID
- AMIDE
r
1. Ni(COD)(TMEDA)z THF ,reflux + CbzHN 2. H3O+
CbzHN
Section 315
0
CO,H
+
(Co2H
CbzHN
(9
1) 60%
1:l mixture when Ni(COD)(bipy)~was used Castailo, A.M.;
Tetrahedron Lett., 1990, 31, 4783. F
N A N F A N a F
CbzHN
w
Py , CH2C12,4 h
CbzHN
89% Bertho, J-N.; Loffet, A.; Pinel, C . ; Reuther, F.; Sennyey, G. Tetrahedron Lett., 1991, 32, 1303.
HOOC-NHCHO 1. Pd(0Ac)z , P(o-Tol)~ c ~-Bu H-N" N- C0,Me 100°C, NET3 , DMF .-
Ad
0
Meoel Q ,24h
OMe
2. NaBH4 ;H3O'
3.3N HCI 66% 4. A c ~ OHCOOH , J
BocHN
7 Co2H
1.3 eq. LDA
P
w
BocHN
23. H3O+
Co2H
48%
De Nicola, A.; Einhorn. J.; m e . J -L, Tetrahedron Lett., 1992, 33, 6461.
C02H M e 4 NH,
Ac2O Hz0, ))I)))
*
Me--(co2H NHAc
Veera Reddy, A.; Ravindranath. B, Synth. Commun., 1992, 22, 257.
96%
Acid - Amine
Section 3 16
SECTION 316: CARBOXYLIC ACID
29 1
- AMINE
1. NaN(TMS)2
NH2 3. 1N aq. HCI ,RT 4.ZnIaq. HCI ,AcOH 5. aq. LiOH ,THF 6. ion exchange
0 2
H02C83%
(>99%ee, R)
ODDolzer. W,; Tamura, 0. Tetrahedron Lett., 1990, 31, 991.
M ~ ANx ph Me
Ph
1. acryloyl chloride
2. NH3 C H K h 3. CICOZBn, NEt3
Nfi
I
*
HOOC
Y Me
NHyHCI
4. Hg(OzCCF3)z 5. NaBH4, MeCN 6. HCI, MeOH ,reflux
Amoroso, R.; Cardillo. G,; Tomasini, C. Tetrahedron Lett., 1990, 31, 6413. I. t-BuLi , THF , -75°C 2. C@
NHBoc
PhSimig, G.;
3.20% HCI ,reflux
8h
*
phTNHBOC 55%
Tetrahedron Lelt., 1991, 32, 1963, 1965. 0
Ph
Y
CO2Et 1.
F
Ph,r C02H
~ NH2 C vTEBA ~
K2CO3, MeCN , 80°C 2. KOH , M e O H , RT,2 h
Br
NH2
64%
Landini. D.; Penso. M.. I Org. . Chem., 1991, 56, 420.
Me-N3
t-Bu -(
N
1. LDA 2. BnBr 3. 6N HCI ,heat
4. Dowex 50W-X8
+
1
HOOC
olll
\
Ph
H2N BZ' 50% Juaristi. E.; Quintana, D.; Lamatsch, B.; Seebach. D,J. Org. Chem., 1991, 56, 2553. REVIEWS: "New Approaches to the Use of Amino Acids as Chiral Building Blocks in Organic Synthesis" Reetz. M.T,Angew. Chem. Int. Ed. Engl., 1991, 30, 1531.
292
Compendium of Organic Synthetic Methods, Vo18
Related Methods:
Section 319
Section 3 15 (Carboxylic Acid - Amide). Section 344 (Amide - Ester). Section 351 (Amine - Ester).
SECTION 317: CARBOXYLIC ACID
Phwco2Et
- ESTER
porcine liver acetone powder H20, pH 7.2, RT, 7 h
- PhyCOzEt
96%
C02H
COzEt
Ahmar, M.; Bloch.;Bortolussi, M. Synth. Commun., 1991, 21, 1071.
SECTION 318:
CARBOXYLIC ACID THIOETHER
OBOM SnBu3 Chan, P.C-M.;
- ETHER, EPOXIDE,
1. BuLi , THF , -78°C
2. co2 3. H+
*
9BOM e C 0 2 H (95%=) 99%
Tetrahedron Lett., 1990, 31, 1985.
0
NaSPh ,aq. iPrOH 0°C -+ RT
*
E C O O H 95%
Breitschuh, R.; m c h . D, Synthesis, 1992, 83.
SECTION 319: CARBOXYLIC ACID
- HALIDE, SULFONATE
1.3 eq. LDA
GMi
Welch. J.T.; Plummer, J.S.; Chou, T.S. J. Org. Chem., 1991, 56, 353. BIyNEtZPh, PhH RT,7h
-
Me
Narayana, C.; Reddy, N.K.; Kahalka. GW, Tetrahedron Lett., 1991, 32.6855.
87%
Acid - Ketone
Section 320
293
Starostin, E.K.; Mazurchik, A.A.; Ignatenko, A.V.; Nikishin. G.1, Synthesis, 1992, 917.
SECTION 320: CARBOXYLIC ACID
-
KETONE
1. AcCl, N-methylmorpholine
+
c
2. AICI3
67%
(>20 : 1) Jefford. C.W.; Tang, Q.; Boukouvalas, J. Tetrahedron Lett., 1990, 31, 995. 1. TFAA
c-
OSiMe3
2.
=(ph
CO,H
, -4O"C, 3h
65%
(>95% ee , S )
Michelon, F.; Pouilhbs, A.; Bac, N.V.; b e l o i s . N. Tetrahedron Lett., 1992, 33, 1743. Br
1.
M
~
~
C
O c-~
E H ~o
Zn, DMF, 70°C. 2 h 2. HCl , 100°C, 1 h Schick.;Ludwig, R. Synthesis, 1992, 369.
o C T M e 0
Also via: Section 360 (Ketone - Ester).
SECTION 321: CARBOXYLIC ACID
- NITRILE
NO ADDITIONAL EXAMPLES Also via:
Section 361 (Nitrile - Ester).
41%
294
\
- ALKENE
-
SECTION 322: CARBOXYLIC ACID
Me-
on 323
Compendium of Organic Synthetic Methods, Vol8
& . 2 eq. LiNEtz 2.0.5 q.12
CO2H
3. hot
62% Tefrahedron,1991, 47, 1997.
Aurell, M.J.; Gil, S.; Parra, M.; Tortajada, A.;
.
1. Mg THF
2. C@
'C02H
HO2C-
with 1. Ba ,THF 2. C 0 2
+
T
C
z
(99
C1)
99%
(2
98)
82%
H
SynLetr, 1992, 593.
Yanagisawa, A.; Yasue, K.;
Section 349 ( h i d e - Alkene). Section 376 (Nitrile - Alkene).
Also via: Section 313 (Alcohol - Carboxylic Acids).
Section 362 (Ester - Alkene).
Mem
SECTION 323: ALCOHOL, THIOL
- ALCOHOL, THIOL
+
Pseudornonas putidt39D Me&H
& OOH
Deluca, M.E.; Hudlickv. T. Tetrahedron Lett., 1990, 31, 13.
"0H
O
Pd(PPh3h , (Me3Sn)z dioxane , sealed lube 1O0-1O5"C124h
*
/
OH
80%
"0H
OH
Kellv. T.R.; Li, Q.; Bhushan, V. Tetrahedron Lett., 1990, 31, 161.
OH
n-C3H7 air , cat. AIBN
ether
89% (=2:1 cis:trans) Kgnai.;Ttimtiskozi, I TetrahedronLett., 1990, 31, 403.
Alcohol - Alcohol
Section 323
295
Hovorka, M.; GunterovB, J.; ZAvada, J. Tetrahedron Lett., 1990, 31,413. 5 9. NaN3 , RT OH W&1. aq. MeOH Me,Si&OH
Me3Si, 0
“%OH
NaN3 in hot DMF gave azido-allylic alcohols
90%
N3
Chakrabortv. T.K,; Reddy, G.V. Tetrahedron Lett.. 1990, 31, 1335.
OH H O A P h
a 0 4
Ph
86%
(47%ee, S) Tomioka. K,; Nakajima, M.;Koga, K. TerrahedronLett., 1990, 31, 1741. Ph
dihydroquinidine pchlorobenzoate OS04,K3Fe(CN)6 KzCO3, aq. r-BuOH
ph-
ooc
Ph
73% improved ee over NMO
Kwong, H-L.; Sorato, C.; Ogino, Y.; Chen, H.;
Tetrahedron Lett., 1990, 31,
2999.
dihydroquinidine
p-chlorobenzoate
p
h
6 Ph
polymer
*
1% 0~04 NMO , 10°C 2-3 d
P h q p h OH
81-87% (85-93% e)
Kim, B.M.; Shagless. K.B. Tetrahedron Lett., 1990, 31, 3003. MgI2, PhH ,AIBN Bu3SnH (added by
syringe pump)
OH
&OH
)-
53%
Me .. Bonlnl.; Di Fahio, R.; Mecozzi, S.; Right, G . Tetrahedron Lett., 1990, 31, 5369.
296
Compendium of Organic Synthetic Methods, Vol8
1. r-BuLi , ether -78OC
2. PhHCO
Me
Section 323
FH Ph80%
Me
Sengupta, S.; Snieckus. V, Tetrahedron Lett., 1990, 31, 4261.
1. P O 0S E M
-
cat. hydroquinone xylene ,reflux H O 2 . 0 ~ 0 4NMO , , aq. THF OH 60%overall SiMe$'h 3. mr, 15% ACOOH AcOH , NaOAc , RT , 1 h Koreeda. M,; Teng, K.; Murat, T.Terrahedron Lett.. 1990, 31, 5997.
* M~ M~
OH
1. (HMe2Si)flH ,NH3 2. [RhCl(ethene)]z, R-BMAP DCE ,30"C ,6.5 d
3.30% HzO2, KF ,K H C G MeOH , THF
M~ +OH OH
60%
(95/5 sydanti; 80%ee)
Tamao. L;Tohma, T.; Inui, N.; Nakayama, 0.;Iray,Tetrahedron Letr., 1990, 31, 7333.
c1
A*
Mo (NOj ;;fi
€I
51%
Ph
Lin, S-H.; Vong, W-J,; Cheng, C-Y.; Wang, S-L.; LiuJLS Terrahedron Lett., 1990, 31, 7645. 0 ~ 0 4 KjFe(CN),j ,
tBuOH, H20,RT K2CO3,24 h
Minato, M.; Yamamoto. K. ; Tsuji, J. J. Org. Chem., 1990, 55, 766.
$, 0
PhCHO , CrC12 THF ,LiI O"C,lh
Fujimura, 0.;Takai.;
Ph OH OH (9 8
+ OH OH 2)
J. Org. Chem.. 1990, 55, 1705.
95%
Section 323
Alcohol - Alcohol
1. catecholborane ,THF -lO°C, 5 h
2. aq. Na K tartrate, MeOH
*
*
297
82%
(101 syn:anti)
Evans. D.A,; Hoveyda, A.H. .I. Org. Chem., 1990, 55, 5190. 0
OH
3 eq. BuLi , 0°C ether-pentane
88%
* 6 ) OBuH
OH
u; AM-El-Aziz, AS.; Lough, A. J. Org. Chein., 1990, 55, 5305. OTBDMS 5% OsO4,25"C
BnO
Brio OTBDMS >H
2 eq. NMO
TBDMS-O HO
TBDMS-0
Brio
OTBDMS
+
C O , ~TBDMS-0
(9
w;Morikawa, Y.;
H O CozEt 96%
1)
J. Org. Chein., 1990, 55, 5429.
aq. Dowex-SOW
71%
reflux, 30 min
Ranu.; Chakraborty, R. Synth. Coinmun., 1990, 20, 1751. 0
OH
Ph
MeTi(OiPr)3, ether LiI , - 7 8 -+~ - 2 0 0 ~
Ph
Ph
Ukaji, Y.; Kanda, H.; Yamamoto, K.; m 0
PhKPh 0
OH OH
Me OH
4
Me
a
,Yb,RT.18h
THF , HMPA
.c
Ph
(99 . T. Chern. Lea., 1990, 597.
1)
OH P h m Hph-& Me +
Ph Me
Ph
OH
37%
46% (90% ee) Takaki, K.; Tanaka, S.; Beppu, F.; Tsubaki, Y.; Fuiiwara. Y,Chein. Left., 1990, 1427.
69%
298
Compendium of Organic Synthetic Methods, Vol8
Section 323
Pseudomonas sp. (BM 2)
OH
G e w , P.J.; P&c&&~ Commun., 1990, 204.
35% 3% Roberts, S.M.; Ryback, G.; Winders, J.A. J. Chem. Soc., Chem.
GOH
1. HzKO (500 psi), PhH [Rh(OAc)2]2 , iOO°C
Op(OEt),
*
2. LiAIH4, ether
72%
OH
Jackson. W.R.; Perlmutter, P.; Tasdelen, E.E. J. Chem. SOC.,Chem. Commun., 1990, 763.
Me- . M e Br Si-
1. Bu$nH, 1-BuOH AIBN , reflux
2.30%H 2 0 2 , THF K H C 0 3 , MeOH reflux Koreeda.; Hamann, L.G. J. Am. Chem. Soc., 1990, 112, 8175.
t-BuMezSiO
G'U""
___L
Me
f-BuMezSiO
(a) SmIz , THF , RT (b) Sml,, THFhexane , RT ( c ) SmI@-Bu , THF , RT
80%
9'"qo o?-B&e2Si0
Me OH
(a)
(b)
(C)
Me
0%
71% 35% 0%
41%
15%
Ilenishi. J,; Masuda, S.; Wakabayashi, S. Tetrahedron Lett., 1991, 32, 5097.
+
Ph
Ph
O s 0 4 , NMO 1 0 1 acetone:H20 +
*
75%
(24%ee , SS)
fk'
Pini, D.; Petri, A.; Nardi, A,; Rosini, C.;
PhxPh HO OH
.
Tetrahedron Lett., I991, 32, 5175.
Section 323
Alcohol - Alcohol
1. I-BuOK , THF -78°C
Ph
2. H202, K F KHC03
t
* 0
PhCHO , SnC12 Bu,NBr, DMI L, 25"C, 1 6 h
&OH
66% Tetrahedron Lett., 1991, 32, 6383.
Matsumoto, K.; Miura, K.; Qshima;
Me
299
M s P h
Ph
+
OH OH
DMI = dimethylimidazolidin-2-one
7)
(93
Masuvama. Y,;Nakata, J.: Kurusu, Y. .I. Chem. SOC., Perkin Trans. 1, 1991, 2598.
89%
1. Li" ,naphthalene ,THF 1 h , -78°C
Yus. I%;
2. iPrCHO , -78°C 3 RT * 3. H 2 0 Rambn, D.J. J. Chem. Soc., Chem. Commun., 1991, 398. Re2O7, H 2 0 2 , 1 6 h
n-C8H17-
/
90"C, dioxane
n-C H
l 7 - " y 0 ~
'"qH phqH L,
OH
62%
Wanvel. S; Klass, M.Rg.; Sojka, M. J. Chem. SOC., Chem. Contmun., 1991, 1578. 1 aq.acetone,25"C . 0 ~ NMO 0 ~ ~
ph\
2.Na2S205
Ph
+
* HO
HO HO
~ 0 ' 'Ph (16
Park, C.Y.; Kim, B.M.; Shamless. K.B. Tetrahedron Lett., 1991, 32, 1003. 1. Bu3SnH, AIBN PhMe
2. TBAF
1)
Ph 87%
-3
59% HO
HO
Hutchinson.J.H.; Daynard, T.S.; Gillard, J.W. Tetrahedron Lefr., 1991, 32, 573.
Section 323
Compendium of Organic Synthetic Methods, Vo18
300
PdC12(PhCN)2 , SnCl2 70 h
0
xq!
-
&OH , TIf F ,0°C
(82:18 syn:anti) Kurusu, Y. Chem. Lett., 1991, 879.
Takahara, J.P.; ;.Y-
N
,
BH3, ~ THF ~ aq. NaOH
~
(90
u, Mckee, S.P.; Sanders, W.M. Tetrahedron Lett., 1991, 32, 711. Ph2CuLi
0
L
-
7
Devine, P.N.;
RMgX ,R2CuLi
10)
86%
BxoH
Bn
similar results with
OH
86%
a:;+ 0::
Tetrahedron Letf., 1991, 32, 883.
C
1.0.1 M S d 2 , THF
CHO I-BuOH , -78°C + 2 5 T CHO 2. 10% Na2S203
(93
Chiara, J.L.; Cahti, W.;
Tetrahedron Letr., 1991, 32, 1125.
'
B(OiPr)* (98:2 E:Z)
Wang, Z.; Meng, X-J.; &&&a.
A
OH N E t 3 , CH2C12 28 h
+
81%
HO Me +OH
*" Me
72%
(97:3 syn:anli)
CHo
HMPA 2.10%aq. Na tartrate
Raw, AS.; & h s g ~ U . J. Org. Chem., 1991, 56, 830. *
7)
C.W. Tetrahedron Len., 1991, 32, 1945.
1.2 eq. VC13(THF)3 I .4 ZII , CH2Cl2
Park, J.;
75%
OH
Tetrahedron, 1992, 48, 2069.
82%
Alcohol - Alcohol
Section 323
Ph-
[Rh(COD)z]+ C1042. NaOH ,HzO
Matsumoto, Y.; HayuhJ, '
B
011 OH
1)
40% ee
U
2. H@z, NaOH
OH OH
*
OH OH
-
Bu
+ B u / Y Me
Me
3. TBAF
(24
When step 1 is 9-BBNITHF/-78"C-25"C
62%
44% ee
Tetrahedron Lett., 1991, 32, 3387.
1. catecholborane ,PPh3 1% [Rh(COD)C1]2
V
OH
OH (3
0SiMe2r-Bu Me
30 1
1)
(1
Bureess. K,; Cassidy, J.; Ohlmeyer, M.J. J. Org. Chem., 1991, 56, 1020.
9)
1. LDBB ,THF ,-78°C 2. Et3AI ,M e e T H F , -70°C 3. iPrCH0
*
+OH
52%
LDBB = 4,4-di-t-butyl biphenylide Mudryk, B.; Cohen. T. J. Org. Chem., 1991, 56, 5760.
0.2%C A N , H 2 0 , MeCN 25 min
+
Ph
1.2.2 eq. SmI2, THF HMPA
O16% H
80%
6
Baltork. I.M.; Zardaloo, F.S. Tetrahedron, 1991, 47, 9861.
N-;.
T
HO,,,
80%
a;H +M
I . Org. Chem.,1992, 57, 3132. Molander. G.A,; McKie, J.A. .
Me-
'.
3/SiPhzC1
-
.NEt3
OH 2.190"c 3. KF , 1 4 2 0 2
Me
(1
Sieburth. S.M,; Fensterbank, L. .1. Org. Chem., 1992, 57, 5279.
1)
71%
Compendium of Organic Synthetic Methods, Vol8
302
Section 323
1 . Li , BFpOEt2, naphthalene 2. iPrCHO
0
+OH
*
3.aq,HCI
76%
Rambn, D.J.; Yus.M. Tetrahedron. 1992, 48, 3585. 1% Os04 , K?Fe(CN)6, HzO
K2CO3, r-BuOH , RT
r.
OH
5% L N ~ O S i P h z l - B u
Oishi, T.;
83%
(41% ee , SS)
OSiPh2l-Bu
Tetrahedron Len., 1992, 33, 639.
OAICI, 2
Sarlori.
\
FeC13, MeN02, RT Sh
+
78%
OMe OMe OMe G; Maggi. R.; Bigi, F.; Arienti, A,; Casnati, G.Tetrahedron Lett., 1992. 33, 2207. O s 0 4 ,aq. MeCN , NMO
Ph
c
polymer-bound dihydroquinidine , 24 h
-;1-"
Ph
86%
OH
(82% ee , RR)
Lohrav. B.B.; Thomas, .-.;Chittxi, P.; Ahuja, J.; Dhal, P.K. Tetrahedron Len.. 1992. 3 1 . BnNEt3 B H 4 , Me3SiCI CHZC12 ,0°C
2. 10%K2C03 Baskaran, S.; Chidambaram, N.; Narasimhan, N.; 33, 6371.
c
rL
HO
HO
5453.
69%
Tetrahedron Lett., 1992,
(90% ee)
m,Tanaka. K.; Miyamoto, H. Tetrahedron Lett., 1992, 33, 4021.
Alcohol - Alcohol
Section 323
303
P h q Ph OH
quant.
(73% ee , RR)
Imada, Y.; Saito, T.; Kawakami, T.; Murahui. S-I. Tetrahedron Left., 1992, 33. 5081.
DHQD-IND , cat. OsO4
Ph/-7Nle DHQD-IND=
72% ee (1R.23
0
J, Am. Chem. Soc.. 1992, II4,7568.
Wang, L.;
Ph
K3Fe(CN)6, K2C02,O"C t-BuOH, H20
Ph
1 % oSo4 , K3Fe(CN)6 +
ph&Ph
DHQD2-PH AL
84%
OH
DHQD2-PHAL = 1,4-bis-(9-O-dihydroquinidinyl)3 +99% eel phthalazine - see J. Org. Chem., 1992, 57, 2768. Xu, D.; Crispino, G.A.; -J. Am. Chem. SOC., 1992, 114, 7570.
3% Ni(mac)2,02 DCE.MS4Am8h 100°C
HO
*OBz
OH
90%
(85: 15 1 ,2-diol:1,3-diol) nickel (11) Ni(rnac);! = bis-(3-methyl-2,4-pentanedionato) Mukaivama.; Irnagawa, K.; Yamada, T.; Takai, T. Chem. Lett., 1992, 231. Ru(acac)3 , tetraglyme P(n-Cd41713 H2 200"C, l-I3Po4,3 h
-c
oH
27%conversion 95% selectivity
Hara, Y.; Inagaki, H.; Nishimura, S.; Wada. K,Chem. 1Rlt.. 1992, 1983.
Compendium of Organic Synthetic Methods, Vo18
304
Section 323
Me3SiCI. NaI , Srn MeCN, 15 min
84% Ph s ! h OHMe Akane, N.; Kanagawa, Y.;Nishiyama, Y.; Ishii. Y, Chem. Lett., 1992, 2431.
b \
.RT
I . 0 3 , CH2C12 , O°C 2. Hz Pd-C , EtOH
OMe
b''OH
*
&OH
+-
+OH
+OH
(3
1)
41%
Culshaw, A.J. Synktt, 1992, 214.
;-
E t f i l , PhH-hexane [PhBrL? sec-BuLi;Al]
Meb
0
H
0°C --t
RT
OH M e A O H
+
Ph Me+OH
Ph
OH
(20
1)
55%
Ahn. K.H; Kim, J.S.; Jin, C.S.; Kang, D.H.; Han, D.S.; Shin, Y.S.; Kim. D.H. SynLeft, 1992, 306.
0
Ph
#
N a B b ,EtOH , RT
N.OMe 0 Me Sibi. M.P. ; Sharma, R. SynLett, 1992, 497.
P hOH V O H
92%
REVIEWS:
"Recent Advances in the Asymmetric Dihydroxylation of Akenes" Lohrav. B.B. Tetrahedron Asymmetry, 1992, 3, 1317. "New Aspects of Stereoselective Syntheses of 1,3-Polyols" Dishi. T,; mats. T. Synthesis, 1990, 635. Also via:
SECTION 324:
Section 327 (Alcohol - Ester); Section 357 (Ester - Ester).
ALCOHOL, THIOL
- ALDEHYDE
Siedlecka, R.; Skarzewski. J.; Mfochowski, J. Tetrahedron k t t . , 1990, 31, 2177.
305
Alcohol - Aldehyde
Section 324
OMe
A
1. PPh3, TMSOTf 2. BuLi , THF, -78°C
3. PhCHO , TMSOTf = H r c H o 4. KOH ,MeOH 77% 5. H+ Kim.;Kim, Y.C. Tefrahedron Lett., 1990, 31, 2901.
0 Me,SiO
THF,-78OC
Li
Kane., Kim, D.H.; Lee, J.H.; Rim,J.G.; Yoon, Y.B.; Kim, K. .I. Org. Chem., 1990, 55, 5555.
1 . MeTi(OiPr)3 ,ether 1 h (>99:1 dr)
2. HCUHzO - ether
Me p Ph
w
H CHO
70% Tetrahedron Lett., 1991, 32, 29 19.
Ukaji, Y.; Yamamoto, K.; Kukui, M.; l&&&yLL 1 . BuzBOTf , iPr2NEt
\)IN A 0
CH2C12,O"C 2.EtfiAICI.CH2C12 hexanes ,-78°C
0
OH 0
V
N
(add enolate to Et2AEIl
'
Me
OH 0
O V I
-
+
N
'
Me
3. iPrCHO
5)
(95
0 O
u
63%
Walker, M.A.; Heathcock. C.H,J. Org. Chem., 1991, 56, 5747.
ph?-tph
TolO2S' N.sNS02Tol , -780c 1.
n-C5H1 ICHO
LC K - H
2.5 h
2. t-BuMe2SiC1, imidazole 3.03
Corev. E.J.; Jones, G.B. Tetrahedron Lett., 1991, 32, 5713.
OSiMe2t-Bu n-~5~11< CHO 98%
306
Section 325
Compendium of Organic Synthetic Methods, Vol8
1. Dibal , PhMe , 0°C 2. satd. NH4CI 3. 1.6N H2S04, 18 h
Ph
69%
Ph
4.9N HCI , 15 h SynLett, 1991, 479.
Hayashi, M.; Yoshiga, T.;
MABR , -78OC
** 0
87%
40 min
Ph-0SiMe2i-Bu I-BU
(98% ee)
I-Bu
MABR = B r q o h i o + B r I-BU Mel-Bu
Maruoka, K.; Ooi, T.; Nagahara, S.;
Tetrahedron, 1991, 47, 6983.
Section 330 (Alcohol - Ketone).
Related Methods:
SECTION 325: ALCOHOL, THIOL
- AMIDE
iPrCHO ,THF LHMDS ,- 100°C
96%
Ph
Ph
(>99% de 3S.4R)
Oiima.;Pei, Y. Tetrahedron Lett., 1990, 31, 977. 1. EbNIO, ,MeOH -78°C 2. cyclopentadiene
HO Ph wNHoH
OH
"5':
H o
Ph
3.Na/Hg,MeOH NaH2PO4
77%
Miller, A.; Procter, G. Tetrahedron Lett., 1990, 31, 1043.
0 N Boc
1. set-BuLi ,TMEDA ether 2. PhCHO
OH m
P
h
N Boc 39% Bealr.;Lee, W.K.J. Org. Cheni., 1990, 55, 2578.
+
J-0 0
~~~
Ph 37%
Section 325
Alcohol - Amide
307
%MeoKPh -78'C
0
PMP
OMe,
HO
1. LDA , THF
2. MeCHO f-78°C -+ RT
0
Ph
PMP
80%
PMP = p-rnethoxyphenyl
Durst.; Sharma, M.K.; Gahe.;Lee, F.L. J. Org. Chem., 1990, 55, 5525. HOCHzCHzNH2, e'
PhC02Me
*
B z H N ~ o H 73%
; Ueda, A.Can. J. Chem., 1990,
Arai, K.; Tamura, S.; Masumizu, T.; Kawai, K.; 68, 903.
3; C1eNHB 1.2.2eq. BuLi 2. 10°C 3. H f l
82%
\ /
Smith.;hitchard, G.J. Angew. Chem. Int. Ed. Engl., 1990, 29, 282. I . BuLi , T H F , -105°C 2. PhCHO
0
0
*
E(2N\Ph
OH
65%
Hiiro, T.; Mogami, T.; Eambe. N,; Fujiwara, S.; Sonoda. N. Synth. Cornmun., 1990, 20, 703.
E:-
OH AI(H6) , aq. THF , ))))))
0 Bn
/
e 0. N - 0 B n
Luzzio.; OHara, L.C. Synth. 0 P
0
Commun., 1990, 20, 3223.
BuMnCl
v NMe,
h
70%
Me
Bu,, 0 Ph@NM+ Me
+-
(>99
HO B u o
Ph/VINMe, Me c1)
98%
Taniguchi, M.; Fujii, H.; Oshima, K.; Utirnoto, K. Tetrahedron Lett., 1992, 33, 4353. piperidine ,AIC13 , 1 h
DCE , 2 5 T
w
H
Lesirnple, P.; J&g. D . C L Synthesis, 1991, 306.
o
q
N
s
91%
Compendium of Organic Synthetic Methods, Vol 8
308
, OMe
dNJ Y
Section 325
OMe BnCHO ,CHzCl2 R T , 15 h
-"II"
~~C~~(THF)~IZ[Z~~CI~I
/
CHO
OH
HO
73%
(80:20 syn:anti) (77*)
Annunziata, R.; Cinauini. M.; m z i . F.; Giaroni, P. Tetrahedron Asymmetry, 1990, 1, 355. P h C O a , PhMe
O2N
02Ny-Jo
c
reflux
B z O A OH
92%
Schmidhauser.;Longley, K.L. Tetrahedron Lett., 1991, 32, 7155. CHO
NHCbz
1. 1 . 1 q.VC13(THP)3 0.6 Zn
2. 1 M HCI
Org. Chem., 1992. 57, 28.
Konradi, A.W.; -..I.
W' h0
0
n
1 . 2 eq. S m 4 , TF
A
CF,
0
Collin, J.; Namy,J.L.; Jones, G.; 0
0
MeA1C12. 0°C hexmdCH2C 12 H v N M e 2 2h
53%
CF,
Tetrahedron Lett., 1992, 33, 2913.
Me OH() € f NMe, ' v i-
Me
":? Me 0
Me
NM%
Me
(97
3)
66%
Fujii, H.; Taniguchi, M.; Oshima. K,; ytimoto. Ic, Tetrahedron Lett., 1992, 33, 4519. 1 . 2 eq. MeZNCHO Na , 8 0 ° C , 5 h
Ph
Ph
OH
Botteghi, C.; Gotta, S.; Marcheti, M.; Melloni. G. Tetrahedron Lett., 1992. 33, 5601.
Alcohol - Amine
Section 326
O H N.C02Ph C 5
Sd2
309
$q-C02Ph
+
OSiMe;?t-Bu
OSiMe2t-Bu 25%
Baldwin.;Turner, S.C.M.; Moloney, M.G.Tetrahedron Lett., 1992, 33, 1517.
I/
NaBH4, EtOH , 0°C pH = 8-10
9>(cH2)S 0 0
9v(cH,), 0 OH
f/
OH 0
36%
30%
Moeller. K.D; Hanau, CE.Tetrahedron Lett., 1992, 33,6041. 1. n-C3H7NH2
*
2. MeOH ,reflux
CO,Et
P
+ 91(cHz)S
N
Amri, H.; El Gaied, M.M.; Ben Ayed, T.; Villeras, J. Tetrahedron Lett., 1992, 33, 6159.
0
ZnBr , THF ,25”C
0
/Jul NHPh
c
bw OH 0
NHPh 91%
Taniguchi, M.; Qshima. K.; Utimoto. K. Chem. Lett., 1992, 2135.
SECTION 326: ALCOHOL, THIOL OH
PhCH2NH2, Zn ,2h NaBH3CN, n-PrOH H2O , reflux
OMe Bernoas. R.C, Tetrahedron Lett., 1990, 31, 469.
HO 1. BuCu
MeHN
- AMINE *
NHBn 82%
,;IoH
. ; LiAIH4 Ph’”
1. BuZnI
HO L
SPh 2. LiAlH4 MeHN 3.Hz.W-C 3. H2, Pd-C Me Couty, F.; Darm, J-C.; Prince, B.; Puchot, C. Telrahedron Len., 1990, 31, 2889.
s;
Section 326
Compendium of Organic Synthetic Methods, Vol8
310
0
e- ,NaOMe ,MeOH Bu4NHS04,15"C Mex=
0
Me
C02H
M~
graphite electrodes 500 m A ,80 h
OH
3.9 v
Me
75% Fasseur, D.; &~Q,&B.; Cauliez. P.; Debacker. M.; Couturier, D. Tetrahedron Lett., 1990, 31, 1713.
Bn
Nq-+
H
Boc.
OH
H
N
H
6)
(1
=
OH 65%
Vara Prasad, J.V.N.; Rich. H. Tetrahedron Left., 1990, 31, 1803.
Me. t-BUN
N
/I
A
1.1-BuLi ,THF -78°C
php +J
Ho
2. PhCHO , -5"; t-BuN 60% Solladik-Cavallo,A,; Bencheqroun, M. Tetrahedron Lett., 1990, 31, 2157. 1. BuLi ,ether 2. MeOMs
N.
3. Y O ; aq. HCI
Me
QyN.
* 0
Simig, G.;Schlosser. M. Tetrahedron Lett., 1990, 31, 3125.
Me
Me
67%
M o ( C O ) ~reflux , H20/MeCN
Me'ph% N*O
MeHN
n-C4H9 2-3 h
OH
78%
Cicchi, S . ; Goti, A; B u n'L L;Guama, A.; De Sarlo, F. Tetrahedron Lett., 1990, 31, 3351.
(73
Mlkami.; Kaneko, M.; Loh, T-P.; Terada, M.;
27)
59%
Tetrahedron Lett., 1990, 31, 3909.
31 1
Alcohol - Amine
Section 326
0 Chini, M.; Crotti. P.;
a
BnNH2, LiC104 MeCN.64h
F
H NHBn
80% Tetrahedron Lett., 1990, 31, 4661.
'
1. Dibal , CHzC12 , -78°C 2. PhMgBr ,ether
Ph
3. aq. NaHC03
Ph
bH
5. H3O+
69%
Polt. It,;Peterson, M.A. Tetrahedron Lett., 1990, 31, 4985.
N3 OH
NaN, , LiCIO, MeCN ,80T
n-c6H 13
24 h
+ +
n-C6H13
HO n-C6H13
N,
92.5) 96%
(7.5
Chini, M.; Crotti. P,; Macchia, F. Tetrahedron Lett., 1990, 31, 5641. Rh2(OAc)4, PhH
o N f M e /
reflux95h
N Me
do Me
OH
Me
77%
Etkin, N.; Babu, S.D.; Fooks, C.J.; Durst...I.Org. Chem., 1990, 55. 1093.
1. BuLi
3. NaBH4, THFEtOH \
NMe2
H
47% overall
Katritzkv. A.R, ; Lue, P.; Chen, Y-X. J . Org. Chem., 1990, 55, 3688.
Re
HSiMezPh , CHzClz, 25°C CsF , 18-cfown-6,9h
0 ; . u~ -
67%
OSiMe,Ph
Rubina, K.; Shymanska, M.; Lukevics, E. Synth. Commun., 1990, 20, 2439.
Compendium of Organic Synthetic Methods, Vo18
312
2 eq.Sml2 ,ethylene glycol HMPA , RT c
N-OBn 4
Ph
Ph
Section 326
d N H O B n 83%
Tetrahedron Lett., 1991, 32, 3555.
Hanamoto, T.;
0
H
.MeCN
Ph 10 kbar , 2 4 h
H
15% at atmospheric preessure Potsuki. K; Nishiuchi, M.; Kobayashi, S.; Nishizawa, H. J. Org. Chem., 1990, 55, 2969. 1. BuLi , ClSiMezH, ether 2. P ~ [ ( C H ~ = C H ~ ) M ~ ~ S ~ I ~ O ) Z 0.2%.RT , 3 0 rmn
NH2
3. EDTA-2 M a , RT * 4.30% H 2 0 2 , KF KHC03 MeOH , THF ,RT I
ph$t
77%
(80:20 syn:anti)
Nakagawa, Y.; Iray,J. Org. Chem., 1990, 55, 3438.
;
OH NHBoc
1.0.5 [V2C13(THF)&
1 h addition of aminoaldehyde 2. 10%aq. Na tartrate
Konradi, A.W.;
&ma J. Org. Chem., 1990, 55, 4506. OH
P h / t Ph OH
Wt.; Ahuja, J.R. J.
1. soc12 ,cc14
2.UN3, DMF , 12OOC * 3. H2, Pd-C
OH
OH Ph &Ph
81%
NH,
(196% ee , RS)
Chem. SOC., Chem. Commun., 1991, 95.
porcine pancreatic lipase EtOAc
k
70%
(>201 dr)
c,
Q Ac
OH
+
( T O H H
(-) ,92%ee , S (9%) (+) ,90%ee , R (90%)
Asensio, G.; Andreu, C.; Marco, J.A. Tetrahedron Lett., 1991, 32, 4197.
Alcohol - Amine
Section 326
PhCHO
'*
TolSOzCH2CN , I % AgOTf 25"C, CH2Cl2 Me
Me
313
OH PhL N H M e
me 96% (83% ee)
PPhz
2. LiAIH4, THF
Sawamura, M.; Hamashima, H.; Ito. Y . J . Org. Chem., 1990, 55, 5935
0 %Me,
@ Me
MeCN t
hv (near UV)
quant.
\
quantum efficiency = 0.56
m; Cao, Q. Tetrahedron Lett., 1991, 32, 3915.
(93
Canas, M.; Poch, M.; Verdageur, X.; Moyano, A.; &j&.&A, 1991, 32, 6931.
OH M e A O H
H' N'CHPh,
7)
96%
Tetrahedron Lett.,
;
1.1 MsCl, 3 NEt3 CHzC12
0°C (8 h); RT (36 h)
Me
CHPh2
77 %
Poch, M.; Verdaguer, X.; Moyano, A.; PericBs, M.A.; Riera, A. Tetrahedron Lett., 1991, 32, 6935.
c
Me02C"'no N
0
1. Phy N=O 2.0~04,NMO
HO,
OH
3. Hz , Pd-C
Defoin. A,; Pires, J.; Streith, J. SynLett, 1991, 417.
H
3 14
Compendium of Organic Synthetic Methods, Vol8
G-
Me
Section 326
1. BF3*OEt2 2. sec-BuLi , THF ,-78OC
3. PhCHO ; 5% HCI
79%
Kessar. S .V,; Singh, P.; Vohra, R.; Kaur, N.P.; Singh, K.N.J. Chem. Soc., Chem. Cornmun., 1991, 568.
A N' Ph \
ph%
Me
.
1. PhCHO h w i s acid 2. Na , iPrOH. THF O°C --f RT 3 . 4 N HCI , THF , 60°C 4.3NKOH, 1 h
QIH2 OH
NH2 OH i-P h v P h
Ph+Ph Me
Me
(39
61)
94%
Barluenea.; Joglar, J.; Gonz&lez, F.J.; Fustero, S.; Kriiger, C.; Tsay, Y-H. Synthesis, 1991, 387.
0;;
0'
MqSiN, , L-(+)-DIPT 10% TiCh(0iPr)z -10°C , 2 0 h
60%
(46% ee)
SynLett, 1991, 774.
Hayashi, M.; Kohrnura, K.; Me3SiN3, THF , 6 d
n-C6H 1 3
cat. Ti(OiPr),
dn-c6H13 OSiMe,
b
N,
Sutowardoyo, K.I.; Emziane, M.; Lhoste, P.;
(92
+ 8)
74%
Tetrahedron, 1991, 47, 1435.
5
C02t-BU n-C6H 13
~-C&I~CHO CH2Cl2 ,
P~C=N-CH~CO~~-BU
89%
OH
(43% dr)
Gasparski, C.M.; Miller. M.J. Tetrahedron, 1991, 47, 5367. NaN3, NH4CI aq. MeOH ,25"C
OH
60 h
w M e 3 X
HO
(3
OH
+
Chakrabortv.;Reddy, G.V. Tetrahedron Lett., 1991, 32, 679.
"XH N3 O H 1)
88%
315
Alcohol - Amine
Section 326
Q
"W%
M.~
NHOMe
.OMe
e- , Sn cathode, C anode = 5% C , iPrOH , EbOTs
Shono. T,; Kise, N.; Fujimoto, T. Tetrahedron Lett., 1991, 32, 525. Shono. T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett., 1991, 2191. 1. NMM
Ph
3. NaBH4, H20 -15°C. 30 see Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; 923.
Ph
Tetrahedron Lett., 1991, 32,
woM
1. LiDBB , THF , -95°C
9 S P h
M e O O C H :
2-
81%
79%
-95"C, 90 & OH LiDBB = lilhium di-t-butylbiphenyl radical anion
Tsunoda.;Fujiwara, K.; Yamamoto, Y.; Ilbs.Tetrahedron Lett., 1991, 32, 1975.
P N
Me
0
Bra
1. NaOMe , PhH , reflux 2. NaBH4
Ph
c1
3. Me02CC1, PhH reflux
0
58%
Me- N C02Me0C02Me
Coates, A.J.; Malone, J.F.; McCarney, M.T.; Stevenson, P.J. Tetrahedron Lett., 2991, 32, 2827. Br OTHP ,
1. Ph+ 0
MeHN-
PPh3f
Br-
Kinder, F.R. Jr.; Jarosinski, M.A.;
2. NaH , THF , heat 3. H+
N I
Me
J. Org. Chem., 1991, 56,6475.
76%
3 16
Compendium of Organic Synthetic Methods, Vol 6
OSjMe2t-Bu
OHC1Me
Section 326
OSiMqt-Bu
1. LiHDMS
* M
2. ally1 MgCi
M
e
+
NH2 (4
. . ; m Giacomini, D.; Mezzina, E.; 1991, 32, 2961.
OSiMqt-Bu
+Me N*2 96)
(82
-nus.
18)
88%
P.; Moursounidis, T. J. Org. Chem., 1991, 56, 1529.
Murakami, M.; Hayashi, M.; =.I.
Ph Me,,
66%
; Zarantonello, P.Tetrahedron Lett.,
Org. Chem., 1992, 57, 193.
1. Dibal , ZnCl2 , THF 2. H 2 0 , OH-
3. LiAIH4, THF
Ph
Ph
*
Ph
3)
(97
92%
Aguilar, E.; w r o . S;. Olano, B.; Viado, A.L. J. Org. Chem., 1992,57, 1219. Bar1ueqga-L ; Aguilar, E.; Olano, B.; Fustero, S. Sydett, 1990, 463.
;-
1. Na(Hg) , aq. MeOH 2. NaOH , aq. EtOH
(96%de)
Martin. S.F.; Hartmann, M.; Josey, J.A. Tetrahedron Lett., 1992, 33, 3583.
HO
Alcohol - Amine
Section 326
OH
1. Dibal 2. NH4Br 3.MeNH2
PhXCN
4.NaBH4
317
OH
t
Ph
A-NHMe
79% Zandbergen, P.; van den Nieuwendijk, A.M.C.H.; Brussee. J,; van der Gen, A.; Kruse, C.G. Tetrahedron, 1992, 48, 3977.
H P
O
8CF3 E t
1. Bn2NH , RT 2. NaBH4, EtOH , RT
- 7:; Bn2N
85%
Ph
Ph
BCgu6, J-P.;Bonnet-Deppon, D.; Sdassi, H. Tetrahedron Lett., 1992, 33, 1879. ral liver microsornes
E~OH,phosphalebuffer
iBz
P h O d o
cj
36°C
c
(86%ee)
Bz
40%
Rao, A.B.; Rao, M.V. Tetrahedron Lett., 1992, 33, 4077.
;
Me,
H
'% NH2
1. BuLi ,THF , -80°C 2. AIMe3, PhMe ,-80°C 3. -80°C -+ 0°C
+
4. NaF, H20
HO
H N,H
Najime, R.; Pilard, S.; Vaultier. M, Tetrahedron Lett., 1992, 33, 5351. 1. BuLi , -5OT 2. r-BuLi , -3O'C -+ 20°C elher, PMDETA
PhHNA
I
3. PhCHO 4. H,O
PhHN
PMDETA = N,N~~".N"-pentamethyldiethylenediamne
Barluenea; Gonzllez, R.; FailanBs, F.J. Tetrahedron Lett., 1992, 33, 7573.
0'
iPrMezSiN3, TMSOTf )3
,O0C,48;
OH
Nupent.J.Am. Chem. SOC., 1992, 114, 2168.
,$t
OSiMe2(iPr)
ON.,
(93% ee)
86%
69%
Section 327
Compendium of Organic Synthetic Methods, Vol8
318
REVIEWS :
"The Synthetic Utility of a-Amino Alkoxides" SynLetl, 1992, 615.
SECTION 327: ALCOHOL, THIOL
- ESTER OH
baker's yeast 20%sucrose
dialysis tube Spiliotis, V.; Papahaatjis, D.; m u s s i s . N, Tetrahedron Lett., 1990, 31, 1615. H20,
nC3H7CHO. I d
SOzN(iPr)z
S02N(iPr)2
70% (42% de)
Baylis-Hillman coupling reaction
Basavaiah.;Gowriswari, V.V.L.; Sarma, P.K.S.;Dharma Rao, P. Tetrahedron kit., 1990, 31, 1621.
OSiMe, Me&
Me
90%
(35 1) Ishikawa, A.; Uchiyama, H.; Katsuki, T.; Yamaguchi, M. Tefrahedron Lect., 1990, 31,2415.
9
cat. OsQ , NMO aq. acetone, RT
C02Me
HO
12h
111
OH
6 " O H CO2Me
85%
Backenstrass, F.; Sueith.;Tschamber, T. Tetrahedron Lett.. 1990, 31. 2139.
HO>
1. BuzSnO , PhMe
Ph reflux , 6 h OH 2. BzCl 3. Me3SiC1
Ph w
Me3Si0 (98
OBz
-t
BzOT(OSiMe3 2)
83%
Reginato, G.; Ricci, A.; Roelens. S,; Scapecchi, S. J. Org. Chem., 1990. 55, 5132.
Alcohol - Ester
Section 327
3 19
YH do -- & OH
porcine pancreatic lipase
o
(n-C3H7C0)Z0
+Y
*
&n-C3H7
n-C3H7
0
O0 n-C3H7 0
1)
(99
Ramaswamy, S.; Morgan, B.; Oehlschlager, A. Tetrahedron Lett., 1990, 31, 3405. ,
A
,
Pseudomom fluorescens
OH OH
lipase
CHCI, 300~
=/OAc
j n + A OAcOH 40%
I
OAcOAc 60%
(>98% ee)
Santaniello, E.; Ferrabuschi, P.; Grisenti, P. Tetrahedron Lett., 1990, 31, 5657. Candida parapsilosis
63%
(>99% R)
Ham, H.; S b i m i u A; Hattori, S.; Yamada, H. J. Org. Chem., 1990, 55, 4377. Ph
wOMe
-
OSiMe2t-Bu PhCHO , TMSCl [CPZYbC112
OSiMe3 Ph\C02Me Ph (82
Gong, L.; Streitwieser. A. J. Org. Chem., 1990, 55, 6235.
+
OSiMe3 Ph+C02Me Ph 18)
70%
Mew0SiMe3 , Sn(0Tf)z PhCHO
*
SEt
Me
'
, Bu$n(OAc)2
E t S T P h Me
85%
(100% syn; >98% ee)
Mukaiyama, T.; Kobayashi, S.; Uchiro, H.; Shiina, I. Chem Lett., 1990, 129. Mukaiyama, T.; Uchiro, H.; Shiina, I.; Kobayashi, S. Chem. Lett., 1990, 1019. Mukaiyama, T.; Shiina, I.; Kobayashi, S . Chem. Lett., 1991, 1901. ;Uchiro, H.; Fujishita, Y.; Shiina, I.; wukaivama. T, J. Am. Chem. Soc., 1991.
113,4247.
320
Compendium of Organic Synthetic Methods, Vo18
immobilized bakers yeast MeOH t
0
) , , CO,Et
Section 327
OH
i./
C02Et 56% (97% ee , S) Naoshima.;Maeda, J.; Munakata, Y.;Nishiyama, T.; Kamezawa, M.; Tachibana, H. .I. Chem. SOC., Chem. Commun., Z990, 964.
.
0 CHzClz
P \ h v '*OH BFyOEt2, (CH20H)y 0 61% 0°C (5 h) + RT (20 h) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai. K. J. Chent. SOC., Chem. Commun., 1990, 1538. PhCHo
iPrCHO , 15% SmIz
9
rk0
OH
>99:1 anti:syn) Evans. D.A.; Hoveyda, A.H. J. Am. Chem SOC.,1990, 112, 6447.
e
95%
1. Li , NH3 ,THF
-78"C, 30 sec
72%
C02n-C8H, 72. aq. NH4CI
CO~~-C~HI~
van der B a n . J.L. ; Bamick, J.W.F.K.; Bickelhaupt, F. Synthesis, 1990, 897. OSiMe,t-Bu 20% Z a t z 1 B PhCHO -b
=(OEt
n A C02SiMe2,-Bu
PhMe , -78°C
OSiMqr-Bu * ELo,Cdph (60% ee)
79%
Mukaiyama, T.; Takashima, T.; Kusaka, H.; Shimpuku, T. Cheni. Lett., 1990, 1777.
*
C02Bn
cat. Mn(dpm)z, 02,PhSiH3 0°C , iPrOH
+
OH d c o 2 B n
Mn(dpm)2 = bis(dipivaloy1methanato) manganese (11) Chem. Lett., 1990, 1869. Inoki, S.; Kato, K.; Isayama, S.;
91%
Alcohol - Ester
Section 327
OH
, ! , , C02Me
32 1
OH OH
1. LDA 2. PhCHO
V
OH OH
+
P h CO,Me
W
(30 1. EtGiCl 2. PhCHO , Tic14 (93 Shirai, F.; Gu, J-H.; mi.T.Chem. Lett., 1990, 1931.
M e g ~ , Tic14 c 0
w
Et02C
*
HO~U
Ti02 , CH2C12 , -80°C
h
CO2Et
OH
I I ~
Me
Me
OSiMe3
P
C02Me 70) 86% 7) 75%
Ali, S.M.; hmguXL SynLett, 1990, 391. Ph3SiClO4, 1.5 h CH2C12, -78°C -+ -30°C@0H m
C02Me 95%
C02Me Inokuchi, T.; Kusornoto. M.; Matsurnoto. S.; Okada, H.;
C02Me
SrnI2, THF-HMPA
Hon.;Lu, L.; Chu, k-P. Synrh.
Me02C
t
f-BuOH
Chem. Left., 1991, 2009.
70% Commun., 1991, 21, 1981
(15
85)
Lei, B.; Fallis. A.G. Can. J. Chem., 1991, 69, 1450.
6 0
C12CeCH2C02Et, THF -78°C
5
HO
*
Liu. H-J.; Zhu. B-Y. Can. J. Chem., 1991, 69, 2008.
CO,Et 96%
75%
322
Compendium of Organic Synthetic Methods, Vol 8
Section 327
Trost. B.M.; Granja, J.R. J. Am, Chem. SOC.,1991, 113, 1044.
B , - O q 0
0
2 eq. SmI2, THF , -78OC
Ph
OH
1)
(>200
76%
Molander.; Etter, J.B.; Hatring, L.S.; Thorel, P-J. J. Am. Chem. SOC., 1991, 113, 8036.
t-Bu0,C
-p-k B.O
enolate (<2:98
OSiMe,
OSiMe, Ph
f-BuQCf..
2. 1. LDA PhCHO
*
3.TMSCl
Z:E)
t y f
Ph
%.% (60
40)
Curtis, A.D.M.; Y&&gJ. Tetrahedron Lett., 1991, 32, 1507 W h i t i a Tetrahedron Lett., 1991, 32, 1503.
j-0-
+q+y
(56:44 in THF at -78°C ; 0100 in THF at 22°C
Wei.;Bakthavatchalam, R. Tetrahedron Lett., 1991, 32, 1535.
/
M:gE;;p2 t
EtOH ,85 min
+
49%
OEt
CHO 5%
. . Shlmlzu.; Watanabe, Y . ;Orita, H.; Hayakawa, T.; T~IUULL Tetrahedron Lett., 1991, 32, '
2053.
Alcohol - Ester
Section 327
323
Sartori, G,; Casnati, G.; Bigi, F.; Baraldi, D. Tetrahedron Lett., 1991, 32, 2153. 1. R*2BBr, NEt3
Br,
C02t-BU
Bu$nH, PhH AIBN,reflux
OH
ph+C02r-B~
-78OC
2. PhCHO CHEl2
OH
*- .
ph+,C02t-B~
Br
74%
86% (98:2 anti:syn) 96% ee
h y . F. J; Cho, S. Tetrahedron Lett., 1991, 32, 2857.
OH
bakers yeast
50°C, + MVK 30 min
&C02Et
Me
:
+
&CO,Et
OH
h C O 2 E t
Me
Me
3) 94% (97 Nakamura.; Kawai, Y.; Ohno, A. Tetrahedron Lett., 1991, 32, 2927. Nakamura.; Kondo, S.; Kawai, Y.; Ohno, A. Terrahedron Leu., 1991, 32, 7075.
OH EtO2C+
1. Soclz 2. LiBr ,acetone, 50°C
CO Et
OH
E ~ ( - J , cCO ~ /2Et
3.2.5 Zn , H 2 0 (cat.)50"C, 2 h
OH
70%
Ga0.y.; Zepp, C.M. Tetrahedron Lett., 1991, 32, 3155. OD HO
-,*.
OAc OEt
Ti(OiPrhOAc,1 h CHC13
HO&OEt
6H
0
OAC OEt i-
HO+OEt OH -2) 95%
(>98
Raifeld. Y.E,; Nikitenko, A.A.; Arshava, B.M.Tetrahedron Asymnzetry, 1991, 2, 1083.
0
H2 (100 atrn), 25OC 0.5 [R~C12Ph]2
(R)-BINAP , 4 0 h Kitamura, M.; Tokunaga, M.; Ohkuma, T.;
.
OH &COW (99% ee , R)
97%
Tetrahedron Lett., 1991, 32, 4163.
Compendium of Organic Synthetic Methods, Vol 8
324
Section 327
OH COzEt CO,Et Me
2 Sm12,THF
de&-JMe 79% (31:l % dr)
Molander.; Kenny, C. J. Org. Chem.. 1991, 56, 1439. 0
0
bakers yeast, 16 h "fermentation
N3
N3
N3
19%(70% ee)
49% (70%ee)
Hudlickv.; Tsunoda, T.; Gadamasetli, K.G.; Murry, J.A.; Keck, G.E. J. Org. Chem., 1991, 56, 3619.
C02Me
RuCI~(COD),, Wt3 PhMe , 140°C, MeOH
-CO,Me
HO
90%
(97%ee) Taber. D.F.; Silverberg, L.J. Tetrahedron Lett., 1991, 32, 4221.
0 Bn2N/OE1
1. mCPBA 2. H2 , Pd(OH)2
*
Me400a
Me
90%
OH
(>95%ee) Reetz.; Lauterbach, E.H. Tetrahedron Lett., 1991, 32,4481.
ph4,/c02u
NaBH4, MnC12
Me Fujii, H.;
w;
i
OH phJyco*Et
+
Me (90
Terrahedron Lett., 1991, 32, 6141.
OH ph+co2Et
Me 10)
90%
Alcohol - Ester
Section 327
325
wmg. 2.;M e w X-J.; Kabalka, G.W. Tetrahedron Lett., 1991, 32, 4619. Me02CA0
BuzBOTf , iPrzNEt -78°C .+ 25°C
Me
(8
55%
92)
QhL; Wrobel, Z.; Rubenstein, S.M. Tetrahedron Lett., 1991, 32,4647. 1. Sn[Co(C0)414 , 1-120
Ph-
Br
pgooH+
Ca(OH)2, CO (65 bar) f-BuOH
Ph
2. H30'
CC13CF3. CISiMe3 e' (Pt cafhode/C anode)
d C F 2 C O 2 M e 89%
Shone.; Kise, N.; Oka, H. Tetrahedron Lett., 1991, 32, 6567.
+*'
0, N
SH
'04 0
COzMe
NaOMe ,MeOH , 4 8 h
2. Ph(C=O)SH , Tic14
w
LC02Me Me
HS
(39% ee) Shono.,Matsumura, Y.; Fujita, T. Tetrahedron Lett., 1991, 32, 6723.
MeC02Me
1. Dibal , -78"C, BFyOEt2 2. Me Me-OEt
C02H
OH
DMF , EWOTs
1.
Ph
C02H
67% Tetrahedron tett., 1991, 32, 4703.
Monflier, E.; Pellegrini, S.; Mortreux.,
ACHO
Ph%zoH
OSiMe3
*
Kivooka. S,; Shirouchi, M.J. Org. Chem., 1992. 57, 1.
67 %
% OH
Me Me
C02Et
Me
70%
Compendium of Organic Synthetic Methods, Vol 8
326
0 menthyl'
s';
1.
..
Me02C&
0
.
. 4 eq. LDA THF -78°C
2.ZnCl2 , Dibal ,THF , -78OC * 3. Ni(R)
Me02C
PDC , I-Bu00H
CH$12,8 h
0
L-
-OH 0
0°C -i 25°C
Chidambaram, N.; Bhat, S.;
82%
J. Org. Chem., 1992, 57, 5013.
0
PhCHO , -4OOC CHzClz
Me ;
.- 7 8 T
OSiMq
M~~~~~
20% BHzTHF
>*Q
H02C
2. TBAF ,THF
-
Me NHTs
-S
Me
E
OH 0 t
P h v S E t Me
-k
13)
(87 (80% ee)
Pannee, E.R.; Hong, Y.; Tempkin, 0.;
OBz
18%
OH 0 PhO
OH Me
Me 70% Olivier, E.; Ouimet, N. Tetrahedron Lett., 1992, 33,457.
PhCHo
81%
(97%ee)
SolladiB. G; Almatio, A. Tetrahedron Lett., 1992, 33, 2477.
-3
Section 327
89%
(94%e)
Tetrahedron Lett., 1992, 33, 1729.
4 eq. Smlz ,THF-HMPA
-78°C + 23°C
I
(35:l)
Enholm. E.L; Jiang, S. Tetrahedron Lett., 1992, 33, 6069, 313,
PhCHO
Ph
BrCH2C02Et , Cp2TiClz-Zn b
THF , RT , 5 min Dine.;Zhao, G . J. Chem. SOC.,Chem. Commun., 1992, 941.
OH
C02Et
90%
327
Alcohol - Ester
Section 327
€!m&&gA;Leijonmarck, H. Tetrahedron Lett., 1992, 33, 3025. iPrCH2CHO ,Tic14
OSiMe2t-Bu 75%
(59:41) Tetrahedron Lett., 1992, 33,
Vasconcellos, M.L.; Desmaele, D.; Costa, P.R.R.; dUg&!J 4921.
~
PhCHO
~
~
~
MeN02, -78°C
"
'
,
phQ0zEt p-NOzPhS02
92%
(90%ee , R)
"
Kivooka. S,; Kaneko, Y.; Kume, K. Tetrahedron Lett., 1992, 33, 4927.
Tetrahedron Lett., 1992, 33, 1465,
Gu, J-H.; Terada, M.; Mikami, K.;
In - ICHZCOzEt THF - pentane cinchonine
PhCHo Johar, P.S.; Araki, S.; m
Y
.
-
OH Phk C 0 z E t
63%
71% ee , R)
. Chem. Soc., Perkin Trans. I, 1992, 711.
RuCI2-n H 2 0 , PhH , RT t-BuOOH, 4 h
0 phAO/\/OH
Murahashi. S.; Oda, Y.; Naota, T. Chem. Lett., 1992, 2237.
79%
328
Compendium of Organic Synthetic Methods, Vol8
cp
2% Ph2 I
h
r
-
B
~
w
@
0
p- Fe'
Bach, T.; Fox, D.N.A.;
p
,20b
+oSiMeZf-Bu OMe
PhCHO
Section 328
COzMe
77%
ReazJIL J. Chem Soc., Chem. Commun., Z992, 1634.
'
OH
C02t-BU Zn ,MegSiCl
0 Br
Br Escudier, J-M.; Baltas, M.;
98%
Tetrahedron Lett., 1992, 33, 1439. Ti(OAc)3, aq. AcOH RT,3h
*
OH
50%
Ferraz. H.M.C,; Ribeiro, C.M.R. Synrh. Commun., 1992, 22, 399, Section 313 (Alcohol - Carboxylic Acid).
Also via:
SECTION 328:
ALCOHOL, THIOL THIOETHER
- ETHER, EPOXIDE,
Bewersdorf, M. Tetrahedron Lett., 1990, 3I, 67.
n-C3H70H, 0.2% DDQ 90 min
IranDoor.;Baltork, I.M. Tetrahedron Lett., 1990, 31, 735.
IranDoor.;Baltork, I.M. Synth. Commun., 2990, 20, 2789.
diastereomers (85:15)
OH 92%
Alcohol - Ether
Section 328
329
55%
9)
(9 1
Alexakis.;Hanriizi, J.; Jachiet, D.; Normant, J-F. Tefrahedron Lett., 1990, 31, 1271.
0+
C02Et t - B u P h ' S i O d
1. TBAF ,THF m 2. Pd(Ph3)4 , THF 11.5 h
r c o 2 y
CozB
OH
OH
8)
(92
82%
Suzuki, T.; Sato, 0.;Hirama. M,Tetrahedron Lea.,1990, 31, 4747.
17)
(1
Angle.;Amaiz, D.O. .I. Org. Cherrt., 1990, 55, 3708.
B F3
0 khavarren.
+
Ho&,,,(H'
0
N- NMe,
NMe,
aJ. Org. Chem., 1990, 55, 4255.
( 5 :1
Molander. G.A,; Harring, L.S. .I. Org. Chem., 1990, 55, 6171.
trans:cis)
71%
67%
330
Compendium of Organic Synthetic Methods, Vol8
OSiMe,
Section 328
1. TMSOTf
M
e
0
4
OMe
2. "MSOTMS , DMAP
Lee.; Cregg, C. S y d e r f , 1990, 317.
V-PILC ,PhH , r-BuOOH
-OH
OH
RT
96%
V-PILC = vanadium-pillared montmorillonitecatalyst
Uuudary. B.M.; Valli, V.L.K.; Prasad, A.D. J. Chem. SOC., Chem. Commun., 1990, 721.
y ' "OH
Dillwed-montmorillonite.35 h *
T
Ti(OiPr)4, (+)-DIPT '
O
H 86%
Choudarv.;Valli, V.L.K.; Prasad, A.D. J.
(94%ee)
Chem. SOC., Chem. Commun., 1990, 1186.
LTA, PhH, RT. 2 h
BySn OH Yamamoto.; Irk,S.; Arase, T.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Chem. Commun., 1990, 1492.
OMe
1. BuLi 2.BughBr
A SnBu3 3. Tic4
n-C,H,,
OMe n-C7H&
~-C~H~SCHO
n-C7Hl OH
+
(99
OMe n-C7H1& n-C7H1 OH 1)
84%
(39:61 in 95% yield with BF3.OEt~ratherthan Tic14
Yamada. J.; Abe, H.; Yamamoto, Y. J. Am. Chem. Soc., 1990, 112, 6118. n-C6H 13
f - 3
oyo Ph
1. MqBBr ,-78°C
2. BH3mTHF
b
r_(n-C6H
HO
(14
OBn
13 +
r(n-c6H'3 BnO
OH
1)
83%
Guindon, Y.; Girard, Y.; Berlhiaume, S.; Gorys, V.; Lemieux, R.; Yoakim, C. Can. J. Chem, 1990, 68, 897.
Alcohol - Ether
Section 328
33 1
20% Co(modp)z, i M H
Ph
t-BuOOH,MS4A.02 50°C, 30 min (-0
0 ' 0
modp =
73%
99% trans selective
0
Inoki, S.; Muka ivama. T,Chem. Lett., 1990, 67.
Q-p 0
Pons, J-M.;
.
Y
TiC14, Mg ,THF
71%
OH
Tetrahedron, 1990, 46, 513. ZrCb-LiAlH4, ether, RT
30 min quant. Shaozu, W.; Tianhui, R.; Yulan, Z. Bull. SOC. Chim. Belg., 1991, 100, 357. Shaozu, W.; Yin, C.; Yulan, Z. Bull. Soc. Chim. Belg., 1991, 100,421 (with CpTiCIyLiAlHq), 1. S d z , THF ,HMPA RT, 10min 2. aq. NH4CI
=-
qyH 55%
Shibuya, K.; Nagaoka, H.; Yamada, Y. .I. Chem. Soc., Chem. Commun., 1991, 1545
2)
(1
72%
Shimada, S.; Saigo, K.; Makamura, H.; Hagegawa, M. Chem. Lett., 1991, 1149. MqSi,
PhCHO
S,
SiMq
TBAF, THF, RT, 20 h
*
Phy OH SMe 98%
Hosomi. A,; Ogata, K.; Ohkuma, M.; Hojo, M. SynLett, 1991, 557.
332
Compendium of Organic Synthetic Methods, Vo18
Section 328
o r -- p*8'' PbSnBu3 1. BuLi , TMEDA , THF -90°C
Ph
OH
2. PhCHO
Ph
Lohse, P.; Loner, H.; Acklin. P.; Slernfeld, F.;
f\l
87%
Tetrahedron Lett., 1991, 32, 615.
1. TMSOTf ,CHzClz
BHpSMeZ, -78°C
O-OH
0 0 P h A P h 2. NaHCO3
P h A P h
95%
Hunter. R.; Bartels, B.; Michael, J.P. Tetrahedron Len., 1991, 32, 1095.
MeC02v +Hov 02CMe
0
porcine pancreatic lipase
pH 6.5 , -5"C, 26 h
0
54% conversion (90%ee)
Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett., 1991, 32, 3043. (OAC
fOH
l.Zn(BH& , DME
OBz
OBZ Panu. B.C.; Basu, M.K. Tetrahedron Lett., 1991, 32, 3243. ZrCh-LiAIH4, ether
ph401 0
;
30°C. 1 2 h
PhJ0>
93% OH
i-
P h 7 7%
OH
Tianhui, R.; Ning, C.; Yulan, Z. Org. Prep. Proceed. Int., 1991, 23, 427.
Me02cwC
'yo
02Me I . MelBBr , 20°C
c-C6H 1 1
2.M&u(CN)Liz -30°C
Me02Cw
C02Me Me02cHC02Me
JMeOH
+
c-C6H 1 1
(17
1)
83%
Guidon.;Simoneau, B.; Yoakim, C.; Gorys, V.; Lemieux, R.; Ogilvie, W. Tetrahedron Letl., 1991, 32, 5453.
Alcohol - Ether
Section 328
dOH
0
333
1.2.2eq. BuLi ,DME ,0°C 2.2.0 eq. B(OMe)3 , 0°C
SiMe$-Bu
ph&oH
3. PhBr , Pd(PPh&, reflux H 2 0 , DME
0
SiMe2t-Bu 68%
Cristofoli, W.A.; b v . B.A. Tetrahedron k i t . , 1991, 32, 5881. CH2C12, MS 4 A ,0°C Id
(80
20)
50%
Mikami. K.; Terada, M.; Sawa, E.; Nakai. T, Tetrahedron Lett., 1991, 32, 6571. mCPBA ,aq. NaHCO3
OH
25"C, 7 h
OH 83% Fringuelli. F.; Germani, R.; Pizzo, F.; Santinelli, F.; Savelli, G. J. Org. Chern., 1992, 57, 1198.
-
SnCI4, MeOH , -30°C 30 min
H Ph+OH Me0
88%
(95% ee)
Moberg.
6; Rakos, L.; Tottie, L. Tetrahedron t e t t . , 1992, 33, 2191. hv (350 nm) PhH,4h
Me
0
c
90%
Ph
Sumathi, T.; Balasubramanian. K.K,Tetrahedron Lett., 1992, 33, 2213.
OH
t - B ~ 0 0 HCHC13 , MS 4 A ,45"C, 72 h
*
+OH
73% Antonioletti, R.; Bonadies, F.; Locati, L.; Screttri. A, Tetrahedron Len., 1992, 33, 3205.
Compendium of Organic Synthetic Methods, Vol8
334
SiMe,
'02,
Section 328
"'Oo Me3Si_
Ti(OiPr)4
*
70%
Adam. W,; Richter, M. Tetrahedron Leu., 1992, 33, 3461.
Re207
OH
%OH
Kennedv.,Tang, S. Tetrahedron Lett., 1992, 33, 3729.
N
0
N
1. LHDMS , THF 2. BnBr 3. LiEt3BH , THFC
0
ePh
H
O
RT
59%
T Ph SPh
92%
Orena, M.; Porzi, G.; Sandri. S . Tetrahedron Lett., 1992, 33, 3797.
Me3Si
0
BuLi ,ether
CHO
-78°C
i)H
HO (29
a
Urabe, H.; Matsuka, T.; &Q&
Bu
Me3Si 71)
75%
Tetrahedron Lett., 1992, 33, 4179.
mMe
Hq
1 . 3 eq. Re207 3.3 eq. 2,6-lutidine
OH 2. NaOOH
Me
62%
H
(5.8:l trans:cis) Tang, S.; K e n n e w Tetrahedron Lett., 1992, 33, 5299, 5303. AIBr3,Oz , PhH
+
6OoC, 18 h
*
%H 85%
EQC
& OH
Antonioletti, R.; Bonadies, F.; Lattanzi, A.; Monteagudo, E.S.; Scettri, A. Tetrahedron Lett., 1992, 33, 5433.
Alcohol - Ether
Section 328
335
OH
OH
0
(9
91)
82%
Li, K.; Hammn, L.G.; Dreeda. M, Tetrahedron Lett, 1992, 33, 6569.
1. SmIz
80% Curran. D.P.; Totleben, M.J. J. Am. Chem. Soc., 1992, 114, 6050.
J
Bu
0
NaBH4-CaC12
THF , 0°C (85
85%
15)
Fujii, H.; Oshima. K.; Utimoto. K, Chem. Lett., 1992, 967.
1. Ph4
N
0 S H$&iZCH$'h
Ph
H @ b MeOH , RT, 5 h Ph 2. aq. HCI ,CHzClz 3. DMSO , PhCH(Me)NIIZ 50°C.30 min Karikomi, M.; Narabu, S.; Yoshida, M.; M C h e m . Lett., 1992, 1655.
80%
REVIEWS: "Rearrangementof Epoxyalcoholsand Related Compounds" Org. Prep. Proceed. Int., 1990, 22, 547. "Transformation of P-Hydmxyalkylselenides to Aldehydes and Ketones. A Review"
Krief.;Laboureur, J.L.; Dumont, W.; Labar, D. Bull. SOC.Chim. Fr., 2990,
127, 681.
"StereocontrolledManipulations of ChromatographicallyResolved Pyranosides"
Mash,&& SynLett, 1991,
529.
Compendium of Organic Synthetic Methods, Vol8
336
- HALIDE, SULFONATE
SECTION 329: ALCOHOL, THIOL
Phv
BuzSnHz ,0°C
+
* phJBu OH
0
Bu
0
(0
with Bu$nHZ/DNB
Section 329
100) 82% 10) 75%
(90
DNB = p-dinitrobenzene (radical inhibitor)
Shlbata.;Nakamura, K.;Baba, A.; Marsuda, H. Tetrahedron Lett., 1990, 31, 6381.
Br PhCHO
(
c1 RT
*
OH P
hc1 h + p
85%
h
13% L
C
l
Ph 2%
+
Y h d e r . P A ; Grissom, J.W.; Hoffmann, U.;M a R. Terrahedron Lett., 1990, 31, 6605. C02&
LDA ,PhCHO F F3CL C02Et -9OOC. 2 h
F,C-p
OH 80%
also undergoes conjugate addition and alkylation reactions Qian, C-P.; Nakai. T, Tetrahedron Lett., 1990, 31, 7043. ByN' H 2 F i , 120°C
KHFz , 8 h
+
Ph
h + F OH
Ph
(39
.. Landml.; as^& Tetrahedron Lett., 1990, 31, 7209.
obtain a 1:l mixture at 2S'C
(7
Alvarez, E.; Nuaez. M.T.; Martin, V.S. J. Org. Chem., 1990, 55, 3429.
Imai.;Mishida, S . J. Org. Cheni., 1990, 55, 4849.
)7
HO
F
61)
1)
74%
89%
Alcohol - Halide
Section 329
6
1. MeOH ,NaI ,NaOH
0°C Me 2. NaOCl , 2 T , 1 h 3. 100/oaq.sodium thiosulfate
m.K.L; Failing, S.N. J. Org. Chem., 1990, 55, 5287 CuO.HBF4,
331
6" OH
I
80%
-&
I2
60%
MeCN , H20
I
Barluenpa.;Roddguez, M.A.; C m p o s , P.J. J. Chem. Snc., Perkin Trans. I, 1990, 2807.
-
1. EtMaBr 2. Ti(GPr),
0 *Ph
b
3. aq. H+
xoH 83%
Ph
Sosnovskii, G.M.; Astapovich, I.V. Zhur. Org. Khim., 1990, 26, 911 (Engl., p. 781).
4
&10~-NaAS03
aq.MeCN,RT 2h
Ohta, H.; Sakata, Y.; Takeuchi, T.; IshijJ
> 4io
25
70%
; Giordano, C. Synthesis, 1990, 327.
B u ~ P H Fneat, ~, 4 h
n-C 1 ZH
26% OH
53% I Chem. Lett., 1990, 733.
4 eq. C13CCOOH , HMPT RT,8h
CHO
Ferraccioli, R.;
+
l0O0C
*
KF
n-C 12H25
F +
n-C I 2H2& 7)
(93
OH 94%
Seto, H.; Qian, Z . ; Yoshioka. H.; Uchibori, Y.; Umeno, M. Chem. Lett., 1991, 1185.
0
ph%o~s
Et2AlCl , CH2C12 -55OC
+ -5°C , 2 F
c1
Cl
Ph+OMs OH
(92 Gao, L.; Saitoh, H.; Feng, F.; Murai. A, Chem. Lett., 1991, 1787.
+
Ph+OMs OH 8)
quant.
338
Compendium of Organic Synthetic Methods, Vol8
Section 329
LizCuBrd, THF , 4 h c "
. . Clacclo.; Heller, E.; Talbot, A. SynLett, 1991, 248.
3Me
CH212, Sm ,THF
t
n-C6H13
Br
p* M~
n-C6H13
93%
diols available from chloromethyl ethers Imamoto. T, ;Harajima, T.; Takiyama, N.; Takeyama, T.; Kamiya. Y.; Yoshizawa, T. SOC., Perkin Trans. I, 1991, 3127. bakers yeast, EtOH , sucrose (ketone added to yeast slurry)
*
Ph
Ph
Lcl 84%
(44% ee) Tetrahedron. 1991, 47,
LiI , AcOH , THF
RT ,20 min
Baiwa. J.S,; Anderson, R.C. Tetrahedron Lett., 1991, 32, 3020.
Ph
6 q.HMDS , DMF , CHF3 e- , Pt electrodes
A,Ph
[CHFdpymlidinonelDM; Bu~NX]
Ph+
CF3 OH Ph
84%
Shone.; Ishifune, M.; Okada, T.; Kashimura, S. J. Org. Chem., 1991, 56,2.
c)'
1. Me3SiCF3 , THF
TBAF
Krishnamurti, R.;Bellew, D.R.;
2.TBAF,THF
J. Org. Chem, 1991, 56,984.
OH
BrCF2CH=CH2,Zn
Ph-CHo Yang, Z-Y.;
THF,O+25"C
Chem.
OH
Noran. P.J.S,; de Carvalho, M.; Okamoto, M.T.; 2073.
0
I
*
J. Org. Chem., 1991, 56, 1037.
A g2 Ph
67%
Alcohol - Halide
Section 329
1. I Z ~ ( C N ) C U ( C H ~ ) & ~ I I THF , -60°C -+ -25°C
PhCHO
c
2. I2 , -70°C + RT
Achyutha Rao, S.;
339
L, 59%
Ph
J. Org. Chem., 1991, 56,4593.
J -Psi Connet-Delpon, D.; Lequeux, T. J. Org. Chem., 1991, 56, 5800.
Abouabdellah, A.; -6.
MgI2, PhMe -60°C
* &OH OH . . Bonml.;Righi, G.; Sotgiu, G. J. Org. Chem., 1991, 56, 6206. "OH
-ae
(Bu3Sn)2, PhH
hv (sunlamp)
BH2CbSMe2, -60°C
*
O
OH
66%
OH
Rawal. V.H.; Iwasa, S. Tetrahedron Lett., 1992, 33, 4687.
H Ph
85%
'k
OH
Ph
OH
(>98:2)
(1,2: 1,3-dioI)
. . Lupattelli. P.; Bersani, M.T.; Mincione, E. Tetrahedron Left., 1992, 33,6181. Bovlcelh.; . . Bovlcelh.;Mincione, E.; Ortaggi, G . Tetrahedron Lett., 1992, 32, 3719. Ph
\
Tic14 - LiCl ,THF -20°C , 15 min
OH Shimizu, M.; Yoshida, A.;
* Ph\ +ph\
HO
(89 SynLett, 1992, 204.
OH
.-' 1)
OH
96%
Compendium of Organic Synthetic Methods, Vol8
340
*
0
OH
0.5 Br2 ,CH2C12
Br
fl\n-C,H,:. Br
n-C6H 13
(0.7j3.0
Konaklieva, M.I.; Dahl,M.L.;
Section 330
A-C,H13 OH
:
1)
54%
Tetrahedron Lett., 1992, 33, 7093.
SECTION 330: ALCOHOL, THIOL
- KETONE
1. dihydroxy acetone phosphate
OH
fructose-1,&diphosphate aldolase (EC 4.1.2.13) 2. acid phophatase pH 4.8
OHwib in (+)-em-brevicomin
40%
Schultz, M.; Waldmann.; Vogt, W.; Kunz, H. Tetrahedron Lett., 1990, 31, 867. OSiMe3
O
H
C
T SiMq
TBAF ,Si@
C
C
l
Ram6n. D.J.; Yus.
M
2. PhCHO , -78°C -+ + 2 0 T
OH
Ph
3.H20
:
Me
Me
-78OC
M = Li , THF
M = SiMeZl-Bu
BF3*OEt2, CHzClz
18
98
Evans.;Gage, J.R. Tetrahedron Lett., 1990, 31, 6129.
n
0 0
AAX 60%
M.Tetrahedron Lett., 1990, 31, 3763, 3767.
OSiEt,
0
H
n 0 0
OH
60%
kee T.V.; Roden, F.S. Tetrahedron Lett., 1990, 31, 2067.
+
34 1
Alcohol - Ketone
Section 330
\rf\\ 0
PhCHO ,EtzMeSiH PPh2Me , To1 -5T, 2h
0
OSiMeEt, 99%
(83:17
syn:anti)
Matsuda I,; Takahashi, K.; Sato, S. Tetrahedron Lett., 1990, 31, 5331. 1. LDA 2.PhCHOb
+
M~
Me,SiO
OSiMe,
E.,&
-
Me
Me,SiO 90)
(10 (99
with CITi(0iPr)J
Panyachotipun, C.; m r n t on.
Ph
1)
Tetrahedron Len., 1990, 31, 6001. (PhSeh , CH2(C02Me)2
Ph
MeOH , NaC104 Inokuchi, T.; Kusumoto, M.;
70%
J. Org. Chem., 1990, 55, 1548. ECHO , ZnCl2 Cl12C12
-
OSiMe, 61%
Moiseenkov, A.M.; Czeskis, B.A.; Ivanova, N.M.; m o v . O.M. Org. Prep. Proceed. Int., 1990, 22, 215. iPrCHO , CH2C12 TiC14, 3.5 h
* z*
OBz
88% (92% dr)
Trost. B.M, : Urabe, H. J. Org. Chem., 1990, 55, 3982. MoOPD
O
*
a safer alternative to M ~ O P H
P&Ph 0
MoOPD = oxodiperoxymolybdenum (pyridine)-1,3-dimetyl3,4,5,6-tetrahydro-2( 1H)pyrimidinone = MoOy Py-DMPU Anderson, J.C.; Smith, S.C. SynLeft, 1990, 107.
47%
Ph
342
Compendium of Organic Synthetic Methods, Vol 8
,JH4Y
Section 330
TFA ,aq. THF
76%
Stone, G.B.; h h s U L L & J. Org. Chem.. 1990, 55, 4614. 0
1.
PhCHO Sasai, H.; Kirio, Y.;
Br
, WOf-Bu)4 THF , -30°C
P h d 2. MsCl , NEt3 , CH2C12 * -78°C -+ -30°C Br 56% J. Org. Chem., 1990, 55, 5306. ‘
1. ethylene glycol ,TsOH PhH , reflux
0
2. LiAlH4, THF , 0°C
M~O 3. wet silica ~gelC A b
Hitchcock, S.R.; Perron, F.; Martin, V.A.;
HO
2ji
81%
Synthesis, 1990, 1059.
YU
PhCHO
91%
(60%ee)
Mukaiyana, T.; Inubushi, A.; Suda, S.; Hara, R.; Kohayashi, S. Chem. Lett., 1990, 1015.
Dh
,
Dl.
1. Yb ,RT
* n *
Takaki.;Beppu, F.; Tanaka, s.; Tsubaki, Y.; Jintoku, T.;
J. Chem. Soc., Chem.
Commun., 1990, 516.
Ph
icf-
0 Ph
B q S n H , PhH ,hv
30 rnin
b
u Ph
p
h
93%
H w g a w a . E.; Ishiyama, K.; Horaguchi, T.; Shimizu, T. .I. Chem. Soc., Chem. Commun., 1990, 550.
Section 330
PhCHO
Alcohol - Ketone
&:L:CHzCIz, Me
E t S v P h Me
SnO + Me3SiOTf
-t
EtS Me
(94 (91 96 ee)
Me
OSiMe,
0
OSme,
0
-78°C
343
6)
82%
Mukaiyama, T.; Uchiro, H.; Kobayashi, S. Chem. Leu., 1990, 1147.
0 PhA TeBu
1. BuLi
2.
t
PhQB :u
85%
OH Me r-Bu 3. H+ Hiiro, T.; Morita, Y.; Inoue, T.; Kambe. N.; Ogawa, A.; Ryu, I.; Sonoda. N, J. Am. Chem. SOC., 1990, 112, 455.
Me Sn(OT02, NEt3 TiCI4, iPr2NEt
(95
5) 83% 99) 86% Evans.;Clark, J.S.; Mettemich, R.; Novack, V.J.; Sheppard, G.S. J. Am. Chem. SOC., 1990, 112. 866. Evans. D.A.; Rieger, D.L.; Bilodeau, M.T.; Urpl, F. J. Am. Chem. Soc., 1991, 113, 1047.
0"
0
(< 1
25"C, 10 h
2q.
b " a $
SbCf
a:, 88%
Schulz.;Kluge, R.; Siviai, L.; Kamm, B. Tetrahedron, 1990, 46, 2371. 1. PhCHO ,BiCl3 CH2Cl2, RT
Phh0siMe3
b
0
OH
25 min PhU P h 2. MeOH , IN HCI Wada. M.; Takeichi, E.; Matsumoto, T. Bull. Chem. SOC.Jpn., 1991, 64, 990.
94%
344
Section 330
Compendium of Organic Synthetic Methods, Vol 8
SnCL4, CHzClz , -78°C
PhCHO
Q N S
" " P h w
Me
OH 0
L,
P h ' v c
Me
Ph
43%
(6S:35 anti:syn)
o Ph
Chikashita. H. ; Tame, S.; Yamada, S.; Itoh, K. Bull. Chem. SOC.Jpn., 1990, 63, 497. 0
HO
P h 5 Ph 0
hv ,MeCN =
SnBy
Me-Ph
2O0C
(89:ll E:Z)
Ph
Ph +
0
Me 0
32) 89% (68 (89:ll E:Z) Takuwa. A,; Nishigaichi, Y.; Yamaoka, T.; Iichama, K. J. Chem. Soc., Chem. Commun., 1991, 1359.
OSiMe, M e & - ph
1. ot ,cat. Ni(mac)z, DCE
iPrCHO , RT
2. KF , MeOH
Ni(rnac)z = bis-(3-methyl-2,4-pentanedionato)nickel (11)
OH
Ph
75%
Takai, T.; Yrunada, T.; Rhode, 0.;W i v a m a . T, Chem. Left.,1991, 281. Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett., 1991, 1499.
4°SiMezr-Bu Me , 10% InCI3 L, u 7 t
PhCHO
ClSiMezi-Bu ,-43°C , 1 .S h
-
B
~ 93%
Me
Mukaiyama, T.; Ohno, T.; Han, J.S.; Kobayashi, S. Cheni. Left.,1991, 949.
MeSSiO Ph&Me
aq. HCIIO ,TIJF Y b(0Tfh
* P h G O H Me
Chem. Lett., 1991, 2087. 1. NaN(TMS)Z, THF , O°C
Ph
)(&
,acetone, -78°C 2 min
Adam.;Prechtl, F. Chem. Ber., 1991, 124, 2369.
Ph .-
Ph
944b
345
Alcohol - Ketone
Section 330
0
Ph
-
Guertin, K.R.;
JL
>X
1. LDA , THF , -78°C
2
Ph &OH
,aceton:
77%
-78"C, 30 min (inverse addition) Tetrahedron Lett., 1991, 32, 715. 1.2-ICr2BH , CDC13 1,5 h , 0°C
0
2.PhCHO 3. H20 2-ICr2BH = di-(2-isocaranyl)borane Boldrini, G.P.; Bortolitti, M.; Tagliavini, E.; Trombini. C,; Umani-Ronchi, A. Tetrahedron Let?., 1991, 32, 1229.
&
J / $
;L . k;iT
OMe
OMe
5 3
66%
(94% ee , R)
Davis. F A ; Kumar, A.; Chen, B-C. J. Org. Chern., 1991, 56, 1143. Davis.;Weismiller, M.C. J. Org. Chern.,1990, 55, 3715. [dimethoxy derivative] 1.2 eq. SmI2
0 2. H30' n-C8H,+ c1
+
n-C H
*
OH 171+n-C,H,, 0
75%
Aryl acid chlorides lead to 1,Zdiketones Collin, J.; Namy,J-L.; Dallemer, F.; Kacan. H.B, J. Org. Chern.,1991, 56, 3118.
OH 0
LDA , THF MgBrz-OEtz
Ph
-70°C-+RT
*
P h g P h i- P h 4 P h Me Me
2) 73% (98 Swiss, K.A.; Choi, W-B.; Liotta. D.C. ; A b d e l - M a; Maryanoff, C.A. J. Org. Chem., 1991, 56, 5978.
346
Section 330
Compendium of Organic Synthetic Methods, Vol8
PCWP = peroxytungsto phosphate
Sakata, Y.; khii. Y.J. Org. Chem., 1991, 56, 6233. e- , Sn cathode
iPrOH , 2 5 T
Me
Me
60% 5% Shono. z; Kise, N,; Fujimoto, T.; Tominagi, N.; Morita, H.J. Org. Chem., 1992, 57, 7175. Shono. T,; Kise, N. Tetrahedron tell., 1990, 31, 1303. Bu3SnSiMe3 BnEt3NCI
&,
~
74%
HO
Br
Mori.; Kaneta, N.: Isono, N.;
Ihmeb, H.; Maggini, M.; Prato.
i. M, Tetrahedron Lea, 1991, 32, 6139.
m, Scorrano, C . Tetrahedron Lett., 1991, 32, 6215.
1. iPrCHO ,CH&& BiC13 , 3 NaI
OSiMe3 2. MeOH ,HCI
0 OH 90% Le Roux, C.; Maravat, M.;Borredon, M.E.; Gaspard-Iloughmane,H.; Qhd Tetrahedron .
Lett., 1992, 33, 1053.
OSiMe-,
0
PhCHO , Gd(OTf),
1:4 (H20:THF), 20 h RT
=-
OH
@Ph (78
mS.: Hachiya, I. Tetrahedron Lett., 1992, 33, 1525.
+
F
P 22)
h 88%
Alcohol - Ketone
Section 330
347
Ph
4OSiMei -c6 min
-CHO
0
c
OSiMe,
[Ru(salen)(NO)(H~O)]' Ph Odenkuk, W.; Whelan, J.; Bosnich. B. Tetrahedron Lett., 1992, 33, 5729. PhI(OzCCF3)z ,TFA , 3 h
0
P h ' v Me
0 Ph J L O H
b
MeCN ,H2O
69%
R.K;Berglund, B.A.; Penmasta, R. Tetrahedron Lett., 1992, 33, 6065. 1.2.2eq. S d z , MeCN
Ph
c1 +
0 PhAMe
2. H30+
c
Ph%H
Me Ph
78%
Ruder. S.M, Tetrahedron Lett., 1992, 33, 2621.
Ikeda, S.; Chatani, N.; Kajikawa, Y.; Ohe, K.; Murai. S. J. Org. Chem., 1992, 57, 2.
(4.2
1)
64%
Motberwell.; Sandham, D.A. Tetrahedron Lett., Z992, 33,6187. OSiMe3
0.5%TiCp~(CF3Cs03)z PhCHO ,CDZCiz <5 min
c
0 OSiMe, Phu p h 90%
Hollis, T.K.;Robinson, N.P.; Bosnich. B. Tetrahedron Lett., 1992, 33, 6423.
b
OSiM%
cat. Mn (salen) derivative PhIO ,MeCN ,25OC 70 min
&,OH
+
&osiMe3
(2.6
(30% ee)
Reddy, D.R.;
J. Chem. SOC., Chem. Commun., 1992, 172.
1)
70%
348
-
Compendium of Organic Synthetic Methods, Vol8
Section 331
35% H z q , 1.6% PCWP
CHCI3 ,H2S04, reflux 24 h
OH
aq. Dowex-50, reflux
0
Ph
Ph+Me Me OH Chakraborty, R.; Das, AX. ; R a n u . S y n r h . Commun., 1992, 22, 1523. 1.
*;
A0
EtCN
ph
N.
Tl
83%
67%
(93% ee)
BB,,
-78°C. 14 h 2. aq. H+ Corev. F.J.; Cywin,C.L.; Roper, T.D. Tetrahedron Lett., 2992, 33, 6907.
REVIEWS : "Uses of the Fries Rearrangement for the Preparation of Hydroxyarylketones"
klixLhA Org. Prep. Proceed. lnf., 1992, 24, 392.
"Selective Oxidation of a$-Unsaturated Ketones at the a-Position" Demir. AS,; Jeganathan, A. Synthesis, 2992, 235.
SECTION 331: ALCOHOL, THIOL BrZnCHzCEN
PhCHo
MqSiCI , THF reflux, 30 min
- NITRILE OSiMe, Phl\/C=N
8646
Palorno.;Aizpurua, J.M.; L6pe2, M.C.;Aurrekoetxea, N. Tetrahedron Lett., 2990, 31, 2205.
Matsubura, S . ; Onishi. H.; U t i m o u Tefrahedroti Lett., 1990, 31, 6209.
Alcohol - Nitrile
Section 33 1
349
''9 n
N-H
2% H - N , + f $
PhCHO
HCN , PhMe , -20°C 8h
Tanaka, K.; Mori, A.; -.I.
0°C , 18 h
CN
97%
(91% ee)
*
pdoSiMe3 CN
95%
(78% ee, R) Chern. SOC., Chern. Comrnun., 1990, 1364.
Hayashi, M.; Matsuda, T.; -.I.
PhCHO
PhR
Org. Chem., 1990, 55, 181. Me3SiCN. Ti(OiPr)4 (+)-DIFT, CH2C12
PhCHO
OH
H
0
PhCHgN , e - , -4OOC DMF-H?O, 80 mi%
HO&CN Ph 75%
+
CN ph& ph 8%
Torii. &; Kawafuchi, H.: Inokuchi, T. Bull. Chern. SOC. .Ipn., 1990, 63, 2430. Me3SiCN - CaO , 60°C heptane
&OAc
X
~
A + GC O
CN
0
OSiMe, 4)
(96
Sugita, K.; Ohta, A.; Onaka.;
A 75%
Chern. Left., 1990, 481.
QauhdL Bull Chem. SOC.Jpn.. 1991, 64, 3143. TMSCN ,CH2Cl2 cat. TMSOTf , -78OC
H
N=C OBn
Molander.;H a , J.P. Jr. J. Am. Chem. Soc.,
3 (7:l dr)
1991, 113, 3608.
OBn
50%
C
350
Section 33 1
Compendium of Organic Synthetic Methods, Vol8
Me3SiCNI CH2C12
PhCHO
@:r~
20% Ti(OiPr)4 -30°C 44h
1"
N-OH
p h i o SCi N Me3
90%
(67% ee , R)
Hayashi, M.; Miyamoto, Y.; Inoue, T.; Qggni. N, J. Chem. Soc., Chem. Commun., 1991, 1752.
, Ti(0liPr)4 , RT
O C H O
l-
Me0
87%
@:
Me0
0
Mori, A.; I n o u e . C h e m . Lett., 1991, 145. Mori, A.; Kinoshita, K.; Osaka, M.; Inoue.Chern. Lett., 1990, 1171. Me3SiCN. CHzClz
phwCHo
10% EtN(iPr)2,O0C
c
Ph4
OSiMe3 C N
*%
Kobayashi, S.; Tsuchiya, Y.; l g h W y m a . T, Chem. Lett., 1991, 537, 541. Me3SiCN , Yb(CN)3 , THF
0°C. 1.5 h
oo:re3 93%
Chem. Lett., 1991, 1447.
Matsubara, S.; Takai, T.; HCN
PhCHO
To% w
Me3AI
-78"C, 102 h (41%, 61% e ,R) -78°C , 7 2 h (87% ,3696 ee ,R)
Bn
C02Me
N<
Mori, A.; Ohno, 11.; Nitta, H.; Tanaka, K.;
Me3SiJ
CN
SynLetr, 1991, 567.
PhCHO , KF 3 min .-
microwaves (440 W)
P h F C N OSiMe3 62%
Latouche, R.; Texier-Boullet.,lbm&nJ, ' Tetrahedron Lett., 1991, 32, 1179.
35 1
Alcohol - Nitrile
Section 33I
Me0
1. LDA , THF , -70°C
OH
36%
CN
BhawaJ, B.M.; Khanapure, S.P.; Zhang, H.; U J. Org. Chem., 1991, 56, 2846. 2 eq. C12CeCHzCN, THF -78°C + RT , 4 0 min
Liu.; Al-Said, N.H.
T
Ir
C
N quant.
Tetrahedron Lett., 1991, 32, 5473.
LiC104, KCN MeCN ,70°C 8h
OH H-LCN
C
+
HIITOH n-C6H 13
n-C6H13
(98.2
1.8)
95%
Chini, M.; Crotti. P.; Favero, L.; Macchia, F. Tetrahedron Left., 1991, 32, 4775.
+
KCN ,znI2, TMS-CN *
Brunet. E; Batra, M.S.; Aguilar, F.J.; -0.
PhCHO
(>95:5 syn:anti) J.L.G. Tetrahedron Lett., 1991. 32, 5423.
BrZnCHzCN ,THF -13'C. 16 h cat
nf'A
p h Y C N OH
76%
OH (93% ee , S ) Me h i . & ; Hirose, Y.; Sakata, S. Tetrahedron Asymmetry, 1992, 3, 677.
reflux , 4 h -11.
-
OH d
D.; Koenig, T.M. Tetrahedron Lelt,, i992, 33, 3281.
C
N
74%
352
Compendium of Organic Synthetic Methods, Vol8
0;;
3.5 eq. LiCN , THF
*
reflux, 4 h
Section 332
"%
a c c i o . J.A.; Stanescu, C.; Bontemps, J. Tetrahedron Lett., 1992, 33, 1431.
oo @:
0'"
TMSCN ,CH2C12,2O0C
80%
18 h
"
Ti(OiPr14
OSiMe3
OH
I
N. SynLett, 1992, 663.
Hayashi, M.; Tamura, M.; @mi.
- ALKENE
SECTION 332: ALCOHOL, THIOL
4
1. CH3CHO
-78°C , 1h
2. NaOH ,H202
65% (90%ee)
OH
'I'
Brown. H.C,; Randad, R.S. Tetrahedron Lett., 1990, 31,455.
SPh
PhCHO ,Me2AICI OH Sph CH2Cl2 , -23°Cw P h~ O T ~
OTBS
20 h
Tanino, K.; Nakamura, T.; Kuwaiima
6 0
B
*#
6
OH SPh
+ p h + ~ ~ ~ ~
Me
Me
(94
6)
G H
Tetrahedron Lett., 1990, 31,2145.
1. Os04, NMO aq. 1-BuOH , RT 24 h
Ph. Ph- pJ
S
2. KOH , DMSO 50°C
Harmat, N.J.S.;W a r r e d Tetrahedron Lett., 1990, 31, 2743. [iPrMgCl , CpzTiClz] ether, Bu3SnC1
Bu
THF,reflux 6h
*
Lautens.;Huboux, A.H. Tetrahedron Lett., 1990, 31, 3105.
75%
Bu
86%
353
Alcohol - Alkene
Section 332
montmorillonite clay
clay catalyzed C l a i m reanangement
53%
Lett., 1990, 31, 3241.
SiMe3
Me3Si
2 e S i M e 3
2.2 TiC14, -78°C
BnO
+
B
n
y
O
/v
OH OSiPh,
CH2C12
88% (2,3 antikyn = 33/1) Shimazaki, M.; Morimoto, M.; Suzuki. K. Tetrahedron Lett.. 1990, 31, 3335. ZdAg-graphite THF , RT , 10 min
*
4 90%
Fiirstner. A, TetrahedronLett.. 1990, 31, 3735. SmI2, THF , HMPA
Me
t-BuOH, 0°C
*
X
Me
H
55%
Shim. SC,; Hwang, J-T.: B n p . H-Y,; Chang, M.H. Tetrahedron Lett., 1990, 31, 4765.
TsO 0
T e , NaBH4
*;: H __
5H 1 1
DMF
91 % Discordia, R.P.; Murphy, C.K.;Dittmer. D.C. TetrahedronLeu., 1990, 31, 5603.
SnBu3 OBn
1. SnC14 , -78°C , 5 min
2. PhCHO , -78°C. h 1* h; ' -
McNeill, A.H.; Thomas. EJ, Tetrahedron Lett., 1990, 31, 6239.
90%
354
Compendium of Organic Synthetic Methods, Vo18
Section 332
1. NBS , CCI, , K2C03 2. KO2, 18-crown-6
4 3
OH
458
Williams, G.M.Terruhedron Len., 1990, 31, 7509. Bnrnble. M.A.; Edmonds, M.K.; 1. PhMe, MS 4A (C6HI 1 0 ) M e 2 S i A B o.f0 o COziPr 2t iPr 2. H a , KHC03, MeOH
CHO
t-BuMe2SiOJ,
t - B u M e 2 S i O G
OH
THP ,55"C
67%
Boush. W.R,; Grover, P.T.; Lin, X. TelrahedronLetr., 1990, 31, 7563. Boush. W.R,; Grover, P.T. Terrahedron Len.,1990, 31, 7567. 1. BBr3 , CH2Cl2
-78°C + 25'C
KSiMe,
2.30%~~0~ 97% 3N NaOH ,reflux Hirai, A.; Suzuki, H.; Sonoda. N., Murai, S . J. Org. Chem,, 1990, 55, 1409.
w;
SiMe3
73 \,,at
HO
1. KH , I 2 , THF
65°C
2. TBAF , THF , 6 5 T
-0 74%
HO
tandem anionic oxy-Cope*allylsilane cyclization Jisheng, L.; GalIardo, T.; J. Org. Chem., 1990, 5.5,5426. 1, iPrCHO
Park, J.; Bdersen. S.F. J. Org. Chem., 1990, 55, 5924.
3 -
0
PhI , 10% Pd(OAc)?, BudNCl 3 HC02Li , 3 EtN(kr);! ,LiCl * DMF ,50°C, 1 d
Ph(79:21
Larock. RC,;Leung, W-Y. J. Org. Chem, 1990, 55, 6244.
' E:Z)
OH 78%
Alcohol - Alkene
Section 332
355
NEt3, CHC13 ,reflux 84% 3.1M HCI ; 1M NaOH Hosomi.; Kohra, S.; Ogata, K.; Yanagi, T.; Tominaga, Y. J. Org. Chem., 1990, 55, 2415.
,RT
Ph-Br
-CHO
Zn , DMF
4
87%
Ph
(75:15 erythro:threo)
Shono.;Ishifune, M.; Kashimura, S. Chem. Len.. 1990, 449. MeZAICI , CH2C12 /X"C
MABR , CH2C12, -78°C t
('
1)
(1
32)
65%
85%
Maruoka, K.; Ooi, T.; Yamamoto. H. J. Am. Chem. SOC.,1990, 112, 9011
SiMe3
0
C \\
SiMe,
E13Al , CH2C12 RT
Dost. B.M; Urabe, H. J. Am. Chem. SOC.,1990, 112, 4982.
OJl cu
1. ICH2ZnI 2. n-C5Hl lCHO
Knochei., Rao, S.A. J. Am. Chem. SOC., 1990,
86% 112, 6146.
356
Section 332
Compendium of Organic Synthetic Methods, Vo18
H
TiC14, -78°C
O
-"OQ
Bu3Sn
I,
+
(77:23 EZ)
1111
26)
(74
quant.
Yoshitake, M.; Yamamoto.; Kohmoto, S.; Yamada, K. J. Chem. SOC.,Perkin Trans, I,
1990, 1226.
-78T
-+
RT
-- d
+ OH
(22
1)
17%
Tanaka, T.; Inoue, T.; Kamei, K.; Murakami, K.; Jwata. C, J. Chem. SOC., Chem. Commun., 1990, 906. Bu3SnH1 AIBN , PhH
OH
HQ
54%
22%
Keck.;Tafesh, A.M. SynLert, 1990, 257. LDA ,t-BuOK
c
Q
88%
0 0 O"C,lh OH Mordini, A.; Ben Rayana, E.; Margot, C.; Schlosser. M.Tetrahedron, 1990, 46, 2401. 1. T i C 4 , O'C, 3.5 h 2. SiOz
Abouabdellah, A.; Auk* C.; Begue, J-P.;Bonnet-Delpon, D.; Guilhem, J. J. Chem. Soc., Perkin Trans. I, 1991, 1391.
Sarandeses, L.A.; Mouriilo, A.;
w. J -I,J. Chem. SOC.,Chem. Commun., 1991, 818.
Alcohol - Alkene
Section 332
BujSnH , AIBN PhH , reflux
357
SiMe3
Me3Si *
46%
syringe pump addition over 8 h
OH
(55:45
OH
EE:ZE)
Clive. D.L.J,; Cole, D.C. J. Chem. Soc., Perkin Trans. I, 1991, 3263. c-C~HIlCHO BF3'0E12
Bu3Sn
OMOM
L
Me
,
OH OH : c - q H , ,+ M e M c - C 6 H
,,
MOM
OMOM 5)
(95
74%
Marshall.; Welmaker, G.S.; Gung, B.W. J. Am. Chem. SOC.,1991, 113, 647. Marshall.;Luke, G.P. J. Org. Chem., 1991, 56, 484. 1. PhClIO , BF3eOEt2, -78°C
M°Cp(Co)2 2. Me3N-0, CH2Clz, 23°C
OH
APh
Lin, S-H.; Yang, Y-J.; Liu, R-S. J. Chem. SO~., Chem. Commun.. 1991, 1004.
6.
1. n-C6H 13MgBr. ether
CuBr.SMe2, -70°C
2.H20
c
Barber, C.; Bury, P.; Kociehski. P.; O'Shea, M. J. Chem. Soc., Chem. Commun., 1991, 1595.
Yf
OH Me
1. Co(dmgH)zPy
2. hv (sunlamp)
Me 76%
Harrowven, D.C.; Pattenden. G , Tetrahedron Lett., 1991, 32, 243.
>
CE
2 eq. Riecke Zn ~ ~ e O f W 0
30 min
60% ( 9 5 5 cktrans) Chou, W-N.; Clark, D.L.; White. J.B, Tetrahedron Left., 1991, 32, 299.
358
Compendium of Organic Synthetic Methods, Vo18
Ph
d
Section 332
10%Bu4NRe04 5 q.TsOH*H20
40%
CH2Cl2,RT Ph Narasaka, K.; Kusama, H.; Hayashi, Y . Chem. Lett., 1991, 1413. 1. Me2CuLi 2. LiAlH4, THF 3. KH ,THF
*
OH e n - C 5 H l l Me
Ito, T.; Yamakawa, I.; Okamoto, S.; Kobayashi, Y.;
aTetrahedron Lett., 1991, 32, 371. 69%
1. PhCHO ,24 h 2. MeOH
I*, CP 1 c 1
d
N O \ M O b
-
If quenched after 1 h:
P Me
h 99%(8% de)
45% yield, 98% de John, J.A. Teirahedron Lett., 2991, 32, 1271. Faller. J.W,; DiVerdi, M.J.;
Me. C
PhH (3 h addition)
HO
6 + bMe
HO
HO
OBn
OBn
(62 38) 80% Rochigneux, I.; Fontanel, M-L.; Malanda, J-C.; Poutheau. k TetrahedronLett., 1991, 32, 2017.
MgCl d
0
Br
1. CeC13 , -2OOC
30min
2.
0
A ,-78'C Bn Bn
Bn-Bn HO Bn
Bn
i-
B n e B : H HO Bn Bn
9%
19%
I . BuLi
Ph$-
2. BuLi-TMEDA
THF 3. PhCHO , 2 h $hen. Y,;Wang, T. Tetrahedron Lett., 1991, 32, 4353.
OH
53%
Alcohol - Alkene
Section 332
359
--
Me
ette. L.A.; Friedrich, D.; Rogers, R.D. J. Org. Chem., 1991, 56, 3841. Philippo, C.M.G.; Vo, N.H. Can. J. Chem., 1992, 70, 1356.
- U & ;
Me$i
)=C=
1.9-BBN, RT 2. n-CsH1lCHO
Me
Me
OH NH?
Gu, Y.G.;
89 %
( 9 8 2 diastereorners)
Tetrahedron Lett., 1991, 32, 3029. 1.1-BuLi ,pentandether -78OC
P
2. +20T
O J1-
HO
3. H30+
94%
Bailev. W.F,; Zarcone, L.M.J. Tetrahedron Lett., 1991, 32, 4425.
J-SiMe3
= C-
ph/\/CHO
TiC14, CHzClz, -95°C 45 min
*
OH 57% Hatakeyama, S.; Sugawara, K.; Kawamura, M.; Takano. S, Tefrahedron Lett., 1991,32,4509. 1. BuLi
2. H,O+
c
HO
Nguyen, T.; IWshLE. Tetrahedron Lett., 1991, 32, 5903.
73%
QSiMe,t-Bu
5 eq. I-BuLi 10 eq. MgBq
Bu
--
OSiMepBu
Lautens.;Chiu, P. Tetrahedron Lett., 1991, 32, 4827.
Me,', =
0 : H
66%
Compendium of Organic Synthetic Methods, Vo18
360
Ph-C=C-H ,SmIz. t-BuOH THF-HMPA ,RT , 5 min
J
Lr
Me
Ph
Section 332
Ph
93%
(%:I4 E:Z)
Inanana.; Kabuki, J.; Ujikama, 0.;Yamaguchi, M. Tetrahedron Lett., 1991, 32, 4921. 1. Dibal, CH2CI2, -78OC 2. EtMgBr ,-78OC - 20°C J
-c
c
0,Me
OH
88%
Marek.; Alexakis, A.; Normant, J-F. Tetrahedron Left., 1991, 32, 5329. 1. MePPh3Qi , BuLi
NHBoc
NHBoc 2. ICH2SiMq
Ph
dCHO
3.TBAF
ph+ (>95:5
OH
65%
syn:anti)
Franciotti, M.; Mann, A.; W d e i. M Tetrahedron Lett., 1991, 32, 6783.
5
CHO BF300Et2 99%
SnBu3 Yamamoto.; Yamada, J.; Kadota, I. Tetrahedron Lett., 1991, 32, 7069. 1. Tack. Zn , DMElPhH
94%
Kataoka, Y .; Miyai, J.; Oshima, K.; Takai. L;m o t o .,(I J. Org. Chem., 1992, 57, 1913. Takai. K,; Kataoka, Y.; Utimoto. K,J. Org. Chem., 2990, 55, 1707. PBQ, THF ,RT 25% DABCO , 1 d
C02Et Roth, F.; Gygax, P.;
Tetrahedron Lett., 1992, 33, 1045.
75%
Section 332
Alcohol - Alkene
36 1
**
1% Bu4N ReO4, CH2CI2 5%p-TsOH*H20,5 min
H 0”’
(2.5: 1 cis:trans) dienes formed with longer reaction times Narasaka; Kusama, H.; Hayashi, Y. Tetrahedron, 1992, 48, 2059.
L
q 2.pph3 1 . ‘a,25,C , CC4
z
~
-
+
-
-
10-20% conversion
(92
8)
Dussault.;Hayden, M.R. Tefrahedron Lett., 1992, 33,451.
J
97%
6 9 5 5 p:m) Singleton. D.A,; Martinez, J.P.; Watson, J.V. Tetrahedron Lett., 1992, 33, 1017. Singleton. D.A,; Martinez, J.P. Tetrahedron Lett., 1991, 32, 7381.
(4:l dr) Rawal. V.H.; Krishnamurthy, V. Tetrahedron Lett., 1992, 33, 3439.
OMe
Ph-
PhCHO [(CpzZrCl2)2/BuLi]
Ph Ito, H.;
.
(10:1 threo:erythro) ;Hanzawa, Y. Tetrahedron Lett., 1992, 33, 1295.
-
362
Compendium of Organic Synthetic Methods, Vol8
Br
Me3Si-
L
, PhCHO
Me3Si*
Br
CrC12, THF , RT , 3 h
Ph
t
/
Me
6Bn
McNeill, A.H.;
-
69%
!%Me3
Hodcson. D.M, ; Wells, C. Tetrahedron Lett., 1992, 33, 4761.
B u 3 S n w
Section 332
Me OH
1. SnC14, -78°C. 5 min
-
B
2. Me B~&, CHO , -7PC
n
o
w
76%
BnO"
(<4% other diastereomers)
TetrahedronLett., 1992, 33, 1369.
x
,,,SnBu3
B uLi
w
OBn 0-
OBn OH 9) 94% Tetrahedron Lett., 1992, 33, 5795. (9 1
Tomooka, K.; Igarashi, T.; Watanabe, M.;
H-Cr C-Bu
1 . CpZZr(H)Cl, CHzC12 RT , 10 min
OH
2. PhCHO
cat. AgC104
Maeta, H.; Hashimoto, T.; Hasegawa, T.; ~ z u k i K, . Tetrahedron Leu., 1992, 33, 5965. 1. LDA , THF , -78°C 2. MesSiCl 3. MeOH ,20"C, lh
Le Nocher, A M . ;
TetrahedronLetr., 1992, 33, 6151.
ph
Me
s.i.ph
Me
2.aq. H F , MeCN
MeOX L.
NaHCO3.1 h RT
Me
Me
1. PhMe (93 mM) 172°C. 24 h c
M~'''' Me02C (1
Craig. D,; Reader, J.C. Tetrahedron Lett., 1992, 33, 6165.
'''rOH Me
Me"' Me02C 1)
Me 75%
Alcohol - Alkene
Section 332
363
1. cu* 2. PhCHO H
83%
3. -c1
Ph
Cu* = zero-vaient copper (from CuCN-2 LCI) Stack, D.E.; Rieke. R.D.Tetrahedron Lett., 1992, 33, 6575. 1. Cp2Bu2, PhMe -78°C -+ RT
7)
2. PhCHO , "X", 3 h -78OC 3. 1N HCI
~
P&
X = no Lewis acid
Ph
+
"1
ox
OH
(35
65) 29)
X = BF3*OEt* (7 1 Ito, H.; B e u chi. T.; Hanzawa. Y. Tetrahedron Leu., 1992, 3. 7873.
Cp2TiCI , THF
70% 82%
OH
b
@+Z)
91%
Yadav.; Shekharam, T.; Srinivas, D.Tetrahedron Lett., 1992, 33, 7973. Yadav.;Shekharam, T.; Gadgil, V.R. .I. Chem. SOC., Chem. Commun., 1990, 843. MeN02 CH3S03Ht 16 h b
75°C
75%
Ph)=N-oH Me
(E+Z)
33% z Blanchot-Courtois, V.; Hanw~I.Tetrahedron Left., 1992, 33, 8087. B,. , AI-InC13 , RT
PhCHO
THF-HzO, 50 h
Araki, S.; Jin, S-J.; Idou, Y.; -Bull.
=
PhCHO -aka.
'*
Bn
SMe
b
OH
&
Ph
88%
Chem. SOC. Jpn., 1992, 65, 1736.
SMe
OH
, BF3eOEt2
CH2C12, -78°C
OH
P
h
V
p
K,; Shibata, T.; Hayashi, Y. Bull. Chem. SOC.Jpn., 1992, 65, 2825.
h 83%
364
Compendium of Organic Synthetic Methods, Vol 8
Section 33-
15)
(85
Fukuzawa. &; Sakai, S. Bull. Chem. SOC.Jpn., 1992, 65, 3308.
97%
I . PhCHO , SnClZ PdCldPhCN)2
-OH
OH i- 9 Ph
15"C,4h 2.
)))>)))))
P
h
RT , 4 8 h
2) 57% (98 (67:33 E:Z) ( 7 0 3 0 syn:anti) Masuvama. Y,; Hayakawa, A.; Kurusu, Y. J. Chem. SOC., Chem. Commun., 1992, 1102.
'r'
1. THF , 160°C, 1 h 2. PdC12(PhCN)2
SnCl2, DMI, HzO
RT,5d
%O
*
OH
35%
(32:68 syn:anti)
Masuvama.;Nimura, Y.; Kurusu, Y. Tetrahedron Lett., 1992, 33, 6477. 1. LDA , r-BuOK
Degl'Innocenti, A.; 1992, 753, 803.
..
; Pecchi, S.; Pinzani, D.; Reginalo, G.; Ricci, A. Syntert,
Allylic and benzylic hydroxylation (C=C-C-H -+ C=C-C-OH,etc.) is listed in Section 41 (Alcohols from Hydrides). Also via: Section 302 (Alkyne - Alcohol).
SECTION 333: ALDEHYDE
- ALDEHYDE
Jlnefa.;Xinhua, X.; Haiying, C.; Anren, J. Tetrahedron, 1992, 48, 3503.
Alcohol - Amide
Section 334
365
OMe
Moeller. K.D.; Tinao, L.V. J. Am. Chem. Soc., 1992, 114, 1033. REVIEWS:
"Oxidative Rearrangement of Fury1 Carbinols to 6-Hydtoxyl2H-pyran-3(6H)ones, a Useful Synthon for the Preparation of a Variety of Heterocyclic Compounds" Georeiadia. M.P,; Albizati, KF.; Georgiadia, T.M. Org. Prep, Proceed. lnt., 1992, 24, 97.
- AMIDE
SECTION 334: ALDEHYDE
0
1.
0
2. silica gel Wasserman. H.H.; Cook, J.D.; Vu, C.B. J. Org. Chem., 1990, 55, 1701. 1. PhMe , NEt3 RT,Sh
Af = 4-(Meo)-C&
Alcaide.;Martin-Cantalejo, Y.; Plumet, J.; Roddquez-L6pez, J.; Sierra, M.A. Tetrahedron Lett., 1991, 32, 803.
Tol0,SHN
&
NBS , DME, H 2 0 , O'C, 2 h ~
OH
N S02Tol
(>9S:S
JPeer. V,; Humer, W. Angew. Chem. Inr. Ed. Engl., 1990, 29, 1171.
dr)
366
Section 335
Compendium of Organic Synthetic Methods, Vol8
r-L ? BOC
q-'* ,NaOCl
OH
NaBr , aq. NaHCO3 ,(lo:
&HO
?J
Boc
82%
(>98% ee)
Leanna.;Sowin, T.J.;Morton, H.E. Tetruhedron Lett., 1992, 33, 5029. SECTION 335: ALDEHYDE
- AMINE
H;F/CO,PPh3
CHO
CHO
PPh2 EIOAC
55°C. 22h
PPh2 64%
<4%
Jackson. W.K.; Perlmutter, P.; Tasdelen, E.E. Tetrahedron Leu., 1990, 31, 2461.
(67
33)
76%
Anastasiou, D.; Campi, E.M.; Chaouk, 11.;W o n . W.B.; McCubbin, Q.J. Tetrahedron Lett., 1991, 33, 2211. 1. MeOH ,reflux, 23 h 2 . 6 N HCI , H2O/CH2C12
reflux, 26 h
c1
De Kimne, N.; Boeykens, M.; Boelens, M.; De B'uck. K.;Cornelis, J. Org. Prep. Proceed. Int., 1992, 24, 679. 1. BuLi , -78°C 2. MgBr2, O°C 3. PhCHO , -65OC
Zhang, P.;
50% (80% ds)
Tetrahedron Lett., 1992, 33, 2945.
Aldehyde - Ester
Section 336
PhNHMe ,cat. DBU THF , -15”C, 40 min
dCHO
-
367
P h M e N d CHO
>95%
Mark6. I.E.; Chesney, A. SynLett, 1992, 275. Chesney, A.; M&&LFL Synth. Commun., 1990, 20, 3167. REVIEWS:
“Synthesis of a-Amino Aldehydes and a-Amino Ketones“ Fisher. L.E.; Muchowski. J.M. Org. Prep. Proceed. Int., 1995, 22, 399.
SECTION 336: ALDEHYDE
- ESTER ,?!
1. EIO’ poEl “zEt
M%N-N-,
KzCO3, reflux
CHO 2.H
Kp , H +
*
H< 85%
CO2Et
cH
0
Schmitt, M.; Bourguignon, J.J.; Wermuth, C.G. Tetrahedron Lett., 1990, 31, 2145.
NMe2
OMe Tsay, S-C.; Robl, J.A.;
I. EtOTf ,CHzC12
RT
2 . 2 eq. L-Selectride THF , -78OC
*
69%
OMe
J. Chem. Sac.. Perkin Trans. I, 1990, 757, 1. NaI , Me3SiCl , DMF
Ph 7CHO 2. NZCHCOzMe, NEt3 heat
H q C 0 2 M e Ph 35%
Cu(acac)2 3. NEt3*HF, CH2C12 - Synthesis, 1990, 43. Kunz, T.; Janowitz, A.; IWigJUL 1. e‘ , NaI , MeOH 2.2.F h o l
also for preparation of ketone-esters
Me H7(yCO2Me 0 C02Me 80%
.. . ~G.I.; Elinson, M.N.; Feducovich, S.K. Tetrahedron Lett., 1991, 32, 799.
368
Compendium of Organic Synthetic Methods, Vol8
Section 337
0
k0,Er
EqEt
c4m
(>99
>90%
I)
Gillard, J.W.; Fortin.,G r i m , E.L.; Maillard, M.; Tjepkema, M.;Bemstein, M.A.; Glaser, R. Tetrahedron Lett., 1991, 32. 1145.
HO
To
(Bu3Sn)zO. 80°C
5h
0
0
80%
Shibata.;Matsuo, F.; Baba, A.; Matsuda, H. J. Org. Chem., 1991, 56, 475.
SECTION 337: ALDEHYDE
- ETHER, EPOXIDE, THIOETHER
PhSH , benzophenone
PhS-
hv , MeCN , 1.7;
&hoH
CHO
75%
Gravel.; Farmer, L.; Ayotle. C. Tetrahedron k i t . , 1990, 31, 63.
nCH0
BF3eOEt2, -78°C
0%
*
CH2C12
n-C3H7
0
n-C3H7
74% Frauenrath. H.; Sawicki, M.Tetrahedron Lett., 1990, 31, 649.
BnSH , PhH ,4OoC 12 h
*
PhC-SAcHo
)-CHO
w, Elmaleh, D.R. Org. Prep. Proceed. Int., 1990, 22, 112.
(77
Polo, A.; Real, J.; Claver, C.; Castill6n. 1990, 600.
48%
23)
98%
&; Bay6n. J.C. J. Chem. Soc., Chem. Commun.,
Aldehyde - Halide
Section 338
369
phvph POC13, DMF 80"C,'jh
Ph
phQrHO * OHC
52%
Ph
Venugopal, M.; Umarani, R.; Perumal. P.T.; -R
phm .Ph S 0
Tetrahedron Lett., 1991, 32, 3235.
1. NaOAc ,Ac20 ,Tf20 2. NaHCO3
c
3.5 eq. K2CO3, MeOH
Ph
-Yh
CHO
55%
NH4C 1 Craip.;Daniels, K.; MacKenzie, A.R. Tetrahedron Lett., 1991, 32, 6973.
H-C;C-n-GH17
I I - C ~ H ~ ~ PhH SH, AIBN ,CO(80atm) w n - C ~ 5 ~ 1 3 ~ - C S H l ?
-
n ~ 6 ~ 1 3~un-GH,,
+
100°C
CHO
9%
70%
; I s o e . J . Chem. Soc., Chem. Commun.. 1992, 880.
Nakatani, S.;
SECTION 338: ALDEHYDE
- HALIDE, SULFONATE
-&QPhz?1. n-BuLi ,-78°C
F
HQPh 51%
2.PhCHzBr
76% Patrick, T.B.; Hosseini, S.; Bains, S. Tetrahedron Lett., 1990, 31, 179. 1. iPrNH2
-CHO
2. NCS , CCl4 3. AlC13 , CS2 4. oxalic acid aq. CH2C12
c
TCHO
c1 32%
Stevens, C.; De Kimpe. N. Org. Prep. Proceed. Int., 1990, 22, 589. DMF , PWI3
Evans.;Lloyd, H.A.; LaBeau, D.; Sokoloski, E.B. Org. Prep. Pruceed. int., Z990, 22,764.
370
Compendium of Organic Synthetic Methods, Vol8
13
(84
Section 339
3)
14%
Duhamel.; Guillemont, J.; Poirier, J-M.; Chahardes, P. Tetrahedron t e t t . , 1992, 33, 5051. 1. LDA , THF, 0°C
N'
4
t-Bu 2. Me3SiCI
3. NCS , C C 4 , RT
63% 4. 10 eq. MeOH ,CC14, RT c1 5. (C02H)z. H20-CH2C12 &&mp%&; Coppens, W.; Krauze, A.; De Corte, B.; Stevens, C.; Welch, J. Bull. Soc. Chim. Fr., 1992, IOl, 237.
SECTION 339: ALDEHYDE
- KETONE
l o
[
PhSCH20Me , THF 1. THF BuLi ,-78"C, , -78°C2 h, M
Me M&
e a z o
Me
SBu 2. HgC12, H+
hemf&L; Panilla A.; Camps, F. Tetrahedron Lett., 1990, 31, 1873.
d-H
1. BuLi , THF , -78°C 2. t-BuOzCCI
4.6N 3.n-CsHlsMgBr NH3
OEt
Savoia.;Concialini, V.; Roffia, S.; Tarsi, L. J.
74% Org. Chem., 1991, 56, 1822.
1. PhSeBr ,HgC12, AgN02 2. DMAP
O d
OEt
3.10% HCI
(38%..
(95%)
bCH
Backvall, J-E.; Karlsson, U.; Chinchilla, R. Tetrahedron Lett., 1991, 32, 5607.
Adger, B.M.; Barrett, C.; Brennan, J.; McKervev. M.A.: Murrav. R.W. J. Chem. SOC.,Chem Commun., 1991, 1553.
Aldehyde - Alkene
Section 34 1
37 1
n
SH SH
CK-H
AI2O3.4 h
Ranu. B.C,; Bhar, S.; Chakraborti, R. J. Org. Chern., 1992, 57, 7349.
x
OSiMe2t-Bu
c
70%
c q
' b SnBu3, CAN
MeCN S , MS 4 A , -23°C
87%
Narasaka.; Okauchi, T.; Arai, N. Chern. Lett., 1992, 1229. SECTION 340: ALDEHYDE
- NITRILE
NO ADDITIONAL EXAMPLES
SECTION 341: ALDEHYDE
-
ALKENE
For the oxidation of allylic alcohols to alkene aldehydes, see Section 48 (Aldehydes from Alcohols). I
PhCHO ZnBr;!
ZnCl;!
cat.
SiMe,
THF
& -
N' -hp
aq.ether
Ph
4 C H O
86%
E only
Gaudernar, M.; Bellassoued, M. Tetrahedron Leu., 2990, 31, 349.
'3 !A
1, t-BuOK ,TlIF
0
EtO-
0
2.PhCHO
3. H30+
-
Ph
-CHO
OEt 86% Duhamel. L,; Guillemont, J.; LeGallic, Y.; Pl6, G.; Poirier, J-M.; Ramondenc, Y.;Chabardes, P. Tetrahedron Lett., 1990, 31, 3129.
Kataoka, H.; Watanabe, K.;SkxdL Tetrahedron Lett., 1990, 31, 4181.
372
Compendium of Organic Synthetic Methods, Vol8
Section 341
60%
Jeffew. T. TetrahedronLett.. 1990, 31,6641.
* \
OH
V-PILC ,rn-xyiene
\
reflux, 1.5 h
r C H O
.c
84%
V-PILC = vanadium-pillared montmorillonite clay Choudarv. B.M,; Prasad, A.D.; Valli, V.L.K. Tetrahedron Left.,1990, 31, 7521. 1 . BuLi , THF , -23°C Ph 2. PhCIIO w
3. H2O C C H O 4. KH , 18-crown-6 36%overall THF Enholm.; Satici, H.; Prasad, G. J. Org. Chem., 1990, 55, 324.
r LDA ,THE - 7 8 ~ n-C5H, ,CHO 2.S i q
1
THF.2h
-CHO n-C5H 1 1 (84: 142 all E2E,4Z:2Z,4E)
78%
Kann, N.; Rein. T,; hennark. B,; Helquist, P. J. Org. Chern., 1990, 55, 5312.
iPr d De K-;i
1. NaOMe , MeOH ,heat 2. (COzH)2*2H20, heat H20.CHzCl2
H
--
T
H
O85-95%
Stevens, C. Bull. SOC. Chim. Belg., 1990, 99,41.
(7:93 EZ)
Nonoshita, K.; Banno, H.; Maruoka, K.;
64%
J. Am. Chem. SOC.,1990. 112, 316.
2
37 3
Aldehyde - Alkene
Section 341
&CHO
Mahrwald, R.;
Ti(OiPr)4 , hexane -68"C, 4 h
aSynthesis, 1990, 592. Li
PhCHo
Ph
2.1N HCI
-CHO
Contreras, B.; Puhamel. L.; Ple, G . Synth. Commun., 1990, 20, 2983.
)&
CH2Cl2 ,-78OC c
&CHO+
2090
CHO
73%
(74% ee)
iPr
Takasu, M.; Yamamoto. H. SynLett, 1990, 194.
-
Sartor, D.; Saffrich, J.;
".;q Me
O +0
4 C H O
95%
(c1:99 endo:exo) (64%ee)
SynLett, 1990, 197.
3M LiClO4, ether
(3JcH
co. P A ; Clark, J.D.; Jagoe, C.T. J. Am. Chem. SOC.,1991, 113, 5488.
Me ; 91%ee) (>99:1 exo:endo Kobayashi, S.; Murakami, M.; Harada, T.; Mukaiyama, T. Chem. Let?., 1991. 1341.
374
Compendium of Organic Synthetic Methods, Vol8
-
PhH
-OH
q-@H%M€)2
no oxidation of non-allylic alcohols Yana. H,; Li, B. Synth. Commun., 1991, 21, 1521. DMF , P O c b 0°C + RT,4 h
OMe
bCHo 81%
Cr$$
wMeo MeO"'
CHO
OMe
Tetrahedron Lett., 1991, 32, 3875.
Ramesh, N.G.;
'OzMe
60%
5% Pd(0Ac)z 15% PPh3, 80°C
HO
CHO
W i n . J-M. Tetrahedron Lett., 1991, 32,6113. dC I SN ~ C I, ~
PhCHO
Section 34 1
DCE , HzO ,25"C, 4 h
Ph
, N*
CHO
57% J3morsv. S.S. ; Badawy, D.S.; Nour, M.A.; Peller, A. Tetrahedron Letl., 1991, 32, 5421.
Menicagli. R,; Malanga, C.; Guagnano, V. Tetrahedron Lett., 2992, 33, 2867. SnC12-2 H2O , CH2C12
*
-CHO 94%
Ford, K.L.; Roskamn. E.J, Tetrahedron Left., 1992, 33, 1135.
H- CSC
l
NH2
2 eq. MezPhSiH , CO , PhH Rb(C0)12, 100°C , 2 h
OHC
Matsuda.; Sakakibara,J.; Inoue, H.; Nagashima, H. TefrahedronLett., 1992, 33, 5799.
Amide - Amide
Section 342
x
375
uCHO, RT. 4 h 10%
(MeOM’’
FP co
D
C
O 64%
H
L
Feltl
THF
Olson, A.S.; Seitz, W.J.; Hossain. M.M. Terruhedron Lell., Z991, 32, 5299. n CI Nd
0
-@
t-Bu
-
C12C=CHCI, 55°C. 48 h
\==
t-BU
CHO
80%
A.&; Scherbakova, I.V.; Taek, R.D.; Steel, P.J.Can. J. Chem., 2992, 70, 2040.
Also via P-Hydroxy aldehydes: Section 324 (Alcohols - Aldehyde).
SECTION 342: AMIDE
- AMIDE
(yg H
*
0
Beckwith, A.L.J.; Dyall, L.K. A m . J. Chem., 2990, 43, 451.
> 0
Ph
N.Me
1. LiNTMSz , THF 2. aq. Ht
95%
0
phf c
0
NHMe NHMe
ph,,.t
0 (70:30 threo:erythro)
70%
w o v . I.V.; Smushkevich, Y.I.J . Chem. SOC., Chem. Cotnmun., 1990, 1686. Ph-
H-N
N-H
NH2
DMF ,aq. dioxane , 10 min
Bannworlh. W.; Knorr, R. Terrahedron Lerr., 1991. 32, 1157.
376
Compendium of Organic Synthetic Methods, Vol8
1.2.5 eq. LDA ,THF
MeHN Ph
NHMe
Ph
Ph
Ph
NHMe Ph
(4
1)
Enda.;Shudo, K. Tetrahedron Leu., 1991, 32,4517.
50%
Section 312 (Carboxylic Acid - Carboxylic Acid) Section 350 (Amines - Amines)
Also via Dicarboxylic Acids: Diamines
SECTION 343: AMIDE
Section 343
- AMINE
b.:Me (ipr)2Nl 1. LDA
Me0
0
(~PI-)~N
63%
O E
2.
Ph
\=N Alcaide. B,; Plumet, J.; Rodrfguez-Lopez,J.; Shche-Cantelejo, Y.M. Tetrahedron Lett., 1990, 31, 2493. 1 . 0 ~ 0 ,4NaIO4 ,NMMO 2. Et3Si1, TFA D-
78%
Holladav. M.W.; Nadzan, A.M. J. Org. Chem., 1991, 56, 3900.
(CO),Crl
NMePh
H
CO ,ether, hv
Sijderberg, B.C.; l k g & ~ L LJ. Org. Chem., 1991, 56, 2209.
Etgbv, J.H,; Qabar, M. J. Am. Chem. SOC.,1991, 113, 8975.
H
Amide - Ester
Section 344
-
c)
N C02Me
Ph4;
, CHC13
NH-NHC02Me
+
RT ,70 min
377
80% Vidal, J.; Drouin, J.; Collet...!.Chem. SOC., Chem. Commun., 1991, 435.
0
Me
CQ
R
H2N /L N H z , A1203
'b' CO,E~
microwaves (125 W) * 15 min
Pilard, J-F.; Klein, B.; Texier-Boullet. F.; Hamelin.
Me 90%
0
J, SynLett, 1992, 219.
REVIEWS : "The Chemistry of Pyrazolidinones" Org. Prep. Proceed. Int.. 1991, 23, 275. Claramunt, R.M.;
SECTION 344: AMIDE
- ESTER
PMB = p-methoxybenzyl Clark. R.D.; Souchet, M. Tetrahedron Lett., 1990, 31, 193.
Na
MeOzC-kCqMe NHAc
Ph
~
OAC
91:g ( 4 C02Me:
2
P
Ph
[ ( Z - C ~ H ~ ) P ~ CMe02C ~]~ COzMe THF , S-BINAP NHAc 120 h ,25"C 92% +
h
Me02C
IIII
COzMe )
A Ph
C02Me NHAc
(95%ee , S) Yamamchi, M.; Shima, T.; Yamaeishi. T,; Hida, M. Tetrahedron Letf., 1990, 31, 5049.
04 N 0 -C 0 z t - B ~ Boc Schoenfelder, A.;
==/-OH
THF , R T , 24 h
Maon.
CO2t-BU
,KCN *
t-Bu02C+NHBoc
Synth. Commun., 1990, 20, 2585.
77%
Section 344
Compendium of Organic Synthetic Methods, Vo18
378
OH
ACO ,r-Bu
1.2 LDA .TMF
(96
4)
85%
Hatanaka.;Park. 0-S.; Ueeda, I. Tetrahedron Lett., Z990, 31, 7631. Me Me
1. phv N-Ts , Tic14
C H F l z , RT
MeoAco2Et Me0
Me
Me
N
Ts
2. EtOH
Me
TS'
Ph
(98
mCPBA , DCC ,DMF 2S°C, 1 h
k02Bn
Ph 2)
UK.; Shimada, S.; Hasegawa, M. Chem. Lett., 1990, 905.
f i C02H O N
Me
+ O G C02Et
04)-Co&t
81%
o + j Q
*
0%ester with free lactam Shiozaki. M,Synthesis, 1990, 691.
c1 42%
'02Bn0
K CH(C02Me)2 , 110°C Mn(OAch, AcOH 10 min
47%
Tetrahedron Lett., 1991, 32, 1011.
del Rosario-Chow, M.; Ungwitayatorn, J.; 1. NaOAc , OsC13 30% MeC03H
H
NHB&
RT
Go*'
0
H
78%
2.5%Na2SO3 Murahashi.; Saito, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Leu., Z991, 32, 2145.
OH
1. Pb(OAc)4 ,EtOAc ,M S 4A 2. DABCO
SEt 86%
Apitz, G.; U l i c h . W. Tetrahedron Lett., 1991, 32, 3163.
Amide - Ester
Section 344
379
1. RuC13-3 H20, NaOAc , AcOH MeCHO, EiOAc , 40°C, 3 h + 2.10% aq. Na2S03
0&(Me H
72%
Murahashi.;Sdto, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Left., 1991, 32, 5991.
Boc-Trp-COOH
+
H2N-Trp-OMe
new peptide coupling reagent
DMF ,iPr2NEt ,RT , I .5 h , - F
K0
96%
Ph- P. Ph F
Chen, S.; Xu,J. Tetrahedron Lett., 1991, 32, 6711
F 0 NHTs
Boc-Trp-Trp-OMe
c
w
PdClz , CuC12, NaOAc CO , MeOH-AcOH ,3OoC
Co2Me
N*Ts
0
I (
87 h
89%
0
(1:7 cis:trans)
Tamaru. Y,; Tanigawa, H.; Itoh, S.; Kimura, M.; Tanaka, S.; Fugami, K.; Sekiyama, T.; Yoshida, Z. Tetrahedron Lett., 1992, 33, 631.
so-
O I y
[aceLophenoneLDA]
C02Et
THF
c
OH 0 phA.A/yC02Et
78%
BOC NHBoc Ezauerra J,; de Mendoza, J.; Pedregal, C.; Ramirez, C. Tetrahedron Lett., 1992,33,5589.
LN.
BOc RhdOoctvl)4, pent& _... L,----,
d o A c o 2 E t
N2 (66% dr , 1R)
Davies.;Huby, N.J.S. Tetrahedron Lett., 1992, 33, 6935. 1. “NaPhSeBHj” ,heat 2. H+ ,CH2N2
OSiPh2r-Bu Pedersen, M.L.;
-
OSiPh,t-Bu SePh 85%
Tetrahedron Lett., 1992, 33, 7315.
Compendium of Organic Synthetic Methods, Vol8
380
0 Ts(Me)N>
9
-
1. TfzO , -($-Bu
-
Section 344
C H g 1 2 , -lOOd-BU
2.RT.
75%
N(Me)Ts
3. H f l , C C 4 , RT 4. mCPBA , NaHC03 CHzClz ,0°C
(93%ee)
Genicot, C.; Ghosez. L Tetrahedron Lett., 1992, 33,1351.
Abe, M.; Sudo, A.; Hasegawa, A. Chem. Lett., 1992, 1445.
Shimada, S.; -K;.
Siozaki. M. Synthesis, 1990, 691.
0
)-CHO
COzMe
M e 0 P 4NHCbz
Me0
CO2Me
DBU ,CH2C12 , -2OOC + RT
NHCbz
quant.
(3:97 E:Z)
Schmidt.;Griesser, H.; Leitenberger,V.; Lieberknecht. A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis, 1992, 487.
C02Me CI+NHCHO Me
2 'W
0
Roos, E.C.; JIiemstra. L;-0. SynLett, 1992, 451. Related Methods:
SiMe3, TMSOTf , 4 h
*
@CO*Me \ NHCHO 84%
W.N.; Kaptein, B.; Kamphuis, J.; Schoemaker, H.E.
Section 315 (Carboxylic Acid - h i d e ) . Section 316 (Carboxylic Acid - Amine). Section 351 (Amine - Ester)
SECTION 345: AMIDE
NHBoc Nemoio, H.; Jimenez, H.N.;
- ETHER, EPOXIDE, THIOETHER 4% RhH(PPh3)4, MeOH sealed tube, 100°C +
9NHBoc OMe
M%
J. Chem. SOC., Chem. Commun., 1990, 1304.
h i d e - Ether
Section 345
a t
C02Me
38 1
-
1. NBS , hv , 1 5 min
Cc4 ,CH$32.
2. EtOH 2,641tidine
9
0
EtOA CO2Me 41%
!%m. C.J; Pitt, M.J. Tetrahedron Lett., 2990, 31, 3471. n-CloH21
4
HBF4, H2NCOzEt 4 5 T . 10 h
+
Ane OH l
NHC02Et Et0,CHN
PhSe
SePh 25%
61%
0
Francisco, C.G.; Hernhndez, R.; Le6n, E.I.;Salazar. J. A%;SuArez, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2417.
3
O
+
phs>Me PhSH ,hv
N
O
b
r
v
L
N
S
P
h
L 12% (2:l cis:trans)
54% (trans)
Naito.; Honda, Y.; Miyata, 0.;Nonomiya, I. Heterocycles, 1991, 32, 2319. 2% VO(dpnh, 02,DCE iBuCHO , RT, 12 h
MM e u y . P h
0
*
MeG~' 87%
Me
Me
0
Me
VO(dpm)r = bis-(dipivaloy1methanato)oxovanadium (IV)
Inoki, S.; Takai, T.; Yamada, T.; Mukaiyama. T. Chem. Left., 2991, 893. TolSo2NH2, PhSeCl , DCE 85%
cat. ZnClz/elher, 24 h
. .
Toshtmltsu.; Kusumoto, T.; Oida, T.; Tanimoto, S. Bull. Chem. Soc. Jpn., 1992, 64, 2148. Me2NCH0, N3C02Et
AOSiMe,
heat
* &OWNMe
CHO
Mitani, M.; Watanabe, K.; Tachizawa, 0.; Koyama, K. Chem. Lett., 2992, 813.
38%
382
Compendium of Organic Synthetic Methods, Vol8
SePh
I .
NHCO2Et
j30,Et
(87 Cooper, MA.;Ward. A.D. Tetrahedron Lett., 1992, 33, 5999.
SECTION 346: AMIDE
Section 346
13)
95%
- HALIDE, SULFONATE -78°C
0
NIS = N-iodosuccinimide cossV.;Thellend, A. Tetrahedron Lett., 1990, 31, 1427.
Cl2, H20,90"C 39%
H
H Ranc. E O r g . Prep. Proceed. Int., 1990, 22, 104. 5% Pd(0Ac)z. RT 2 eq. benzoquinone 2 eq. LiCl , 8 h
c1
acetone -H20
(>98%cis) Backvall. J -B; Andersson, P.G. .I. Am. Chem. SOC., 1990, 112, 3683.
Me
c1H
~
0
BuNH2
0 ~
Cundida t cylindrucea lipase
Me+
c1
NHBu
62% (95% ee) Gotor..,Brieva, R.;GonzBlez. C.; Rebolledo, F. Tetrahedron, 1991, 47,9207. Brieva, R.; Rebolledo, F.; -.I. Chem. SOC., Chem. Commun., 1990, 1386 [with subtilisinl.
Amide - Ketone
Section 347
0
383
1. LiN(SiMq)Z
Me OMe
OMe
(1
Araki, K.; Wichtowski, J.A.; N!ekhJL
Tetrahedron Lett., 1991, 32, 5461.
O
1. LDA
0 i N X B U
HMe o
O
t
0"
N
O L B
3.5) 68%
u
HMe F
Ph
88%
Ph
(97% de)
0 2
Davis. F.AA;Han, W. TetrahedronLett., 1992, 33, 1153. 12, s-collidine , RT
0 Ph-
\
NEt,
CH2Cht18 h
I Kitagawa, 0.;Hanano, T.; Hirata, T.; Inoue, T.;
_id
12, THF
*
84%
Tetrahedron Len., 1992, 33, 1299.
'
d)+&$
0
MeS \ N
Bn I
in
Bn
I
56%
4% D h h a t a . H,; Wang, E-C.; Ikuro, K.; Yamazaki, T.; Momose. T, Heterocycles, 1992, 34,435.
SECTION 347: AMIDE
6
Si(iPr1,
N
- KETONE
1. ROCOCl 2. MeMgCl , -78°C
PhMeITHF 3. H30+
R = 8-phenylmenthol
*
hcl bcl
M~'''\ I?
+
C02R
Me
major
92% (91% de)
N
COzR minor
Comins. D.L.; Guehring, R.R.; Joseph, S.P.; OConnor, S. J. Org. Chem., 2990. 55, 2574.
3 84
Compendium of Organic Synthetic Methods, Vol8
Section 347
0
1.
0
MeOH , CH2CI2 2. pyridinium p-toluenesulfonate CH2C12, reflux, 1 h 5821.
0
; Henke, S.L.; Luce, P.; Nakanishi, E.; Schulte. G. .I. Org. Chetn.. 1990, 55,
GN
ETn
1. Bn-N=C=O , NaN ,THE
2'H20
O
*
U
N 75%
Ognyanov, V.I.; Hesse. M.Helv. Chitti. Acra, 1990. 73, 272. 1. Ac.BF4-bIeCN
d d L
%
2.aq.NaOH Gridnev, I.D.; Balenkova, E.S. Zhur. Org. Khitn., 1990, 26, 46 (Engl., p. 37). MeO-
OSiMe,
N * Cbz 1-Bu
TMSOTf
*
&
304%
Cbz I
t-BU
85%
Earle, M.J.; Fairhurst, R.A.; Heanev. H,; Papageorgiou, G. SynLeft, 1990, 621. 1.20% HC1
NHiPr 2. MsCl , Bu4N HSO4 C02Me H20/CHC13
Buchholz, R.;
Ph
iPr
Helv. Chini. Acta. 1991, 74, 1213. PhI(02CCF3)2 , MeOH RT, 10min
* -0
NHAc 76%
Kits.; Tohma, H.; Kikuchi, K.; Inagaki, M.;Yakura, T. J. Org. Chetn., 1991, 56, 435.
385
Amide - Ketone
Section 347
Linde, R.G. 11; Deroncic, L.O.;
J. Org. Chem., 1991, 56, 2534. Rh2(0Ac)4 , CHC13 25°C ,45 min
0
79% 0
Padwa.;Chinn, R.L.; Hornbuckle, S.F.; Zhang, Z.J. J. Org. Chem., 1991, 56, 3271. 0
0
0
1. TIC4 , CH2C12
iPrZNEt, 0°C , 1 h b
Bn
2.
&
0
OAN&
Bn
-25"C, 0.75 h
Me
88%
(>99: 1)
Evans. D.A,; Bilodeau, M.T.; Somers, T.C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem., 1991, 56, 5750. hv ( h = 313 nm) , MeCN
k
N. B0 nBZ
( l o 2 M) , 7 5 min
z* B::&
70%
0
Le Blanc, S.; Pete, J-P.;Piva. 0, Tetrahedron Letf.,1992, 33, 1993.
230°C, 5 h
cossV.;Bouzide, A. Tetrahedron Left., 1992, 33, 2505.
Me
(85
15)
95%
Compendium of Organic Synthetic Methods, Vol8
386
3
Section 349
1. NEt3 , Me3SiCI NaI , MeCN
2. MeNHSOZCI , NEL MeCN Vega, J.A.; Molina, A.; Alajm'n, R.; Vaquero, J.J.; Garcfa Navlo, J.; A l v a r e z - B u i u Tetrahedron Lett., 1992, 33, 3677. BQO, DMF ,55"C
Ph
3h
Ph
ShiDton. M .R. SynLetr, 1992. 491.
SECTION 348: AMIDE
- NITRILE
*
Ph
NC
8OoC, 17 h
fL
b
c
P
?
NC
h
+
"Me
fi.,.Ph
NC
Ac (5
N, "Me Ac 1)
Teng, M.; Fowler. F.W, J. Org. Chem., 1990. 55, 5646.
NC
CO,Et
1. LiNHBn , THF , -70°C 2. EtOH *
NC h N H B n 0
Bhawal, B.M.; Khanapure, S.P.; Biehl. E.R. Synth. Commun., 1990, 20, 3235.
SECTION 349: AMIDE
- ALKENE
Phfi'N% 93% Georg.;He, P.; Kant, J.; Mudd, J. Tetrahedron Lett., 1990, 31, 451.
3%
0
A HCO~AC 'pp:
ONH:O
Baldwin.;Aldous, D.J.; O'Neil, LA. Tetrahedron Lett., 1990, 31, 2051.
75%
80%
Amide - Alkene
Section 349
0
1.LDA.THF
4N'n-Bu
A J
387
0
0
+ fiI+pBu
2.% xylene k H,4hn - B u 135°C (99.5
0.5)
:
92%
Tsunoda.;Sasaki, 0.; It8, S Tetrahedron Lett, 1990, 31, 727. Me H-CiC+Me OH
2
C%.BuNHz
*
PBu3, 110°C
56%
BU"'fo
0 Fournier, J.; Bruneau, C.; Dixneuf, P.H. Tetrahedron Lett., 2990, 31, 1721.
qN,o 3.85%HQ04
n-C6Hi3 N-H
H
PhMe , 60°C
Me Barluenpa.; Tom& M.; Subez-Sobrino, A.; Rubio, E. Tetrahedron Lett., 1990, 31, 2189.
*
\
see Tetrahedron Lett., 1988, 29,4855
PhCHO , PPh3 iPrOH ,reflux * 48 h
Me
N-BW
Ph9NH Me 71%
EZ) Dellaria, J.F. Jr.; Sallin, K.J.Tetrahedron Lett., 1990, 31, 2661. (2:l
1. LiN(TMSh ; TMSCl THF , 0°C
-pJ
=CHO
2. c , L 3. xylene, reflux, 20 h
Uvehara.; Suzuki, I.;
57%
Tetrahedron Lett., 1990, 31, 3753.
pTol-N=C=O
dioxane
N- To1
0
76%
Ljebeskind.;Johnson, S.A.; McCallum, J.S. Tetrahedron Lett., 1990, 31, 4397.
Compendium of Organic Synthetic Methods, Vo18
388
B
NHBoc n o A O
Section 349
0
1. t-BuMeZSiOTf 2.6-lutidine
H'NKo
h 2. TBAF ,THF ,RT
10%Pd(PPh3)4, 1 h
78%
BnO
(9:l syn:anti) Spears, G.W.; Nakanishi, K.; Qhfune. Y,Tetrahedron Lert., 1990, 31, 5339.
8h
KnaDD.; Gibson, F.S.; Choe, Y.H. Tetrahedron Len., 1990, 31, 5397.
84%
Ru BuMgBr
Bu C02t-BU
C02t-Bu
+ BF3oOEt2 + CuBr
+ 0) 100)
(100
(0
63% 77%
Shono. T,; Terauchi, J.; Ohki, Y.; Matsumura, Y. Tetrahedron Letf., 1990, 31, 6385.
BocHN-CHO
1. (CHz=CH)2ZnCI 2. A c ~ O 3. HzC(COZEt)z,NaHPd(PPh3)4 , THF
CO,Et
B~~HN-
--
CO,Et
87% ThomDson. W.J,; Tucker, T.J.;Schwering, J.E.; Barnes, J.L. TefruhedronLeff.,1990, 31, 6819. 1. THF, KH , -78°C
/y
H k
p
Ph 0
3
-Br
2. MeCN , 105°C 12 h
0S,2
CCl,
Ph
70% (4 diastereomers) 51:31:12:7 syn ax.:anti ax.:anti:eq.:syneq. Guv. 4; Crailiot, Y . Terrahedron Left., 1990, 31. 7315.
Amide - Alkene
Section 349
389
1. RuC12(PPh3)3
PhH , t-Bu00H 2. Na bisulfite
C02Me
C02Me Naota, T.; Nakato, T.;
89% Tetrahedron Lett., 1990, 31, 1475.
'
PhI , NEt3 , 3% Pd(0Ac)Z
C02Me
C02Me
Nilsson, K,; Hallbere. k J. Org. Chem., 1990. 55, 2464.
fi N
SiMq
S ~ C I ~
*
CH2C12, -78°C. 30 min
CO2Et (50
CO2Et 1) 90%
&
W k o w s k i . A.P,; Park, P. J. Org. Chem., 1990, 55, 4668. ,DMF KOAc ,8O0C. 4 d Bu~CI
Larock.;Yum, E.K. SynLett, 1990, 529. PhN,
1. PPh3 , PhMe , RT 2. adipoyl chloride, PhMe
reflux, 3 h
-
-
0
45%
cN:Ph
Aubert, T.; Farnier, M.;sjuilard. R, Synthesis, 1990, 149.
77%
c1
1. Ac*BF4-MeCN
2. MeCN
3.aq.NaOH
&WAC
60430%
Gridnev, I.D.; Balenkova, E.S. Zhur. Org. Khim., 1990, 26, 50 (En& p. 40).
390
Compendium of Organic Synthetic Methods, Vo18
(3
x
0
-
Section 349
1. LDA ,THF ,-78°C
2.
Br
77%
Diels- Alder reportedpreviously Chockalingam, K.; Harirchian, B.; BaUJlL Synth. Commun., 1990, 20, 189.
Braisted, A.C.; Schultz. P.G, J. Am. Chem. SOC.,1990, 112. 7430. 1 . 1 2 , THF 2. NaH , DMPU ,THF
NHTs DMPU = N,Ndimethylpropylene urea Shaw, R.; Anderson, M.;
I
+s
+
"41 TS
83%
10%
SynLett, 1990, 584.
Yamapuchi.; Hamasaki, T.; Utimoto, K.; Kozima, S.; Takaya, H. Chem. Lea., 1990, 2161.
Bz. N
-78°C -+ 55°C
Kim. D.; Kim, H.S.; Yoo, J.Y.Tetrahedron Letr., 1991, 32, 1577.
62%
Section 349
Amide - Alkene
Ph-CkC-H
39 1
hNEt2
5% PdCIz(PPh,),, 5% PPh3 10%Me1 ,NHEtz , 120°C
-
CO (5 a m ) , 6 h
Ph
81%
0 Torii.;Okumoto, H.; Sadakane, M.; Xu, L.H. Chem. Lett., 1991, 1673.
Giesler, A.; Steckhan. E.; Wiest, 0.;Knoch, F. J. Org. Chem., 1991, 56, 1405.
Co&
- 1 3 g , so2
*
a surfactant diene \ H 2 0 * ' o h
X
o,,,,,,
e n - T * H 1 302s_ \ 0 - n ~ ~ 1 3 02s \ Ph
x o
-+
Ph
x o
(80
X = NHCOz(CH&NMq+ Bf
20)
98%
laeper.,Shinozaki, H.; Goodson, P.A. J. Org. Chem., 1991, 56, 2482.
(i+
1
!J 0
2eq. MezAICl CHzClz ,-30°C
-
Snider. B.B,;Zhang, Q. J. Org. Chem., 1991, 56, 4908.
(-$ 0 , Me
OMe
*
BX
0'Li+
THF ,reflux, 12 h
e I
Me (5.5
Coates, B.; Montgomery, D.;
a Me (64%) p Me (14%
Me 1)
Tetrahedron Lett., 1991, 32, 4199.
64%
Section 349
Compendium of Organic Synthetic Methods, Vol8
392
phi
0 xylene ,reflux
N
0
(>95:5
YPh
76%
H
E:Z)
Janecki, T.; &&l&JL ' Tetrahedron Lett., 1991, 32,6231.
5 q.A c ~ O
*
H o
- Hy
60%
H
0 OMe tralI. ; w c . W.N Tetrahedron Lett., 1992, 32,6633. Roos, E.C.; Bemaw. P.; IL.
Q
HZN
OMe
m4(c0)12,DBU t-BuMezSi-H ,CO
t - B u M e 2 s i p
PhH , 100°C
C&-H
H
oQo
64%
Sakakibara, J.; Nagashima H. Tetrahedron Lett., 1992, 32, 743 1.
-
RuHz(PPh3)4, DME HzO , 120°C , 2 4 h
94%
H Sasao, S.; Saito, E.; Naota, T. J. Org. Chem., 2992, 57, 2521.
;-
CSCH2 0
K 0
NHTs
PdClZ(PhCN)z, THF N E t 3 , RT
+C1
-
f
-
oyN- Ts 0
P 53%
Kimura, M.; Fugami, K.; Tanaka, S.; ~&MJLX,J. Org. Chem., 1992, 57. 6377. Tetrahedron Lett., Kirnura, M.; Kure, S.; Yoshida, Z.; Tanaka, S.; Fugami, K.; 1990, 31, 4887 [with CuCI, NEt31. Terrahedron k t t . , 2991, 32, 6359 [with Kimura, M.; Fugami, K.; Tanaka, S.; AgNCO] .
Amide - Alkene
Section 349
0
393
0
PhCHO , PPE , 2 4 h 35°C
Ph
I
63% Me PPE - see J. Org. Chem., 1969, 34, 2665 Marson.;Grabowska, U.; Walsgrove, T. J. Org. Chem., 1992, 57, 5045.
Me
A. ph 0 N' bMe Et
5% PdC12(PhCN)2 THF,20°C, 16h
1
c
N-Ph
0
79%
Metz.;Mues, C.; Schoop, A. Tetrahedron, 1992, 48, 1071.
0
OTf , DMF , K2C03
-f
Co2H MCbz
=
&yC02H
10% Pd(OAc)z, Bu~NCI
20% P(o-Tol)3 Criso.;Glink, P.T. Tetrahedron, 1992, 48, 3541.
0 p
EtO- , EtO
77%
NHCbz
0
n-C6H13CHO, ether n-C&,3 a N . ~ ~80% e NaH ,0°C + RT /
he
7 P . . 0 M e94% 0 Me
l h
(955 E Z )
Netz, D.F.; Seidel. J.I. Tetrahedron Lett., 1992. 33, 1957.
&(cH2)8NHBoc
2. 1. 3. TFA NMI hv ()i=340 nm)
CHzC'2
(
2 0
0
52%
Ouinkert. G.; Nestler, H.P.; Schumacher, B.; del Grosso, M.; Diirner, G.; Bats, J.W. Tetrahedron Lett., 1992, 33, 1977. = / C 0 Z M e DME , ,02
'H
5% PdC12(MeCN)2 5% CuCl ,60°C Hosokawa. T,; Takano, M.; Kuroki, Y . ;Murahashi. S-I. Tetrahedron Lett., 1992, 33. 6643.
Section 349
Compendium of Organic Synthetic Methods, Vo18
394
l.PhCH0, PhH ,80°C (Dean-Stark) 2.4 eq. NaBH4, MeOH Ph 3. AcCI, NEt3 A c - N J 60% 4. PhCHO, THF ,TBAF RT (35:65 E Z ) Palomo. C. ; Aizpurua, J.M.; Legido, M.; Picard, J.P.; Dunogues, J.; Constantieux, T. Tetrahedron Lett., 1992, 33, 3903.
Fn
H 2 N y SiMe3 SiMe3
*'
Bu /
OSiPh2t-Bu cat. PdC12(PhCN)2
0
>N-H
OSiPh2t-Bu
*
PhH
72%
C13C
(88% ee)
cc13
Mehmandoust, M.; Petit, Y.;Larchev&que,M. Tetrahedron Lett., 1992,33,4313.
0
f
MedN
1.LHMDS.THF -78°C
Ph
2. 120-C , 6h
+
Me4
Me (92
8)
-8
80%
Tsunoda. T.; Sakai, M.; Sasaki, 0.; Sako, Y.;Hondo, Y.; It& S. Tetrahedron Lett., 1992, 33, 1651.
0 X
OSiMe3
1.
hosiM,e;" H
2. 02, ether
\ /
X = C02Me
Wv.J.H,;
87%
Ateeq, H.S.; Krueger, A.C. Tetrahedron Lett., 1992, 33, 5873.
Q ,CHzC12, -8OOC
%&% Ph
Ph
-
lMgI2 ,24 h
m e v . E.J,; Ishihara, K. Tetrahedron Lett., 1992, 33, 6807.
N
0
O 82%
(9554.7 enantioselectivity) (97:3 endo:exo)
Amide - Alkene
Section 349
H-CI C ~ N H T
395
1. BuLi ,THF 2. 5% Pd(0Ac)z. THF S 10% PPhj 3 . 3 eq. PhI ,60°C
& Ph N
c
is
57%
Luo. F-T,; Wang, R-T. Tetrahedron Dtt., 1992, 33, 6835.
I
0
3. PhN=C=O 4. aq. NaOH
Kataoka, Y.; Oguchi, Y.; Yoshizumi, K.; Miwatashi, S . ; Takai. K,; Ytimoto. K,Bull. Chem. SOC. Jpn., 1992, 65, 1543. Takai. K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K, Chem. Lett., 1991, 1479.
0
10% Pd(0Ac)z , THF 2 q.CuC1~,02,6OoC 24 h
Anderson, P.G.; Backvall. J-E.J. Am. Chem. SOC.,1992, 114, 8696.
9
BrbN .Bu3As PhCHO
0
ph
> N S
25% Pd(PPh3)d 0
30%
Shen. Y.; Zhou, Y. Synth. Commun., 1992, 22, 657. Zheng, J.; Wang, Z.; D e n . Y. Synth. Commun., 1992, 22, 1611 [with Zn, B u ~ P70%]. ,
0
0
f i c ~ oPh3PCH2C3H7 Br
O
N
BuLi , THF
Smith. M.B,; Kwon, T.W. Synth. Commun., 1992, 22, 2865. REVIEWS :
"N-Dienyl h i d e s and Lactams: Preparation and Diels-Alder Reactivity" Smith. M.B, Org. Prep. Proceed. Int., 1990, 22, 315. Also via Alkenyl Acids: Section 322 (Carboxylic Acid -Alkene)
Section 350
Compendium of Organic Synthetic Methods, Vol8
396
SECTION 350: AMINE
- AMINE
Rossi.;Celentano, G.; Stradi, R.; Strada, A, Tetrahedron Lett., 1990, 31, 903. N H ~ PhCHO ,TFA PhH ,reflux
Dean Slark trap
H H Narayanan, K.; Cook. J.M. Telrahedron Lett., 1990,31, 3389.
75%
Uenishi, J.; Tanaka, T.; Wakahavashi. S;,@gJ.,Tetrahedron LRtt., 1990, 31, 4625. 1. LiI
4.Mefl-0
Me
Chamchaang, W.;
I
BnHN
I 3 n h u U . .I. Org. Chem., 1990, 55, 2531. MeNHCH2COzEt
Ph NMe2
Me2N&
c
NaOEt ,EtOH ,20h
reflux Krolikowski, D.A.; Yu, R.H.; Riesinger, S.W.; 1990, 55, 4135.
;-
Ph
.
phh N I Me '
coZEt
87%
J. Org. Chem.,
1. NH3, Pd-C , EtOH , 12 h
NY .
40%
Ph J. Indian Chem. Soc., 1990, 67, 470.
+
NH2
Ph , ) , , NH,
80%
Arnine - Amine
Section 351
1.2 eq. SmI2 ,65"C 2. H2O
Ph7\ N- Ph
397
Ph+ph
b
1. SmI2 ,THF ,reflux 2. MeOH , silica gel
93%
NHPh
Imamoto.:Nishimura, S. Chem. Lett., 1990, 1141. Bn
NHPh
*
69%
F.nholm. E.L; Forbes, D.C.; Holub, D.P. Synfh. Cornrnun., 1990, 20, 981.
Ph
H O T OHPh Oi, R.;
Ph
xso2
>:
Ph_4N-H
N H ~
Ph
DMF, reflux 15 h
Ph
Tetrahedron Lett., 1991, 32, 999.
Me P h , rj
1$H
Ph N 72%
Me
BuLi , ether ____c
Ph
N ~ N - N M ~ , Me
Me
H
60%
eN;;
(>99% de)
Alexakis. A,; Lensen, N.; Mangeney, P. Tetrahedron Lett., 1991, 32, 1171.
a
Me 1. N2O4, ether (28%) 2. H 2 , Pd(OH)2IC
*
Me 97% Zhang, W.; Jacobsen. E.N. Tetrahedron Lett., 1991, 32, 1711.
Me
1. P B u ~PhH , 2. BH3, THF
91%
Takeuchi, H.; Matsushita, Y.;
J. Org. Chem., 1991, 56, 1535.
398
Section 35 I
Compendium of Organic Synthetic Methods, Vo18
fl
@
1. S n , 12 N HCI 2. NaOH ,CH2C12
*
NO2
&Ma; Nakayama, I.; Wilson, R.B.
NH2
82%
Jr. J. Org. Chem., 1992, 57, 778.
1. PhNCO ,PhMe ,reflux
30 rnin
oNa
b N = p p h : PhMe ,reflux, 20 h d N H P h 45% Noeuchi.;Onimura, K.; Isomura, Y.;Kajigaeshi, S. J. Her. Chem., 1991, 28, 885.
oNH2
1. oxalyl chloride ,THF reflux 2.NaBH4,TFA * PhHN25OC Nutaitis. C.F. Synth. Commun., 1992, 22, 1081.
NHPh
13%
REVIEWS:
"The Chemistry of 1,3-Dioximes" Kotali. A.; P w oreiou. V.P, Org. Prep. Proceed. h i . , 1991, 23, 595.
SECTION 351: AMINE
- ESTER
B q S n H , AIBN PhMe .9O0C ,8h
C02Me 92%
(35:65cis:trans)
Esch, P.M.; Hiemstra. &;Speckamp. W.N, Tetrahedron Lett., 1990, 31, 159.
M e O G C02Me b-. C0,Me Skrinjar, M.;
-
BuCu Bs
Bu'"
n rlJC o 2 M e + C02Me (96
Tetrahedron Lett., 1990, 31, 1115.
N
Bu
C0,Me
C0,Me 4)
84%
Amine - Ester
Section 35 1
E~O~C,,,,CO~E~
MeqC02Et
LiMe2Cu ,ether -78°C
N
399
c
+s
8
NHTs 68%
EtO2C
Tanner. D,; Birgersson, C.; Dhaliwal, H.K. Tefrahedron Lett., 1990, 31, 1903.
*
Boc-NHNH2
.
80%
MeCN reflux
ONs
NHNHB~~
ONs = 2-nosyloxy - 2-(((4-nitrobenzene)sulfonyl)oxy) Hoffman. R.V.; Kim, H - 0 . Tetrahedron Left., 1990, 31, 2953. 1. LDA ,THF , -78°C 2. DIOP (-) , -50°C. 4h
SOWY, 0
80% (99% de)
Ph C I - e P d
Ph
Genet, J.P.; Kopola, N.; Juge, S.; Ruiz-Montes, J.; Antunes, O.A.C.; Tanier, S . Tetrahedron Lett., 1990, 31, 3133. 1. methyl acrylate
2. B u S n H
*
Q ' Co2Me
LN \
83%
C02Me 12%
Boivin, J.; Fouquet, E.; &ad. S.Z, Tetrahedron Lett., 1990, 31, 3545.
Ph,C= N-(
C02Me
OAc
NaCH(C02Me)z MeCN ,25'C, 2 h
cat. Pd(PPh3)4 =- P I I , C : N - ~ [ O ' ~ ~
Me02C
CO2Me
ODonnell, M.J,; Yang, X.; Li, M. Tetrahedron Left., 1990, 31, 5135.
MOM0
N
1.3 L D A , THF -78°C
C02t-Bu . .
2. BnBr
MoMQ
-P
CO,t-Bu
Ph
Wdllams.;Benbow, J.W. Tetrahedron Lett., 1990, 31, 5881.
66%
79%
Section 35 1
Compendium of Organic Synthetic Methods, Vo18
400
P(OEt)3 ,PhMe
RT 73%
Luheshi, A-B.N.; Salem, S.M.; U l l e v , R.K. Tetrahedron Lett., 1990, 31, 6561.
A
1. LiBr, D B U , THF
NYCO,Me Me
AN&C02Me 2*
M 6 C02Me
-COzMe
61%
Kanemasa.;Uchida, 0.; Wada, E. J. Org. Chem., 1990, 55,4411,
*
ye
LDA*Bn2NCH2C02Et, THF
C02Me
c
-78°C
f i NBnz
Me02C
threo selective Yamaeuchi.; Torisu, K.;Minami, T. Chem. Lett., 1990, 377.
-
OSiMe3
Phv N-Ph
MeAOMe
,-78°C
5% TrSbCb, CH2CIz 15 min
NHPh
+
*Ph
NHPh phhc02Me
Me
Me 8)
(92
other Lewis acids used, with varying selectivity Mukaiyama, T.; Akamatsu, H.; Han, J.S. Chem. Lett., 1990, 889. Kato, K.; Mukaiyama, T. Chem. Lett., 1990, 1917.
NHC02SiMe,t-Bu
Me02C
c1
2 eq. AgF ,MeCN RT , 2 4 h
M:02C
56%
co2Et
95%
0
0
9 9
H.NK*
(3 Sakaitani, M.; Qhfune. Y. J. Am. Chem. SOC., 1990, 112, 1150.
+
H.
K N O
Me02C
2)
63%
NBn2 hv , co (60 psi), MeOH C02Me c M e 4 87% (CO),Crd NBn2 Me Ileeedus.;Schwindt, M.A.; DeLombaen, S.; Imwinkelried, R. J. Am. Chem. SOC.,1990, 112,2264.
Section 35 1
40I
Amine - Ester
flCo2'
O
Ru-C , AcOOH
t
H
G O A c O H
82%
Murahashi. S; Naota, T.; Kuwahara, T.; Saito, T.; Kumohayashi, H.; Akutagawa, S. J. Am. Chem. SOC., 1990, 112, 7820. Ti(OiPr)4 , TMSN3 CH2C12, RT , 2 h
Me3Si0 tn
OAC 70%
Sutowardoyo, K.I.; Sinou. D, Bull. SOC. Chim. Fr., 1991, 128, 387.
N.OH
10%Co (salen derivative) BuONO , PhSiH3, THF
--
-0Bn 0
+OBn
RT.47h
Kate.; Mukaiyama, T. Bull. Chem. SOC.Jpn., 1991, 64, 2948. Kato, K.; Mukaiyama, T. Chem. Letr., 1990, 1917.
1. BnO2CCH2NHS02Ts1 r-BuOK 2. POC13 , Py
0
Me
La&). T.D.;
=
3. t-BuOK
89%
0
Me
Q,o,,n H
Hoehner, M.C. J. Her. Chem., 1991, 28, 1671.
Mertin, A.; Thiemann, T.; Hanss, I.; &J&j&gA
9
Bn' N,CHO Bn Pe cam. A.E.;
SynLerf, 1991, 87.
1. ( i P r O ) C l 2 T i . 3 OEt 24 h , 0°C
-
2. AcOH , PhMe
35%
*
B n2N Bn (>20: 1
good yield 4R,5S)
Kawaguchi. A.T.; Vofante, R.P.; Shinkai, I. Telrahedron Len., 1991, 32, 1867.
Compendium of Organ;:: :ynthetic Methods, Vo18
402
Section 35 1
EIO~CI(CHO
Nz
PhCN
2% Rh2(0Ac)4 45% 7OoC, 6 h Connell, R.D.; Tebbe. M.; Helaulst. . P ; hermark, B. Tetrahedron Lett., 1991, 32, 17. n-C6H1
THF ,-10°C
- N.SiMe,
3-
t-Buo2Cwn-C6HI
*
+t-Buozcw Y n-C6H1 3
Y
pPLi c1 Of-Bu
H
H
(100
0)
52%
Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett., 1991, 32, 121.
0
Bz
1. 1.1 eq. LDA
"02CEt
NHBz
\
2. THF'ooC7 CH2N2, THFhh
54%
Bz O N o M e
+
M ,e Me
39%
Endo.;Hizatate, S.; Shudo, K. Tetrahedron Lett., 1991, 32, 2803. (CO2F-t
TSFA , PhH ,5"C 7h
NO2 -d.
C@Et
w
HO'
N 4
Ph
70%
TSFA = triflic acid J-M.; Jacquesy, J-C.; Violeau, B. Tetrahedron Lett., 1991, 32, 3075.
,&
1. BrySMe2, NEt3
CH2C12 , -20°C
C02Me + Ph 2. mCPBA , CH2C12 -20°C Ph NHPh 85% 3. MeC07Me, LDA -78°C Palomo. C,; Cossio, F.P.; Rubiales, G.; ApAricio, D. Tetrahedron Lett.. 1991, 32, 3115.
R
wN
C02Me
C02Me
CuCl , DME 2,2-bipyridine
*
(&:2Me b02Me
47% (30:70)
+
5
N C02Me C02Me 12%
Udding, J.H.; J&umaJL ; van Zanden, M.N.A.; SoeckamD. W.NTetrahedron Lett., 1991, 32, 3123.
Amine - Ester
Section 35 1
403
LDA ,EtONO
Moorhoff, C.M.;
CH=NOH CO2Et 46%
THF - pet ether
0
J. Org. Chem., 1991, 56, 703.
Meo2c9CEC-H 1. NaH, THF 2.
Me02C
Ph
3. reflux Tavlor.,Macor, J.E.; French, L.G. J. Org. Chem., 1991, 56, 1807
C02Et
Me2N-
PhCHO ,LDA BEt3, -20°C
-
OH
Ph+CO@l GMe2
+
41%
OH ph&C02Et
NMq <5)
(295
93%
b r e . G.L;Akgiin, E. Tetrahedron Lett., 1991, 32, 5521.
ph&
hna&~&;
BnNH?. EtOH bake; yeast C02Ec
Ph /
P-cyclodextrin,37"C pH 7 . 2 . 4 8 h
C02Et NHBn 70%
(73% ee)
Nageswar. Y.V.D.; Kumar,H.M.S. Tetrahedron Lett., 1991, 32, 6611.
c0,a
Na2SzOa. AgN03 H2SO4, CH2C12 reflux.1.5h 0 E l 0 5 OH 0
C02Et+ 58% 84% conversion
N 27%
Copa, F.; Fontana, F.; Lazzarini, E.; Jvlinisci. F; Pianese, G.; Zhao. L. Tetrahedron Lett., 1992, 33, 3057.
f i NEt2
d
C02Me
,NMp
Ru(COD)(COT) , 7OoC 20 h
Mitsudo.; Zhang, S-W.; Satake, N.; Kondo, T.;
Me Tetrahedron Lett., 1992, 33, 5533.
404
Compendium of Organic Synthetic Methods, Vol8
1. MeLi
Me $0
Bn-‘ *N
Section 35 1
Ph
2. NaBH4 3’ H2S04
B n - N g ;
0
51%
0
(4:l p:a methyl) Fray, A.H.; Mgyers. A.L Tetrahedron Lett., 1992, 33, 3575. Et02Cy
1. NaHMDS , 2. 1N HCI , RT
-
N=CHPh
Br
WH2 0
COZEt
53%
Kotha, S.; Kuki. A, Tetrahedron Lett., 1992, 33, 1565.
(85
15)
72%
hXliiI&; Marion, P. Tetrahedron Letf.,1992, 33, 5339.
Yamamoto.; Asao, N.; Uyehara, T. .I. Am. Chem.Soc., 1992, 114, 5427. REVIEWS :
;J-
”The Asymmetric Michael Addition Reaction Using C h i d Imines” Desmaele. D.; Dumas, F.; Guingant, A. Tetrahedron Asymnlefry, 1992, 3, 227. Related Methods:
Section 315 (Carboxylic Acid - Amide). Section 316 (Carboxylic Acid - Amine). Section 344 (Amide - Ester)
Amine - Ether
Section 352
405
- ETHER, EPOXIDE, THIOETHER
SECTION 352: AMINE
1. MEGiCl , NEt, 2. TBAF
Y NO2 0-
74% (>99: 1 trans:cis)
Dehaen, W.; Hassner. A. Tetrahedron Len., 1990, 1990, 743. PhCHO Au[c-C&I~1-N=C]zBF4
CO,Me
CHgl2
1
Phwco2M
OWN
cat.
OWN
12)
(89 92% ee
cat.=
1% ee
F~ PPhp. Me
Pastor. S.D. ; Togni, A. Tefrahedron Lett., 1990. 31, 839. baker’s yeast
C1
Ph
pH 7.2 buffer
lower selectivity with ethyl cinnamate or 2.4.6-trimethylphenyl nitrile oxide
Rao.;Bhanumathi, N.; Srinivasan, T.N.; Sattur, P.B. Tefruhedron Leff.,1990, 31, 899, 0‘ Na’
” j f H
Me0
\’
+
DMF. l z p -
, -
Br
%H
\ I H
(4
1)
61%
Grip? R.; Markandu, J.; Surendrakumar, S. Tetrahedron Lett., 1990, 31, 1191.
NHMe
Hg(OAc)2, MeOH,RT AcOH
%Me
Maiumdar.;De, R.N.; Saha, S. Tefruhedron Left., 1990, 31, 1207.
80%
406
Section 352
Compendium of Organic Synthetic Methods, Vol 8
n-Bu. N- H n-B;
n-Bu. 0.15M malonic acid MeCN , t-BUSH
~ /OEt z
n-B;
69%
2. 2.6 eq. =\oEt Newcomb, M.; Kumar, M.U. Tetrahedron Lett., 1990, 31, 1675. 1. 1.5 Hg(0Ac)z
MeCN , 25°C R2
2.3. P aq. 2 NaCl LiBH4
THF , - 7 R T
&Dz2 0
0
Me
-I- e
3
Me
,
0
t
R
2 R'
0
R' = OBn; R 2 = H (>50 1) 89% R' = H;R~ = O B ~ ( I >50) 78% Helle, M.A.; Sanyal, B.J.; Eberspacher, T.A. Tetrahedron Lett., 1990, 31,6765. PhCO3H, BnEt3NCI CH2C12 - H 2 0
M e 4 N<
*
85-95%
0
Balachkova, A.I.; Koldobskii, (3.1.; Drozdetskii, A.G.; Tereshchenko, G.F. Zhur. Org. Khim., 1990, 26, 216 (En& p. 185).
3Me
0, Me_
OH
n-BuLi-t-BuLi THF , KT
Me,
Me
(85
15)
Roussi.;Zhang, J. Tetrahedron Lett., 1991, 32, 1443. d
O N
M
e
saPh 0
MewMe
-oo+ oo =d-
80%
&gBr_
THF
79%
Me0
Shibutani, T.; Fujihara, H.; Furukawa. N. Tetrahedron Lett., 2991, 32, 2943.
Amine - Ether
Section 352
@
%Ygl,,Me*
w
0.004 M
407
yNo58%
0
Boner.;Yohannes, D. J. Org. Chem., 1991, 56, 1763.
Ph
H o
MezNCH(0Me)z DMF ,PhH , reflux
{IMe HzNgoH OH
81%
Ph
Amberlite , 1 6 h
c&
Leonard, W.R.; Romine, J.L.; Meyers, A.I. J. Org. Chem., 1991, 56, 1961.
N
.Bu
TiC13(0iPr) , CHzC12 -78°C
\/\//
98%
Newcomb.; Ha, C. Tetrahedron Left., 1991, 32, 6493. J F - B u Me,Si'
OMe
BuLi , THF
*
N
BuCuMgBrbBF3 THF , MDS
OMe
B u d M e NH2
B u g M e NH2
i-
(2
*
98)
46%
1)
54%
(99
Cainelli. G,; Giacomini, D.; Panunzio, M.; Zarantonello, P. Tetrahedron Letf., 1992, 33, 7783. ( W 2 x
>A;o.tone 0
(W2NJ t
05 0
93%
N(iPr)2
Adam.;Peters, E-M.; Peters, K.;von Schnering, H.G.; Voerckel, V. Chem. Ber., 1992, 125, 1263.
REVIEWS:
"Preparation of Diaminoethers and Polyamines" Bradshaw. J& ; Krakowiak, K.E.;Izatt, R.M. Tetrahedron, 1992, 48,4475.
408
Section 353
Compendium of Organic Synthetic Methods, Vol8
SECTION 353: AMINE
- HALIDE, SULFONATE Ph-CTC*
OMe Ph
0 CF3
Me0
NH2
"FA, reflux 2h
Me0
48% Linderman.;Kirollos, K.S. Tetrahedron ,!,ell.. 1990, 31, 2689.
1)
76%
Friesen. R.W, Tetrahedron Lett., 1990, 31, 4249. AcCl , NaI , MeCN reflux, 24 h 55%
Corcoran.;Bang, S.H. Tetrahedron Lett., 1990, 31, 6757.
0
AcOF ,CH2Br2
N
kfi
Hebel, D.; Ibzen.3 J. Org. Chem., 1991, 56, 6298.
0-
1. PhOPh , reflux 2. wc13
MeskCN N
N
Br
60%
c1
C02Me
49%
SMe
H
Tominapa. Y,; Michioka, T.; Moriyama, K.;Hosomi, A. J. Her. Chem., 1990, 27, 1217. MesSiN3 ,CH2C12-MeN02 NBS , -5°C + RT
or3 67%
Olah.;Wang, Q.; Li. X-Y.;
SynLett, 1990,487.
Amine - Ketone
Section 354
t-Bu C1
409
BH3*SMe2, CH2Cl2
H
reflux, 7 h
C1
w; Stevens, C. Tetrahedron, 1991, 47, 3407.
,$
N yN
1. benzyne ,dioxane
reflux, iAmONO
2.aq. KOH
C1 Cl Gonsalves, A.M.d'A.R.; Pinho e Melo, T.M.V.D.; Gilchrist, T.L. Tetrahedron, 2992, 48, 6821.
-
SECTION 354: AMINE
KETONE
____c
3h
Bn NHBn 65% Vatele, J-M.; Dumas, D.; Gore, .I. Tetrahedron Lett., 1990, 31, 2277.
-
OH
NaH , PhH 80°C
88%
Br
Wassenan.;Cook, J.D.; Vu, C.B. Tetrahedron Lett., 1990, 31, 4945. 1. NaN(CHOh, EtOH RT --f 50°C 2. HCI , reflux
Br Ph Yinglin. H.; Hongwen, H. Synthesis, 1990, 615.
*
0
a,
" 2. PhMe , reflux
Ph
0 b
Ph
+q+ P
Ph
12
:
(0.67
q
H'
11
1)
95%
Cordero, F.M.; Brandi. A,; Querci, C.; Goti, A.; DeSarlo, F.: Guarno, A. .I. Org. Cheni., 1990, 55, 1762.
Compendium of Organic Synthetic Methods, Vol8
410
0
iPr
1. LDA ,THF ,0°C
*
2. PhCO2Me , THF 0°C
0
NHiPr 68%
Ph
Bartoli.;Cimarelli. C.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Synthesis,
N i3
N
i3
Kraus. G.A,; Shi, J. J. Org. Chenz., 1990, 55, 5423,
Et2N-
73%
Et2Ny
t-BuOK ,DMSO
0
1990, 895.
Meo2C+pph
-78°C PhLi ,+ THF OoCw
Me02cf&Br
Section 354
52%
Arenz, T.;
Angew. Chetii. Int. Ed. Engl., 1990, 29, 932.
0 Br
0 p
%
0 NEt3
CO2R
nIchihara, ; Y.; Mori, T.; Kamio, C.;
46%
Et02C '
J. Het. Chem., 1990, 27, 263.
Noien. E.G.; Ailocco, A.; Vitarius, J.; McSorely, K. J. Chem. Snc., Chetn. Cotnmun., 2990, 1532.
A
DCA = 9,10-dicyanoanthracene
Jeon, Y.T.; Lee, C-P.; Mariano. P.S. .I. Am. Chem. Soc., 1991, 113, 8847.
Amine - Ketone
Section 354
41 1
3 eq. [3 THF-Mg2C120-TiNCOI 5% Pd(PPh3)4, NMP, 12 h
6
\
100°C
Uozumi, Y .; Mori.;
Me
0
'
* b
H
e 87%
4'
J. Chem. Soc., Chem. Commun., 1991, 81.
BnNH2, AcOH , PhMe reflux
Me
67%
NHBn
Synthesis, 1991, 1 IS.
Otto, A.;
M
%
1. BnNH2, CH2CI2
MeOH
2. NaOMe , MeOH
N Bn
65%
a o u . S-S.E; Yuan, T-M. Synthesis, 1991, 171.
0
Ph
NHiPr
AA
1. LiTMP , THF , 0°C 2.MeI
0 4
Ph
NHiPr Me
86% Bartoll.;Bosco, M.; Cimarelli, C.; Dalpozzo, R.; Palmieri, G. SynLett, 1991, 229.
Baxter, G.; Melville, J.C.; Robins. D.J, SynLea, 1991, 359.
OBBU, P
h
k
+
M%Ny
NM%
0
CHzClz
P h v P h Me
Ph -78'C
33%
(4
0
NMe2 +
NMe2
P h v P h Me
RT 95% (1 Nolen. E.G.; Allocco, A.; Broody, M.; Zuppa, A. Tetruhedron Lett., 1991, 32, 13.
1) 17)
412
Section 354
Compendium of Organic Synthetic Methods, Vol 8
a
Ph-CGCH , CO 5 % PdClz(PPh3)~
I
NH2
Et2NHt 120°C 6h
Ph
H
90%
Toni.;Okumoto, H.; Xu,L.H. Teiruhedron Left., 1992, 32, 237.
JyJ
0
Phl(OzCCF3)2 CF3CH20H RT ,30 min
N
H
b@JJ
o
H o
51%
J(ita. Y.;Tohma, H.; Inagaki. M.; Hatanaka, K.; Kikuchi, K.; Yakura, T. Tefrahedron Leff., 1991, 32, 2035.
1. TNHTos
(CO),CO
OH
BFyOEt2, -7EC CHzClz 85% 2. Me3N-0,Oz CHzC12 , RT , 1 h Jeonc. N.; Yoo. &; Lee, S.J.; Lee, S.H.; Chung. Y.K. Tefruhedron Lett., 1991 32, 2137.
co
Q b
l.PhCH0,
GNH2
conc. HCI 2.10% aq. NaHC03
H\
P
I
h
88%
Yi, L.; Zou, J.; Lei, H.; Lin, X.; Zhang, M. Org. Prep. Proceed. Inf., 1991, 23, 673.
Ph
kc
Ph
e- (graphiteelectrodes) MeOH , PhH ,NaOH (-1.78 V) , 30"C, 8 h*
Ph
hPh 65%
H
Rajanarayanan, A,; levaraman. R, TefruhedronLeft.,1991, 32,3873.
Amine - Ketone
Section 354
413
(98
De Kimne. N,; DHondt, L.; Moens, L. Tetrahedron, 1992, 48, 3183. P h - C S - H , PdCl2(dppf) COEtzNH (20 atin) ,autoclave , 120°C. 1 h
*
2) ‘ 1 2 %
dph 70%
H Kalinin. V.N,; Shostakovsky, M.V.; Ponomaryov, A.B. Tetrahedron Lett., 1992, 33, 373.
4
0si(ipr)3
5 eq, NaN3 5 eq. CAN
-
&N’
72%
Maenus. P.; Barth, L. Terrahedron Lett., 1992, 33, 2789. Bn.
PhMe , R O T , I h
*
BiiHN
UO%
Desmaele, D.; Champion, N. Tetrahedron Lett., 1992, 33, 4447.
Ded’Innocenti.~.; Capperucci, A,; Reginato, G.; Mordini, A; Ricci, A. Tetrahedron Lett., 1992, 33, 1507. 1,
Bu BCI,
.PhMe. 12h
-78°C - RT
2. BnN3 3. MeOH
Noiret, N.; Youssofi, A.; Carboni, B.; 1105.
+
D,”””“ Bu
72%
.I. Chetn. SOC.,Chem. Cotntnun., 1992,
Section 356
Compendium of Organic Synthetic Methods, Vol8
414
REVIEWS :
"Synthesis of a-Amino Aldehydes and a-Amino Ketones" Org. Prep. Proceed. Int., 1990, 22, 399. "Further Advances in the Chemistry of Mannich Bases" Tramontini, M.; Angiolini, L. Tetrahedron, 1990, 46, 1791.
a
- NITRILE
SECTION 355: AMINE
1. hv ,02, DAP+2 (visible light)
2. Me3SiCN , 1 h
H
DAP+2 = N,"-dimethyl-2,7-deazapyrenium bis-tetrafluorohorate 90% Santamaria, J.; Kaddachi, M.T.; Riglaudy, J. Tetrahedron Lett., 1990, 31,4735.
phxN-Ts
2 MeqSiCN ,THF 0.5 Yb(CN)3,65"C Ph 3h
Matsubara, S . ; Kodama, T.; Utirnoto.
SECTION 356: AMINE Ph ph)=
TsHN Tetrahedron Lett., 1990, 31,6379.
- ALKENE
1. Ph3P=CHEl, PhMe
Ny C02t-Bu
ooc
2.2S°C,30 min
0
Nx
Ph ph);
Cost-Bu
85%
O'Donnell, M.J,; Arasappan, A.; Homback, W.J.; Huffman, J.C. Tetrahedron Lett., 1990, 31, 157.
'NHNMez
@ PhjP-
1. I-BuOK, THF 2. ~ - C ~ H I ~ C H O wn-C7H 15
350C.20h
B P yields lower with ketones J=ristau. H.-J,; Gasc, M.-B. Tetruhedron Lett., 2990, 31,341.
-
MQN+ E
N
-
H
N G B ~
Et 85:15
% - N- NMe,
H
80%
1. scc-BuLi 2. BrCHzCH=CH2
Nt-Bu 3.N2H4 or LiAIH,
Beeley, L.J.; B f z M U J X Tetruhedron Lett., 1990, 31,417.
Z:E
39%
Amine - Alkene
Section 356
-0
K 0
(PhCH&NH OOC, 9 0 h
OMe
PPh,
-
415
+
NBu,
3)
(97 84%ee,S
&eH Ph2P
-NBu, 87%
91:9 E:Z
:
N Me
OH
HO*
Havashi. T.; Kishi, K.; Yamamoto, A.;
Tefrahedron Letf., 2990. 31, 1743.
OTf
N(Boc)2
B u ~ N,DMF ,80"C 5% Pd(OAc)*(PPh3)2 5h
36%
Arcadi, A.; Bernocchi, E.; Cacchi, S.; Caglioti, L.; Marinelli, F. Tetrahedron Letf., 1990, 31, 2463.
>
CHo
1. BnNH, 2. NCS
rn
r..~
3. 1.3 I-BuOK ,R r ether, 5h
/
De Kimpe. N.; Yao, Z-P.; Boeykens, M.; Nagy, M. Tetrahedron Len.,1990, 31, 2771. N.Bn - ~ r
J'
Ph
THF
,cat.TiCi4 7
A h
*
P
h
c
83%
Tanaka,H.; Inoue, K.; Pokorski, U.; Taniguichi, M.; Toni. S. Tetrahedron Left., 1990, 31, 3023. ,OBn AlBN,80°C
2. AcOH ,MeOH
&
(Bn0)HN
1. BusSnH, PhH
*
82%
C02Me
Enholm. E.J.; Burroff, J.A.; Jarmillo, L.M. Telrahedron Left., 2990, 31, 3727.
Ding, Z.;
Synfh. Conimun.. 1990, 20, 227.
416
Compendium of Organic Synthetic Methods, Vol8
phq
Section 356
BuLi , THF
NHMe
Ph'($b
-78°C -+ -loo(?
Ph
-/'
85%
LiAIH4 86% Tetrahedron Lett., 1990, 31, 5353.
Tokuda.;Fujita, H.;
\:hP
he
Ph
0
-?
1. C N - H
CN
b
0
2. NaN(TMS)2 3. i K H O
81%
~ L ~ & Merino, & L JI.;.Palacios, ; F. Tetrahedron Left., 1990, 31, 6713.
Tsuda.;Kiyoi, T.; -.I.
Org. Chern., 1990, 55, 3388.
K2C03, H 2 0 , CS2 TEBA , CkIzC12
wph
W " - O H Albanese, D.; Landini, D.;
=C-(
Bn SMe
Synthesis, 1990, 333.
iPrCH=NBn , AIC13 , PhMe
RT
52%
81%
(3: 1 cktrans)
Hayashi, Y.; Shibata, T.; Narasaka, K. Chem. Lett., 1990, 1693.
',""?
PhNHZ*HCI 140°C
60%
Abdrakhmanov, I.B.; Gataullin, R.R.; Mustafin, A.G.; Tolstikov, G.A.; Baikova I.P.; Fatykhov, A.A.; Panasenko, A.A. Zhur. Org. Khim., 1990, 26, 1527 (Engl., p. 1319).
Amine - Alkene
Section 356
Et2N
NHEt2, MeCN
Ets---lfCF3
RT,2h
0
417
74%
0
Hoio. M; Masuda, R.; Okada, E. Chem. Lett., 1990, 2095. 1. TfOH , -78°C
NHPh
2. PhNHEt .21"C
*
3.80°C
72%
4. Me-CS-Me 5.H'
Grossman, R.B.; Davis, W.M.; -..I.
(>95% ee) Am. Chem. SOC., 1991, 113, 2321.
5 eq. n-C3HT-CS-n-C3H7
H
NH2 5% Pd(OAc)*, 5% PPh3 DMF , 2 4 h
Larock.;Yum,E.K. J. Am. Chetn. SOC., 1991, 113, 6689.
\ S , F ~ CSF Ph-
THF.RT.15h .
80%
NHPh
I
Ph-CH=N-Ph
n-C3H7
I
94%
Me
(74:29 erythro:threo)
Kira.;Hino, T.;
Ph'Na
'
Chetn. Lett.. 1991, 277.
Cu , PhMe , reflux 4h
+
Ph
9
)=c
0
Ph
70%
(82:18 E:Z)
Sekiguchi. M.; Ogawa.; Kambe, N.; SQU&L.&
Chetn. Len., 1991, 315.
I . BuLi , iPrlNH, t-BuOK 12 h , -5OOC
Me,Si-
N(SiMe3)2
2, PhCHO, -50°C + RT
Me3Si c-
Me3Si*
Nk Ph
Degl'Innocenti, A,; Mordini. A,; Pinzani, D.; Reginato, G.; Ricci, A. SynLett, 1991, 712.
418
Compendium of Organic Synthetic Methods, Vol8
m
1. LDA ,THF 2. MeCHO , -78°C + RT
Schuster, E.; Hesse, C.;
Me Ph
F3C
32%
SynLett, 1991, 916.
*Br
.ether
>Np'h
Bocoum, A,; Boga, C.; Savoia.;
k
*
3. DCC , cat. CuCl , ether 3h
N
PhA'NX
Section 356
'
H (4357diastereomers)
Tetrahedron Lett., 1991, 32. 1367.
Ne fh dPh ,P m e , ~
2 ~ 0 3
Pd2(dba)yCHC13 6S"C, 26 h
F3C
Unevama.~.; Watanabe, H. Tetrahedron Left.,1991, 32, 1459.
W'uts. P.Q.hL; Jung, Y-W. J. Org. Chern., 1991, 56, 365. Bu$nH, AIBN , ACN PhH ,reflux, 3 h
-Q+
slow addition of tin hydride
A C N = azobis(cyc1ohexane)carbonitrile
65%
Zlegler.; Jeroncic, L.O. J. Org. Chem., 1991, 56, 3479.
TNY L
quant.
0.3 eq.HCI , dioxane 1 0 l ° C , 20 h
Cook, G.R.; Stille. J.R, J. Org. Chetti., 1991, 56. 5578.
N+
95%
Amine - Alkene
Section 356
419
-o$g 0
PhI(02CCF3)2 CF3CH20H RT ,30 min
N
H o
H
o
51%
Kita, Y,; Tohma, H.; Inagaki, M.; Hatanaka, K.; Kikuchi, K.; Yakura, T. Tetruhedron Lett.,
1991, 32, 2035.
n
H-C’C%Me
0 N H LJ
Hg(OAc)z,NEt3 THF , Rr
Kr:;f-
Katritzkv. A.R.; Long, Q-H.; h e , P. Tetrahedron Lett., 1991, 32, 3597.
0
OSiMe2t-Bu CDC13
.t
BU
.SiMel
= N,
56%
AiC13
Tanino, K.; Takahashi, M.; Murayama, K.; Kuwaiima. I. J. Org. Chern. 1991, 57, 7009.
, 40%aq.HCHO
MeCN ,TFA
0 0
Gregoire, P.J.; Meilor.;Merriman, G.D. Tetrahedron Lett., 1991, 32, 7099.
420
CompenJ:um of Organic Synthetic Methods, VOI8
N(SiMe,), H-CE C--/ Corriu. R.J.P,; Bolin, G.; More-
1. Bu$nH, AIBN 2. PhBr ,PhMe 2% Pd(PPhj)q, 72 h
Ph
W NHz 65%
Terrahedron Left.. 1991, 32, 4121.
1. PhNHMe
OH
m
Section 356
2’ Y B r BiClyAI , aq. THF*
-L
NMePh
85%
Kalrilzkv.;Shoban, N.; Harris, P.A. Tefrahedron Lett.. 1991, 32, 4247.
Neumann.;Rogic, M.M.; Dunn, T.J. Terrahedron Lett., 1991, 32, 5865. n
10 eq. HCOOH THF
0
49%
0 Rutjes, F.P.J.T.; Paz, M.M.; Hiernstra. K; Sneckamn. W.N, Tetrahedron Lett., 1991, 32, 6629.
1. xylene/PhMe , -78°C Tic14 2. LiAIH4
71%
Cook, G.R.; Bark, N.S.; .I. Org. Chem., 1992, 57,461. J. Org. Chem., 1992, 57,7188. Barta, N.S.; Cook, G.R.; Landis, M.S.;
\ QNHTs Harris, G.D. Jr.; Herr, R.J.;
5% Pd(OAc)z, DMF P(o-T01)3 ,NazC03
N B u ~ C I75”C, , 22 h
meTS
Me
J. Org. Chem., 1992, 57,2528.
67%
Amine - Alkene
Section 356
1. LDA , THF , -78°C 2. (EtO)2POCI
42 1
85%
fln-CdH9
+
n-C4H9
4. hexanal Hiehet. R.J.; Jones, T.H. J. Org. Cheni., 1992. 57, 4038. Sn[N(iPr)z] , ether
FJN3 ph+CHO
w
Ph-
N(iPr)2 70%
Burnell-Curly, C.; Roskamn. E.J, J. Org. Chem., 1992, 57, 5063.
Meq
Bu3SnH. AIBN THF ,reflux
N - Phth
D
LN
16%
1)
(1
Tefrahedron, 1992, 48, 1317.
Dickinson, J.M.;
TFA , CHzClz
* G0 > S i Me Me3
96%
Me
OoC
Gelas-Mialhe, Y.;Gramain, J-C.; Louvet, A.; Remuson, R. Tefruhedron Left.. 1992. 33, 73.
*
Pd(PPh3)4, K2CO3 , 2 h
~
H
B H
Arcadi, A.; Cacchi. S,; Marinelli, F. Tetrahedron Leff.,1992, 33, 3915.
Me
(c"'c'
NHBn
2 eq. MeCHO ,MeCN 5 eq. B u ~ N I120°C , *
2 eq. MeS03H , 18 h
& ef. N Me Bn
Overman. L.E,; Sarkar, A.K. Tetrahedron Leff.,1992, 33,4103.
71%
82%
u
Section 356
Compendium of Organic Synthetic Methods, Vol 8
422
P
Me0
NHt-Bu
N- t-Bu
heat
* Y
w; De buck, K.; Booten, K . Tetrahedron Lett., 1992, 33, 393. 1 . Pd(PPh3h H ~ N CO (40 psi) 55°C
(-JOT'
HO
2. soc12
t
m,
Mevers. A.L; Rohichaud, A.J.; McKennon, M.J. Tetrahedron Lett., 1992, 33, 1181. 1. TfOSiMe$-Bu ?h , 2OoCc Q Ph
OSiMe,
Ph
+
P
OSiMe-,
better selectivity-lower yield with AlCb
Ph
OSiMe3
(54
28)
86%
e
92%
Nogue, D.; Paugam, R.; Wartski, L. Tetrahedron Lett., 1992, 33, 1265. 1.9-BBN
Me3Si
N @ CHO
Me)=C=
W
3. NaOOH , 1 h
(98:2
M Z:E)
Tetrahedron Lett., 1992, 33, 5025.
Sattsangi, P.D.;
SiMe3 c
Et
hv , DCN , MeCN:H20 10 h
70%
Pandev. G,; Rani, K.S.; Lakshmaiah, G . Tetrahedron Lett.. 1992, 33, 5107. 1. CF3S03H , 0°C
CH2CI2
b
2. NaOH
&won. N!.H.; Schkeryantz, J.M. Tetrahedron Lett., 1992, 33, 5291.
71%
Amine - Alkene
Section 356
<
Davis, J.M.;
1. Cp2ZrCl2 , 2 BuLi , THF , -78OC 2.n-C3H7 CS C- n-C3H7 , THF
PhNC ,20°C 4 6 7 T , 3 h
H
n-C3H7
4. 3.MeOH H20 ; Jaxa-Chamiec, A. Tetrahedron Lett., 1992, 33, 5655.
Ph Ph
423
56%
NHPh
6Br
D
In,THF, 1 h
91%
Ph
Beuchet, P.; Le Marrec, N.; Mosset. P. Tetrahedron Lett., 1992, 33, 5959 1. CpzTiMe2, PhH
PCN
60°C. 5 d
2.Na2S04
quant.
Barluenea.;del Pozo Losada, C.; Olano, B. Tetrahedron Lett., 1992, 33, 7579. Sm,SmI*,THF . 4 h
&N
67°C
Ph
(78162
72%
EIZ)
Opawa.;Takami, N.;Sekiguchi, M.; Ryu, I.; Kambe, N.; mods. N,./. Ant. Chem. Soc., 1992, 114, 8729.
PhNHOH ,dioxane , 100°C MoOl(dipoc)(HMPA), 8 h
II
NHPh
52%
d i p = 2.6-pyridinedicarboxylate Srivastava, A.; Ma, Y . ; Pankayatselvan, R.; Dinges, W.; Nicholas. K.M,.I. Chem. Soc., Chem. Commun.. 1992, 853.
I . TaC15, Zn , DME PhH 2. MeqAI THF
.
4.aq. NaOH
Takai.;Miwatashi, S.; Kataoka, Y.;
H-N.
NMe2
Chem. Lett., 1992, 99.
80%
424
Section 357
Compendium of Organic Synthetic Methods, Vol 8
1. BuLi
2. CpaZrMeCl ,59"C, 6 h
PhHN--(
3. n-C3H7C&n-C3H7 4. MeOH
phH 92%
Coles, N.; Whitbv. R.L; Blagg, J. SynLeft, 1992, 143. 3 eq. (CH201, , MeCN 6 eq. BudNI, 80°C
NHBn CI C-Me
1.3 eq. MeSO$l
&Me 1
+
62% Ovennan. L.E.; Rodriguez-Campos, I.M. SynLeff, 1992,995.
Bn"D 9%
REVIEWS: "Diels-Alder Reactions of Azadienes: Scope and Limitations" Boeer. D.I, Bull. SOC. Chim. Belg.. 1990, 99, 599. "ElectronicallyNeutral 2-Aza-1,3-dienes: Are They Useful Intermediates in Organic Synthesis?" B a r l u e n m l ; Joglar, J.; GonzAlez, F.J.; Fustero, S. SynLerr, 1990, 129. "The aza-Wittig Reaction in Heterocyclic Synthesis" Emchi. S,; Matsushita, Y.; Yamashita, K. Org. Prep. Proceed. lnr., 1992, 24, 209.
SECTION 357: ESTER
- ESTER Pd(OAc)2, NEt3 , MeCN CO , RT ovenlight
Me &LU&&&;
80%
0
Langlois, P.; Okano, T.; Ozbalik, N. Terrahedron Lett., 1990, 31, 325.
u; Jung, K.W.; Kim, Y.S. Tetrahedron Lea., 1990, 31, 1023.
10%
Ester - Ester
Section 357
425
Me
0
H
(1
Bode, H.E.; Sowell, C.G.;
1)
Tetrahedron Lett., 1990, 31, 2525.
>
90%
1. acetyl bromide ,ZnCI2 2. ZflHFIDMSO 3. CuCN , 2 LiCl ,O°C
CHO
4. THF , LiCl , -78°C +Br
Chou, T-S.;
Me
B u a B r , -2.1 V
95% C02Et
J. Org. Chem.. 1990, 55, 4791. 1. deposit on Celite powder
la2-lo4 mbar
57%
Enereaction Choi, S.S-M.; JCirbv. G.W.; Mahajan, M.P.J. Chem. SOC., Chem. Commun., 1990, 138. PhI(OAc)z , HBF, , 6 h
%CN
& OAc 0
+
aq. AcOH
0
83%
Tiecco. M; Testaferri, L.; Tincoli. M,; Bartoli, D. Tetrahedron, 1990, 46, 7139. 1. p-NBSP
-
OSiMe3 2. NaOAc , DMF ,60°C Me/-\OMe
MeYCozMe 33% OAc
p-NBSP = p-((nitrobenzene)sulfonyl)peroxide
Hoffman. R.V.; Stoll, D. Synth. Commun., 1991, 21, 211.
L
A
SPh
C02Me
"base", DMF -78°C
* / F h
*-
C02Me
(>90% de)
Rodriguez, C.M.; Martfn, V.S. Tetrahedron Let?., 1991, 32, 2165.
88%
426
Compendium of Organic Synthetic Methods, Vo18
0.
10%PdC12, cuc12 1 a m . C O , RT, 1 d
OH
Section 357
111
-
propylene oxide, MeOH MeC(OEt)3 , CH2C12
C02Me
55%
Tamaru.;Hojo, M.; Yoshida, Z. J. Org. Chem., 1991, 56, 1099. LiI , DMF
"'C02Et
40 min
61%
3 : 0 2 E t
Kasalkin.; Kulak, A.N.; Tolstikov, G.A.; Shitikova, O.V. Tetrahedron Lett., 1991,32, 4591.
1. SrnI2, THF , O°C 2. A c P DMAP w
aoAc phx 68%
C02Me
Br
Inanaea.;Yokoyama, Y.; Handa, Y.; Yamaguchi, M. Tetrahedron Lett., 1991, 32, 6371. S d 2 - T H F . HMPA MeOH ,RT
C 0 2 M e 70% C02Me
Ph
(1.91 dr)
Inanaga.;Handa, Y.; Tabuchi, T.; Otsubo, K.; Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett., 1991, 32, 6557.
C02n-C,SH2 5 porcine pancreatic lipae
A
H COz1-Bu
28 h
~
r-BuO,CLrC)c 0
o +
37% (49 l e e )
I C02t-B~
Sbi. M.P.; Gaboury, J.A. Tetrahedron Lett., 1992, 33, 5681. e' , PI cathode/Cu anode NaI , 0. I M Et4NC104
77%
DMF
(36:64 tramcis)
Tokuda. M.; Hayashi, A,; Syrinome. H,Bull. Chern. SOC.Jpn., 1991, 64, 2590.
Ester - Ether
Section 358
427
IOeq. -CO2Et , AIBN 0.1 Bu$nCl, t-BuOH
EtO
2 eq. NaBH3CnI reflux
I
0
Stork.;Franklin, P.J.Aust. J. Chem., 1991, 44, 275.
65%
Bi(OAc)3 , I2
6 " O A c -I- 6 , , A c OAc OAc (70
30)
71%
Trainor, R.W.; Deacon, G.B.; Jackson, W.R.; Giunta, N. Aust. J. Chettz., 1992, 45, 1265. Also via Dicarboxylic Acids: Section 312 (Carboxylic Acids - Carhoxylic Acids). Diols Section 323 (Alcohol - Alcohol) Hydroxy-esters Section 327 (Alcohol - Ester).
SECTION 358: ESTER
- ETHER, EPOXIDE, THIOETWER
Yadav. J.S,; Rao, E.S.; Rao, V.S.;Choudm. B.M, Tetrahedron Len., 1990, 31, 2491. 2 iodosobenzene , TMOF conc. H2S04, overnight w
Ph
Ph
TMOF = trimethylorthoformate Sineh. O.V. TetrahedronLett., 1990, 31, 3055.
PhSe+Co2Et CO,Et
=/
n-C6H13
hv (sunlamp), PhH* reflux
XMe
C02Me 82%
Eto2ue
EtO2C
Bvers. J.H.; Lane, G.H. Tetrahedron Lett., 1990, 31, 5697.
95%
n-C6H 13
Compendium of Organic Synthetic Methods, Vol8
428
Ph
2
1. p l y L-leucine ,H202 NaOH , CC14
Baures, P.W.; Eggleston, D.S.; El.&&J&
B
0 0
ph 2. mCPBA , CH2C12
JJ, Tetrahedron Lett., 1990, 31, 6501.
,
o
~
. .OTf
Section 358
Ph
m
OPh
56% (>99%ee) ; Gombatz, K.; Lantos.;Mendelson, W.; Remich.
O Me'''
Me'
0
C0,Me
80%
Witty, D.R.; Feet. G W L , Choi, S.; Vogt, K.; Wilson, F.X.; Wang, Y.; Storer, R.; Myers, P.L.; Wallis, C.J. Tetrahedron Lett., 1990, 31, 6927. 1. HOOCCH2C02Me ,CH2C12 DCC , DMAP ,30°C 2. TsN3, MeCN , NEt3
SPh
3. Rhz(OAc)3 , PhH , reflux
M e h O H
*
MePo 40%
PhS Et0,C
Kido, F.; Kazi, A.B.; Yosh ikoshi. A. Chem. Lett., 1990, 613.
(1%OH
n-C7Hl~Br,MeCN , 100°C KCNO, Bu4NBr
Tomesch, J.C.; Houlihan, W.J. Synthesis, 1990, 477.
; .M-
61%
Jarvis, B.B.; Wells, K.M.; Kaufmann, T. Synthesis, 1990, 1079. 1. = r O H CH2C 12
EtO-
\
COEt
.ms
2. Cr(OAc), , aq. THF
RT
(1:3.9 cis Me:trans Me) Lubbers, T.; Schafer, H.J. SynLelr, 1990, 44.
Section 358
Ester - Ether
MeO-0
K0
429
Rhz(MEPY)d, CH2C12
CHN,
reflux
*
oJ
62%
OMe
(91% ee, S) Dovle. M.P.; Van Oeveren, A.; Westrum, L.J.; Protopopova, M.N.; Clayton, T.W. Jr. .I Am. . Chem. SOC., 1991, 113, 8982.
t-Bu
,t-Bu
BnEt3NCI. CHC13 K2CO3, H 2 0 . 3 h
* j y/ N 0
oxone, pH 1.5
O2N
83%
O2N
Bulachkova, A.I.; Koldobskii, G.I.; Drozdetskii, A.G.; Tereshchenko, G.F. Zhur. Org. Khitn., 1991, 27, 215 (Engl., p. 189). BF30OEt2, -78°C + 0°C
OMe Ph
*
OMe
Me0
0
Ph
40SiMe3 C02Et
CO2Et
86%
Sugimura. H,; Shigekawa, Y.; Uematsu, M. SynLett. 1991, 153. PPTS , EtOAc
H t-Bu cyclohexane t-BuH:To HOJ''Me ' ~ ~ 0 Dean-Starlctrapc H H 80°C
x
Co2H
it-Bu
Me
Chapel, N.; Greiner. A,; Ortholand, J-Y.Terrahedron Lett., 1991, 32, 1441. Greiner. A,; Ortholand, J-Y. Tetrahedron Len., 1990, 31, 2135.
Et
59%
BunSnH ,AIBN , PhH reflux , 6 h
=cT 0
(Jh
Me 3)
(97
CO2Et
CO2Et
(35:65 cis:&ans)
77%
80% E Loikema, L.D.M.; Hiemstra. H, ; Ghouch, A.A.A.; Speckamn. W.N. Tetrahedron Lett., 1991, 32, 1491.
EtO' 0 P-( I'
EtO ;-
.
Section 358
Compendium of Organic Synthetic Methods, Vol 8
430
C02H SMe
12.. 2 eq. T BuLi C H, THF O , -78°C
-
HO
A
68%
3. H30'
.
Midura, W.H. SynLetr, 1991, 245.
SynLett, 1991, 771.
Kornaisu, M.; Suehiro, I.; Horiguchi, Y.;
# 0
b m
1. (TBDMS-OTf/NaMn(CO)5]
2. =/ COzMe 3. hv 4. CSA Rybczynski, P.J. .I. Org. Chetn., 1991, 56, 3207.
Me*Me
BnSH , BuLi THF ,0°C
C02Me
*
0
76%
Me
Me
MeHMe + BnS
BnS
(98
C02Me 2)
98%
Miyata, 0.;Shinada, T.; Ninorniya, I.; Nruto.; Date, T.; Okamura, K.; Inagaki, S.J. Or& Chem., 1991, 56, 6556.
OBn OBn
HO,,+OH
4 eq. Cundidu cylindruceu
OBn OBn A~O+OH
hexanes ,0005 M
OBn
d
OAc
,2S0C,48h
OBn (98% de)
Bureess.K.; Henderson, I. Tetrahedron Lett., 1991, 32, 5701.
CSPh 1. Zn ,AcOH ,60°C 2. NaCl , DMSO/H 150°C
@ h:
COZEt
56%
Kido.;Kawada, Y.; Kato. M.; Yoshikoshi, A. Tetrahedron Lett,, 1991, 32, 6159.
58%
Ester - Ether
Section 358
43 1
OMeOMe
M e O l C02Me
&C02Me
SnCb , BTMSA CHfllz, 20°C, 2 b
-+
Me0
0
BTMSA = MeA N ( S i M q h
Earle, M.J.; Fairhurst, R.A.; &mey&
COzMe 74%
3.9)
(6.1
Tetrahedron Lett., 1991, 32, 6171. 1 . (PhTe)2,NaBH4 EtOH
'COzMe
MsO-
9 OMe
CI
PyS"&O2Me
*
-
()
54%
Barton.;Dalko, P.I.; Gero, S.D. Tetrahedron Lett., 1991, 32, 4713. 0
-4.-
CO,Et
t
Mn(OAch
Mellor. J.M.; Mohammed, S. Tetrahedron Lett., 1991. 32, 7107, 7111.
53%
1. LiNTMSz , THF
-78°C ~ RT Me 2. TMSCI , - 7 8 -+ 3. TMS-OTP
-
Wilson, L.J.;
SPh (3.7:l trans:cis)
J. Org. Chem., 1992, 57, 1948.
0 -/S-Ph
,WAA
-
TFA , -20°C 4RT ,24h
Brichard, M-W.; Janousek, 2.; Mereny, R.; Brichard, M-H.; Musick, H.; Janousek, Z.;
0 F 3 C 2 ' "
Tetrahedron Lett., 1992, 33, 251 1.
w,H.G. Synth. Cornmun., 1990, 20, 2379. C0,Me
1. iPrCu(MgBr2) ,-1 5°C 3h
2 : x : h
H
65%
2. CH2N2 (94% dr)
Heckmann, B.; Mioskowski. C,; Yu, J.; F a l c k . , Tetrahedron Left., 1992, 33, 5201.
432
Compendium of Organic Synthetic Methods, Vo18
N2=CHC02Et, C H s 1 2 cat. RhzfOAck
- G
0 , BocHN BocHN Hlavacek, J.; Kral, V. Coll. Czech. Chern. Cornrnun., 1992, 57, 525.
-
o^..
5% Pd(OAc)z
ACO,, *
2 eq. p-benzoquinone
/
Section 359
c0,Et
&
83%
87%
H
Bgckvall.;Anderson, P.G. J. Am. Chern. SOC.,1992, 114, 6374. TI(OAc)3 , PhH ,reflux
OH
(OAc 0
83%
Mihailovik, M.Lj.; Vukikvik, R.; r
Ann. Chem.. 1992, 305.
SECTION 359: ESTER
-
HALIDE, SULFONATE
reflux hv (sunlamp)
62%
I Bar& F.; 0 - Y a m . C. Tetrahedron Lett., 1990, 31, 1121.
q
Ph
Ph
4
e' , 3F/mol, NEt3
M e 0 &oQ
3HF-MeCN 65% (60%de)
Kabore, L.; Chebli, S.; Faure, R.; Laurent, E.; Marquet, B. Tetrahedron Lett., 1990, 31, 3137.
r3f/
30% CuCl , MeCN llO°C1 16 h
0
0
Pyrex tube (capped)
99%
m s h i m a , H,; Seki. K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J . J. Org. Chem., 1990, 55, 985.
Ester - Halide
Section 359
433
1. BulP=CFC02Et, THF
n-C7HI5-Br
-7 8°C w H-C~HI~CFHCO~E~ 2. aq. NaHCO3 Thenappan, A.; lh&nJLL J. Org. Chem, 1990, 55, 231 1.
0
CF,
ether, reflux
C02Et
2. TBAF ,THF
83%
Shi, G.; Xu. YiJ. Org. Chem., 1990, 55, 3383. Ca(OC1)2, AcOH CH2CI2, H 2 0
>=(c,,t
w
m h e w . L;Alink, B. J. Org. Chea., 1990, 55, 3850.
0 0
OH Me Me
4''
c02et 80%
1. Tf20*NEt(iPr)2 CH2C12 , -78°C 2. PhI(OAc)Z, hv
Kaino, M.; Naruse, Y.; Ishihara, K.; TFA , CuC12
Pb(OAc)4
*o
I Me
J. Org. Cheni., 1990, 55, 5814.
O,CCF,
"'c1
83%
Serguchev, Yu.A.; Gutsulyak, R.B. Zhur. Org. Khim., 1990, 26, 2066 (Engl., p. 1784).
OCO~H
CHC13, iPr2NEt DMSO-TMSBr reflux,l2h
/\1-0 B
r
/-
q 0
55%
Iwata. C,; Tanaka, A.; Mizuno, H.; Miyashita, K. Heterocycles, 1990, 31, 987.
OSiMe,t-Bu
40n-C~H17
60%
CHBr3, BEt3,1.5 h
C02n-CBH 17
Sugimoto, J.; Miura, K.; Oshima. K.; Utimoto. K. Cheni. Left., 1991, 1319.
434
Compendium of Organic Synthetic Methods, Volt?
0
12, aq. THF ,RT c
n-c6H,3+e2
HO
HO
ICFzCOzMe , DMF Cu,6h
Me
I)
cc'
+
-
OH &Me
, , C02Me
.
.
(23:l cktrans)
T. Chem. Lett., 1991, 177.
1. LDA , THF , -78°C 2. THF , -78°C
Ph
&.
y C02Me + F
Ph F
(95
F
Q&&ULE.;
-1v70 ,,,,,
/(0x0
1 Kitagawa, 0.; Sato, T.; -chi.
79%
CF2C02Me
1 . Ti(OiPr)4 , 0°C , 2 h 2. NIS , CH2C12
CO,H
C02Me F 5)
0 2
Riiegg, G.M.; Lang, R.W. Tetrahedron Lett., 1991'32, 1779. 1. LDA , THF, 0°C
Me
)- C02Et
Ph
Resnati, G.; Des m
60%
(5:3 trans:cis) Cheni. Len., 1990, 1011.
'
Kitagawa, 0.;Miura, A.; Kohayashi, Y.;
--I (7
Bpw;tLzE;Li, X . Helerocycles, 1990, 31, 1205.
Ph
Section 359
2. (CF3SO2)2NF -80°C
MexC02Et Ph
a1
u . D.D.J. Org. Chem., 1991, 56, 4925. ICF2C02MeI Cu 55°C
-
F
83%
CF2C02Me
Yang, Z-Y.; l2umJU J. Org. Cheni., 1991, 56,5125. Yang, Z-Y.; J. Chem. Soc., Chem. Commun.. 1992, 233.
78%
40%
435
Ester - Halide
Section 359
q+
TMPAP ,dioxane
Q:,k
RT
0 TMPAP = trimethyl(pheny1)ammonium perbromide
0
52%
Collado, I.G.; Massanet, G.M.; Alonso. M.S. Tetrahedron Lett., 1991, 32, 3217.
fl-
AgN03. Br2 NaOH , MeCN/H@
Br
74%
c
C H
NBS , KHC03 CH2C I f l 2 0
*
CO2H
93%
Dai, W.; J
6
C02Et
Br-
/
60%
Hirao. T,; Fujii, T.; Miyata, S.; Qhshiro. Y,.I. Org. Chern., 1991, 56, 2264.
0
F:%
Ph
1. PhLi ,ether , -78T 2. HgO , I , , PhH w
3. hv , 2 5 T
0
Kobayashi, K.; Sasaki. A,; Kanno, Y.; Sueinome. H . Tetrahedron, 1991, 47, 7245.
\CO2H
1. Br2 , PBr3,120°C, 6 h 2. CH2C12, PhSH , RT 16 h
b.11-J.; Luo, W.Synth. Commun., 1991, 21, 2097. THF 1% BPO ,170,reflux AIBN
Eto*c*FF Me ;-
12 h
0
Br
Eto2c&
c
BPO = benzoyl peroxide Burgess, J.P. Tetrahedron Lett., 1992, 33, 1683.
73%
Compendium of Organic Synthetic Method", Vol8
436
Ti(Ot-Bu)d, 12 CH2CI2,RT
COzMe A
C
0
2
M
e
-
C02Me C02Me
ct,
74%
I
Kitagawa, 0.;Inoue, T.; XagwKL ' Tetrahedron Lett., 1992, 33, 2167.
-
Section 359
Fuchimmi. T.; Hayashi, T.; Konno, A. Tetrahedron Lett., 1992, 33, 3161. Cu(bpy)CI , reflux
O
K
CHC1, PhH (0.1 M) , 18 h
0
G
C
l
92%
E:Z) Pirmng, F.O.H.; Steeman,W.J.M.; JkmuaJL ;;Kaptein, B.; Boesten, W.H.J.; Schoemaker, H.E.; Kamphuis, J. Tetrahedron Lett., 1992, 33, 5141. (70:30
IBr , PhMe , -80°C *
I&
- 1 (21. I Duan, J.J-W.; Sprengeler, P.A.; smith. A.B.
1) 89%
Tetrahedron Leu., 1992, 33, 6439.
% - Go$
1. MezNEt , THF , -78°C
G
C Br
l
2.
HO
c1(85% dr)
Durst, T.; Koh, K, Tetrahedron Lett., 1992, 33, 6799. DMF (1M HCI) , RT oxone, 1 h Kim, J.N.; Kim, H.R.; Pvu. E . S Synth. Comrnun., 1992, 22, 2521.
71%
F
'
h0 q
437
Ester - Ketone
Section 360
C1 P h A P h
BzCI , BuzSnCl~PPh3 7OoC , 15 h
OBz P h A P h
OBz
0 SnCI2, PPh3, BzCl 70T. 11 h
+
(87
80%
13)
99)
(1
t
c1
0
58%
Shibata I,; Yoshimura, N.; Baba, A.; Matsuda, H. Tetrahedron Leti., 1992, 33, 7149. CH2(C02Et)2
TPh OH
C02Me
Me02C
NaH,THF,2S°C 2h
Ph (2
3)
66%
Lawrence, R.M.; I W m W B L Chem. Letf., 1992, 305.
SECTION 360: ESTER
- KETONE "zMe
?Po
Mn(0Ac)s
C U ( O A C ) AcOH ~, 25"C, 3h
61%
H
CO2Me
Method extended to include formation of bridged molecules White.;Somers, T.C.; Yager, K.M. Tetrahedron Lett., 1990, 31, 59.
OMe Me0 2. aq. NaHC03
Me0
C02Me 0 Me Me 60%
Collins. D.L; Dosen, M.; Jhingran, A.G. Tetrahedron Left., 1990, 31, 421.
Ph2S2, AIBN
Ph PhCl , hv (sunlamp)
C0,Me (1
Feldman. K.S.; Vong, A.K.K. Tetrahedron Lett., 1990, 31, 823.
C02Me 1)
46%
438
Section 360
Compendium of Organic Synthetic Methods, Vol8
0
PhI(0H)OTs
CHzCl2 ,reflux* 15h 0 Moriartv. R.M,; Vaid, R.K. Hopkins, T.E.; Vaid, B.K.; Prakash, 0. Tetrahedron Lett., 1990, 31, 201.
Ph
C02H
1.03
74%
,CH2C12 , MeOH -78°C
2. PhH , CH2C12,0°C
A
C
O
SnC12
2
E
63% 0
Holmquist, C.R.; Roskamo. E.L Tetrahedron Lert., 1990, 31, 4991. 1.
PPh3
(
C02r-BU
COZt-Bu
2. oxone, aq. THF RT
86%
Wasserman. H.H,; Vu, C.B. Tetrahedron Lett., 1990, 31, 5205. 1. LDA , THF , -78°C 2. PhzSiClz
$,,
C02Me C02Me
0
4. PhH , reflux , 4 h 5. KH , MeOH
61%overall
intramolecular Diels-Alder using a "disposabletether" Shea. K.J.; Zandi, K.S.; Staab, A.J.; Cam, R. Tetrahedron Lett., 2990, 31, 5885.
72%
CO2H Karim, M.R.; $amn son. P, J. Org. Chem., 1990, 55, 598.
0
t
Ester - Ketone
Section 360
439
HI, AczO, RT
0
0
quant.
Zoeller. J.R.; Ackerman, C.J. J. Org. Chem., 1990, 55, 1354.
Q
1.
Br
2. TMSI , HMDS -20°C -+ RT 3. HC104, aq. THF Eto2C 76% v. T.; Heard, N.E.; Fleming, A. J. Org. Chem., 1990, 55, 2570.
e- (4 F/mol) TMS-CI-DMF
6
76%
CO2Et
W o . T.; Kise, N.; Uematsu, N.; Morimoto, S. J. Org. Chern., 1990, 55, 5037.
0
0
(2
3)
84%
Crandall, J.K,; Rambo, E. J. Org. Chem., 1990, 55, 5929.
EtO2C
0
k
M e O K 0 y 0 ~
CO2Et
Pd(OAc)2, PPh3 , THF reflux , 4 h
Ikeda, I.; Gu, X-P.; Okuhara, T.; -Synthesis,
0 &C02Et
Bu
1. NaOEt ,EtOH 2.03
3. Me2S
Si, Z-X.; Jiao, X-Y.; Hu, B-F Synthesis, 1990, 509.
c
EtO2C
CO2Et
1990, 32.
0 BuAC02Et
48%
84%
440
Section 360
Compendium of Organic Synthetic Methods, Vo18
~
&
1.2 eq.MeLi ,THF , HMPA 2. BnBr ~ ~ ~
*
0
2
t
3.H' Ph/ J I C 0 2 M e 57% 4. CH2N2 Tapia, 1.; Alcazar, V.;Moran. J.R.; Caballero, C.; Grande, M. Chem. Lett., 1990, 697.
Me
Po
Scholz, G.; Konusch, J.; Tochtermann. W, Liebigs Ann. Chem., 1990, 593.
SePh
63%
d C02Me
Bu3SnH, AIBN
C02Me
1990, 112, 4003, 4008. Boger. D.L,; Mathvink, R.J. J. Am. Chem. SOC., B e e r . D.L; Mathvink, R.J. J. Org. Chem., 1992, 57, 1429.
Me 0 Me%J 0
1. LDA ,ether
Ph
2. *e&C02Me,
0
-100°C
* Me+C02Me Me
" )Me CN 4. 3. aq. CuSO4, NH&IH2O Me'
60%
(93% ee , R)
p,,,,8
Enders.;Gerdes, P.; Kipphardt, H. Angew. Chern. Int. Ed. Engl, 1990, 29, 179. 0 ~
&f$H$g
.c
/ C
O
Z
reflux M
~
0
H
+
C02Me
HO
(90
1)
82%
Enholm. E.L; Kinter, K.S. J. Am. Chem. SOC.,1991, 113, 7784.
n-CTH ISCHO Chen, C.; Q&&J,
1. Zn , 'IMF 2. AQO, Py 3. NBS , AgOAc
+
OAc 0
4. t-BuOOH , OsO,, MeOH n-C,H,s epichlorohydrin J. Chem. SOC.,Chem. Commun., 1991, 1289.
C02Me 60%
44 I
Ester - Ketone
Section 360
MeoA
1. PhC02Me , Tic14
Et
CHzCl2 Et 2. MeOH , -78°C 4 0°C * Me02C V 3. NEt3
OMe co2Et
OMe e10 OMe P h i- Me0,C Ph C02Et c0,Et 0%
90%
Shimada, S.; Saigo, K.; Hashimoto, Y.; Maekawa, Y.; Yamashita, T.: Yamamoto, T.; Hasegawa, M. Chem. Lett,, 1991, 1475.
)-CHO
1. (C02Et)z ,NaOMe , 2 h
MeOH , 10°C
2. conc. HCI ,RT , 1 h
Ham. H.; Morishita, T.; Akutsu, S.; Kawamura, M. Synthesis, 1991, 289.
3
Fujimura, T.; Aoki, S.; J%kamura. E. J. Org. Chem., 1991, 56, 2809.
C02a
z:; fi
1. LiN(SiMe3)z
-785
N M 2.~ aq.~HC1
Ph
0
0
CqEt 63%
with NhOAdAcOH at 60°C
McComb ie. S.W,; Metz, W.A.; Nazareno, D.; Shankar, B.B.; Tagat, J. J. Org. Chem., 1991, 56. 4963.
Schinzer.; Kalesse, M. Tetrahedron Lett., 1991, 32, 4691.
Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Scettri, A. Tetrahedron Lett., 1991, 32, 5373.
442
Compendium of Organic Synthetic Methods, Vol 8
PhI(OAc)z, I2 CHzC12 ,hv (Pyrex)
+
w a s . P.; Millan, S.D. Tetrahedron Lett.. 1991, 32, 7493.
Section 360
&
54%
hz:Me3
,TASF ,-78°C
64% TASF = tris(dime~y1amino)sulfonium trimethyl difluorosiliconate Klimko, P.G.; m e t o n . D.A, J. Org. Chem., 1992, 57, 1733.
C02Me
1. TosN3 , A1203 KF , THF , RT
4
2. Rhz(OAc)4, RT
OMe
C02Me 46%
Ceccherelli, P.; Curini. M.; Marcotullio, M.C.; Rosati, 0. Org. Prep. Proceed. Int., 1992, 24, 497.
.
Me
NMO C02(CO)6 CHzC12,5 h
0
m
Krafft.,Romero, R.H.; Scott, I.L. J. Org. Chem., 1992, 57, 5277.
I
Bu3SnH, AIBN PhH , reflux C02Me +
Dowd. P.; Choi, S-C. Tetrahedron, 1992, 48, 4773. Dowd. P,; Choi, S-C. Tetrahedron Lett., 1991. 32, 565.
66%
443
Ester - Ketone
Section 360
2%Rh2(TPA)4
CYC12,O"C. 1.5 h
N2
C02Me
C02Me
C02Me
"PA = triphenyl acetate (96 Hashimoto, S.; Watanabe, N.; i Tetrahedron Lett., 1992, 33, 2709. Hashimoto, S.; Watanabe, N.; mi. S, Tetrahedron Lett., 1990, 31, 5173.
4)
75%
68%
Sartori. G.; Bigi, F.; Tao, X.; Casnati, G.; Canali, G. Tetrahedron Left., 1992, 33, 4771. 1 . pyrrolidine
2. LDA , THF
3. Me1 ,-78OC + RT 4. H30+
Hodgson, A.; Marshall, J.; Hallett, P.; W g h er. T. J. Chem. SOC.,Perkin Trans. I, 1992, 2169. Kh4n04*CuS04*5 H20 cat. H 2 0 , CHzClz, 7 h
47 96
0
6
Baskaran, S.; Islam, I.; Vankar, P.S.; Chandrasekaran. S. J. Chem. SOC., Chem. Commun., 1992, 626.
PhI(OzCCF3)2, MeCN
ooc
COZH
83%
k0 0
McKillop. 4,; McLaren, L.; Taylor, R.J.K.; Watson, R.J.; Lewis, N. SynLett, 1992, 201. Also via Ketoacids Hydroxyketones
Section 320 (Carboxylic Acid - Ketone) Section 330 (Alcohol - Ketone)
444
Compendium of Organic Synthetic Methods, Vol8
SECTION 361: ESTER
Section 362
- NITRILE
iPrOH, CH2C12
CN ~ 0 2 ( ~ ~ ) 8 ~ 1 3 OCN 0 C CN
d
200 bar
*
+
NC-CO~~P~
q c o 2 89% i p r
8%
Sisak.;U n g v w , F.; Markb, L. J. Org. Chem., 1990, 55, 2508.
C02Me
1. BuzCuLi , THF -30°C 2. BuBr
Me
* T
M
e
80%
Calb.;Lopez, L.; Pesce, (3. Gazz. Chim. Iial., 1990, 120, 203. CICH2CNt DMSO
PhCOOH
NazCO3
c
PhKOwCN 0
97% Bvers. J.H.; Baran, R.C.; Craig, M.E.; Jackson, J.T. Org. Prep. Proceed. Int., 1991, 23, 373. CICH2CN, NEt3
PhCOOH 80%
+
+
PhCO2CH2CsN 90%
Na2S ,aq. acetone
Hupel.;Bhaskar, K.V.; Longmore, R.W. Synth. Commun., 1992, 22, 693.
SECTION 362: ESTER
- ALKENE
This section contains syntheses of enol esters and esters of unsaturated acids as well as ester molecules bearing a remote alkenyl unit. 1. 1.2 eq. LDA
2. 2 eq. HgC12
LizPdC14 THF-HMPA
25OC ,4d
Larock. R.C.; Stinn, D.E.; Kuo, M-Y.Tetrahedron Lett., 1990, 31, 17. 1. ACZO
OH 2. KHMDS SnBu3 t-BuMe2SiCi
/d
3. heat Ritter. K, Tetrahedron Lett., 1990, 31, 869.
63%
Ester - Alkene
Section 362
2. TMSCl
445
0 +
C12P
0 50)
(50 '
Pellon, P.; Himdi-Kabbab, S.; Rault, I.; Tonnard, F.; 1147.
*CHO
1. I-BuOK , THF -78°C , 0.5 M
Tetrahedron Lett., 1990, 31,
-OKoEt
2. CIC02Et
83% De Cusati, P.F.; Qlofson. R.A, Tetrahedron Lett., 1990, 31, 1405. CO (600 psi) NEt3, THF-MeCN
-
0
I 7 07
5% 100°C. Pd(PPh3)4 overnight w
%
Shimoyama, I.; Zhang, Y.; Wu,G.; &jgi&i& TetrahedronLett., 1990, 31, 2841.
OTs
p(=
1. Pd(dha)z/dppe THF , RT
CO Me 602Me
2. MeCH(C02Me)2) NaH
82% Stolle, A.; Salaun, J.; Tetrahedron Lett., 1990, 31, 4593. Stolle, A.; Salaun, J.; de Meijere, A. SynLetf, 1991, 321.
NaCo(C0)d. CHglz
€3-cic-€3 2.0"C. EDA, 8 h 3. HCI
* El E$to
Et
17%
Krafft.;Pankowski, J. TetrahedronLett., 1990. 31, 5139. Krafft. M.E,; Pankowski, J. SynLett, 1991, 865. NzC(C02Meh SbBu3, PhH
PhCHo
cat. CuI , 4 h , 7 F C
phYCo2Me
also works with ketones Liao, Y.; h n g . Y-7. TetrahedronLett., 1990. 31, 5897.
C02Me
98%
446
Section 362
Compendium of Organic Synthetic Methods, Vo18
+
1. t-BuOK , -3OoC, 14 h
0
C02Me
2. PhI , Pd(dba)z, 2 h 5% dppe
*
ph&
88% Fournet, G.; Balme, G.; Van Hemelryck, B.; Gore, I. Tetrahedron Lett., 1990, 31, 5147.
-
'7
.
MeOH ,CO RT 3%Pd@"hJ)p, 1 h
n-C6H
n-C,H,
- n-Cd-4
1
v
n-C,H13 C02Me
CO,Me
97%
(1:l E:Z)
Nokami. J,; Maihara, A.; l&jUTetrahedron Lett., 1990, 31, 5629.
-&c02et
,30%EtOH
[co2Et
CO,Et
bakers yeast, 48 h pH 7 . 2 , 37OC
74%
Co2Et
(endo:exo
0 100)
Rama Rao. K,; Srinivasan, T.N.; Bhanumalhi, N. Tetrahedron Lett., 1990, 31, 5959. C02Me MqSi S
C
a
M
e
Ph$+ BFd', MeCN RT.5h MeOzC
\
prepared from alkenes and 2-2-(silylethyl) dienes
Iiosomi.;Masunari, T.; Tominaga, Y.; Yanagi, T.; Hojo, M. Tetrahedron Letf., 1990, 31, 6201.
Me3Si-
csCT
1. iBuMpBr
Me
OH
cat. CpzTiClz
2. coz 3.H30'
c
Ito, T.; Okamoto, S.; &to. F, Tetrahedron Left., 1990, 3I, 6399.
62%
Crale.; Reader, J.C. Tetrahedron Letf.,1990, 31, 6585.
O
G Me 63%
54%
Ester - Alkene
Section 362
447
1. ClCOziBu 2. CH2Nz
.
A
Thijs, L.; Dommerholt, F.J.; Leemhuis, F.M.C.; Zwanenburp B, Tetrahedron Lett., 1990, 31, 6589.
H- C: C- C02Me
MesSnH ,THF
+Co2Me
2% Pd(PPh3)4 SnMe3 71% ~J.c.; Bronk, B.S.; Terrence, K.M.; Phillips, H.K. Tetrahedron Lett., 1990, 31, 6621.
CO2Me
1. LDA 2. Me1 3. mCPBA 4. TFA , CHC13
40%
Cow. R.M; Ritchie, B.M.; Shrier, A.M. Tetrahedron Lett., 1990, 31, 6789. C02Me
Pd(OAc)z, NEt3
Br
Br
MeCN ,100"C
I Tao, W.; Nesbitt, S.; fleck. R.S.J. Org. Chern., 1990. 55, 63.
C1
- j
C02Me CU", DMSO ,25"C
X c1 C02Me
5h
46%
C02Me
C?3t:ie1ci
Me02C
64% conversion
70% E isomer Tezuka. Y,;Hashimoto, A,; Ushizaka, K.;Imai. K. J. Org. Chem, 1990, 55, 329. 1. LiCHBr2 ; BuLi , TIPS-Cl P h e CHO
2.
n-C.jH1ICO2Et
TiC14, CH2C12
=
3. MeOH , -78"C+ RT Kowalski, C.J.; Sakdarat, S. J. Org. Chem., 1990, 55, 1977.
C02Me
n-C5H11'
Y P h 91%
448
Compendium of Organic Synthetic Methods, Vol8
CO$t
Section 362
1. LDA , THF , HMPA
-78°C
2. AcOH ,ether, -98°C
98%
Piers.;Gavai, A.V. J. Org. Chern., 1990, 55, 2374,
s ~ M ~ 0.1 , PdC12(MeCN)2 CH2C12 , RT , 18 h
bAc
c
Panek.;sparks, M.A. J. Org. Chem, 1990, 55, 5564. 1. sec-BSi ,TMEDA ,THF (inverse addition) , -78°C
d
NEt2
2. CuCN.2 LiCI , 0°C
-c
Sengupta, S . ; Sni&u,J
C1
-
J. Org. Chem., 2990, 55, 5680.
q i e
0
SiMe,
OAC 0
\
)L NEt,
Go
&Me
LDA , THF -78°C -+ RT
Me Me
Ph- CI C<
THF (0.05M) , 50°C
c
62%
Me
96%
0
Wender. P.A.; Manly, C.J. J. Am. Chem. Sac., 2990, 112, 8579. 0
71%
+.$
0
Ph
OMe
Brandvold, T.A.; Wulff.;Rheingold, A.L. .I. Atn. Chem. Soc., 1990, 112, 1645. 5% Pd(OAc), , ACOH acetone
cat. benzoquinone
D O A c AcO
85%
(83~17cktrans) Backvall. J-E.; Grandberg, K.L.; Hopkins, R.B. Acfa Chem. Scad., 1990, 44, 492.
73%
Ester - Alkene
Section 362
449
1. NaH 2. 5% PdZ(dba)3*CHC13
OAC 15% DMSO , 5 min
(4
1)
61%
Hanzawa, Y.;Ishizawa, S.; Ito, H.; Kobayashi, Y.; Bguchi. T,.I. Chem. Soc., Chem. Commun., 1990, 394.
+-$ 0
Bu3SnH , AIBN , PhH 5 mM , reflux, 48 h
Bu3Sn
34%
0
Baldwin.;Adlington, R.M.; Mitchell, M.B.; Robertson, J. J.
no lactone was formed
Commun., 1990, 1574.
1 . 0 3 , CHzC12, -78°C >
2. PhP=CHC02Me
Chem. Soc., Chem.
-C02Me 89%
H!m. Y-S.; Lu, L.; Li, S-Y. J. CO2Et
@02Et /
I
B
Chem. Soc., Chem. Commun., 1990, 1627.
u
c02et c02et
A ,DMF
5% Pd)OAc)z. Bu4NCl Na2CO3 , PPh3,60°C Id
Larock.;Fried, C.A. J. Am. Chem. Soc.. 1990, 112, 5882. l-BuSiMe2H. PhH M~
M>
HO
+
G C - H CO , DBU, 100°Cc Rh2(CO)n
0
79%
H
O OHC
L SiMe2t-Bu
6%
Matsuda. 1,; Ogiso, A.; Sato, S. .I. Am. Chem. Soc., 1990, 112, 6120. IrHs(P[iPr13 - PBu3
C: C- C02Me
PhMe ,80"C, 30 h
Ma, D.; Lu,& Tetrahedron, 1990, 46, 3189.
c-
-C02Me 87%
450
Compendium of Organic Synthetic Methods, Vo18
Section 362
( B z O ) ~reflux , (3huanp. C-P.SynLet1, 1990, 527.
Batty, D.; Crich. D, Synthesis, 1990, 273. e- (Pt electrodes) , 2 4 h
'-
/-yo0
Kbpy)(trpy)R~OI+~ pH 8 buffer
42%
trpy = 2,2',6,2"-terpyridine
Camps, J.L.; De Giovani, W.F.;
Synthesis, 1990, 597.
4C02Me
PhSSPh , THF , reflux
dco2Me 81%
(98:2 EZ) Miyata, 0.;Shinada, T.; Ninomiya, I.; paito. T, Synrhesis, 1990. 1123.
0 EtO- PEtO
0
C02Et
0
,LiBr
NEt3 ,25"C
Rathke. M.W,; Bouhlel, E. Synth. Commun., 1990, 20, 869.
-
Br2C(C02Et)2, THF 2 eq. BuzTe, 50°C
PhCHO
~
Ph-
CO2Et
CO2Et
93%
Zhou, Z-L.; Shi. L-L,; Huang. Y-2,Synth. Commun., 1991, 21, 1027.
BCl,
NzCHCOzEt, ether -65OC
Brown.;Salunkhe, A.M. SynLett, 1992, 684.
c
CO2Et
65%
Ester - Alkene
Section 362
cviy
45 1
MeOH ,80°C.
-
CQMe Me02C
Gruseck, U.; Heus&mnn. M, Chem. Ber., 1990, 123, 1911, 1905. 1. MezCuLi , elher, -20°C
Ph- Cr C\
CO2Et
2.2N H2SO.q. 25°C
c
M$ Ph*cyco~~ H
I(tause. N . Chern. Ber., 1990, 123, 2173. 1. 19% HCI , 25"C, 1 d 2. NEt3 , 25°C , 2 d
OH
c1
-*o
C02Me
66% (>96% ee)
Tsuboi. S,; Sakamoto, J.; Sakai, T.; Utaka, M. SynLeir, 1991, 867. 1. Pd(OAc)z, TEBA , K2C03 2. Ag2CO3, PhMe ,80°C 48% Arcadi, A.; Bernocchi, E.; Cacchi.; Marinelli, F. Tetrahedron, 1991. 47, 1525.
H- Cr c
Me02C
d
PhI , t-BuOK , DMSO 5% Pd(dba)z , 14 h Ic C02Me 30°C
Ph 80%
Fournet, G.; Balme, G.; Gore, J. Tetrahedron, 1991, 47, 6293.
4
C02Me
C02Me
20% BuSSBu hv (>300 nm)
4 Me02C Me02C
77%
Singleton. D.A,; Huval, C.C.; Church, K.M.; Priestley, E.S. Tetrahedron Lerr., 1991, 32, 5765.
452
Compendium of Organic Synthetic Methods, Vol8
CqMe
H-C5 C-CO2I3
=/
.AIDN c
Bu3SnH , PhH (0.2 M) reflux, 2 h
Bu3Sn
Section 362
C02Et +
u
62% (3:l Z:E)
31%
Lee.;Hur, C.U. Tetrahedron Left., 1991, 32, 5101.
O0
+
do
C1
Me
Li
COZLi ;
l.2. PhSOgI , Py * 92% 3. MgBn , CH2Cl2 BJack.;McDermott, T.S.; Brown, G.A. Tefrakedron Lett., 1991, 32, 6501.
TfO
66%
Pd(OAc)2, 2 PPh3
CO,Et TIIF, 55°C. 6 h IIounis. I.N, Tetrahedron Leu.,1991, 32, 6675.
,Me+ICI -78°C
(97.5:Z.S)
WS.; Cheng, X-M.; Chnprich, K.A. Tetrahedron Leu., 1991, 32, 6839.
(93 89% endo (2% exo)
Gras.;Pellissier, 11. Tefruhedron Lem, 1991, 32, 7043.
Ilofer, J.; Doucet, H.; Brmieau, C.; Dixneuf, P.H. Te/rahedron Leu., 1991, 32, 7409.
Section 362
453
Ester - Alkene
oo
0
0
EtO. P EtO
a SEt
0 *
NaH , TIIF, 20°C 19 h Liu, H-J.; Rose, P.A.; Sasaki, D.J. Can. J. Chem., 1991, 69, 934.
SEt
87%
NEt3, CO , MeOH
NHBn
RT,3h
c*
H
C02Me
Shaw, R.; Lathburg, D.; Anderson, M.; Gallagher, T. J. Chem. SOC.,Perkin Trans. I, 1991, 659. HCOOH , 120"C, 15 h
Bu-CZ C- H
[Ru(p-cymene)(PPh3)Cl2] *
Neveux, M.; Bruneau, C.; Philippot, K.; Devanne, D.;
BUTocHo 78%
J. Chem. Soc., Perkin Trans. I, 1991, 1197. J. Chem. SOC.,Chem. Commun., 1990, 1199.
1. C12CLiCO2Li 2. PhSOzCI, Py
3. MgBr2, ether
c
71%
B k k . T.R; McDermott, T.S. J. Chem. Soc., Chem. Commun., 1991, 184. Black.;McDermott, T.S. Synth. Commun., 1990, 20, 2959.
Ph 0
\
Fe(C0)4(acetone), PhMe 145"C, sealed tube, 60 h CO (55 psi)
87%
Pearson. A.L; Dubbert, R.A. J. Chem. Soc., Chem. Commun., 1991, 202.
cozMe, Ph- Cr C-Ph
Ru(COD)(COT) , 20 h
Mitsudo.;Zhang, S-W.; Nagao, M.; 598.
Py ,80"C
Ph PhAC02Me 87% J. Chem. Sac., Chem. Commun., 1991,
Compendium of Organic Synthetic Methods, Vol8
454
Me
Section 362
M~
Pd-SnC12 ,80"C DMI-H20 , 7 2 h
(96 Masuvama; Nimura, Y.; Kurusu, Y. Tetrahedron Lett., 1991, 32, 225.
1. AgOTf, CH2Cl2, RT
'Y0
4)
38%
~r
2. DBU , -78°C 63% (84:6:6:4)
Tahir, S.H.; Olrnstead, M.M.; &ut&ML Tetrahedron Let., 1991, 32, 335. BICH~CO~E P ~B,u ~ 25% Pd(PPh3)4 , 2 4 h
PhCHO (86:14
6CO+t
Ph
1 10°C -)
1OO:O E:Z for various aryl aldehydes
Shen.;Zhou, Y.Tetrahedron Lett., 1991, 32, 513.
:,& ''
i M H O , THF
0OEt 2266-telramethyl piperidine * p r i 2 E t +
Me
fi
85%
qi2E 8)
(92 Patois, C.; Savignac, P. Tetrahedron Lett., 1991, 32, 1317. OAc
=/
,NEt3
Pd(OAc)2, PPh3LDMF, 60°C , 7 h
Ciattini, P.G.; Morera, E.;
93%
Alto* I
(3.3:l EZ) Tetrahedron k i t . , 1991, 32, 1579.
79%
Ester - Alkene
Section 362
455
'uco2Me 1. I-BuOK 2. Pd(0) ,dppe
Me02C
1 q. t-B~0K/O"C124h 40 /20°C/9 h 35 0.2 q.t-BuOK/78"C/3 h 0 76 +18-crown-6 fl8"C/18 h Monteiro, N.; Balme, G.; Gore, J. Tetrahedron Lett., 1991, 32, 1645.
Ph/=
c=
C0,Me 43 75 0
45
CH2(C02Et)2, THF vinyl bromide, 65°C CH(CO,Et),
Pd(dbaI2ldppe
Ph
CH(CO,Et),
9)
(9 1
69%
p8%
(35:65 E:Z) Chaptal, N.; Colovray-Goteland,V.;Grandjean. C.; Cazes, B.; Gore, J. Tetrahedron Lett., 1991, 32, 1795.
M e 0M e2 0 C e
62 5% AIMe3, elher
Me02C
Harvey. D.F,; Brown, M.F. Tetrahedron Lett., 1991, 32, 2871.
Ph
OAc
13 k b a , CH2C12 7d
Prapansiri, V.;l&mkm&R
C0,Me
OTHP
(60:40 diastereomers)
*Ph
Tetrahedron Lett., 1991, 32, 3147.
Mkc
,NEt3,KBr 5% Pd(OAc)2,10% PPh3 aq. DMF ,70"C, 2 h n-C6HI 3
=/
Me n-C6H 13- C- CE CJ
76%
-
OC02Me 71% C02Me Mandai. T,; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuii. J. Tetrahedron Lett., 1991, 32, 3397.
456
Compendium of Organic Synthetic Methods, Vol8
Section 362
XSMe Bu3SnH, AIBN PhMe ,80°C
lh
*
58%
4
C5-H a$ (9010) Iwasa, S.;Yamamoto. M,; Kohmoto, S.; Yamada, K. J. Org. Chem., 1991, 56, 2849.
(y*.* SePh
Ph3SnH. AIBN
C0,Et
CO2Et
H
92%
Clive.;Daigneault, S. J. Org. Chem., 1991, 56, 3801.
a
Davies. H.M.L,; Clark, T.J.; Smith,H.D. J. Org. Chem., 1992, 56, 3817.
H-CZC
PhI , CO (300 psi) , PhH Pd(0Ac)z , PPh3 ,NEt3 120OC. 24 h
OMe
Huang, Y.;A1Der.H..Org. Chem., 1991, 56, 4534.
5% PdC12(PhCN)2 AcOH ,RT
OMe
65%
Ph
clX t
0
81%
0
Ma, S.; J,u. X. J. Org. Chem., 1991, 56, 5120. Ma, S.; Lu. X. J. Chem. SOC., Chem. Commun., 1990, 733. BnO-OMe OMe
+
MewoMe 1. TMSOTf ,CHzClz
-78°C. 10 h
PhMqSi
Panek.;Yang, M. J.
C02Me 2. aq. NaHC03
Org. Chem., 1991, 56, 5755.
OMe
OMe
* B n o w C 0 2 M e Me
(30:l syn:anti)
8590
Ester - Alkene
Section 362
457
5)
(95
Takai.;Tezuka, M.;
76%
J. Org. Chem., 1991, S6, 5980.
x
,,,C02Me
C02Me (92% ee)
Devine, P.N.;Oh. T. J. Org. Chetn., 1992, 57, 396.
P h o O T f
+
c
cfC-H
CO2H
Pd(OAc)z( PP h3 )2 NEt3 , BqNC1 MeCN , 60°C 45 min
79%
*
Lqyh
0
0
74%
Arcadi, A.; Burini, A.; (3acchi.; Delmasuo. M.; Marinelli, F.; Pietroni, B.R. .I. Org. Chem., 1992, 57, 976.
75%
Pavies. H.M.L.; Hu, B . J. Org. Chetn.. 1992, 57, 3186. Pd(Pph&~.CO
OTf
*w
N B u 3 , LiCl ,65OC
0
83%
Crisn. G.T,; Meyer, A.G. J. Org. Chem.. 1992, 57, 6972. I.Mg*,THF,RT 2. acetone 3. c02 4. H30'
Mg* = activated Mg
Xiong, H.; Rieke. R.D.J.Org. Chem., 1992, 57, 7007,
68%
458
Compendhm of Organic Synthetic Methods, Vol 8
0
& csc-H
Section 362
Ph$nH, AIBN PhH ,reflux , 7 h 4 mM 63%
MQ-l
Baldwin.;Adlington, R.M.;Ramcharitar, S.H. Tetrahedron, 1992, 48, 3417. BrZnCHzCN , THF
P h Y C N OH
-13°C. 16 h
PhCHO
cat.
h Me
16%
(93% ee , S )
OH
Yang. S-K.; Kim, S-G.; Lee, J-S.TefrahedronAsymmetry, 1992, 3, 1139. =/
80"C
+
-CO,Me
4% N-methylpiperidine Ru(COD)(COT) 30 min also with conjugated amides
h
C0,Me
(90
10)
75%
Meo2cG.
Mitsudo.; Zhang, S-W.; Kondo, T.;
Ni(C0)4, f-BuOH
*
Me02C
Tetrahedron Leu., 1992, 33, 341.
Me02C Me02C
Llebarla.;Camps, F.: Morelb, J.M. Tetrahedron Lett., 1992, 33, 3683.
''Bonete, P.;
Ph- Cr C-H
1 . 2 eq. BuLi 2. iPrCHO
C02H
3. TFAA 4. DBU
Tetrahedron Lett., 1992, 33, 4065.
Pd(PPh3)4, PhH CO (15 atm) , 3 0 h 100°C
+ 0
(95
Itoh, K.;Miura. M,; Nomura, M. Tetrahedron Left., 1992, 33, 5369.
0 4)
Me 88%
Ester - Alkene
Section 362
PhCHO , CF12C12
0
alumina
459
w'"
-
0
93%
Varma.;V m , M. Tetrahedron Lett., 1992, 33, 5937. hv , EtOH ,O°C
Me
Me +
0
0
CqH
0
CO2H
(91
C W
9)
Charlton. J.L; Pham, V.C.; Pete. J-P, Tetrahedron Lett., 1992, 33, 6073. Piva, 0.;Pete. J-P. Terrahedron Lett., 1990, 31, 5157.
(2.3
1)
87%
Friesen. R.W.;Kolaczewska, A.E.; Khazanovich, N. Tetrahedron Lett., 1992, 33,6715.
Me- CE C- C02Bn
cat. Pd(OAc)z, RT
c
AcOH , LiOAc AcO 8.5 h Lu. X.; Zhu, G.; Ma, S. Terrahedron Lett., 1992, 33, 7205.
b
C02Bn 78%
1. LiN(SiMe3)z , DME 2. Cp2Zr(H)CI ,0°C -+ RT c
dcozM61%
Godfrey, A.G.; Ganem. B. Tetrahedron Lett., 1992, 33, 7461. ECHO , BzCl , EbNCl
SnMe3
Bu2SnC12
OB z
Yano, K.; Baba.;Matsuda, 11. Bulf. Chern. SOC.Jpn., 1992, 65, 66. Pd2(dba)3*CHC13
c-
OAc
AcOK , PPh3 , PhMe
77%
reflux OAc Trost.;Brieden, W.; Barringhaus, K.H. Angew. Chern. Int. Ed. Engl., 1992, 31, 1335.
Compendium of Organic Synthetic Methods, Vol8
460
O0 K0
Section 362
0
Bando, T.; Tanaka S.; Fugami, K.; Yoshida, Z.; T a m a r u . Y . u l 1 . Chetn. SOC.Jpn., 1992, 65, 97.
~ C - (H (M~CN)~[E-EIO~CCH=CHCO$~]~C~) H- N H-*cozE COZEt 4 O C - H I/CqE , PhMe , 0°C , 3 0 min Zhou, Z.; Costa.
86%
m, Chiusoli, G.P. .I. Chetn. Soc., Perkin Truns. 1, 1992, 1399. 1407. 1 . BulICuCN(Zn1
(80:20 cis:trans) Sidduri, A.R.; Knochel..I. Am. Chetn. Soc.. 1992, 114, 7579.
O
,TMSOTf,MeOTs
4 y o A
CH2C12, -4SOC
0
66%
0
(98:2 'para:meta') Mashimoto, Y.; Nagashima, T.; Ilasegawa. M.; Saipo. K. Chetn. Letf., 1992, 1353.
TBACN = tetrahutylammonium cerium (IV) nitrate Narasaka, K.; Okauchi, T.; Tanaka, K.; Murakami, M. Chent. Leff.,1992, 2099.
Bu
1.
BuCHO
C02Et
Sn , THF , aq. NH4Cl
2.
n+
0
Zhou, J.; Lu, G.; Wu. S . Synfh. Cornniun., 1992, 22, 481.
s 0
81%
Ether - Ether
Section 363
46 1
Related Methods: Section 60A (Protection of Aldehydes). Section 180A (Protectionof Ketones). Also via Acetylenic Esters: Section 306 (Alkyne - Ester). Alkenyl Acids: Section 322 (Carboxylic Acid - Alkene). P-Hydroxy-esters: Section 327 (Alcohol - Ester).
SECTION 363:
ETHER, EPOXIDE, THIOETHER EPOXIDE, THIOETHER
- ETHER,
See Section 60A (Protection of Aldehydes) and Section 180A (Protection of Ketones) for reactions involving formation of Acetals and Kecals.
acetone, MeCN , RT
0
"near quant." Bujons, J.; Camps, F.; I k k s u a A Tetrahedron Lett., 1990, 31, 5235. PhSeSePh , MeOH (NH&(O$O-OS03)
OH
G S e P h
reflux ,1.5 h
91%
Tiecco.;Testaferri, L.; Tinpoli.;Bartoli, D.; Balducci, R. .I. Org. Chem., 1990, 55, 429.
58% Mudryk, B.; Shook, C.A.; Cohen..l.Am. Chem. SOC., 1990, 112, 6389.
OMe
Ph
4OMe
5% PbBr;?, A1 , TFA
PhJe
THF ,1 h
OMe
Ph
83%
Dhimane, H.; Tanaka, H.; Torii. S. Bull. SOC.Chirn. Fr., 1990, 127, 283.
95% Sasaoka, S.; Uno, M.; Joh, T.; Imazaki, H.; 1991. 86.
'
.I. Chem. SOC.,Chenz. Commun.,
Compendium of Organic Synthetic Methods, Vol 8
462
e-50% , Pt anode, MeOH-THF LiC104
$ye
$,
+
Section 363
4:
Me0
Me0
(5.3
1)
73%
Moeller.; Manabadi, M.R.; New, D.G.; Chiang, M.Y.; Keith, S. .I Am. . Chem. soc., 1990, 112, 6123.
PhSeCi , CH2C12 RT,24h
OSiPh2t-Bu
c
p h ~ ~ ~ h 2 t - 1 3 u
PhSe"'
74%
(1:1.4 a$)
m g .
S.K; Hwang, T.S.; Kim, W.J.; Lim,J.K. Terrahedron Lett., 1991, 32, 4015.
CHO
Me3Si0v SPh
Me3SiSPh, -78°C 5% 'I'MSOTf .0.3 h CH2C12
93%
Kusche, A.; Hoffmann, R.; Munster, I.; Keiner, P.; Bruckner, R. Terrahedron Lett., 1991, 32, 467. 1. (MesSi)$iH, PhMe 2. AlBN , @O°C,1 h
*
-
3
oo-
S-Si(TMS)3 84%
Arva.~.; Lesage, M.; Wayner, D.D.M. Terrahedron Lett.,
-
1991, 32, 2853.
PhSSPh , PhSeSePh , hv
V
45"C, 30 h
S
m; Tanaka, H.; Yokoyama, H.; Obayashi, R.; Yokoyma, K.;
P SePh
h 74% .I. erg.
Chem., 1992, 57, 111.
OH
;-
PhSeSePh ,DCN , hv MeCN
*
P S e P h
Somasekhar, B.B.V. .I. Org. Chem., 1992, 57, 4019.
60%
Ether - Ether
Section 363
MeSeSeMe , SnC14 CH2C12, RT ,0.2 h
/--7
Me
'
MeSe
t
Me
Hermans, B.; Colard, N.;
463
SeMe
Me-Me
82%
Tetrahedron Lett., 1992, 33, 4629.
e- , Hg cathode , Pt anode N E t 3 , EkNCIO4, MeCN
O J o
85%
Br Bhuvaneswari, N.; Venkatachalam. C.S.; Balasuhramanian. K.K, Tetrahedron Lett., 1992, 33, 1499.
\y-J -.
9 I.+'
Bu3SnH. AIBN , PhH 80°C ,45 min -c
0B
0.
0B
Dalla, V.; I3k.P. Tetrahedron Lett., 1992, 33, 7857.
M e OCHC13 o T e f 1 3
* f ! O M e 98%
Comasseto, J.V,; Grazini, M.V.A. Synth. Commun., 1992, 22, 1061.
OMe n-C5H1 I-(
PhSeTMS , cat. TMSOTf CHzC12, -25°C. 15 min
*
OMe
OMe n-C5H,,<
SePh
91%
Sakakibara, M.; Katsumata, K.; Watanabe, Y.; Toru, T.; Ueno. Y, SynLert, 1992, 965.
SECTION 364:
ETHER, EPOXIDE, THIOETHER SULFONATE XeF2(SPh)2 +
-SePh
CH2C12, -20°C
Unevama.; Kanai, M. Tetrahedron Lett., 2990, 31, 3583.
63%
- HALIDE, F
464
Compendium of Organic Synthetic Methods, Vsl 8
Section 364
GhMe, 110°C. 36 h
n-C7H1s'C02Me
OMe
Bunndle..;
2. Et2N-SF3, CH2CI2 55% McKinnis, B.R.; Narayanan, B.A. J. Org. Chern., 2990, 55, 768.
Fuchipaml.; Yamamoto, K.; Nakagawa, Y. .I. Org. Chetti., 2991, 56, 137.
via HOF*MeCN Hung, M.H.; Smart, B.E.; Feiring. A.E.; Rozen. S,.I. Org. Chertt., 2991, 56, 3187. CF3CHzO-Na+ , 1 10°C 10%CuBr , S d
PhOCH2CF3
7wo Rec. Trav. Chitii. Pays-Bas, 1991, 110, 299.
Keegstra, M.A.;
0
0
1. MeS-SMe2 BF4 , C H Q 2 2. NEt? , 3 HF ,0°C 3. aq. NH3
"'SMe
70%
Haufe. G.; Alvernhe, G.; Anker. D.; Iarent, A.; Saluzzo, C. .I. Org. Chern., 2992, 57, 714. Saluzzo, C.; Alvernhe, G.; Anker. D. Terruhedron Lerr., 2990, 31, 663. 0~~
Mn02-TMSCI
OMe
c1
Bellesia, F.; Boni, M.; Ghelfi.; Grandi, R.; Pagnoni, U.M.; Pinetti, A, Teirahedron, 1992,
48, 4519.
6
1 2 . MeCN
-20°C +RT
Or-BU
Marek.; Lefragois, J-M.; -1.
I
J -F. Terrahedron Lerr., 1992, 33, 1741.
94%
Ether - Ketone
Section 365
465
(37:63 cktrans)
U Ju& l;,?.
Gum, L.; Kim, S.W.; Kim,
Y.S.Tetrahedron Lett., 1992, 33, 3969.
SOC12, DMSO , RT -+ 70°C
SMe
,8t
Bellesia, F.; Boni, M.; Ghelfi.;Pagnoni, U.M.; Pinetti, A. Synlh. Cotnmun., 1992, 22, 1101.
SECTION 365: ETHER, EPOXIDE, THIOETHER Me
1.1 eq. HC(OEt)3, -78OC
OSiMe:,
1.2 eq. S n C 4 , 3 0 min
*
- KETONE
tLEt 88%
93:7 cistrans
Marlin, V.A.; Perron, F.; Alhizak K.F, Tetrahedron Lett., 1990, 31, 301.
-
0
4 O E t n - w1I
MeCN 20.C. 2 h
II-CSH1 1
Il-C-jH1 1 (3.1
Iqbal,- .J
n-C5H1 1
28%
1 ) 63%
aph
Tetrahedron kt~., 1990, 31, 1485.
KOPh,NEt3 C acetone
0
75%
OPh Hassner.;Naidorf-Meir, S.; Gottlieh, H.E. Tetrahedron Left.,1990, 31, 2181. +
j
PhSe
SiM% AgBF4, CH2ClzDCE , -5OOC -+ RT -
03
PhSe
Yamazaki. S.; Hama, M.; Yamahe, S. Terrahedron Lett., 1990, 31, 2917.
47%
466
Compendium of Organic Synthetic Methods, Vol8
25% overall
Paterson.;Osborne, S . Tetrahedron Lett., 1990, 31, 2213. MOMO
Me0
0
hv
Section 366
MOMO
OMOM
no yields Kraus. G.A, ; Thomas, P.J.; Schwinden, M.D. Tetrahedron Lett., 1990, 31, 1819.
84%
(70leman.;Grant,
E.B. Tetrahedron Lett. 1990, 31, 3677. e- , Pt anode, LiCIO4 CH2CI2, AQO
Me
1-2 mA/cm2
0 (p:o
Tetrahedron Lett., 1990, 31, 3933.
0:*
OH
.
PhCkCH ,NHEtz PdC12(dppf) 12OoC 20atmCO,2 h autoclave
=
56%
21:))
dph 81%
.. Kallnln.; Shostakovsky, M.V.; Ponomaryav, A.B. Tetrahedron Lett., 1990, 31,4073. PPhs , CC14, THF RT , overnight
78%
Arimoto, H.; Nishiyama, S.;
TefrahedronLett., 1990, 31, 5619.
Section 365
Ether - Ketone
467
3 NIS , 3 Li2CO3 16 MeOH , PhH e
hv (infrared lamp)
35°C
77% McDonald, C.E.; Holcomb, H.; Leathers, T.;Ampadu-Nyarko, F.; Frommer. J. Jr. Tetrahedron Lett., 1990, 31, 6283.
.
Ph-Pb(OAc)3
c o 2 i p r TMG THF , 3 d
OH
Ph
cat. Pd(OAc),, PPh3
0 71% TMG = N,N,N,N-ietramethylgu~idine Barton, D.H.R.; -v. D . U ; Finet, J-P.; Guiry, P.J.;Kielty, J.M. Tetrahedron Lett., 1990, 31, 6631.
ENo2 2 eq. PhSNa
78%
700C'3h
hl~~3-k; Kusama, Y . ; Oda, D. .I. Org. Chem., 1990, 55, 595.
1. MeOCH2CHN2,ether
NEt3
c1 2. Fthz(OAc)d Hudlickv. T,; Olivo, H.F.; Natchus, M.G.; Umpierrez, E.F.; Pandolfi, E.; Volonterio, C. J. Org. Chem., 1990, 55, 4767.
Et-CI C-Bu
PCWP , H202 CHC1-j. reflux
24h PCWP = peroxotungstophosphate* Ishii.;Sakata, Y . J. Org. Chent., 1990, 55, 5545. NaOCl , aq. MeCN , RT
OH
Foucaud. A,; le RouillB, E. Synthesis, 1990, 787.
q7% P
h
0
p C02Me
92%
468
Compendium of Organic Synthetic Methods, Vol8
Section 366
2 .THF
Me0
I.
Li-C3C
Crimmins. M.?'.; O'Mahony, R. .I. Org. Cheni., 1990, 55, 5894.
Ph
L
'Ph
PL = H
Itsuno.;Sakakura, M.; Ito, K. .I. Ph
wc1
Org. Chern., 1990.55, 6047. OSiMe,
. -78OC+ O°C * PhQ 2. NH4CI , H 2 0
1. Ph4CN
0
Ph
3. NE13.3 HF , 3 d 4. KOH ,ether, 15 h Marschner, C. Chem. Ber., 1990, 123, 107.
39%
m:
QPh
Phl(O1I)OTs , MeCN
Ph 75% * 0 0 Prakash.:Pahuja, S.; Goyal, S.; Sawhney, S.N.; Moriarty, R.M. SynLeu, 1990, 337. BFjeOEt? , CHzCI;! -78°C
(&&
82%
0
Kicci, A.; Derl'Innocenti. A,; Capperucci, A.; Faggi, C.; Seconi, G.; Favaretlo. L. SynLelt,
1990, 471.
Soderberg, B.C.: ;-
Sierra, M.A. J. Am. Chem. SOC., 1990, 112, 4364.
Section 365
Ether - Ketone
469
4'-Bu OSiMe3 , 5 % TMSOTf MeCN ,-4OOC. 30 min
OMe
*
92%
OMe 0
(92:8 anti:syn)
&ig~&; Kudo, K.; Hashimoto, Y.; Kimoto, H.; Hasegawa, M. Chetn. Left., 1990, 941.
SnBu3
Bu3SnH. AIBN , hv 0.8 h , 2OoC
* 62%
H . . Nlshlda.; Takahashi, H.; Takeda, H.; Takada, N.; Yonemitsu, 0. J. Atn. Chetn. Soc., 1990, 112, 902.
Co(acac)3, reflux, 150AcOH min
Ph
p+?-4h
c
Ph
0 Ph Me Nishino. H,; Yoshida, T.; Kurosawa K. Bull. Ckem. SOC..Ipn., 1991, 64, 1108. Me
.
10%
.
i TsOH ECHO
Me-OH Hopkins, M.H.; ;Rishton, G.M. .I. Atn. Chetn. Soc.. 1991, 113, 5354. Brown, M.J.; Harrison, T.; Herrinton, P.M.; Hopkins, M.H.; Hutchinson, K.D.; Mishra, P.; -.I. Am. Chetn. Soc., 1991, 113, 5365. OSiMe3
2eq.
PhS-
dph ,MeCN.RT 2 eq. CAN
0 t
ph+
75%
SPh
Narasaka, K.; Okauchi, T. Chetn. Letf., 1991, 515. 1 . BuzBOTf, iPr2NEt
phi
CH2C12, -78°C -+ O°C
2. PhSCl, -78°C
Paterson.;Oshome, S . SynLett, 1991. 145.
0
P h L S P h
"%
470
Section 366
Compendium of Organic Synthetic Methods, Vo18
Adam. W.; Hadjiarapoglou, L.; Smerz, A. Chent. Ber., 1991, 124, 227. 1. Meldrum'sacid&
.
Eid, C.N. Jr.;
8
>W% Tetrahedron Let(., 1991, 32, 461.
VO(OiPr)Cl2, N2 iPrOH-CH2C12 0°C (3 h); RT (5 h)
6
c1 (>98
67%
c2)
Hirao. T.; Mikami, S.; Mori, M.; Dhshiro, Y, Terruhedron Lett., 1991, 32, 1741. PhCH(OMe)2, Py TMSOTf , CH2C12
-78°C
RT
p:e Q0 91%
Kim. S.; Kim, Y.G.; Park,J.H. Tetrahedron Let(., 1991, 32, 2043. O'IUSOTMS
Ad
OMe
TMSOTf
0
C0,Me
Me
56%
MoIander. G.A,; Cameron, K.O. .1. 5rg. Chem., 1991, 56, 2617. ELOH, I-120, RT
SOzPh EtO+
0 also reacts with other nucleophiles
Weichert, A.; Hoffmann. H.M.R,.I. Org. Chem., 1991, 54, 4098.
0
90%
Ether - Ketone
Section 365
d OH
47 1
1 . 3 eq. LDA , TMSCl
TEA 2. TiC14, BnCHO 3. H2S04, AcOH
&ph 78%
also reacts with TiClhetones
Kellv. S.E.; Vanderplas, B.C. .I. Org. Chem., 1991, 56, 1325. PhSeSePh , MeOH (NH4)2S208 , 1.5 h
Me0 OMe
30%
Tiecco.;Testaferri, L.; CO.
Bartoli, D.; Marini, F. J. Org. Chem., 1991, 56, 5207. M.; Testaferri, L.; Tiopoli. K; Bartoli, D. .I. Org. Chem., 1990, 55, 4523.
Pirruae. Mac,; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269.
Pirrune. M.C.; Zhang, J. Tetrahedron Lert., 1992, 33, 5987.
Genicot, C.; Gobeaux, B. Ghosez. L Tetrahedron Lett., 1991, 32, 3821.
0 Bn,N/ Me'
Me
f-BuOOH ,f-BuOK 'MFlNH3
Me& NBn,
Me
+
(95
;-
Lauterbach, E.H. Tetrahedron Lert., 1991, 32,4477.
Singh, O.V.;
Kanil.;Gag, C.P.; Kapoor, R.P. Terrahedron Lett.,
M e e o M e NBn, 5)
65%
1991, 32, 5619.
472
Compendium of Organic Synthetic Methods, Vo18
Section 366
R = Me 8 6 % 0 R = iBu 72% Tetrahedron Lett., 1991, 32, 5465.
B a r , K.J.; Watson, B.T.;
0.1 MeAlC12 , 2 h
Me
-6S"C
-
JPo Me
69%
(31:69 dr)
Rogers, C.; m v . B.G Tetrahedron Lett.. 1991, 32, 6477.
Kobbing, S.; Maitav. J. Tetrahedron Lett., 1992, 33, 927.
="u-
SiMe,
'"G
SnC14
+=( SePh
Me$i
66%
Yamazaki. S.; Fujitsuka, H.; Yamabe, S.; Tamura, H. J. Org. Chem., 1992, 57, 5610. PhCHO , THF ,60T Mey-0 c1
Bu3Sn-N(Et)C02Me +
M e G 0 P h 59% (1387 &:trans)
Yamasaki, H.; Baba, A.; Matsuda, H. .I. Org. Chern., 2992, 57, 6909. Shibaca.; Yamasaki, H.; Baba, A.; Matsuda, H. SynLeit. 1990, 490.
(24
Spero, D.M.;
Tetrahedron Lett., 1992, 33, 1143.
b
o
T
413
Ether - Ketone
Section 365
C
O
,
M
e
0
*&
.
1. MsNj NEt3, MeCN , 2 5 T
2.
a&p.2';.,
C02Me
RhdHCWz
(
54%
Ye, T.; McCann.; Murphy, E.; Doyle, M.P. Tetrahedron
McCarthy, ;N.; . A .MLett., 1992, 33, 5983.
B
OSiMe,
bSPh
CH2C12,O"C , 3 0 rnin N-TS
Ph-
s.y.SPh
75%
Ts
Maonus. P,; Rigollier, P. Tetrahedron Lett., 1992, 33, 61 11.
hv , PhH , reflux
96%
0Chen, C.; Crich. D.; Papadatos, A. J. Am. Chem. SOC., 1992, 114, 8313.
0
0
ph
1. TMSOTf , EtN(iPr)2 CH2C12 2. MgBryOEt2
L
S
P
h 90%
Kosugi. H,; Hoshino, K.; Uda, H. .I. Chem. SOC., Chem. Commun., 1992, 560. TMSOTf , PhMe
PhS (97
3)
62%
Kudo, K.; Saieo. K.; Hashimoto, Y.: Saito. K.; Hasegawa, M. Chem. LRtt., 1992, 1449. 1. PhCHO , SnCl2 2. EtOH
OAc
3.NCS,CHzC12
*
phYY 84% EtO 0
m; Kobayashi, Y.; Yanagi, R.; Kurusu, Y. Chem. Lett., 1992, 2039.
474
Section 366
Compendium of Organic Synthetic Methods, Vo18
SECTION 366: ETHER, EPOXIDE, THIOETHER
Br
- NITRILE
Br
41%
8%
Baldwln.;ONeil, LA. Tetrahedron Left., 1990, 31, 2047.
C
1. Ph3C-CkN-O , PhH 25°C
I
2.12, CH2C12
(1:4 cis:trans)
Kurth.; Rodriguez, M.J.; Olmstead, M.M. J. Org. Chem., 1990, 55, 283. TMS-CN ,CoC12
Ph+OEt OEt
*
CHzC12 Soga, T.; Takenoshita, H.; Yamada, M.; Muk&uuJ 3122.
&cHo
CICHzCN ,aq. NaOH Et3BnNCI ,20°C,
Ph
98%
Bull. Chem. SOC. Jpn., 1990, 63,
6-1.. Me
77%
m n d a m . Y.S, ; Leelavati, P. .I. Id.Chem. Soc., 1990, 67, 253.
c1
n-C9H
i$- SPh
MejSiCN , SnCI4 CH2C12
Fortes.;Okino, E.A. Synth. Commun..
t
68%
1990, 20, 1943.
:-AIEt2 ,ZnC12
OMe
E~~&LH.H.; Yamanaka, T.; Yakuma, K.; Miyazaki, M.; KitaY.. Chem Soc., Chem. Commun., 1991, 533.
Ether - Alkene
Section 367
475
SECTION 367: ETHER, EPOXIDE, THIOETHER
- ALKENE
Enol ethers are found in this section as well as alkenyl ethers.
reflux
0 Geng, L.; !,&ATetrahedron , Lett., 1990, 31, 111.
Me
65%
-x
Bu3SnLi. THF 0°C ,20 min
CI
Ph
Ph
98%
Fujiwara, S.; Katsumura.; Isoe. S . Tetrahedron Lett., 2990, 31, 691.
6
1, M e h S i L i 2.n-BuLi. THF
OSiMezPh
* &Me
3.MeI
Brook reanangement
40%
Koreeda.; Koo, S. Tetrahedron Lett., 1990, 31, 831.
Me02C
0
EtO
NPhth
NPhth
(1
1.3) 91%
230 h
Tietze.;Hartfiel, U. Tetrahedron Lett., 1990, 31, 1697. OSiMe3
SiMe3
TMSOTf
t
OMe
&
75%
Lee. T.V,; Roden, F.S.; Yeoh, H.T-L. Tetrahedron Lett., 1990, 31, 2063.
Ph- ci
'-
B(SeMeb ,RT CH2CI;!,30 mine
Ph
Phy
MeSe)=
61%
i-
MeSe
SeMe 18%
Kataoka, T.; Yoshirnatsu, M.; Shirnizu, H.; Hori. M. Tetrahedron Lett., 1990, 31, 5927.
476
Compendium of Organic Synthetic Methods, Vol8
Section 367
Saiuzzo, C.; Alvemhe, G.; linker. D, Tetrahedron Letf.,1990, 31, 2127.
9
C02Et
es- 103"C,5d
2-
0
+
C0,B
OTBS
50%
1)
(7.3
Block.;Zhao, S.H. Tetrahedron Lett., 1990, 31, 5003.
OTBS
TBS = SiMqf-Bu
Friesen. R.W.; Siurino, C.F. .I. Org. Chem., 1990, 55, 2572.
.r-Bu
Revis.;Hilty, T.K.J. Org.
80%
Chem., 1990, 55, 2972.
5% P ~ ( O A C NaOAc )~, 100°C , PPh3 ,BusNCl
68%
Larock. R.C,; Berrios-PeAa, N.; Narayanan, K. J. Org. Chem, 1990, 55, 3447. n-C7H15
Me<
0
cT'ie
RhCI(PPh3h , MeCN 90°C , 15 min
n-C7HI5
4
also with allenic aldehydes
Marshall.: Robinson, ED. .I. Org. Chem., 1990, 55, 3450.
Me
Me 80%
Ether - Alkene
Section 367
477
* Q
O A ~ CC14, 135°C , 12 h
Me3S i
OAc
Me3S i
94%
Clark, D.L.; Chou, W-N.; White. J,B,.I. Org. Chem., 1990, 55, 3975. Chou, W-N.; White. J.& Tetrahedron Lett., 1991, 32, 157.
00
1. LiHMDS , THF-HMPA
2. PhN(SOEF3)2 3. BuzCuLi
Tsushima, K.: Mural.A. . Chem. Left., 1990, 761.
w;Hashimoto, Y.; Kihara, N.; Hara, K.; Hasegawa, M. Chetti. Lett., 1990, 1097. n
s s
x Ph Me
T d h , CH2CIz. RT
n
Ms
S
t
58%
Me
Ph
Tani. H.; Inamasu, T.; Tamura, R.; Suzuki, H. Chetti. Lett., 1990, 1323.
\/\/\\ SnCI4, CH2C12, .O"C3 h
Me@C
q:
* A Me02C
63%
0 '%b
Sera.;Ohara, M.; Yamada, H.; Egashira, E.; Ueda, N.; Setsune, J. Chetn. Letf., 1990, 2043.
0
TiCb ,Zn
dioxane ,reflux
;
55%
Me
Me
Nagak, S.K. J. Chetn. SOC.,Chetn. Cotnmun., 1990, 150. AIzO3, PhOII
Me02C- Cr C- C02Me
c
PhO
)-7
Me02C
COzMe
91%
Kodoman.; Sakamoto, T.; Yoshitorni, S. .I. Chetti. SOC., Chetti. Comntun., 1990, 701.
47 8
Compendium of Organic Synthetic Methods, Vol8
Section 367
Me I
Arya, P.;Chan. T - a J. Chem. SOC., Chem. Commun., 1990, 967.
0
0
rTe(iBu);, Br
PhCHO
=/
Ph<
-t
KOH(solid) RT78 h THF (trace water)
n 96%
t
Zhou, Z-L.; Sun, Y-S.;
m
a::
Bi. L-L.: H u n g . Y - Z , J . Chem. Soc,, Chem. Commun., 1990, 1439. 2 eq. EtSH , 12 h cyclohexane
0 Me
(70:30 cktrans)
c1
c,
-5"CjRT
Me
75-88%
v . I.G.; Ramazanov, G.A.; Keriomov, F.F.; Abbasov, I.M.; Zefirov. N.S. Zhur. Org. Khim., 1990, 26, 1638 (Engl., p. 1416). 2,6-di-f-butylpyridine 2 eq. SnC14, -10°C
L O
300 min 13%
25%
Blumenkopf, T.A.; Bratz, M.; Casmeda, A.; Look, G.C.; Overman.;Rodriguez, D.; Thompson, A S . J. Am. Chem. SOC.,1990, 112, 4386. Cp2TiMe2 , PhMe ,65"C
*
eph
a
41%
Petasis. N.A,; Bzowej, E.I. J. Am. Chem. SOC., 1990, 112, 6392. 1. (Se), ,90°C
2 Ph,P=CHPh 2.
H
* Ph
34%
Okuma.;Komiya, Y.; Kaneko, I. ; Tachibana, Y.; Iwata, E.; Ohta, 11. Bull. Chem. SOC. Jpn., 1990, 63, 1653.
Ether - Alkene
Section 367
MeS
1
0
Ph
Bu3SnH. BEt,
- \ = \ SPh
Ph%
SPh SPh Nozaki, K.; Oshima.,
479
70%
(92:8 E:Z)
Bull. Chem. SOC. Jpn., 1990, 63, 2578.
Mesu
1. BuLi , HMPA 2. Me1
*
SiMe,
70%
(66:34 E:Z)
Miura, K.; Qshima. K.; Utimoto. K*Eull. Chem. SOC.Jpn., 1990, 63, 2584. Na ,CISiMe3 ,THF ,0°C 105 min .)))))>)
Fadel, A,; Canet, J-L.; Blaiin.
0~~
t
J.SynLert, 1990, 89.
00SiMe3 83% OSiMe,
ui
1. PPhJ , TMSOTf ,THF , -3OOC 2. BuLi ,THF ,-78OC Ph
d o M e 4.3.BnBr KOH ,MeOH Kim.; Kim, Y.C. SynLett, 1990, 115. 1. BuLi 2. BuI , THF ,HMF’T 3. r-BuOK. THF. refluxC
t-Buo-
71%
Or-Bu 67% (21:79 E:Z)
Julia.;Uguen, D.; Verpeaux, J-N.; Zhang, Ph0zSbS02Ph
D. S y n k f t , 1991, 505.
1. LDA ; Me1 2, BLSiMe,
*
Et2AlCIz , C H E 5
Me
38%
SimDkins. N.S. Tetrahedron, 1991, 47, 323.
0 Me Jj&&J,;
n-GH11
‘OZMe
Co(OAc)l, 0 2
Bhatia, B.; Nayyar, N.K. Tetrahedron. 1991, 47,6457.
58%
Compendium of Organic Synthetic Methods, Vol8
480
BuzSn(OT92, DCE BuzSn(SPh)z, 35°C
-OMe OMe
Section 367
/
PhSL s p h
12h
71%
(72:28 E:Z) Sam, T.; Otera.; Nozaki,H. SynLert, 1991, 903.
1. PhCHO , PhSH , TsOH 2. BuLi
Ph
-
3. MeCH2X SPh H 4. BF3 Afridi, AS.; Kuzmierkiewicz, W. Helv. C h k . Acta, 1991, 74, 1931.
;-
1 . EtCu(CN)ZnEt-2 LiCl 0°C , 1 h 2.
Bu- C5 C- SMe
Bu
Br
6
e:M OMe
OMe e- (RVC anode)
LiClO4, CI12C12
20%CD30D
92%
SMe
J. Am, Cheni. Soc.. 1991, 113, 5735.
Rao, S.A.;
92%
*
SiMe,
-I60%
10%
OMe
Ifudson, C.M.; Marzabadi, M.R.; Moeller. KD-;New, D.G. 1. Am. Chem. Soc., 1991, 113, 7372.
*s-~ Pi01
0 V M c ~ B ~ -78°C -+ RT
\
+
85%
u; Maezaki, N.; Kurumada, T.; Fukuyama, 11.; Sugiyama, K.; Imanishi, T. J. Cheni. W O
SOC.,Chem. Commun., 1991, 1408.
Me&
-ue3 10%Et3A1, CHzClz 15"C, 20 h
Fujiwara, T.; Suda, A.;
Cheni. Lett.. 1992, 1619.
82%
Ether - Alkene
Section 367
F:::
C S 2 , 2 eq. Me1 ,MeCN KF , A1203 , RT
58%
Villemin. D,; Ben Alloum, A. Synthesis, 1991, 301.
Tmst.B M ; Tometzki, G.B. Synthesis,
48 1
1991, 1235.
*
SnBu3 7 CH2C12
t
t-B uMe2SiOTf
82%
Kim., Lee, J.M. Synth.
Cornntun., 1991, 21, 25.
Me0
MeOv
1. MejSi-Jl,,SPh Tic14
)7-Br2. (Bu3Sn)z. Phli hv , 10°C
Me0
33%
95%for step 1; 35% for step 2
Ward.; Kaller, B.F. Tetrahedron Lett., 1991. 32, 843.
OMe
, -30°C
CH2C12,48 h Me02C-CHO
c
“‘CO ,Me (78
(94%ee)
Terada, M.; Mlkami.; N&iJ.
Tetmhedron Lett., 1991. 32, 935.
(9
Koerber, K.; Gore, J.; Vatele, J-M. Tetrahedron Lett., 1991, 32, 1187.
22) 77% (990% ee)
91)
72%
482
Compendium of Organic Synthetic Methods, Vol8
AIiquat 366,O"C do]2%THF, t-BuOK ,2h
Br
0
Bailey, W.J.; Zhou. L-I,Tetrahedron Lett., 1991, 32, 1539.
]I+
68%
PhSCl
Me
-
SiMe3
Ph
Section 367
P
h b SPh 72%
(90% de) Nativi, C.; Palio, G.; Taddei. M, Tetrahedron Lett., 1991, 32, 1583.
iM;
DMUPhH ,Zncl2
microwavcs (600 w)
CH(OMe),
Me
~
5min
Me
"CH(OMe),
with no microwaves. at 140°C, 0%yield
CH(OMe),
Me
82%
Stambouli, A.; Chasuette, M.; Soufiaoui, M. Tetrahedron Lett., 1991, 32, 1723.
NaH ,THF
*
Me0
SiMe, 95%
Pegram, J.J.; Anderson, C.B. Tetrahedron Lett., 1991, 32, 2197.
du
0.2 eq. AgNO3 ,H20 CaCO3 , acetone, RT c
Me '
Me
0
COzMe 95%
0"'"
Marshall.: Wang, X . J. Org. Chem., 1991, 56, 960. Li2CO3 ,acetone-AcOH
2 eqp-benzoquinone 5% Pd(OAc)z, 20°C
c
Aco"'
Backvall. J-E,; Anderson, P.G. J. 5rg. Chem., 1991, 56, 2274.
(>98%Irans)
86%
Ether - Alkene
Section 367
AgOS02To1, MeCN PhSeCl , RT
Ph- CZ C-Me
-
483
To102so>-<”” Ph SePh
75%
Back.;Muralidharan, K.R. J. Org. Chem, 1991, 56, 2781.
Back.:Muralidharan, K.R. Tetrahedron Lett., 1990, 31, 1957.
PhCHO
1. IZn(CN)Cu(CH2)-ZnI THF , -60°C -+ -25°C
2. I2 , -70°C + RT
c
59%
Ph
Hudlickv. T,; Barbieri, G. J. Org. Chem., 1991, 56, 4598. 1. MeLi 2. PhMezSiCl
OSiMe3
L O S i M e 2 P h
93% Duhamel. L,; Guillemont, J.; Poirier, J-M.; Chabardes, P. Tetrahedron Lett., 1991, 32, 4495, 4499. 1. SnC14
2. Ph-OMe , MS 4A
SnBu3 OMe
Takeda.,Kanamori, F.; Masuda, M.; Fujiwara, T. Tetrahedron Lett., 1991, 32,5567. Takeda.:Kanamori, F.; Matsusita, H.; Fujiwara, T. Tetrahedron Lett., 1991, 32, 6563 [with NBS; AIC131.
r-Bu02C- C: C. C02r-Bu
Me
OH
K2CO3 , acetone, 80°C 20 h
c
MenC02t-B~ OH Me”
0
C02t-Bu 88%
Jauch. J,; Schurig, V. Tetrahedron Lett., 1991, 32, 4687.
PhS- Cr C-Me
Pd(PPh&, PhH Bu3SnH
Mapriotis. P.A,; Brown, J.T.; Scott, M.E. Tetrahedron Lett., 1991, 32, 5041.
484
Compendium of Organic Synthetic Methods, Vo18
Section 367
1 . 2 eq. 1-BuLi , ether 2. allylmagnesium bromide 3. ZnBq 4. aq. HCI
Ot-Bu 81%
(955 dr) Marek. L;Lefrancois, J-M.; F Tetrahedron Lett., 1991. 32, 5969. Marek, I.; Normant, J.F. Terrahedron Lett.. 1991, 32, 5973. Marek.; Alexakis, A.; Normant. J-F, Tetrahedron Lett., 1991, 32, 6337. (95%yield)
H- Ci C-(
OEt
OEt
1. BusSnCu(Bu)CNLiz THF , -78'C, 2 h *
2.H20
Bu3sn-roEt OEt
Beaudet, I.; Parrain, J-L.; Quintard. J -P, Tetrahedron Lett., 1991, 32, 6333.
(92
\
c1
/
96%
RT Telrah.edronLett., 1991, 32, 6633.
Balasubramanian, T.;
p h y c l
p-TsOH,PhH
8)
1. (Bu3Sn)zSe 2. TBAF.3 H 2 0 , THF
3.
4
Q
Ph
7990
(5941 endo:exo)
SePi.;Kato, M.; Nakajima, T.Tetrahedron Lett., 1991, 32, 7427. Ph- Cr C-H
PhSeSePh , neat hv (sunlighVpyrex)
c
PhSe PhhSePh
83%
(82:18 E:Z) Ocawa. A; Yokoyama, H.; Yokoyama, K.; Masawaki, T.; Kambe, N.; Sonoda. N, .I. Org. Chem., 1991, 56, 5721. Qgawa. A,; Obayashi, R.; Sekiguchi, M.; Masawaki, T.; Kambe, N.; Sonoda. N, Terrahedron Lett., 1992, 33, 1329.
Ether - Alkene
Section 367
Ph2CHCI
Ph
S 8 , DBU , MeCN
25°C
+
485
60%
Abelman. M.M. Tetrahedron Lett., 1991, 32, 7390, n-C6H I
gz C>
5% PdCIz(MeCN)2
Me MeCN-H2O , 2 h
flMe
4
0
n-C6Hl3 0 76% Fukuda, Y.; Shiragami, H.; Utimoto. K,; Nozaki, H. J . Org. Cherrz.. 1991, 56, 5816. Kataoka, Y.; Tezuka, M.; Takai. K,; 1Jtimoto. K, Tetrahedron, 1992, 48, 3495.
Phqo OMe
reflux
Cp2TiBn2, PhMe 55°C
Ph b
Ph
Me0
84% (1436 E:Z)
N . G ; Bzowej, E.I. .I. Org. Chein., 1992, 57, 1327. n-CrjH,,CHO, CCb
Me3Si0
-
83%
cat. TMS-OTf, PrOTMS
20oc 0 ?l-C6H13 M a k L J J L Mekhalfia, A.; Bayston, D.J.; Adams, H. J. Org. Chern., 1992, 57, 221 1 .
Mekhalfia, A.; Markb, I.E.; Adams, H. Tetrahedron Lett., 1991, 32, 4783.
UH
2
(1
8)
72%
Luo. F-T,; Schreuder, 1.; Wang, R-T. .I. Org. Chem., 1992, 57, 2213.
Ph
>cs CJ
Bu
PhI ,CO , PhH-NEt3 PdCI2(PPh,),
Ph
Ph
0
0
Bu
65%
Okuro, K.; Furuune, M.; Miura. M,; Nomura, M. J. Org. Chem., 1992, 57, 4754.
Br
NaOMe , 10%CuBr 85°C. NMP , 1 h
m.M.A. Tetrahedron. 1992, 48, 2681.
70%
486
Compendium of Organic Synthetic Methods, Vol8
d
o
o
o+
Section 367
Ti-graphite ,THF reflux, 8 h
88%
Ph
Furstner.;Jumbam, D.N. Tetrahedron, 1992,48, 5991. Furstner.
; Jumbam, D.N.; Weidmann, H. Tetrahedron Letf., 1991, 32,6695.
Mc
I-BuOK
Br
Aben, R.W.M.; Scheeren. J.W. Rec. Trav. Chim. Pays-Bas, 1992, 109, 399.
Fe(acac)3/2,2'- bipy A1Et-j 3.
OSiMeat-Bu
Takacs.;Myoung, Y.C. Tetrahedron Letf., 1992, 33, 317.
JSnBu3
Ph- , 0
AcCl, CH2Cl2
c
7
(E + Z)
PhS
"goodyield"
OSiMe,t-Bu
JL OAc
50%
Beddoes, R.L.; MacLeod, D.; Moorcroft, D.; (hale. P,; Zhao, Y. Tetrahedron Lert.. 1992, 33,
417.
alan. A.S,; Prieto, R.; Mueller, B.; Peters, D. Tetrahedron Lett., 1992, 33, 1679.
y)@
Me0
1. Co(1) salophen , THF 2. hv (sunlamp) F
Me0
&s88(
Me
Ali, A.; Ilarrowvcn, D.C.; Pattenden. G, Tetrahedron Lett., 1992, 33, 2851.
Me
43%
Ether - Alkene
Section 367
n-C5HI,-CI C-0 "
Q
487
-.,,,Q
n - w ,i
LiAIH4, THF
Ph Ph Sob, L.; Castro, J.; Movano.;I?&&J ;U Riera. A. Tetrahedron Lett., 1992, 33, 2863.
Br ,
" . k qOAc
y)
Br
K2CO3, MeOH 10 min
*
0
99%
0
Grandjean, D.; pale. P.; Chuche, J. Tetrahedron Letr., 1992, 33, 4905. BuLi , THF
Jin, F.; Jiang, B.; XILY.Tetrahedron Left., 1992, 33, 1221.
OSi(iPr),
95%
Bn
OH SMe
n-C&II3CHO
OSi(iPr),
1.2 eq. MezAICI
94%
"a oooPh
(85: 15 threo:erythro , 83% ee) Tanino, K.; Shoda, H.; Nakamura, T.; JCuwaiima. I , Tetruhedron Lett., 1992, 33, 1337.
0 0
'
Pd(OAc)Z, (R)-BINAP PhH , PhOTf , 9 d
c
0
l!&ph
quant.
(71
29)
(>96%ee)
(17% ee)
Ozawa. F: Kubo, A.; Havashi. T, Tetrahedron Lett., 1992, 33, 1485.
9
EtO-P~ ~ 0 CH3'
1 . 3 eq. LDA ,THF , -78OC 2 . 2 eq. PhSeBr ,60°C
c
3.PhCH0,RT
Ph
*
Shin, W.S.; Lee, K.; Oh. D.Y.Tetrahedron Lett., 1992, 33, 5375.
-
BuCH(0Me)Z. CHF12 TMSOTf, -78°C
SePh SePh
97%
Ma
SiMe3 Bu Hojo, M.;Ohsumi, K.;Hosomi. A, Tefruhedron Lett., 1992, 33, 5981.
85%
Compendium of Organic Synthetic Methods, Volt?
488
1. PhSeBr , THF , -78°C
2.H30’
Et
SePh
Et Tetrahedron Lett., 1992. 33, 5097.
Chung, H.S.;
,EtOH NEt9CaC12
Section 367
71%
Et
so+ 65%
pjnto. I.Lk;Buckle, D.R.; Rami, H.K.; Smich, D.G. Tetrahedron Len., 1992, 33, 7597. 1. BuLi ,THF ,-78°C. 1-BuOK ; BuLi
2 . M e e C H 0
Wang, W-B.; floskam-
*
TBSO
0
TBSO
3. S i 0 2 M 2 0 , microwaves 5 min 4. TBSCl , imidazole , DMF
(1
75%
1)
Tetrahedron Lett., 1992, 33, 7631. > I 80°C
(3
quant.
1)
Detert, H.; Anthony-Mayer, C.;W A n g e w . Chem. Inf. Ed. Engl., 1992, 31, 791.
9
Ph’S&
i . NaOMe ,MeOH +
0 /Jcco,E3
2. CI3CC02H1A y O PhMe ,reflux 3. mCPBA ,CH~CIZ
c
QMe CO2Et
38%
Chan. W.H.; Lee. A.W.M.; Chan, E.T.T. $1. Chem. Soc., Perkin Trans 1, 1992, 945.
n-C,H,$CZ C
t-BuOK , t-BuOH 18-cro~n-6
t
MOM0
Marshall.; BuBay, W.J. J. Am. Chem. Soc.,
70% 1992, 114, 1450.
Ether - Alkene
Section 367
OHC
-
Ph 4ph
489
,Znlz, PhH
RT, 48 h
C
1
W
P
h
87% Ph CI Dvorak, D.; David, S.; Arnold, Z.; Ivana, C.; Petricek, V. Coll. Czech. Cheni. Commun.. 1992, 57. 2331.
(iPr),Si
Ri. iPr
1 . F-
'0
pri. .iPr
0
Bu o O M e
2. *siMe,C T ~ O H B(OTO)~ ~+ -5OC ,30min
Bu 1)
(23
85%
s. A.P.; Hegarty, S.C. .I. Am. Chem. SOC., 1992, 114, 2145.
HO
-3-
C=C-H
$
PhSH , Pd(0Ac)z THF ,67"C, 16 h
SPh
86%
Kuniyasu, H.; OPawa. A.; Sato, K-I.; Ryu, I.; Kambe, N.; Sonoda. N..I. Am. Chem. Soc.,
1992, 114, 5902.
Kuniyasu, H.; Ogawa. &; Sato, K-I.; Ryu, I.; Sonoda. N, Tetrahedron Lea., 1992, 33, 5525.
.
4 O ; N:
Bu-C€-SMe PhMe TiClz(OiPr)2 0°C
0
pet ether
U
*
92%
Bu
SMe (998% ee)
Narasaka.; Hayashi, Y.; Shimadzu, H.; Niihata, S. .I. Am. Chem. SOC., 1992, 114, 8869.
a1 OH
PhCECH , PdC12(PPh3)2 CUI, NEt3 , DMF 60°C, 16 h
m u . N . G ; Pal, M.; Mahanty, J.S.; Dasgupta, S.K. J. Chem. SOC., Chem. Commun., 1992, 41.
Ph
0
c1
B+*)
*
+
vo
EtdCI, DCE ,60°C Ph l h Yano, K.; Hatta, Y.; Baba.;Matsuda, H. Synthesis, 1992,693.
76%
490
Compendium of Organic Synthetic Methods, Vo18
Shimada. K.; Jin, N.; Fujimura, M.; Nagano, Y.; Kudoh, E.; 1843.
Section 367
Chem. Lett., 1992,
1.48%HBr , ZnBrz 5 eq. PhSH
OMe Kwon, T.W.;
2. Cu(0Tf)z ,NEt(iPr12 3.450"C
OMe
Synth. Cornmun., 1992, 22, 2213.
Ni, Z.; Padwa. A, SynLeft, 1992, 869.
Degl'Innocenti.;Ulivi, P.; Capperucci, A.; Mordini, A.; Reginato, G.; Ricci, A. SynLRtt, 1992, 499.
KOH. TBAB. ))>)>>I
-
Br
4:)
68%
Diez-Barra, E.; de la Hoz, A:, Diaz-Ortiz. A;, Prieto, P. SynLetr, 1992,893. Related Methods:
SECTION 368:
Section 180A (Protection of Ketones)
HALIDE, SULFONATE
- HALIDE, SULFONATE
I lalocyclopropanations are found in Section 74F (Alkyls from Alkenes).
IICOzNa, 4OoC
Hu.C-M,;Qing, P L . Tetrahedron Lett., 1990, 31, 1307.
87%
Section 368
Halide
- Halide
49 1
0.1
3 NIS , A1F3, DME 3 NH4HF2, 6O"C, lh
Ichihara.J.;Funabiki, K.; Hanafusa, T. Tetrahedron Lett., 1990, 31, 3167. BrCCl3, cat. SmI2 4nC6H 13
MeCN , 7 O 0 C , 10 h *
C13cvBr n-C6H 71%
13
Ma, S.; Lu. X,J. Chern. SOC., Perkin Trans. I, 1990, 2031.
; Fukushima, T.; Terakawa, Y.; Yoshida, M.; Sawada, H. J. Chern. Soc., Perkin Trans. I , 1991,627.
NIS , TBAH2F2
e
n-C10H21 CHzC12 , 0°C , y h
n-CloH21
87%
TBAHzF3 = tembutylammonium dihydrogen trifluoride
-
Kuroboshi, M.; Hivama. T, Tetrahedron Lett., 1991, 32, 1215. Kuroboshi, M.; Hiyama. T. SynLeft., 1991, 185.
n-CsH1 1
-1
BnEt3+ MnO4 , oxalyl chloride CH2C12, -40°C. 30 min
L C l ~2-CsH11
CH2C12 , 3 0 min
75%
Mark6, I.E.; Richardson, P.F. Tetrahedron Lett., 1991, 32, 1831. IPy2BF4.2 HBF4 CH2CI2, -60°C
I
-1
F
Barluenea.; Camps, P.J.; GonzAlez, J.M.; SuLez, J.L.; Asensio, G. .I. 56, 2234.
BrCC13, AcOH , AcOK Mn(0Ac)z ,RT * e- (0.06 F/mol)
c c 1 3 95%
78%
Org. Chern.. 1991,
Br
Nohair, K.; Lachaise, I.; Paugram, J-P.;Nedetec. J-Y, Tetrahedron Left., 1992, 33, 213.
492
Compendium of Organic Synthetic Methods, Vol8
SECTION 369: HALIDE, SULFONATE 0
- KETONE 0
MgBrpOEt,, elher
SiMe3 S02Ph
Me Hewkin, C.T.;
Section 369
Me)(CSiMea M e Br
2ooc*4
49%
Tetrahedron Lett.. 1990, 31, 1877.
P h y Sph
0
e- ,MeCN , Et$*3 HF ~t electrodes, RT
*
I . l O V , 1.6Frnol-'
Ph$SPh 84%
Brigaud, T.; Laurent E. Tetrahedron Lett.. 1990, 31, 2287.
4 0
Me Na
DMF , -65OC -+ RT overnight
0
Ymemoto. T.; Ishihara, S. Tetrahedron Lett., 1990, 31, 3579.
83%
Hoffman. R.V,;Wilson, A.L.; Kim, H-0. J. Org. Chem., 1990, 55, 1267. 2% RuC12(PPh3)3 PhH, 155°C. 24 h
+ Cl 77%
Lee, G.M.; Weinreb.
S.w.I. Org. Chem.. 1990, 55, 1281.
Rozen.;Hebel. D. J. Org. Chem., 1990, 55, 2621
8%
Section 369
Halide - Ketone
4
493
1. MeOTf , TiC14, ether 2. 1.8-bis-(dimethylamino)- w
C+
Cl+
naphthalene, MeCN 3. H30' Welch. J.T,; De Corte, B.; De Kimpe, N. J. Org. Chem., 1990, 55, 4981. 1. SOC12, CHZCI~, RT , 1 h
2.50% aq. H2SO4,6 h * reflux
& c1
w; Brunet, P. Synthesis, 1990, 595.
35%
81%
Barluenga, J.; Llavona, L.; Yus, M.; ConceI16n, J.M. Synthesis, 1990, 1003. mCPBA , HCI , DMF
OH
Me
PhJ
25"C, 6 h
*
P h L C I
80%
Kim, H.J.; Kim, H.R.; Byu. E.K, Synfh. Cornrum., 1990, 20, 1625.
\ I
Me0-Me
CuClrDMSO 1 h dioxane,reflux
~
0 Sahasrabhuddhe, AS.; B i v a . B.Llnd. J. Chem., 1990, 298, 61.
0
TsS02NC12, MeCN
P h T
40°C. 1.5 h
*
P h x , ,
80%
Kim.;Lee, I S . ; Lim, S.C. Chem. Letf., 1990, 1125.
J
1. LiBr , CICI-121,-78°C 2. 1.6 eq. MeLi ,-78°C
qpl
* 64% 3. HCI- ether 4. HCI - H 2 0 0 Barluenea. JJ Llavona, L.; Concellh, J.M. J. Chen. Soc., Perkin Trans I, 1990, 417. CO,Et
494
Compendium of Organic Synthetic Methods, Vo18
COzEt
Section 369
4
1 . 2 eq. BrCH2CI Br2CH2
2 . 2 eq. LDA , -78°C 83% 3. Me2CuLi c1 4. aq. HCI , 0°C Barluenga, J.; Llavona, L.; Yus, M.; Concellbn, J.M.J. Chem. Soc., Perkin Trans. I, 1991, 2890. PhiCl2 ,CH2C12
0
I ’ h w Ph 54%
0
c1
Moskovkina, T.V.; Vysotskii, V.I. Zhur. Org. Khint., 1991, 27, 717. 1. LDA 2. F-N(S02Ph)2, THF
J
q
+
Ph
. . R&x&g&.~.;
PhI(OAc)z, I2 cyclohexane hv (sunlamp)
*
@
Tetrahedron Lett., 1991, 32, 1583.
a
s. F A ; Han, W. Tetrahedron Lett,, 1991, 32, 1631.
Br
KerdeSk-;.
h
85%
F
also for fluorination of Ar-H Ofner, H. SynLRlt, 1991. 187.
Me Ellwood, C.W.; l%&a&a&
p
1. BuLi , CuBr-DMS
2. TFAA
Basha, A. Tetrahedron Lett.. 1991, 32, 2003.
84%
78%
Halide - Ketone
Section 369
NBS , cat. AgBF4
HO
)-cz c--/
495
- *5 7040%
Angara, G.J.; McNelis, E. Tetm..dron Lett., 1991, 32, 2099.
OSiMe,
CU(NO~)~, MeCN , RT
Cort. A.D. J. Org. Chem., 1991. 56, 6708. TI ( S O ~ T O I,)MeCN ~
0
*
OTs Ph Ph Khanna, M.S.;Garg, C.P.;~QQQLRL Tetrahedron Lett., 1992, 33, 1495.
92%
FU.SynLerr, 1992, 393.
Khanna, M.S.; Garg, C.P.; b o o r .
94%
MeOH-NEt3, CHzClz Tetrahedron Lett., 1992, 33, 6021.
Raina, S.; Bhuniya, D.;
PhI(0H)OTs MeCN
h0-
0
T
-I-
)”))
s
O
A
0 91% Tuncav. A,; Dustman, J.A.; Fisher, G.; Tuncay, C.I.; Suslick, K.S.Tetrahedron Lett., 1992, 33, 7647. KI-KI03-H2S04,45h
PhYMe 0
86%
0 *
Okamoto, T.; Kakinami, T.; Nishimura, T.; Hermawan, T.; Jpn., 1992, 65, 1731. 1. [AgF/PhSeBr/ ))))))) ]
2.30% aq. H202
*
Bull. Chem. SOC.
bF 52%
Usuki, Y . ; Iwaoka, M.; l j x n ~ & A J Chem. Soc., Chem. Commun., 1992, 1148.
496
Compendium of Organic Synthetic Methods, Vol8
0
oxone, HCI , DMF
Ph- CE C-Me
Section 37 1
* P
25°C. 2 h
h v c1 c1
94%
Kim, K.K.; Kim, J.N.;Kim, K.M.; Kim, H.R.; Ryu, E.K. Chem. Lett., 1992, 603.
- NITRILE
SECTION 370: HALIDE, SULFONATE
N C I
p
Pd(PPh3)4, HMPA proton sponge, 65°C
NcK1 N COZPh
4. N C02Ph Mori. M,; Kubo, Y.; Ban, Y. Heterocycles, 1990, 31, 433.
Rodriguez, J.; Duldre. J-P. SynLett, 1991, 477.
SECTION 371: HALIDE, SULFONATE
10"
Me0
rn
- ALKENE
1 . PhSeCl , MeCN AgF , RT , 18 h
*
2.03 , CCl4 , -2°C ~~0 3. iPr2N€I,reflux 44% 16 h v. J.FLMatthhews, D.P.; Barney, C.L. TefrahedronLett., 1990, 31, 973. /
1 . Red-A1 , ether, 0°C
2.12, -78°C + 2 3 T , PhS- Cr C 7 OH 3. HoMOH * NaOzC
. .
COzK
lh
Ph 80%
Maeno!ls.;Doyle, T.J.; Kim, K.D. Tetrahedron Lett., 1990, 31, 2541.
Me H- CEC 4 . OTs
67%
C F ~ C UDMF ,
* F,CHG C: CHMe 65%
Burton.;Hartgraves, G.A.; Hsu, J. TefruhedronLen., 1990, 31, 3699.
Section 37 1
Halide - Alkene
H- CE C-
497
C & I + ~ ,DMSO
Br
20°C
* C6F13HC- C=CH, 75%
Huns. H-H, Tetrahedron Lett., 1990, 31, 3703.
Roush. W.R.; Moriarty, K.J.; Brown, B.B. Tetrahedron Lett., 1990, 31, 6509.
Ph- CE C- H
IPy2 BF4, AcOH CH2C12, HBF4
*
12h
Ph
AcO'
53%
Barluenga.;RodHguez, M.A.; Campos, P.J. J. Org. Chem., 1990, 55, 3104. b h m g d . ; Rodriquez, M.A.; C a m p s , P.J. Tetrahedron Lett., 1990, 31, 2751. Cmpos, P.J.; Lbpez, F.; Llorente, I.; Rodriguez, M.A. Tetrahedron Lett., 1990, 31, 7375. BarluenPa.;Rodriguez, M.A.; Gonzhlez, J.M.; Camps, P.J. Tetrahedron Lett., 1990, 31, 4207.
u; F,C
1
OEt
Thenappan, A.;
F
1. Dibal ,THF b
2. (E(O)~POCFCO~CO~EL Li CO2Et -78°C - +25"C 63% (83:17 E:Z) D.J. .I. Org. Chem., 1990, 55,4639.
m.
F ~ C O ~ T Ml.LDA P
SiMe,
2. PhCHO
CO*TMP 49%
TMP = 2,4,6-lrimethylphenyI
(1:29 E:Z) Welch.: Herbert, R.W. J. Org. Chem., 1990, 55, 4782.
1. KHMDS , -100°C (33212
n-C6H13
1
4
2. PhOIS-qLi B
(84:16
n-C6H13
E:Z)
Chmeau, P.; Julia, M.; Verpeaux, J.N. Bull. SOC. Chim. Fr., 1990, 127, 275.
OBr
'' Br Bandodakar, B.S.; -Synthesis,
morpholine ,DMSO , 8 5 T KOH,EtOH
1990, 843.
66%
eBr 80%
498
Compendium of Organic Synthetic Methods, Vol 8
Section 37 1
CBrC13,2 eq. VCl2 DMF , 80°C, 20 h
c
C
c
l
3 63%
Hirao, T.; Ohshiro, Y. SynLett, 1990, 217.
Bu- Cr C-Et
Me3SiCI , Nal , MeCN O.SHzO.RT, 1 h Ic
Bu)=;l Et I
Kamiya, N.; Chikami, Y.; Jshii. Y. Syntett, 1990, 675.
-
>98%
- dCF* qxF2
1. AIC13, 150°C , 3 d 2. 2 eq. Zn ,DMF
CF3CFBrCF2Br 3. lriglyrne , 25OC. 48 h c1
Morken, P.A.; Lu, H.; Nakamura, A.;
F,C- CH,
+
Tetrahedron Lett., 1991, 32, 4271.
1. sec-BuLi 2. n-C,H,3CHO
n-C6H 1 3
3. DAST ,CH2C12
b
C
CF3
DAST = diethylaminosulfur trifluoride
50-60%
Tellier, F.; SauvStre, R. Tetrahedron Lett., 1991, 32, 5963.
j
0 O M OMee
SiMe
,CH2C12
SnBr2-AcBr , RT , 1 h
Orivama. T.; Iwanami, K.; Tsukamoto, K.; Ichimura, Y.; Koga, G. Bull. Chem. Soc. Jpn., 1991, 64, 1410. 4 eq. M0C15,24 h
c1
34%
brae. T.; Nagata, S.; Yamaguchi, M.; O s h i r o . B u l l . Chem. Soc. Jpn., 1991. 64, 1717.
CHO
(CF$0)20 , Zn-Cu , MS CF3CC12C02Me. THF 60°C
=
m F : 0 2 " " 88% (65:35
Allmendinger. T,; Lang, R.W. Tetrahedron Lett., 1991, 32, 339.
ZE)
Halide - Alkene
Section 37 1
0.33 benzene PhCSAICI - CHg12,O°C
499
*% /
44%
wMe
c.., L.
Bhaskar Ready, G.;Hanamoto, T.; Hivama. T. Tetrahedron Lett., 1991, 32, 521.
Ph
Me3SiC1, NaI MeCN
OAc
*
50%
Me
Amouroux. R,;Ejjiyar, S . Tetrahedron Lem., 1991, 32, 3059.
4CF3 TMEDA ZnBr
.r
-
cat. Pd(PPh3)4, THF
96%
UB.; XLLY.J. Org. C h e w 1991, 56, 7336. a; &LX, Tetrahedron Lett., 1992, 33, Sll[coupling of two vinyl halides]. H- Cr C-C02Et
Lil ,AcOH ,MeCN
*
I
reflux, 21 h
c02Et 87%
Ma, S.; U; Li. 2.J. Org. Chern., 1992, 57, 709. Ma, S.; Tetrahedron Lett., 1990, 31, 7653. Ma, S.; U J . Chern. Soc., Chern. Commun., 1990, 1643 [with LiBr]. MegSi- C: Cf
Me Me CI
TiC14, CH2Clz
*
H Me MuL&H.; Bguml, E.; Cibura, G.; Koschinsky, R. .I. Org. Chern., 1992, 57, 768. 4.2 eq. 1 2 , RT ,24 h
Me
*
&I
Me
57%
Johnson.;Adams, J.P.; Braun, M.P.; Senanayake, C.B.W.; Wovkulich, P.M.; UskokoviC, M.R. Tetrahedron Lett., 1992, 33, 917.
Compendium of Organic Synthetic Methods, Vol8
500
1. TfzO, CHzC12
-CHO
fl'' >
Section 37 1
-1
0°C. 12 h 2647% 2. MgIz (96:4 E Z ) 3. DBU Martinez.;Alvarez, R.M.; GonzAlez, S.M.; Subramanian, L.R.; Conrad, M. Tetrahedron Lett., 1992, 33, 2043. 1 . 2 eq. BuLi , THF 2. B B u ~LiF ,
90% 3. CuI ,THF-HMPA Ph 4. 2% Pdz(dba)3-PPh3 PhI,RT,lh Ichikawa. J,: Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett., 2992,33,3779.
CF3CHzoTs
no
1. LDA
t-Bu
t
t-Bu
2. " i n N
0"' 87%
NTfi
-78"C, 2h Comins. D.L,;Dehghani, A. Tetrahedron Lett., 1992. 33, 6299. Bu3SnSnBuj, hv (sunlamp)
SPh
oI
, PhH , 3 0 min
Cuman. D.P,; Yoo, B. Tetrahedron Lett., 1992, 33, 6931. POC13, DMF ,RT ClCHCC12 , 3 d
Cbz Al-awar. R.S.; Joseph, S.P.; Comins.
3
96%
Cbz D L Tetrahedron Lett., 1992, 33, 7635.
1. thexylBHz , THF 2. (MezN)3P=O t n-C4Hg-C=C-H C U C I ~HzO/THF , Bu 3.20"C + 70°C Masuda. Y,;Hoshi, M.; Arase, A. J. Chem. SOC.,Perkin Trans. 1, 1992, 2725.
+
c1
72%
Ketone - Ketone
Section 372
501
5%
49% (1:9 E:Z)
Albrecht, U.; Warthow, R.; Hoffmann, H.M.R. Angew. Chem. Int Ed. Engl., 1992, 31, 910. AgBF4, AIC13, 10 min microwaves (650 W)
. . Vlllemln.; Labiad. B. Synth. Commun., 1992, 22, 2043. CFS , MeOH
€
'
h
e SnMe3
t
P
h
o
F
48%
CFS = cesium fluoroxysulfate Hodson, H.F.; Madge, D.J.;
SynLetl, 1992, 831.
SECTION 372: KETONE
-
KETONE
-L
hv (Hg lamp) ,2.S h
Ni(II)/Co(II) filter
0
2S°C ,air
95%
0
Macias, F.A.; Molinillo, J.M.G.; Collado, I.G.; Massanet, G.M.; Rodriquez-Luis, F. Tetrahedron Lett., 1990, 31, 3063.
0
2 0
0
,FeCb ,2O"C
claynick, 24 h %?
claynick = [K-10 montrmorillonite/NiBr/MeCN/280°C]
Laszb.;Montaufier,
M-T.; Randriamahefa, S.L. Tetrahedron Lett., 1990, 31,4867. 0
SePh
hv (100 W Hg m l :)
PhH , RT, 3 h
Watanabe, Y.; Yoneda, T.; Ueno, Y.; Tom T, Tetrahedron Lett., 1990, 31, 6669.
Compendium of Organic Synthetic Methods, Vol 8
502
Section 372
LDA ,THF ,25"C, 6 h
Gu, X-P.; Kirito, Y.; Ikeda, 1.;
Ph
J. Org. Chem., 1990, 55, 3390.
il
-
ECHO, SnC12 CH2C12, RT
CHN2
0
Ph
0
JUL88%
Padwa.;Hornbuckle, S.F.; Zhang, 2.; Zhi, L. J. Org. Chern., 1990, 55, 5297. C02Me v C 0 2 t - B ~ c s 2 c o 3 , CIiC13 0 2. PTSA
@ J 0
73%
Me
Ruel, K.;Hogan, K.T.; Deslongchamos.SynLeii, 1990, 516. OSnBu, dMeRT, 1.HMPT h
M
0
e
0
d
p
h
+ M 0e m Ph o 12%
13%
Baba.;Yasuda, M.; Yano, K.; Shibata, I.; Mahuda, H. J. Chem. Soc., Perkin Trans. I, 1990, 3205.
*
Me
NO2
0-Li+ 1. =( ,THF,-78"C Bu
2.10% HCI , RT , 5 h
Miyashita, M.; Awen, B.Z.E.;
.
.
OSiMe3 P h W B F 3
-
BudM 65%
0
Synthesis, 1990, 563.
*
-78°C -+ -10°C
74%
Zefirov, N.S.; Samoniya, N.Sh.; Jutateladze, T.G.; Zhdankin, V.V. Zhur. Org. Khim., 1991, 27, 220 (Engl., p. 194).
503
Ketone - Ketone
Section 372
PdC12(MeCN)2
OC""
cs c-
H 2 0 , THF , RT
n-C6H13
-
&GH13 63%
Mahrwald, R.; Schick. H.Angew. Chem. Inr. Ed. EngL, 1991, 30,593. OSiMe7t-Bu
=.(
Ph
IDMF
Ph30H 2.4 eq. Mn(pic)3
80%
Ph
0°C Mn(pic)3 = manganese (111) 2-pyridinecarboxylate Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka.Chern. Leff., 1991, 1193. 12, DMSO , 155°C. 10 h
Ph+
Ph
p h q P h
85%
0 Yusybov, M.S.; m o v . V.D. Synthesis, 1991, 131.
2
kC02Et
l.Na,ether 2. SOCl;1, - 1 8 T -+ RT
Olah.;Wu, A. Synfhesis, 1991, 1177.
0
French. L.G,; Fenlon, E.E.; Charlton. T.P. Tetrahedron Left.. 1991, 32, 851.
,CsHC03, MeOH 2OoC, 2 h 2.4N Ii2SO4,6ODC,4 h 3. 3MsCl,5NEt3 cat. DMAP , CH2C12 20"C, 30 min P ' A n c e l d ; Gomez-Pardo, D. Tetrahedron Leff.,1991, 32, 3063.
24% overall
504
Compendium of Organic Synthetic Methods, Vol 8
0
1 . e- , SmCl3 , Mg anode
P h h P h 0
2.H30t
PhC02Me
Section 372
68%
Htbri, H.; Duaach. EL Heintz, M.; Troupei, M.; Ptrichon, J. SynLetf, 1991,901.
P
h
q Ph 0 83%
Olah. G.A.; Wu, A. J. Org. Cheni., 1991, 56, 902.
2 eq. BuLi , -110OC
-CO2Me
* Bu
0 Sevferth.;Weinstein, R.M.; Hui, R.C.; Wang, W-L.; Archer, C.M. .I. Org. Chem., 1991, 56, 5768.
HO
)-c: c<
OH
IrHg(PiPr3)2, PhMe reflux , 4 0 h
0
Lu.; Ji, J.; Ma, D.; Shen, W. .I. Org. Chem., 1991, 56, 5774. C02Me
CN
70%
2 eq. Mn(OAc)3*2 H 2 0 EtOH,24h
Me
Me
Snider.;Buckman, B.O. .I. Org. Chem., 1992, 57, 322.
5% Bu2Sn(OTD2 -78"C, 5 h 2.1N HCl , THF , RT
-
p
7
0
0
Sato, T.; Wakahara, Y.; Otera.; Nozaki, H. Tefrahedron,1991. 47, 9773. Sato, T.; Wakahara, Y.; Dtera. J.; Nozaki, H. Tetrahedron Lett., 1990, 31, 1581.
%
Section 372
505
Ketone - Ketone
&
1. iPrNH2 ,Tic14 - ether 16 h , 0°C -+ RT
2.LDA,THF 3. EtI 0 0 4. oxalic acid, H201CH2C12 reflux, 1 h De Kimne. N,; D’Hondt, L.; Stanoeva, E. Tetrahedron Lett., 1991, 32, 3879.
n
1. BuLi , THF, -78°C 2.PhCHO
’Y
3. NBS ,aq. acetone -5°C
Ph
L-
0
58%
66%
Pace. P.C.B,; Graham, A.E.; Park, B.K. Tetruhedron, 1992, 48,7265. 1. NalFe(C0)s , CO , THF 2. CuCl , 25OC , 1.5 h 3. aq. CAN
n - C 9 H Z Br
0 n-C 10H%n-C10H21 21 0
80%
Tetruhedron LRtt., 1992, 33, 1227.
Devasagayara, A.;
8
OSiMe,
3 eq. VO(OEt)CI, -75°C + -40°C 71%
Fujii, T.; Hirao. T.; Ohshiro. Y. Tetrahedron Lett., 1992, 33, 5823. n-CfiH13Br
0
d~~ Me2NAc
0 +
n - C 6 H h Me 0
70%
m a s h i t a . M,; Tashika, H.; Uchida, M. Bull. Chem. Soc. Jpn., 1992, 65, 1257.
M
e O
1. BuLi ,ether-hexane , -50°C 2. H3P04, H20,20°c
n N
u
Wedler, C.; &kkJ.
0
12h
Synthesis, 1992, 543.
Ir
M
e 0
d
B
u
SF%
506
Compendium of Organic Synthetic Methods, Vol8
SECTION 373: KETONE
- NITRILE
BnCN ,2O0C. 3 h 2 eq. HWCO)(PPh$
ph
also with conjugated esters, but in lower yield
Section 373
4 CN
85%
Papanelll.;Schionato, A.; Dotleghi, C. Tetrahedron Lett., 1991, 32, 2807. CN
n-C6HI3-I
, PhH , 8 0 T t
Bu3SnH, AIBN n-C6H 13 LCN CO (80 a m ) , 2 h 74% Rvu. I,; Kusano, K.; Ymazaki, H.; Sonoda. N, .I. Org. Chem., 1991, 56, 5003.
PhCOzMe
e' ,(Mg anode ,NifCd cathode) Bu4N BF4, PhBr , MeCN
Ph
I
Y C N 0
83%
Barhadi, R.; Gal, J.; Heintz, M.; Troupel. M, .I, Chein. Soc., Chein. Coinmun., 1992, SO.
PhC0,Me
1. e- , 10%SmC13 MeCN , t-BuOH
Ph r(-C N
2. H3O+ HCbri, H.; puaach. E,; PCrichon, J. SynLefl, 1992, 293.
0
75%
REVIEWS:
"Stereocon@oll&Construction of Complex Cyclic Ketones via oxy-Cope Rearrangement" Paauette. L.A.Angew. Cheni. Int. Ed. Engl., 1990, 29, 609.
SECTION 374: KETONE
- ALKENE
For the oxidation of allylic alcohols to alkene ketones, see Section 168 (Ketones from Alcohols and Phenols)
For the oxidation of allylic methylene groups (C=C-CH2 Section 170 (Ketones from Alkyls and Methylenes).
+ C=C-C=O),see
For the alkylation of alkene ketones, also see Section 177 (Ketones from Ketones) and for conjugate alkylations see Section 74E (Alkyls from Alkenes).
Ketone - Alkene
Section 374
0"
(PhIOX, , RT , 15h n-Bu4NF THFICH2CI2
GosiMe?
507
+
PhI
12%
Moriartv. R.M; Vaid, R.K.; Hopkins, E.; Vaid, B.K.; Prakash, 0. Tetrahedron Lett., 1990, 31, 197.
M n ( 0 A c ) ~ Cu(0Ac)z . Pb@ ,Py , AcOH 2d , RT Breuilles, P.; UgmJL Tetrahedron Lett., 1990, 31, 357.
8
& COZEt
COzEt
91%
1. PhCHO ,CH2Ck2 Tic4 , Ti(0iPr)d , PPh3 -50°C + RT ,8h *
2. 10%K2C03
83%
Takanami, T.; Suda. K.; Ohmori, H. Telruhedron Lett., 1990, 31, 677.
64% (8:l transcis)
Takacs. J.M.; Zhu, J. Tetrahedron Lett., 1990, 31, 1 1 17.
OTBDMS
MeCN , reflux
t
McLoughlin, J.I.; Brahma, R.; Campopiano, 0.;Little. R.D. Tetrahedron Lett., 1990, 31, 1377.
x
OCOZEt cat. Tic4 , RT , 5 d
79%
De Cusati, P.F.; Qlofson. R.A. Tetrahedron Lett., 1990, 31, 1409.
20%
508
Compendium of Organic Synthetic Methods, Vol8
@Ph
1. TI(OAc)3,
reflux, 3 h
2. ice, H20
0
Singh, O.V.;
Section 374
96%
0
Tetrahedron Len., 1990, 31, 1459. 1. DMP ,MeOH
' ' B o H
2. PCC HC104 , PhH
- .
3. (Me0)2POCH2Li
GH~H
Oxo
42%
Ali, S.M.; Ramesh, K.; Borchardt. rtT, Tetrahedron Lett., 1990, 31, 1509.
0
(150 W lamp)
79%
0
on. D.H.R.; Sarma, J.C. Tetruhedron Lett., 1990, 31, 1965.
Ph,P--\
LeRoux, J.;
1. AcCl 2. BuLi , HCHO
Me
n
*
3. 150-170°C 30 min
Me
66%
Tetrahedron Lett., 1990, 31, 2591. 1. BuLi ,THF
0
-78OC
P h 3 p u c F 3
Bu 0
2. PhCHO
Shen. Y,;Wang, T. Tetrahedron Lea., 1990, 31. 3161. OSiMe2r-hexyl
%/
OC0,Me
63%
- do
BF3*OEt2, CH2CI2 O°C , 15 min
good yield
',.,A
43%ee Ollivier, J.; Legros, J-Y.; Fiaud, .I-C.; de Meiiere. A.; Salaun, J. Tetrahedron Lett., 1990, 31,
4135.
Section 374
Ketone - Alkene
509
MeOH
67% Callinan, A.; Chen, Y.; Morrow, G.W.; SwmmJA Tetrahedron Lett., 1990, 31, 4551.
2 '
Co(CO)6, NMO
0
CH2C12, RT
\ \
85%
Shambayati, S.; Crowe, W.E.; SdudmAL Tetrahedron Lett., 1990, 31, 5289. BusSnH , AIBN PhH ,reflux 1.S h
0
(&
8 " *
0
LanPe.;Gottardo, C . Tetrahedron Lett,, 1990, 31, 5985. EtAIC12,Phfl SO min
90%
70%
Fujiwxa, T.; l3k&J, Tetrahedron Lett.. 1990, 31, 6027, I . Ph3C' Clod
OSiMeJ Me+Me SiMeg-Bu
2. aq. HBF4 , THF 200C
c
M e h ; ; Me (>95% ee)
Lahray. B.B.; Zirnbiniski, R. Tetrahedron Lett., 1990, 31, 7273.
Me
Me
Toru.;Okumura, T.; Ueno, Y. .I. Org. Chent.,1990, 55, 1277.
764
48%
5 10
Compendium of Organic Synthetic Methods, Vol 8
Section 374
reflux, 16 h 38% (3.2:l diastereomeric ratio) Poch, M.; Valenti, E.: Movano.; PericAs, M.A.; Castro, J.; DeNicola, A.; Tetrahedron Lett., 1990, 31, 7505.
A 0
15 min MMPP'H20
*
c
W%
MMPP = Mg monoperoxy phlhalate 0 Dominguez, C.; Cs&y, A.G.; ~UJXTetrahedron U.. Lett., 1990, 31, 7669, 1. AcCl
2. Me-CS C
Hcr(c0)5 xoH* 0-Me4N+ 3. PhMe , renux Herndon.;Matasi, J.J. .I.
Org. Chein.. 1990, 55, 786.
$J
34%
(65:35 transcis)
&
( 2 . 5 1 Z:E)
Cheng, M.; Nuke. M.J. Org. Cherti., I990. 55, 964.
2 Mn(OAc)3*2 H2O
C02Et
-
&iy +
I
OAc
39% ( 2 5 1 P:a) Kales, S.A.; Dombroski, M.A.; Snider. B.B,.I. Org. Cheni., 1990, 55, 2427.
70%
Section 374
Ketone - Alkene
y
iPrCHO , THF , 2 0 h P(n-CgH17)3, 100°C
n-C3H7€: C-n-C3H7
Ni(COD)2
+
511
93%
(93:7 E:Z)
Org. Chem., 1990, 55, 2554.
Tsuda, T.; Kiyoi, T.; -..I.
1. +OEt
SnMq
, 3 eq. Licl
2% Pd(PPh3)4, THF reflux, 16 h Kwon, H.B.; McKee, B.H.; Stille. J.K.J. Org. Chem., 1990, 55, 3114.
wph
1. disiamyl h o m e 2. NaOH ,H202
*
3. ;ml,c~~gide/DMSO
&
Ph
4 . 1 N HClMeOH , reflux 15 min 79% Collins.; Hong, Y.; Kataoka, M.; Nguyen, T. .I. Org. Chem., 1990, 55, 3395.
8
I . LiC(SPh)l
n
2.
3. AgOTf
32%
Posner.;Asirvatham, E.; Hamill, T.G.; Webb, K.S. .I.
J& Cl
Org. Chem., 1990, 55, 2132.
PhSCHzLilIUEDA THF ,-70°C
C02Et
Me
Mathew. J, J. Org. Chem., 1990, 55, 5294. 1. NBS , CC14, reflux
Me
2. aniline, 15 C hC I ~RT ,
.-
&Me
48%
Shimazaki, M.; Huang, Z-H.; Goto, M.; Suzuki, N.; Qhta. 4.Synthesis. 1990, 677.
512
Compendium of Organic Synthetic Methods, Vol 8
PhI , 5% BnClPd(PPh3)z 10%CuI ,DMF , RT
Foxo
Bu3Sn
* 'Ox0
Liebeskind.;FengI, R.W. J. Org. Chem., 1990, 55, 5359.
N O OEt siMe3
Ph
II
CO,Et n-C5H1 1
& Ci C- COzEt
n-CSHI
9
99%
-4-
MOM0
. . Crlmmms.; Nantermet, P.G. .I.
0
0
1. ZnClz , ether ))>)I) 25°C 2. CuBr-SMez , HMPA 9
Ph'
Section 374
OMOM
Org. Chetn., 1990, 55,4235.
Bu3SnH. AIBN 80°C, PhH
&)
c-..
(44%
8M
Me CHPh
cistrans ring juncture)
Boger. D.L,; Mathvink, R.J. J. Org. Chetn., 1990, 55, 5442. 0
Me
11 ,-BuA
I BF3
F
1
0
t-Bu
CHzCl2
2.aq.NaHC03
Me
'bb
72%
(1:2 EZ)
Verleletskii, P.V.; Balenkova, E.S. Zhur. Org. Khim., 1990, 26, 2446 (Engl., p, 2113).
0
OSiMe3
Ph-(OMe OMe
, SnC12
AcCl ,CH2C12, RT , 2 h
Oriyama. T,; Iwanami, K.; Miyauchi, Y.; Koga, G. Bull. Chem. Soc. Jpn.. 1990, 63, 3716.
6
OSiMe3
0
-ouov
,DME
4% Pdz(dba)yCHC13 / S i Q
dPPe
Baba.;Nakano, K.; Nishiyama, S.; Tsurya, S. J. Chetn. SOC., Chetn. Commun., 1990, 348.
Ketone - Alkene
Section 374
?A 0
513
g:;f;;u
-2OoC, 24 h
SiMq
b s i M e 3 99% (88% ee , S)
0
SiPhzt-Bu
Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. SOC.,1990, 112, 7791.
PDC , CHK12, RT 32 h
0
Mukhopadhyay, A.; Suryawanshi. S.N.; Bhakuni. D.S,lnd. ,I. Chent., 1990, 298, 1060.
doMe
1.1-BuLi , THF , -78°C 2. PhCHO
N
Boc
3. (C02Hh. MeOH , RT 15 h
B°C
36%
Giles, M.; Hadley, M.S.;Gallagher, T. J. Chem. SOC., Chenz. Commun., 1990, 831. n
SMe = C* SiMe,
1
SMe 77%
CH2C12,O"C
Hayashi, Y.; Niihata, S.; Narasaka, K. Chem. Lett., 1990, 2091.
0 >Me
cB-Br, PhCHO
Me
PhH , RT , 1 d
62%
0
Br
Shimizu, H.; Hara, S.; Suzuki. A,Synrh. Commun., 1990, 20, 540. 1 . BuLi , BF3*OEt,
PhSo2Me
2- O P nC,H1, 3. Jones oxidation 4. DBU
L.
Marczak, S.; W i c h a . S y n t h . Cornmun., 1990, 20, 1511.
>n-C5Hll
0
60%
5 14
Compendium of Organic Synthetic Methods, Vol 8
Section 314
1. TMSCl , NEt3 2. Pb(OAc)z, MeCN
benzoquinone
52%
Kim, M.; Applegate, L.A.; Park, 0-S.; Vasudevan, S.; W a t t . S y n t h . Commun., Z990, 20, 985.
Fph
H-CS-CHzOMe CH2C12,4 h
Rf2(pfb)4 syring pump addition
N2
Ph
Me0 (82
pfb = perfluorobutyrate
OMe
0
80%
18)
Dole, M.P.; Bagheri, V.; Claxton, E.E. J. Chem. SOC.,Chem. Commun., 1990, 46. NO2
30%MeCN H202,3N , 7OoC, HCI3 h
*
dMe 72%
0
Gupta, K.B.; Franck, R.W. SynLett, 1990, 355.
Me3Si0
OSiMe3 Me
Pelerson.;Kirchhoff, E.W. H
PhCHO , TiC14, -78°C CH2C12 , 4 h
66%
Ph SynLett, 1990, 394.
1. TMSOTf 2. T i c 4 3. Pb(OAc)4
0
Me
&
Me0
Ls.T.V.; Porter, J.R.; Roden, F.S.Tetrahedron, 1991, 47, 139.
48%
Section 314
Ketone - Alkene
SnBu-,
515
Q
Bu3SnH , AIBN PhH ,reflux
77%
Baldwin. J.E.; Adlington, R.M.; Robertson, J. Tetrahedron, 1991, 47, 6795. Me1 , CO (1 atrn) , 4OoC Mnz(C0)lo. CTAB+
n-C5H 1\= 1 C=
+
a-(%H$
CH2Cl2, NaOH 40% CTAB = cetyltrirnethylammoniombromide Satyanarayana, N.; A~QuJLJ. Chem. Soc., Cheni. Cownun., 1991, 8.
OH Me0
MMP , MeCN , 2 0 ° C , 1 h cat. Fe"' (TF4PS4P)
0
~
pH 3 (tartrate buffer)
OMe
7%
85%
Me0
MMP = magnesium monapemxyphthalate Fe (TF4PS4P) = iron-rneso-tetrakis(2,3,5,6-tc~afluorophenyl) tetrasulfonatoporphyrin
0
Artaud, I.; Aziza, K.B.; Chopard, C.; Mansuy, D. .I. Chern. Soc.. Chem. Conimun., 1991, 31.
Me3Si
SiMe3
0
1. BzCI-AlCh , 0°C CHZC1, 2. C-,H,5COCI-AICI, * Ph CHZCI,, O°C -+ RT
0
55%
Babudri, F.; Fiandanese, V.; Marchese, G.; Naw. F. .I. Chem. Soc., Chern. Corrtmun., 1991,
237.
H
O
G OH
BnMe3N Br3, NaOAc CH2C12, RT quant.
Qiieaeshi. &; Morikawa, Y.; Fujisaki, S.; Kakinami, T.; Nishihara, K. Bull. Chern. Soc. Jpn.. 1991, 64, 336.
0
PhCliO , In1 , THF #
Ph
Br
PhLPh
Araki. SJ Butsugan, Y . Bull. Chern. Soc. .Ipn., 1991, 64, 727.
74%
Compendium of Organic Synthetic Methods, Vol8
516
Section 314
(c'B-n-C8H17 Bu4
w
I
CO , Pd(PPh3)4,25"C dioxane , K3P04
Ishiyama, T.; Miyaura, N.; n-C5H117_
csc'
B,,
OMe Fukuda, Y.;
'
98%
Bull. Chem. SOC. Jpn., 1991, 64, 1999.
10%H20 in MeOH 5% NaAuC104 c
0 n-C5H1 bI
reflux, 2 h
B
u
79%
Bull. Chem. SOC.Jpn., 1991, 64, 2013.
bMe PhCHO
TMSOTf
06Me 67%
Sato.;Hayase, K. Bull. Cheni. SOC.Jpn., 1991, 64, 3384.
Honda.;Ishige, H.; Tsubuki, M.; Naito. K.; Suzuki, Y. J. Chem. Soc., Perkin Trans. I, 1991, 954.
JCrafft. M.E.; Juliano, C.A.; Scott, 1.L.; Wright, C.; McEachin, M.D. J. Am. Chem. Soc., 1991, 113, 1693.
02
OSiMe3
Pd(2-furyl)$12 , xylene reflux , 3 6 h
Hetuick, C.M.; Scott. W.J. J. Am. Chem. SOC., 1991, 113, 4903.
Ketone - Alkene
Section 374
Ph
0
Ph -
>Me
0
517
,DMF
0 I-ph BF4 Cat. Pd(OAc12, RT
-
\Me
73%
NaHC03
0 Moriartv.;Epa, W.R.; Awasthi, A.K. J. Am. Chem. SOC.,1991, 113, 6315. 1. t-BuCOS02F , CHK12
-70°C
2. NEt3 0 Gavrishova, T.I.; Shastin, A.V.; Balenkova, E.S. Zhur. Org. Khim., 1991, 27, 673 (Engl., p. 580).
.
Q
1. BuLi THF 2. PhCN ,-78T 4 -5OC
OEt
3' M e 0 0 CHO, -5°C +*RT
E~O-P-Me
86%
OMe
4.5N H2S04 , RT , 1 h
Lee, K.; Dh. D.Y, Synthesis, 1991, 213.
K
MqSn
Degl'Innocenti, A.;
SnMq
0 THF, reflux, 2 h 2. PdBnCl(PPh& O°C 4 RT .2h
m;
n Me C:C,fMe
*
-t).o
0
; Ricci, A.; Seconi, G. Synthesis, 1991, 267.
n-Bu-1 ,THF -78°C + -35°C
OMe
n
. . Maletlch.; Leigh, A.J.; Condon, S. Tetrahedron Lett., 1991, 32, 605. . . -G.;
65%
n-C4H9 61%
Leigh, A.J. Tetrahedron Lett., 1991, 32, 609.
0.016M , 1M LiBF4 12 h , 25°C
0 Smith.;Houk, K.N.Tetrahedron Leu., Z991, 32. 1549.
quant.
Compendium of Organic Synthetic Methods, Vo18
518
' 0
A C 0 2 M e
Section 374
ECHO , COCI~ AczO ,MeCN 25"C,8h
Iabal.;Srivastava. R.R. Tetrahedron Lett., 1991, 32, 1663. CHO
LDA , TMSCl -78"C-+ RT 98 % Herscovici.;Bournaim, L.; Antonakis, K. Tetrahedron Lett., 1991, 32. 1791.
Ph
OEt
0
Po)
)LC 0 2 Et 6
PhCN
*
P
h
,24h
3 SOsNa
97%
4 CO2Et
Pd(dha)z Safi, M.; ~ Q L Q . Tetrahedron Len., 1991, 32, 2025.
10% CpRuCl(PPh3)z dioxane ,reflux , 1 h
Ph
* A Ph
Tray.B.M.; Kulawiec, R.J.Tetrahedron Letr., 1991, 32, 3039.
k% 74%
5% Pd(PPh)3)4, reflux, 1 h THF* Ph
Ph
E m . S,; Uh, K.H.; Lee, S.;Park, J.H. Tetrahedron Lett., 1991, 32, 3395.
1. EtAIC12, PhMe
2. aq. NH&I
Me
.-
c
Me
44%
Me
. . m; Hull, K.; Casares, A.M.; Khetani, V . J. Org. Chem., 1991, 56, 3958.
23%
Ketone - Alkene
Section 314
Php
A O A c
OH
519
,THF
Ru(C0)3(PPh3)2 , 12 'h K2CO3 ,150"C CO (10 Kg/cm2)
2Mi
Ph 76%
J, Org. Chem., 1991, 56, 487.
Kondo, T.; Mukai, T.;
LDA , THF , HMPA
+
0
&Me Me
61%
Mathew. J, J. Org. Chem., 1991, 56, 713. =ISnBu',THF,8O0C
&o
Pd(PPh314, LiBr 36 h
69%
Hettrick, C.M.; Kling, J.K.;Scott. W.J. .f. Org. Chem., 1991, 56, 1489.
NaOMe ,MeOH
fi
Me0
e- ,C anode, 13 F h o l stainless steel cathode =-
OMe
55%
M e 0 OMe Barba.;Chinchilla, R.; Gbmez, C. .I. Org. Chem., 1991, 56, 3673. 1. PhLi
2. aq. NH&l
do
3. 138°C
t-BuO
0
4.AgzO,K2C03
0
Heerding, J.M.; Moore. H.W,.I. Org. Chem., 1991, 56, 4048. 1. MeO2CCSC02Me , PhH 110"DC.2 h
b
Me,SiO
2. aq. H+
63%
' t-BuO
fi
C02Me
0
67%
C02Me
Thiemann, T.; Kohlstruk, S.; Schw*, G.; Pe Meiiere. A, Tetrahedron Lett., 199Z, 32, 3483.
Compendium of Organic Synthetic Methods, Vol8
520
Ph
Ph
H
"KO0
Section 374
1. PdCb(PhCN)2 2 eq. NEt3 NaCH ( C 4 M e ) t
2. co 3.
gc)@ 6 &....
Masters, J.J.;
SnMq
m; Tamariz, J. J. Org. Chem, 1991, 56, 5666. Cu(0Ac)z. 2 eq. Mn(OAc)3 AcOH
50%
18%
Snider.;Memtt, J.E. Tetrahedron, 1991, 47, 8663.
Me
hv ,CH2C12, EtI
SnMe3
-
*TGsph
Sato,;Takezoe, K. Tetrahedron Lett., 1991, 32,4003.
SPh OAc
Kudo, K.;
4311.
OSiMq
+
10%MegiOTf, CH2C12
-78OC --t RT
a; Hashimolo, Y.; Houchigai, H.; Hasegawa, M. Tetrahedron Lett., 1991, 32, (94
6)
1 . M g , THF 2. MeGnCl
<si~,,
3. AcCl , CHC13.1; 2% BnPd(PPh3)zCl 65OC
SiMe, 81%
Lane K-TJ Kim, S.S.; Lee, J.C. Tetrahedron Lett., 1991, 32, 4341. (BuCH=CH)2Zn, THF-DMF PdC12(PPh,)2 , 2 BuLi
87%
Neglshi.; Owczaczyk, Z.R.; Swanson, D.R. Tetrahedron Lett., 1991, 32, 4453.
688
’30)
Ketone - Alkene
Section 374
52 1
0
1.
p&Br
t-BuOK, THF , RT
CO2Et
2.2M HCIICH2CIz
RT
COzEt
*
82%
Ph
Hatanaka. M,; Himeda, Y.; Ueda. 1. Tetrahedron Lett., 1991,32,4521.
2. MeOH
hq,tI( +
0
C02Me
17%
57% J&Q. C-C,; Wei, C-P. Tetrahedron Lett., 1991, 32, 4553.
20%Cut, NMP air, benzoquinone
Me
0
Me
c
SnBu,
Liebeskind. L.&; Riesinger, S.W. Tetrahedron Lett., 1991, 32, 5681. 1 . 2 eq. Mg , THF 2. CuBreSMe2 0
0
Me
8WO
c
, -30°C
65°C
CI
Canonne. P,;Boulanger, R.;Angers, P. Tetrahedron Lett., 1991, 32, 5861.
aO O , , ~ ~ -- -.
I
Q
2 eq. CHzC12 KzCOJ.0.2 NaI
r-BuMe2Sid t-BuMe,SiO Larock.; Lee, N.H. Tetrahedron Lett., 1991. 32, 591 1 .
.
n- C5H1 1
0
62%
522
Compendium of Organic Synthetic Methods, Vol 8
Ph0,S
'd
Leon, F.M.; Carretero.
1.
0
,35h
Section 374
*
2. NaOEt ,EtOH ,0°C 25 min
91%
Tetrahedron Lett., 1991, 32, 5405.
&
PhSSPh , AIBN , hv
Tile &
Kim.;Lee, S . Tetrahedron Lett., 1991, 32, 6575. QSiMe,
snC14, Ck12C12 -70°C + -23":
Me0 Johnson,T.O.; i
/Lcsc
82%
,, OMe 68%
(6:l dr)
k a m ~ UTetrahedron , Lett., 1991, 32, 7361.
1<,. C-
1% IrHs(iP13)z 4% P B u ~, PhH
reflux, 31 h
0
c
73%
Guo, C.; !A,-& letrahedron Leu., 1991, 32, 7549.
0
C02Et
TMS-OTf ,CH2C12
RT
+y
31%
Andrews, J.F.P.; Remn, A.C. Tetrahedron Lett., 1991, 32, 7731. 1. SnC14, CH2C12 , 0°C 2. TMEDA, 20°C, 15 min
Nn-C6H'3 OSiMe3
Po
n-C6Hl3 /
90%
Nakahira, H.; Rvu. I,; Ikehe, M.; Oku, Y.; Ogawa, A.; Kambe, N.; Sonoda. N.;Murai. S . J. Org. Chetii., 1992, 57, 17. Nakahira, H.; Rvu. I,; Han, L.; K'ambe, N.; Sonoda. N, Tetrahedron Lett., 1991, 32, 229 [with TeC141.
Ketone - Alkene
Section 374
OH ( = ~R' T~, M 3h tio ether ~,
523
&f$+J
0
0
LL Od
U
85%
Pearson. WMt; Schkeryantz, J.M. -1. Org. Chern., 1992, 57, 2986.
Me- Cr*C
BF3*OEt2 , CH2C12
0 Me
24 h
Sisko, J.; Balog, A,; Curran. D.P,.I. Org. Chetti., 1992, 57, 4341.
Me)qo Ph OMe
iPrO
4.140"C,xy\ene 5 . CAN, aq. MeCN
Liebeskind.;Granberg, K.L.; Zh'ang, I. .I.
@ye n
1. BuLi
2. TFAA 3. 10%aq. NH4CI
c
57%
/
Bu
0
Org. Chetii., 1992, 57, 4345.
Pd(PPh3)4 , dioxane reflux
Bu3Sn\_ SnBu3
++ cC1
63%
Perez, M.; Castailo, A.M.; Escavarren. A.M. J. Orx. Chetn., 1992, 57, 5047. 1 . 2 eq. EtMgBr ,THF CRTiClz, -78°C
O k X - Ph
2. co,CHC13
Grossman, R.B.; Buchwa Id. S.L.J. Org. Chetti., 1992, 57, 5841.
r. R.L;Dixon, B.R.; Gleason, R.W. .I. Org. Cheai., 1992, 57. 6094.
49%
Compendium of Organic Synthetic Methods, Vo18
524
Section 374
Bu$n-CH=CH2 5% Pd(OAc)2, 3 LiCl
F
dppp , DMF ,90°C’ 24 h
86%
Badone.;Cecchi, R.; Guzzi, U. J . Org. Chem., 1992, 57, 6321. PhMe , 100°C , C O (3 atm) PdCI*(PPh3)2
*
CI
SnBu,
n-C6H 13&
tl-C6H13
58%
e2M
Baldwin, J.E.; Adlington, R.M.; Ramcharitar, S.H. Tetrahedron, 1992, 48, 2957. Me-CX-COzMe Ni(C0)4 , MeOH , RT
-
Me
72%
Me02C H
Camps, F.; Llebaria, A,; Moret6, J.M.; Pages, L. Tetrahedron Lett., 2992, 33, 113.
S02Ph
AA
1. MeN02 , DBU , RT 2. I-BuOK ,THF
Backvall, J-E.; Ericsson, A.M.; Plobeck, N.A.; Junlunen, S.K. Tetrahedron Lett., 1992, 33, 131. 1 . 2 eq. BuLi ,THF 2. B u ~ B 3. cuI
CF3CH20Ts
t
4. BzCl ,THF/HMPA
RT
F2C
Bu
78%
Ichikawa. J.; Hamada, S.; Sonoda, T.; Kobayashi, €I. Tetrahedron Left., 1992, 33, 337.
c o*t-Bu
1.2eq.LDA
0
2. PhiP-
COZt-Bu /
0
62%
Br
3. MqCHCHO
White.;Jensen, M.S. Tetrahedron Lett., 1992, 33, 577.
(16:l E,Z:E,E)
Ketone - Alkene
Section 374
Me
2p
,m p
=/S"J3"3
525
5% Pd(PhCN)zC12 10%CuI ,90°C, 20 min
81%
Me
Johnson. C.R,; Adams, J.P.; Braun, M.P.; Senanayake, C.B.W. Tetrahedron Lett.. 1992, 33, 019.
n-c3H76 6 Q 1. TI(NO3)z , MeOH
0
K2C03
OMe
2. hv h (310 (0.02nm/U M) glass)
C02Me
H ,.&
50%
Hong, F-T.; Lee, K-S.; Liao. C-C. Tetruhedron Lett., 1992, 33, 2155.
0s i( iPrh I
0
1 . PhlO ,TMS-N3, CH2C12 - 15OC
2. TBAF , THF , O°C
0
0
U
0
U
68%
Maenus. P.; Evans, A.; Lacour, .I. Tetrahedron Letf., 1992, 33, 2933.
&
FeC13 ,0.02M
CH,C12, -3°C
SiMe,
2h
*
49%
Kane. K-T.; Kim, S.S.; Lee, J.C.; Sun, U.J. Tetrahedron Lett., 1992, 33, 3495. 1.2 eq. BrClCHLi ,ether-THF -100°C
Ph
/
y C1
I1-C+I1 1
2. PhCHO , Et2AICI , Zn cat. CuBr , THF , -10°C O 59% Narita.; Takahashi, A.; Sato, H.; Aoki, T.; Yamada, S.; Shibasaki, M. Tetrahedron Lett., 1992, 33, 4041.
n-C5Hl
1. LHMDS
2. PhCH(Me)CtIO
0
OSiMe,
I)SiMe3
0
3. Me3SiC1 4.500"C. <1 sec (>98
2)
Ahmar. M.; Bloch. R,; Mandville. G.; Romain, I. Tetrahedron Lett., 1992, 33, 2501.
72%
Compendium of Organic Synthetic Methods, Vol8
526
cdMe
Ph ph>
rnCPBA ,CHzCl2
+
Section 314
Ph p h A * i M e 50%
Me
0
Sugila, H.; bkumJS. ; Saito, T.;
Tetrahedron Lett., 1992, 33, 2539.
;
’ & -
Kim.;Uh, K.H. Tetrahedron Let., 1992, 33, 4325. Pd(OAc)*, PPh,
CO2Me
[ KzCO3 P h M e,, R 16Th
Me
&Me Me02C 0’
76%
m; Benoit, S.; Kumanovic, S.; Sivavamakrishnan, H. Tetruhedron Lett., 1992, 33, 1407, 1403.
a, - & + &
Hunter.;Michael, J.P.; Walter, D.S. Tetrahedron Lett.. 1992, 33, 5413. B~
Sm12, 25°CTHF/MeOH , 2 in
(98
with NallTe , ElOH
Beerli, R.; Brunner, E.J.;
//
,&Fe(co)3
H
(< 1
2)
- Tetruhedrnn Lett., 1992, 33,6449. R eq. AICI3, CO (100 atm)
4 eq. Fe(CO)S, CH2C12 100°C. 12 h
t
H
>99)
85%
9S%
9’ 70%
Fmnck-Neumann, M,; Michelotd, EL.; Sirnler, R.; Vernier, J-M. 7etrahedron Lett., Z992, 33,
7361.
Ketone - Alkene
Section 374
P
527
Bu~S~H AIBN , 54%
Ph
Yamamoto. M.; Furusawa, A,; Iwasa, S.; Kohmoto, S.; Yamada, K. Bull. Chem. SOC. Jpn., 1992, 65, 1550.
,-
65, 2594.
Oikawa, H.; Ohrai, S . ; Sashiwa, H.; Saimoto, €1. Bull. Chem. Soc. Jppn.,. 1992, OSiMel
1.
Ph_
==iCpE t , BF3-OEt2
C H g l 2 , -78OC -+ 0°C) 2. s i q , PhH , reflux
0
Ph&c02&
88%
Sueimura.~.; Yoshida, K. Bull. Chem. SOC.Jpn., 1992, 6.5. 3209.
cf(co),
Ph-CsZ-Ph , reflux 1% aq. dioxane , 6 h syringe pump addition
phh 78%
Ph
OMe
(85:15
trans:&)
Tumer, S.U.; Herndon. J. W,; McMullen, L A . J. Am. Chem. SOC.,1992, 114, 8394.
8 0
Dowd. P.: Zhang, W. J. Am. Cheni. SOC.,1992, 114, 10084.
Iwasawa. N. Chem. Lett., 1992, 413.
48%
Compendium of Organic Synthetic Methods, Vo18
528
H
D
I 11
h
d
’I N ,c‘
*.
c
OEt
l.(CO)SCI=i Me 2. [FeC14] [Fe(DMF)3CI,]
b
Section 374
0
O
Y
53%
Ts
+S
Mori.;Watanuki, S. J. Cheni. SOC., Chetn. Commun., 1992, 1082. 1. LDA , -78°C fn-c7H1S
S02Ph
2.
-r
0
db
e
n-C7HlS
NO2
3 . 0 3 , CH2Cl2 4. Me2S , 0°C Awen, B.Z.;
84%
; Shiratani, T.; Yoshikoshi, A.; Irie, H. Cheni. Lett., 1992, 767.
CHzC12 CoTDCPP = [5,10,15,20-te~ra(2,6-dichlorophenyl)porphinato] cobalt (11)
Matsushita.;Sugarnoto, K.; Matsui, T. Chetti. Lett., 1992, 2165.
Fleck, A.E.; Hobart, J.A.; Morrow. G.W.Synrh. Cottittlun., 1992, 22, 179.
&
1.
OSiMe, , TiC14, 1 h
4Ph
*
2. TFAA , I5 min 3. NEtJ 4. H 2 0
Bouchlel, E.;
57%
Synth. Cottimun., 1992, 22, 2183.
c-..c
jtt’
CSC,
Pd(OAc)z, PPh3 PhMe, IIO°C,30h
“‘C3H7 Guo, C.; U SynLett, 1992, 405. n-qlI;
3”2’”
r
0 69%
Nitriie - Alkene
Section 376
529
REVIEWS : "Diels-Alder Reactions of Cycloakenones in Organic Synthesis" Frinyuelfi. F.; Taticchi, A.; Wenkert. E. Org. Prep. Proceed. lnt., 1990, 22, 131. "Regiospecific Alkylation of Cyclohexenones" Podraza. K.F, Org. Prep. Proceed. fnt., 1991, 23, 219.
"Symposia-in-Print - Organotitanium Reagents in Organic Chemistry" Reetz. M.T, (Ed.) Tetrahedron, 1992, 48, 5557-5754. "Recent Studies on the Peterson Olefination Reaction" Barrett, A.G.M.; Hill, J.M.; Wallace, E.M.; Flygare, J.A. SynLetr, 1991, 764.
SECTION 375: NITRILE
- NITRILE
(89
19)
:
6170
Curran. D.P,; Seong, C.M. J. Am. Chem. SOC., 1990, 112, 9401.
SECTION 376: NITRILE
PhCHO
- ALKENE SiMe3
Zn* ,THF , reflux 30 min
C=N
9s o/o
35:65 E:Z
palom0.c.;Aizpurua, J.M.; Aurrekoetuea, N. Tetrahedron Lett., 1990,31,2209.
OMe A
I/
N-OH
<SiMe3 10% TMSOTf CH$32.0°C.6h
L
C
N
61%
Fuiioka. H,; Miyazaki, M.; Yamanaka, T.; Yamamoto, H.; JCita. Y. Tetrahedron Lett., 1990, 31, 5951. 1. KzC03, H2O , CS2
TBAB , CHS12 2. aq. NaOH ,CS2
=-
(yCN 37%
RT Albanese, D.; Landini, D.; Penso. ILL; Pozzi, G. Synth. Commun., 1990, 20, 965.
530
Section 376
Compendium of Organic Synthetic Methods, Vo18
1. LDA , THF , -78°C 2. MOM-CI ,-78°C
Me$'> CN
3. NH4CI. H 2 0
Me C I A C N
b
76%
(58:42 ZE) Mauze, B.; M&M&L Synth. Commun., 1990, 20, 2251. BrCH2CN , PBu3, Zn
PhCHO
lOO"C, 16 h
*
PhCH=CHCN
68%
(75:25 E:Z)
Zheng, J.; Yu, Y.; Shen.
Bu-Cr C-H
Y, Synth. Contmun., 1990, 20, 3277. 1. siamylzBH, THF, -15°C 2. CuCN ,THF
Bu
\=i
b
65%
3. (Me2N)3PO CN 4. CU(OAC)~*H~O, THF Masuda.; Hoshi, M.; Arase, A. .I. Chem. Soc., Chem. Commun.. 1991, 748.
Et0'
s? .
1. LDA , THF 2. iPrCHO , -78°C 3 RT
*
OEt Et
A
E
t
Janecki. T, Synthesis, 1991, 167.
PhCHO
BnCN ,K2C03, MeOH b
65"C, 15 min
APh
Ph
CN
Ladhar, F.; El Gharbi, R. Synth. Contmun., 1991, 21, 413.
TsN,
Pi
0 ** S
LiCN ,DMF ,RT
e
Ph
Bailey, P.L.; Jackson. R.F.W.Tetrahedron Lett., 1991, 32, 3119.
Ph 6 N,
95%
~~
1. PPh3 2. Ph2C=C=OI RT
Z
P
h 81%
51%
Molina. P.; Alaiarin. M,; Lopez-Leonardo, C. TefrahedronLett., 1991, 32,4041.
55%
Section 377
53 1
Alkene - Alkene
PhCHO
+
CCN CN
ZnClz , 100°C
*
10min
PhwcN CN
91%
Rao, P.S.; Venkataraatnam, R.V. Tetrahedron Lett., 1991, 32, 5821.
Curran. D.P,; Seong, C.M.Tetrahedron, 1992, 48, 2157, 275.
c’c JSjMe3
0%
’& lI
Amberlyst 15
Me
[ p M e
r-
Schinzer. D,; Kabhara, J.; Ringe, K. Tetrahedron Lett., 1992, 33, 8017.
SECTION 377: ALKENE
80%
Me
- ALKENE
D
Y
I
5% PdCIz(MeCN)2, DMF , 2 0 ” C ,24h
Kende.;DeVita, R.J. Tetrahedron Lett., 1990, 31, 307. 1. BuLi , THF , 0°C
n-cd13CHO n-C,H , 0°C -+ 20°C
Ph3p\2h
’
Bi
SiMe3
H\ 82%
SiMe,
1E.3E: 1E,3Z 80:20
Shen.;Wang, T. Tefrahedron Lett., 1990, 31, 543. Na .DMF
Pavenli, M.; Hav. A S , Synthesis, 1990, 878.
532
Section 377
Compendium of Organic Synthetic Methods, Vol8
[Me3SiCI/NaI] m
35% (EZEE = 0.23) Hill. R.K,; Pendalwar, S.L.; Kielbasinski, K.; Baevsky, M.F.; Nugara, P.N. Synth. Commun., 1990, 20, 1877.
OH
MeCN , 15 min
OH
Ni(COD)2, dppb *
q c 6 H 1 3
Hj0
(>99
+
&c6H13
<1)
79%
7
Keller, T.H.; Kuo, D.L.; Pachinger, W. Tetrahedron Leff.,1990, 31, 1265.
;-
I.-O.COZE~
+ Pd(PPh3)4, "€IF -78°C -+ 40"C, 24 h (87:13 E Z ) 2. AcOH ,25"C, 6h Chen, Y.; Li, N-S.; pene_.M-2, Tetrahedron Lett.. 1990, 31, 2405. BU-
Ci C- B(n-C6H13)3
"""%
TBAF, THF n-C6H13 5% Pd(PPh3)4, 50°C n-C H
Hatanaka, Y.;
30 min
13+SiMeF7
99%
*w
Tefrahedron Lett., 1990, 31, 2719.
&A
Ph
1 . 4 eq. t-BuLi , -78°C 2. MeOH , -78°C
Theobald, P.G.; Okamura. W.H,.I. Org. Chem., 1990, 55, 741.
Ph
2
( &;u(CN)Li2
Ph
THF, -78°C
-B.H.;Elworthy, T.R. J. Org. Chem., 1990, 55, 1695.
82%
Alkene - Alkene
Section 311
533
(82:18 ZE) Tucker, C.E.; Rao, S.A.; Knochel. P. J. Org. Chem., 1990, 55, 5446.
OSiEt,
Tic13 I CBKI DME
Clive. D.L.L; Murthy, K.S.K.; Zhang, C.; Hayward, W.D.; Daigneault, S. .I. Chem. Soc., Chem. Commun., 1990, 509. 0 A
x ; r : 3
0
B
EtO2C
r ,12h
96%
NaHC03, CHzC1; RT
Hatanaka. M,; Himeda, Y.; Ueda. I,.I. Chem. Soc., Cherti. Commun., 1990, 526.
Ph-
'' '-
1. BuLi 2. AIMe2CI
- L+ L
3. CpzTi(Me)CI Ph 4. CH2=CH2, HMPA/THF 5. HClgaS),-78°C 6. aq. NaHCO3
Me
(4
1)
Dennehy, R.D.; Whitbv. R.L.I. Chem. Soc., Chem. Commun., 1990, 1060.
SiMezPhQH
KH ,THF , RT
(99.6:0.4 trans,trans:trans,cis)
Flemine. I,; Morgan, I.T.; Sarkar, A.K. ./. Chem. Soc., Chent. Contmun, 1990, 1575.
Karabelas, K.; Hallbern. A, Acta Chem. Scad., 1990, 44, 257.
534
Compendium of Organic Synthetic M e t h o d s , Vol8
n
phv
MeMgI , 5% NiC12(PPh3)2
*
PhH , 2 0 h
Ph
Section 377
61%
SiMe3
Ni, 2-J.; Yang, P-F.; Ng, D.K.P.; Tzeng, Y-L.; Luh. T-Y, J. Am. Chem. Sac., 1990, 112, 9356. 0.5 eq. Mo(C0)6 ,H 2 0
20 h
OAc
t
Ph
50%
(1:l E:Z)
m a . Y.; Maekawa. K.; Kurihara, T.; Kurusu, Y . Bull. Chem. Sac. Jpn., 1991, 64, 2311. 1. MesSiCH2MgCl
PhCHO
2. c r o # y
*
'"p 56%
3. CHZ=CHMgBr 4. AcOH , NaOAc Brown, P.A.; Bonnert, R.V.; ;Lawrence, N.J.; Selim, M.R. .I. Chem. Sac., Perkin Trans. 1, 1991, 1893.
ci c-H
&
2.5% Pd2(dba)&HC13
EtO2C ELO~C
P(n-Tol)3 , RT , PhMet
EtO$ EtO2C
85%
Trost. B.M,; Shi, Y.J. Am. Chetii. Sac., 1991, 113, 701. Trost. B.M,; Lautens, M.; Chan, C.; Jebaratnam, D.J.; Mueller, T. J. Atti. Chetii. Sac., 1991, 113, 636.
(2.8
a
I)
Trost.;Trost, M.K. J. Am. Chetii. Sac., 1991, 113, 1850.
Q
1.
0
2. l'y , reflux
new allene equivalent
46%
w.R.V. ; Chauhan, K. .I. Chem. Sac., Chetii. Conitnun., 1991, 1672.
60%
Section 377
a \
Alkene - Alkene
0
N
S
seA
1.
ph
Shibaa, K.; Shiono, H.;
535
=(M ~ c ~ BF3'OEtZ *
*
CH2C12-THFI 0°C 2. PPh3 3 . 2 eq. NaH ,THF
Ph
98%
Chem. Lett., 1991, 661.
t-Bu
Me3S=O+ I- , NaH DMSO , 130"C, 30 z n
Yurchenko. A.G. ; Kyrij, A.B.; Likhotvorik. LR,; Melnik, N.N.; Zaharzh, P.; Bzhezovski, V.V.; Kushko, A.D. Synthesis, 1991, 393. 1. Brz , CHzC12, -78°C 2. ZnClz , J OSiMe:,
dOEt
b
3. Zn ,EtOH
Ohm, S.; BPuml, E.;
Cheni. Ber., 1991, 124, 2785.
t-BUOK, DMSO , 140°C
t
0
87%
7
59%
kOA -
Arenz, T.; Vostell, M.; Frauenrath. H. SynLetf, 1991, 23.
c1
F M s C l , T H F
OAc
CuCN.2 LiCl , 0°C 0.3 h
+ \
88%
8%
OAC
BH
Yanagisawa, A.; Noritake, Y .; Nomura, N.; Y amamoto. H, SynLetr, 1991, 25 1.
K
SnMq
1. LDA ; PhN(SqCF,), -48OC .+ RT 2. 5% Pd(PPh3)4, THF ,RT
~
Piers.%;Friesen, R.W.; Keay, B.A. Tetrahedron, 1991,47, 4555
0
0
K
60%
536
Compendium of Organic Synthetic Methods, Vol 8
Section 377
p
1. bBuLi , TMSCl 2. Na ,DMAN NHEt2
SiMe,
(E/z > 10)
-x
61%
Chan. T.H,; Labrecque, D. Tetrahedron Lett., 1991, 32, 1149. acetone, PhMe , 6OoC
798%
Doxsee.;Mouser, J.K.M. Tetrahedron Lett., 1991, 32, 1687.
c1
c: c 7c1
2 eq. n-CsH17 - Zn Br
" " R H ~ n " 8 ~ ~ ~
CuCN.2 LiBr , THF
Zhu, L.; Rieke. R.D. Tetrahedron Lett., 1991, 32, 2865.
Bu
'qPh I-BuOH , r-BuOK 8OoC
6
78%
Sellen, M.; Backvall. J-E,; yelauist. P, J. Org. Chern., 2991, 56, 835.
Q
'.
Me,Si
b
B
Me THF,9h
2. NaOH , YO2 , 3 h
61%
Wane. K.K,; Liu, C.; Gu, Y.G.; Bumett, F.N.; Sattsangi, P.D. J. Org. Chein., 1991, 56, 1914. PdCl(croty1h
c1 n-C5H I 1
nC5H ~ L
~zrcpzc' "€IF , -7PC - RT *
7R)
(22
Hutzinger, M.W.;
. J. Org. Chetn., 1991, 56, 2918.
0
OH
1. Ph' s2. 100°C
-
n-C,H
C(OEt)3, H+
t
EtO,C
11
87%
75%
Posner. G.H.; Crouch, R.D.; Kinter, C.M.; Carry, J-C. .1. Org. Chern., 1991, 56, 6981.
537
Alkene - Alkene
Section 377
1.5 eq. BuMgBr 0.3 eq. Cul
OAc
*
THF,2h
n-C7H 15
Bu
n-C7H1 5
83% (909 EE:EZ) Nakanishi, N.; Matsubara, S.; Utimoto. K.; Kozima. S.; '.maguchi, R. .I. Or& Chern., 99 56, 3278.
P
h
S
-78°C -+ -30°C
1. BuLi , ether, -60°C
.
e OMe 2. MeOH RT
P
h
W
B
U
50%
(60:40 lE,3E:1Z:3E)
Gaonac'h, 0.;Maddaluno, J.; Chauvin, J.; h b 5 L L . . l . Org. Chern., 1991, 56, 4045.
Bu-B' Brown.=;
tJ
1.
Bu
Bu
%
Li
*
2. EtC02H
\
Bu
70%
Bhat, N.G.; Iyer, R.R. Tetrahedron Lett., 1991, 32, 3655.
Zair, T.; Santelli-Rouvier, C.;
'
Tetrahedron Lett., 1991, 32, 4501.
-
%c1 ,THF , -30°C
Pd(dbah , PPh3 ,40 min
T2%
Nystriim, J-E.; VBgberg, J.O.; Siiderberg. B.C. Tetrahedron Lett., 1991, 32, 5247.
Me0
OH
OMe
pOCI3, Py
Me0
*
90%
OMe
Runk, C.S.; Haverty, S.M.; Klein, D.A.; McCrea, W.R.; Strobel, E.D.; Pinnick. H.W. Tetrahedron Lett., 1992, 33, 2665.
538
Compendium of Organic Synthetic Methods, Vol8
Section 377
D M S O , 16OOC
&Ph Ph Patro, B.; U;
5h
*
Ph
Ph
85 96
Tetrahedron Lett., 1992, 33, 809. PhI ,cat. Pd(0Ac)t ,DMF
81%
Jeffery. T. Tetrahedron Lett., 1992, 33, 1989.
2. HzO
(65
35)
Araki, S . ; Imai, A.; Shimizu, K.;W m n . Y ,Tetrahedron Lett., 1992, 33, 2581.
0
0
0
I-Ph BF4
ph-SnBq
*
(
PdCl2(MeCN)2, 1 h DMF Epa, W.R. Tetrahedron Lett., 1992, 33, 4095.
;-
OH
Et
1. Bu3SnH ,AIBN ,W"C
LC
91%
p
h 63%
&
L C T
F C . ~ - 2~. MsCl ~ ~,N,E t~3 , CH2& O°C 4 RT
n-C6H 13
71%
Konoike.,Araki, Y .Tetrahedron Left., 1992, 33, 5093.
24)
(76
Take&. T.; Takagi, Y.;Takano, H . ; Fujiwara, T. Tetrahedron Lett., 1992, 33, 5381.
H- CE CJ Maeta, H.;
SiMe3
.
1. CpzZr(H)C1
2. n-CloH21CH0, CH2C12 cat. AgC104 , RT , 1 h 3. reflux, 1 h
Tetrahedron Lett., 1992, 33, 5969.
*
76%
*
n-C ]OH21 (97:3
E:Z)
82%
Ph-C=C-SnMe3 Mes = mesityl
-;Smith.;
1. (Mes)zBH 2. Mes-Li 3.PhCH0
Takacs.;Zhu, J.; t-BuMe2Si 0
61%
4. TFAA
Jones, K.D. .I. Chem. Soc., Perkin Trans. I, 1992, 141.
2 eq. PPh3 ,65"C
Meo2c<Me
PhCH=C=CHPh
>
Me0,C-
5% Pd(OAc)z, THF
Me02C
539
Alkene - ALkene
Section 377
\
-- Me0,C
'..
3
wB:
Me 9s%
Chandramouli, S. J. Am. Chetn. SOC., 1992, 114, 113. P ~ I M ~r
- B u M e Z S i O m
5% Pd(0Ac)z * 15% PPhj, NEt3
62%
Trost. B.M.; Pfrengle, W.;Urabe, H.; Dumas, J. J. Am. Chein. Soc., 1992, 1 1 4 , 1923. 1. PhLi ,ether 2. NaH ;Me1 , TAS
Me3s4+
3.ZnBr2, CH2C12 RT, 1 h
(92:8
E:Z)
Fujiwara, T.; Suda, A.; Takeda. T, Chetti. Lett., 1992, 1631. 1. M e 3 S i A B r
PhCHo ;
CrC12, cat. NiCl2, DMF* 2. aq. HCI, THF
Ph% 14% (>10:1 transcis)
Parsons, P.J.; Naylor, A.; Tyrrell, E. SynLett, 1992, 599.
REVIEWS:
"Synthetic and Mechanistic aspects of 1.3-Diene Photooxidation" -Tetrahedron, 1991, 47, 1343. "Nickel (0)-Mediated Intramolecular Cyclizations of Enynes, Dienynes, bis-Dienes,
and Diynes"
Tamao.; Kobayashi. K.; ]to. Y. SynLett, 1992, 539.
540
Compendium of Organic Synthetic Methods, VOI8
SECTION 378: OXIDES
f
-
Section 380
ALKYNES
0
0 fCzef'OMe
P(OMe)3
Cf C-I-Ph
RT
*
'OTs
90% J. Org. Chem., 1990, 55, 1513.
Lodaya, J.S.; Koser.
iPr2NH1 Tf20,O"C
0
SOzPh
Et
CHzClz
* Et-CrC-SO,Ph
81%
SynLett, 1992, 825.
Clasby, M.C.;
SECTION 379: OXIDES
- ACID DERIVATIVES
NO ADDITIONAL EXAMPLES
SECTION 380: OXIDES
-
- ALCOHOLS, THIOLS 1. pyridine, THF 2. n-BuLi , -45°C
,qN ~ I o ~ , M ~ O fi H s v s
S
o.S,
0
3. n-BuCHO -78°C. 10min 4 . 2 N HCI
B~
Bli
49%
34%
m a l . V.K.;Davies, I.W.; Maddock, J.; Mahon, M.F.; Molloy, K.C. Tetrahedron Lett., 1990, 31, 135.
p:5
SiMe3
OH
PhCHO , TBAF
THF , -70°C
p:Yop:
75%
Cheng, H-C.; &u,-T. Terrahedron Lett., 2990, 31, 673.
0 EtO' p# EtO
Br
1. Z n , THF, 30°C 2. CuCN , 2 LiCl 3. PhCHO *
0 EtO'P'/YPh OH EtO
also with ketones, acid chlorides, conjugate addition
Retherford, C.; Chou, T-S.; Schelkun, R.M.; Km&AJ,
964 - - ..
Tetrahedron Lett., 1990, 31, 1833.
Oxide - Amide
Section 382
PhOZS,
SOT01
MeCN ,
,y
0°C
CHO
5h . Tetrahedron Letf.,1990, 31. 2487.
Dominguez, E.;
1.2.2 eq. LDA
Ph. S+OH
0' 5
0
54 1
THF ,-7 - -20°C t 2. Me1 , -78OC .+ RT
86%
Me Ph.S/COH
(j
ye
+
Ph,S+OH
(jt
0
-00
(7 Ohta. H,; Matsumoto, S.; Sugai, T. Tefrahedron Lelr., 1990, 31, 2895. I . BuLi, THF
P h 0 2 S y y Me - 7 8 ~ OMOM 2. KF MeOH Me,Si
Bu Ph@S+Me
9
(89
0
1)
85%
Bu + P h 0 2 S 4 M e
OMOM
11)
OMOM 85%
Alcaraz, C.; Carretero. J.C.; Dominguez, E. Tefruhedron Leff.. 1991. 32, 1385.
Trost. B.M.; Granja, J.R. Tefruhedron Left., 1991, 32, 2193.
(67:33 ery1hro:lhreo)
; Vilchez, J.E. TefruhedronLeft.,1991, 32, 3225.
FernAndez, R.; Gasch, C.;
Bu
P h 0 2 S J S -(->'I
CHO
'
1
B
c
MeCN , piperidine ,RT
u
p S02Ph
OH
79%
oO"
Trost. B . W ; Grese, T.A. .I Org. . Chetn., 1991, 56, 3189. rnontlnorillonite , 15 h
TolS02NaI Hfllacetnne PhH , RT
-
75%
"'S0,Tol
Biswas, G.K.; Bhattachaw. !a. P. Synfh. Commun., 1991, 21, 569.
Compendium of Orgbnic Synthetic Methods, Vo18
542
Section 380
Solladie.;Colobert, F.; Ruiz, P.; Hamdouch, C.; Carrello, M.C.; Garcfa Ruano, J.L. Tetrahedron Lett., 1991, 32, 3695.
OH
-/
OAc
Ph0,S
46% (>98% ee ,S)
(>95% ee , R) . ;Femhdez-Mayoralas, A.; Conde, S. Tetrahedron Lett., 1991,
Dominguez, E.; 32, 5159.
p$ 0
+ P h O 47% , S y
PhQS*
. t
0,
QAc
OH
.
, iPnO.5.5 h
1. NaHDMS ,0°C 2. PhCHO ,0°C
3. HCI, EtOH
Ph
-
0
0 (96
4)
87%
Aggmval. V . L ; Franklin, R.J.; Rice, M.J. Tetrahedron Lett., 1991, 32, 7743.
0
7'1 Ph
1. LDA , THF , -78°C 2. iPrCHO , -78°C , 5 min
OH
3.H30'
Bn
Bn
1)
(4
Caset.;Muxhejee, I.; Trabsa, H. Tetrahedron Lett., 1992, 33, 127. OH
Zn(BH4)2, DME
* &NO2
5 min
Ranu.; Das, A.R. Tetrahedron Lett., 1992, 33, 2363.
73%
(40:60)
!?
EtO.y-CH,/BuLi,THF OEI
fh
-78°C
2. BF3*OEt2 , -70°C 2h
Racha, S.; Li, Z . ; El-Subbagh, H.;
*
Q
EtO-P-ph OEt
OH quant.
Tetrahedron Lett., 1992, 33, 5491.
90%
543
Oxide - Amide
Section 382
SECTION 381: OXIDES
- ALDEHYDES
9 do?- OMe
1.
0 0-f- ()Me OMe CHO
,acetone/CH2Clz
-10°C 20"C, 2 h 2.RT. 1 2 h
OMe
n-C5H1 1
>c8
n-CSH1ly 99%
Adam. W.; Hadjiarapoglou, L.; Klicic, J. Terrahedron Lett., 1990, 32,6517. 1. CHz=N-NMez CHZC12, RT 2.03
yNo2
-
OZNyCH0
74%
3. DMS Cassaletta. J-M,; FemAndez, R. Tetrahedron Lett., 1992, 33, 3691.
SECTION 382: OXIDES
MeS
f
- AMIDES 1. MeCN, 30°C
OZ
.cN.,, 4 NO2
2. Hg+2,aq. MeCN 30°C
SMe
>70%
treatment wih NazS led to thioamides Manjunatha, S.G.; Reddy, K.V.; & .& ap
CbzHN ,-
J+COzH
S. Tetrahedron Lett., 1990, 31, 1327.
1. Pb(0Ac)d , DMF 2. P(OMe)3 , Tic14
CbzHN
&OMe
P,
0 OMe 76%
Green, 1.M Tetrahedron Lett., 1990, 31,6827. 1. BnNH2, 30"C, THF, 18 h 2. NEt3 , THF , 19 h Pb-cz c q c , , NO,
3. t-BuOH ,THF ,30"C cat. Triton B , 4 8 h
t
0
Bn
49%
Patra R.; Maiti, S.B.; Uumje~A ;Chakravarty, A.K. Tetrahedron Lett., 1991, 32, 1363.
Compendium of Organic Synthetic Methods, Vol8
544
Me
*N-Ph
NO, 3 eq. Et3SiH , DCE 5% Co (salen) derivative
Me
ON
RT
0
Section 383
77%
0
Kato, K.; Mukaiyama, T. Chern. Lett., 1990, 1395.
0N CH,
To1 1. LDA, e
2. LDA , CH2=CHC02Me
Hua. D.H.; Bhafathi, S.N.; Panangadan, J.A.K.; Tsujimolo, A.
S02Ph
Bn
N=\/\,OBn
+
(0
cop
Green, D.L.C.; -C.M.
,i.Org. Chern., 1991, 56, 6998.
CoB S O2Ph
B F,*OEt, THF, -78°C
76%
0
Tetrahedron Lett., 1991, 32, 5051.
SECTION 383: OXIDES
- AMINES 1. (CHZO),
NaOMe 2. P(OMe),
0.OMe
H rP\
Tic14
Ha.;Nam, G-S.; Park, K.P. Tetrahedron Lett., 1990, 31, 1567. N S
DBU ,o-xylene reflux, 18 h
'@
oo
79%
Chucholowski, A.W.; Uhlendorf, S. Tetrahedron Lett., 1990, 31, 1949.
phQsx
1 . BnNH2 , CH$&/MeOH 2. NaOMe
PhQS
*
Padwa. A, ; Norman, B.H. J. Org. Chern., 1990, 55, 4801.
rrPh J !
Bn
quant
Oxide - Amine
Section 383
0
i,,,N H M ~1. BuLi, THF
Me' \
PhHN
*g
____c
2. ECH=NPh
Ph
545
PhHN Et
+
-
(94 Dikic, B. Tetrahedron Lett., 1990, 31, 5231.
&RLS&;
6)
68%
- Q-0
TolS02CH2CI Bu3SnHI AIBN
n
Ph
H MeHN
MeHN
GNU0
PhH , reflux
54%
S02T0l
(84:16 cis:trans) Renaud.; Schubert, S.Angew. Chem. Int. Ed. Engl, 1990, 29,433. **#.
p
To1°'s4
Me NHBn
L-Selectride ,CH2Ci2 -20°C , 6 h
57%
Tol'
Qeura.;Tomori, H.; Fujita, M. Chem. Lett., 1991, 1407.
(97:3 RR:RS)
Bn
Bn
I. LDA , THF , -78°C 2. BnBr
Bu
Bu
(34 Bell, S.I.; Parvez, M.; p J. Org. Chem., 1991, 56, 373.
PhO,S Ph
N - H ,25"C
SO2Ph
c
66)
qih
96%
!)o%
SOZPh
W w a . A.; Gareau, Y.; Harrison, B.; Norman, B.H. J. Org. Chem., 1991, 56, 2713. N O 2 . 0 3 ,
(4.4
1)
98%
Suzuki.;Ishibashi, T.; Murashhna, T.; Tsukamoto, K. Tetrahedron Lett., 1991, 32, 6591.
546
Compendium of Organic Synthetic Methods, Vol 8
9
-
n-CsHj4kN-O ))))))))
Me
9h - 9-j
P
Me
Ph
4
4
a Ph-,P+9 Ph
+
86%
Pli Me
= NiCb.6 H20, NaBH4, MeOH
OH NH2 Me
79%
0-
' 0 Ph
a
'
Section 383
Me
95%
h s u o n g , S.K.;Warren. L; Collington, E.W.; Naylor. A. Tetrahedron Lett., 1991, 32, 4171.
H
Y
cat. Os04
NMO
Priebe.;Grynkiewicz, G. Tetrahedron Lett., 1991, 32, 7353. 1. PhCH2NH2 2.ZnBr2 , Dihal
To1
Ph
*
3h
BnHN
0
;5
Ph
..
+
To1
BnHN ph&
(>97
Ruano.;Lorente, A.; Rodriguez, J.11. Tetrahedron Lett.. 1992, 33, 5637. 1. t-BuLi ; BnBr 2. HCl-HzO, pH 2-3
Ph. q
h
h
3. H2 Pd(OH)2/C MeOH
Me0- P-, '"0 OMe
I
9
-
MeO'bMe pq
(76%ee, R) Maury, C.: Royer, J.; Husson, H-P. Tetrahedron Lett., 1992, 33, 6127.
ccs s."
/& gbb
95 m o l 8 AgOS02CF3
CHzClz
phJ-
Ph
00
Ph+
@
'Ph
(major)
+
<3)
9
%l;.bl 80%
NH2
Ph 26% overall
Q.., Ph-&PO
81% (95% dr)
@
Ph
Davies, I.W.: Gallagher. T.: Lamont, R.B.; Scopes, D.I.C. J. Chem. Soc., Chem. Commun., 1992, 335.
Section 384
Oxide - Ester
0
HN3, PhH , DEAD, PPh3
EtO' EtO
CH2Cl2, -10°C
OH
547
'<
0
-+ RTc
EtO' * EtO
WT.; Matusiak, M. Synthesis, 1992, 367. &Me2
1. t-BuLiRT ,pentane
NMe2
2. EtSSEt , THF 0°C 3. NaB03.4 " 2 0 AcOH.RT,lSh
~
+
88%
N3
M
e
5- Ex
S- Et A 0
0
13%
76%
Shimazaki, M.; Takahashi. M.; Kornabu, H.; Ohta. A,; Kajii, K.; Kodama. Y. Synthesis. 1992, 555.
SECTION 384: OXIDES
- ESTERS 1 . LDA .THF . -78°C: 2. TOISO~F, T~IF
>r
)-Co2Me
RT,3h 3. aq. NH4CI Kende. AS,; Mendoza, J.S. .I. Org. Chern.. 1990, 55, 112.5.
*
C02Me
E t N Q , K2CO3,2 h Aliquat 336 , ))))))
87%
$-YC02Me 90%
NO2
Jouglet, B.; Blanco, L.;
SynLett, 1991, 907.
0
C02t-Bu C02H
*
COzMe SOZTol
CHzCl2 -20"c
&!-,.ol
&!.
To1
+
CO3H
COzt-BU COZH
co,t-ETu
(89
75.85%
6)
Alonso, I.; w e r o . J.C,; RWQQJJ& Tetrahedron Lett., 1991, 32, 947.
p h o 2 s ~ ~ M e
1 . CH2(0Me)2, P2O5 CHCI3
2. BuLi , THF, -78°C * 3. Amberlite IR , Me011 CF3SO31I
Carretero.;Rojo, J. Tetrahedron Lett., 1992, 33,
7407.
PhO2S
0
0
42%
Me
2
Compendium of Organic Synthetic Methods, Vo18
548
Section 385
Bllini. R,; Petrini, M.; Polzonetti, V. Synfhesis, 1992, 355.
SECTION 385: OXIDES
-
ETHERS, EPOXIDES, THIOETHERS
1. PhSeBr ,THF ,-78°C 2. HgClz , AgNOz
0
MeCN
3. Hz@, MeOH * NaOH , 5 min Najera, C.; Yus, M.; Karlsson, U.; Gogoll, A.; BSLckvall, J-E. Tetrahedron Lett. 1990, 31, 4199.
OEt
TolS02CH2Cl
r=/
Bu3SnH, AIBN PhH penaud. P, Tetrahedron Lett., 1990, 31, 4601.
*
PhSH , MeCN , RT 0.1 eq. NEt3
TolO2S-OEt
40%
1. PhS-, THF, RT
2. AcOH , -78°C (88:12 transxis , 88%)
(0:lOO trans:cis , 88%)
Kamimura. A,; Sasatani, 11.; Hashimoto, T.; Kawai, T.; Hori, K.;Ono, N. 1. Org. Chem., 1990, 55, 2431.
NaH ,t-BuOK , THF
-4- 0''L ! 302Ph 80%
Padwa. A,; Murphree, S.S.; Yeske, P.E. J. Org. Chem., 1990, 55, 4241.
1. MeLi
Me
Ph
S02Tol
2. so2
ph&Me S
40%
S02T0l
Braverman, S.; van Asten, P.F.T.M.; van der Linden, J.B.; Zwanenbu rc. B, Tetrahedron Lett., 1991, 32, 3861.
Section 386
Oxide - Halide
t-BuOK, t-BuOH
-
THF , 2 5 T , 4 0 min
549
Ph02S*
(57
43)
81%
Grain. D,; Smith, A.M. Tetrahedron Lea., 1992, 33, 695.
OH
-
1. TsI ,MeCN RT (overnight)
2. K2CO3, MeOH reflux, 5 h Edwards.G.L,; Walker, K.A. Terrahedron Lett., 1992, 33, 1779.
SECTION 386: OXIDES
- HALIDES, SULFONATES FCH2S02Ph (Et0)2P(O)CI
P h q F SOzPh
LDA
95%
( 1 3 1 E:Z) McCarthv. J.R,; Malthews, D.P.; Wwards, M.L.; Sremerick, D.M.; Jarvi, E.T. Tetrahedron Lett., 1990, 31, 5449.
e
c1
CuC12, AlBN c
S0,Cl
150°C
\cjso2
12%
Culshaw, P.N.; ~~IQILK Tetrohedron Lett., 1990, 31, 6433. 1. sec-BuLi , THF, -105°C 2. SiMe3
3. H 2 0 4. TBAF hmJd. J. Org. Chem., 1990, 55, 3622,
0
''
M
e
0 SOzNClz
79%
/
-
S02Ph
'c
0
MeMeCN ,20"C Kim. Y.H,; Lim, S.C.; Kim, H.R.; Yoon, D.C. Chetn. Lefr.. 1990, 79. Me'
Me
c1
80%
550
Compendium of Organic Synthetic Methods, Vol8
F
o
P- OEt
F OEt Yang, Z-Y.;
Section 387
F
:
E
t
85%
Tetrahedron Letf., 1991, 32, 1019.
BzzOz, PhSOzCHzI 1 0 0 ~ tube) ~ ;
~
~
66%
Mw&M, Tetrahedron Left., 1991, 32, 3259.
RT,48h 18%
2. aq. NaOH Walters. T.R.;Z&g. W.W. Jr,; Woods, J.M..I. Org. Chem, 1991, 56,316.
0 EtO- P- CHF, EtO
1. LDA, THF 2. C ~ H I ~ C H THF O , , -78°C 3.
0 P h o l CI
0
EtO'
p-
c/-
OEt F2
4. Bu3SnH , AIBN reflux Martin.; Dean, D.W.; Wagman, A S . Tetrahedron Lett., 1992, 33, 1839.
SECTION 387: OXIDES
C6H 13
73%
- KETONES
Swindell.;Blase, F.R.; Eggleston, D.S.; Krause, J.
(85:15 diastereomeric ratio)
Tetrahedron Left., 1990, 31, 5409.
Oxide - Ketone
Section 387
O '
I . Ph-C=CH, heat
55 1
* Ph
0A To12. heat '
0
96%
Heifer, K-P.; Himbert G,Tetrahedron Lett., 1990, 31, 5725.
@
Br PhO,S<
B~
excess NaOMe
C02Me
*
MeOH,25'C
0
52%
Murphree, S.S.;Muller, C.L.; Padwa. A. Tetrahedron Lett., 1990, 31, 6145. 1. LDA ,THF, -78'C 2. Ph2PCI , THF , -78OC 3 . 0 2 , THF , RT
*
0
9- Ph
h& :
88%
Mikohjczyk, M.; Kielbasihski, P.; Wieczorek. M.W.; Blaszczyk, J.; Kolhe, A. J. Org. Chem., 1990, 55. 1198.
Ph.;-Cl 0
1. LDA ; n-C9H&HO 2. LDA
0
c
Ph'
0
'G n-C9H
Satoh, T.; Fujii, T.; Yamakawa. K . Bull. Chem. SOC.Jpn., 1990, 63, 1266. Satoh, T.; Hayashi, Y.; Mizu, Y.; YamJawa. K.Tetruhedron Lett., 1992, 33, 7181. &C02)4
1. CH2CI2, cat. N SOzPh Ph02S
2. aq. NaOH 3. aq. NH4CI
-8
930/0
Rh2
,I* S O 2 P h
M~ >90% (30% ee) Kennedy, M.; McKervey. M.A.; Maguire, A.R.; Roos, G.H.P. .I. Chern. Soc., Chem. Commun., 2990, 361. 0
,lager. V,; Seidel, B.; Guntrum, E. Synthesis, 1991, 629.
552
Compendium of Organic Synthetic Methods, Vo18
+oSiMe21-Bu Ph
.
-
OSiMe$-Bu DMF RT , 1 d
2.5 eq. Mn(pic)3
+
02NQph 74%
Section 387
nPh 6%
phq -*pH
Mn(pic)3 = manganese (UI) 2-pyridinecarboxylate Narasaka, K.; Iwakura, K.; Okauchi, T. Chem. Len., 1991, 423. 2 eq. Mn(OAc)y2 H2O Ph Cu(OAc)yH20125"C w
?!
0
AcOH , 1 4 h
40%
Snider. B.B; Wan, B.Y-F.; Buckman, B.O.; Foxman, B.M. J. Org. Chetn., 1991, 56, 328.
0
KH , DMSO ,20"C 45 min
*
0
carbanion acceleraied Claisen rearrangement Denmark.;Marlin, J.E. J. Org. Chetn., 1991, 56, 1003.
0
phO!+ Ph Me
74%
60% aq. AcOH , 100°C PhSO$Ja, 12 h
SOZPh W w a . A; Bullock, W.H.; Dyszlewski, A.D.; ; Shankar, B.B.; Ganguly, A.K. J, Org. Chem., 1991, 56, 3556. Padwa.;Bullock, W.H.; Dyszlewski, A.D. J. Org. Chetii.,1990, 55, 955 [with vinyl sulfides]. 1 . LDA , ether 2. (Et0)2POCl
3. air
Lee, K.; Wiemer. D.F, J. Org. Chenz., 1992, 56, 5556.
A
1. P(OEt3)
2. NBS , CH2C12. -5OC-
5
McClure.;Grote, C.W. TetrahedronLett., 1991, 32, 5313.
OEt P'OEt 0
78%
Oxide - Alkene
Section 389
& 0
0
?yOl
SnMe)
9
CH2CI2 , - 7 8 T
TiC1,
553
c
6 ,,,& Me
Me
(40
1) erythrotthreo
Tetrahedron Lett., 1992, 33, 1469.
Pan, L-R.;
1 . 3 q.LDA , THF-HMPA Et -35°C c
.
2.EU -35°C + RT , 3 h
+
NO2
Et
NO2
(84
16)
65%
Ballini, R.; Bartoli. G.; Castagnani, R.; Marcantoni, E.; Petrini, M. SynLett, 1992, 64. REVIEWS:
"Recent Progress in the Synthesis and Reactivity of Nitokelones" Rosini. G,; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proceed. Int., 1990, 22, 707.
SECTION 388: OXIDES
- NITRILES 0
90%
Garcia Ruano, J.C.; Martin Castro, A.M.; Rodriguez, J.H. Tetrahedron Lett., 1991, 32, 3195.
SECTION 389: OXIDES
- ALKENES 1. n-BuLi
3. Na(Hg), RT H3P04.4 h
63%
Chou. S-S.P.; Sun, C-M. Tetrahedron Lett., 1990, 31, 1035.
=c
SO,Ph
1. LDA ,THF , -78°C
2.
Me&C02E7
3. aq. HCI
phQs*
Me' 75%
C0,Et
Ghera. E.; Yechezkel, T.; Hassner. A, Tetrahedron Lett., 1990, 31, 3653.
Compendium of Organic Synthetic Methods, Vol8
554
Section 389
5)
(95
72%
W r a . K,; Yahata, N.; Fujimori, T.; Fujita, M. Tetrahedron Lett., 1990, 31, 4621.
1 . 2 LDA ,THF, -78OC 2 . 2 TIPS OTf
& P- OH
-78°C
81%
Lett.. 1990, 31, 4831.
De, B.; -Tetrahedron
3 eq .
OiBu 4
BuSSBu
SO2Ph
;-&
OiBu
Ph02S
~IV
with MeSSMe. 31:69 &:trans, 66%
81% (67:33 cktrans)
Sineleton. D.A.; Church, K.M.; Lucero, M.J. Tetrahedron Let[., 1990, 31, 5551.
Ph
1 . 2.2 eq. LiTMP , THF 2.Seq.DMF 3. TsCl
0
i,
'
TBDMSN
Me 4. Bu$h(CN)Li2 ether, -40°C
4
Ph
+TBDMsij 0°C
Paleu.; Snow, S.R. Tetrahedron Lett., 1990, 31, 5853.
FNo2
48%
Bu
H G C C Q M e , KF DMSO.Bu4NCI
C02Me 90%
Anderson, D.A.; Hwu. J.R,.l. Org. Chem., 1990, 55, 511.
Ph-O.
s.oII
Pdz(dbah. P WRT th PhH ,dioxane, 18 h
ph&o-s*o-
0 II
0 0 Tamaru. Y. ; Nagao, K.; Bando, T.; Yoshida, Z. J. Org. Chem., 1990, 55, 1823.
Oxide - Alkene
Section 389
555
TolSOzSePh , CHC13 AIBN , reflux
Y C i C - H
92% (8:l E:Z) Back.; Lai, E.K.Y.;Muralidharan, K.R.J. Org. Chem., 1990, 55, 4595.
d + X
hv , BuSSBu neat
\
SO2Ph
PhO2S
D.A.; Church, K.M..I. Org. Chem., 1990, 55, 4780. 1 . (Et0)zPCl , NEt3 elher 2.80°C, 3 h
OH
--
Janecki, T.; Bodalski. R. Synthesis, 1990, 799. 1.
P h 0 , S - f -LiC1
EtO'q'C1 OEt
,-78"C
EtO- P Etd
t
C02Me
Ph\=(
82Yo
(93:7 E:Z)
Lee, J.W.; o h . D.Y.Synth. Commun., 1990, 20, 273.
kF
c1
SOZPh
2. PhCHO
Li
68%
hv Ph C02Me CC14 , 8 h * Ph02S& =CS02ph 2.NEt3 58% Harvey, I.W.; Phillips, E.D.; Whitham. G.H, J. Chem. Soc., Chem. Commun., 1990, 481.
C02Me
0
SiMe3
1.
dPh, PhSO21,
30% 5% Pd(OAc)2 P(OiPr)3
dioxane , BSA
SO2Ph
l0O0C
SO2Ph
(1 Trost.;Grese, T.A. J. Am. Chem. Sac., 1991, 113, 7363.
7.2)
72%
556
Section 389
Compendium of Organic Synthetic Methods, Vo18
I . Py , CHCI3,2O0C 0
Ph0zS.)-
0
+
SOzPh
2. LDA ,TMS-CI , -78°C -+ 20°C 3. NaHCOs , DMF ,100"C
I
PhOzS
10 h
I)
(15
L
60%
Davidson. A.H.; Eggleton, N.; Wallace, I.H. .I. Chem. Soc., Chem. Comntun., 1991, 378. P h 0 2 S ~ C0,Et
PhO,S
PhCHO , KF-AIzQ ("dry") t
microwaves (280 W) , 5 min
)I--.
Et02C
Ph
. . Vlllemln.; Ben Alloum. A. Synth. Commun., 1991, 21, 63.
58%
Retherford, C.; Knochel. P, Tetruhedron Lett., 1991, 32,441. Ph-CS-H
OBannon, P.E.;
w. W.P. J. Org. Chem., 1991,56, 2258. BuJSnH , AIBN , PhH
c!
reflux
S- Ph
Q-Mc
~
=C-I Crandall.; Ayers, T.A. Tetrahedron Lett., 1991, 32, 3659. PhSH , NEt3 ,reflux
0
i. A .** C=C-H
To1
T01w k
11
Guillot, C.; Maiman. C, Tetrahedron Lett., 1991, 32, 4907.
n-CgH17
0
CZC-I-Ph
1. PhSOzH ,MeOH 2. Bu$JCI, 4.5 h
CH2C12
s-Ph
0
t
***
69%
dSPh 76%
n-CgH17
PhOZS*Cl
B F4O Dchiai. M,; Oshima, K.; Masaki, Y. Tetrahedron Lett., 1991, 32, 7711.
95%
Oxide - Alkene
Section 389
1. T0lS021 , CH2C12 , RT 2.1NNaOH
557
TolO,S&
rc
I
n-C&
13
75%
(70:30 Z:E)
n-C6H13
Vaultier. M,; El Louzi, A.; Titouani, S.L.; Soufiaoui. M, SynLett, 1991 267.
Ph'
0 S
BuzCuLi , THF , -5°C
\
Q
ph'L Bu
w
65%
Br
(80:20
E:Z)
Cardellicchio, C.; Fiandnese, V.; Naso...I.Org. Cheni., 1992, 57, 1718. alumina, CH2C12 40°C. 7 h -R;.
..
NO2 Castagnani, R.; Petrini, M. .I. Org. Chem., 1992, 57, 2160.
(20
80)
44%
Trost.;Vos, B.A.; Brzezowski, C.M.; Markina, D.P. Tetrahedron Lett., 1992, 33, 717.
3
Ph3P-
Me
1. EtBr
2. NaOEt ,THF
+
0 Pphh;P+OEt
86%
Me
Ruder. S.M,; Norwood, B.K. Tetrahedron Lett., 1992, 33, 861.
0
0
Ak** To1
1. LDA , THF , -78°C
c
2. t-BuMezSiOTf, -78OC
t-BuMe2Si0
0 S<** To1
85%
Solladie. G.; Maugein, N.; Morreno, I.; Alrnario, A.; Carreiio, M.C.; Garcia-Ruano,J.L. Tetrahedron Lett., 1992, 33, 4561. SolladiC. G,; Ruiz, P.; Colobert. F.; Carreiio, M.C.; Garcia-Ruano, J.L. Synthesis, 1991, 1011.
558
Compendium of Organic Synthetic Methods, Vol8
Section 389
Zhi, L. Tetrahedron Lett., 1992, 33, 1831.
To1,,,0
Bonfand, E.; Gosselin, P.;
H- C: C-
0
1. NEt3 , DMF ,20°C 2. Me3SiCI
I
.
v,,o
Tetrahedron Lett., 1992, 33, 2347.
ZnI2, PhH , RT 15 h
To1
+
rle la l'caldh R.F.; Morente, M.;
*
1-s;o
4
To1
*.*
87%
Tetrahedron Lert., 1992, 33, 6101.
Tetrahedron Lert., 1992, 33, 6311. 1 . 0 2 , PhSh
CEC-H 2. oxone
-
3. PhSCl , NEt3 ,CHzC12 4. NEt3 ,CHzClz 5. H 2 0 2 , AcOH
Ni, Z.; Wang,X.;
S0,Ph
;l3ktm,A Tetrahedron Lett., 1992, 33, 7303.
REVIEWS:
"TheChemistry of Vinyl Sulphones" N.S, Tetrahedron, 1990, 46, 6951. S ymposia-in-Print:"Nitroalkanesand Nitroalkenes in Synthesis" Tetrahedron, 1990, 46, 73133798. " 1,2-bis(Arylsulfonyl)alkenes" cossu, s.; ; Fabbri, D.; Licini, G.; Pasquato, L. Org. Prep. Proceed Int., 1991, 23, 573. '
559
Oxide - Oxide
Section 390
SECTION 390: OXIDES
-
OXIDES
e- (Hg pooVAg-AgI-IDMF, -1.35 V
Ph02sl
EkN' ClO4-
Delaunay, J.; Mabon, G.; Orliac, A,;
Tetrahedron Left., 1990, 31, 667.
[ (79:4
E:z)
(8:9 syn:anti)
1
93%
Ghera. E,; Ben-Yaakov, E.; Yechezkel, T.; Hassner. A. Tetrahedron Lett., 1992, 33, 2741.
Ph
+CHo
1. NbCIS , 3 PPh2H CH2C12 , -78°C
2 . 2 eq. BF3*OEt2
0
0
q rhPh 75% Ph Efashimoto, T.; Maeta, H.; Matsumoto, T.; Morooka, M.; Ohba, S.; k u k i.,.(I SynLett. 1992,
340.
Ph' p Ph
Compendium of Organic Synthetic Methods, Volume 8 Edited by Michael B. Smith Copyright 0 1995 by John Wiley & Sons, Inc.
Author Index
A!udA
Abbasov, I.M. Abd-El-Aziz, A.S. Abdallah, Y.M. Abdel-Baky, S. AbdeI-MrgLQ. Abdrakhmanov, I.B. Abe, F. Abe, H. Ahe, J. Abe, M. Abe, S. Abel, T. Abell, C.
v Aben, R.W.M.
A!&QA
Abouabdellah, A. Abraham, A.C. Abramovitch, A. Abramovitch, D.A. -itch. R.4. Ahreo, M.A. Abt, D.C.
-
Achiwa. K. Achyucha Rao, S. Ackennan, C.J. Acklin, P.
il&tLX
344,407,470, 543 Adhnek, F. ad am^, H.
AdmLL
Adams, J.P. Adger, B.M. Adlington, R.M. Aerrsens, M.H.P.J. Afonso, C.A.M. Alridi, A S .
Awmx. A&xamux Agoston, G.E. Aguilar, E. Aguilar, F.J.
A
283 478 031,291 078 162 155,345 416 019, 245,258 330
561
Agullb, C. Aiman, J. Ahmar, M.
AibLKL
Ahuja, J. Ah uja, J .R. Aida, T. Aizpurua, J.M.
060
380 078, 090 207 132 485 486 017, 109 339, 356 124 286 088 088 032 134 542 055 082,086 099,339 439 332 194, 241, 334, 208 485 472 499, 525 370 449, 458, 515, 524 248 253 480 309 540, 542 026 316 351
Aj.jou, A.N.
Bkahori. S,
Akai, 11. Akai, S. h i c h i . KSL Akwnatsu, H. Akruie, N. Nrazoine, M . Ntgiin, E. Nthmedov, I.M. Akhinedov, M.A. Akiyema. T, Nclitopoulou, I. Nrula, M.R. Ntutagawa, S. Akutsu, S. Al Neiraheyeh, M. AI-owx, R.S. Al-Said, N.H.
Alajarin, R. Akuni, M. Alarid-Sargent, M. Alayrac, C. Albanese, D. . . K.F. &all. Alhrecht, I T . 14lc;lide. B. AIcw'w, C. AIGWX, V. Aldous, D.J. Aldous, S.C. Alexakis. A. Alexander, C.W. Alcxzider, M.D.
283 143 292, 525 304 302 235, 312 198,250 002, 129 148, 252, 348, 304, 529 223,288 142, 201 259 169, 238,283 056 400 304 147, 162, 226 178. 170, 372,402 403 111 111 033,052,053 26 1 156 378, 379,401 441 172 500 35 1 530 386 099, 286 020 176 416, 529 342, 365,465 50 1 365,376 54 1 440 003. 386 003 069, 329, 360, 397,484 104 119
562
-
Compendium of Organic Synthetic Methods, Vo18
Ali, A. Ali, H.M. Ali, S.M. Alink, B. Allainmat, M. Allmang, G. Allocco, A. Almario, A. Alo, B.I. Alonso, I. Alonso, J.M. Alonso, M.S. Alonso,F.
iilm3L
Alphand, V. Altenburger, J.M. Alvarado, J.
AiYauzc
Alvarez, E. Alvarez, R. Alvarez, R.M. Alvarez-Manzaneda, R. Alvemhe, G. Amano, S. Amanokura, N. Amato, G.S. Amiya, T. Amoroso, R. Amougay, A.
AQlmmmA
Ampadu-Nyarko, F. Amri, H. Anastasiou, D. Andersen, M.W. Andersh, B. Anderson, C.B. Anderson, C.L. Anderson, D.A. Anderson, J.C. Anderson, M. Anderson, K.C.
486 093 321, 508 433 164 284 498 410,411 326,557 124 547 204 435 102 006, 012, 046, 054, 081, 094, 131, 169, 170, 210, 262, 287, 456,515 180 119 243 243 336 122 058,500 386 037 464,476 06 1 206 232 166 29 1 224 499 467 309 128,366 235 035 482 039 554 34 1 390,453 049,338
Anderson, R.E.
Andersson, P.G. Ando, R.
AuaL
Andreae, S . Andreoli, P. Andrks, C. Andreu, C. Andrews, J.F.P. Angara. G.J.
l3usU-R
Angers, P. Angiolini, L.
ilu?L=
Anjeh, T.E.N.
slukd2.
Annunziata, R. Anren, J. Anthony-Mayer, C. Antonakis, K. Antonioletti, R. Antunes, O.A.C. Aoki, M. Aoki. S. Aoki, T. Aoki, Y. Aoyama, M.
IkuamaL
ApAricio, D. Apitz, G. Applegate, L A . Arai, K. Arai, M. Arai, N. Araki, K.
AmkiA
Araki, Y. Arasappan, A.
AJXuL
Arase, T. Arhuzov, B.A. Arcadi, A.
Authors
119 315 084 382, 395,432,482 257 27 1 1 63 157 171 312 522 207,495 539 521
414
069,329 25 1 464,476 308 364 488 518 333,334,441 399 139 036,441 525 096 095 184 402 378 5 14 307 076,234 37 1 383 075, 327, 363, 515, 538 538 414 046,047, 500, 530 330 273 075, 092, 094, 286, 415, 421, 45 1,457
Archelas, A. Archer, C.M. Arenz, T. Arienti, A. Arimoto, H. Arjona, 0. Armstrong, S.K. Amaiz, D.O. Am6, M. Amold, Z. Amswald, M. Arora, P.K. Arshava, B.M. Artaud, I.
AuaL A?alaaL A s m i . M. Asao, N. Asaoka, M.
AfmzJkE
Asensio, G. Asirvatham, E. Astapovich, I.V. Atagi, L.M. Ateeq, H.S.
AukL
Aubert, C. Aubert, T. Aufranc, P. Augustine, B. Aurell, M.J. Aurrekoetxea, N. Austin, D.J. Austin, R.E. Avendaiio, C. Avila, M. Awad, M.M.A. Awasthi, A.K. Awen, B.Z. Awen, B.Z.E. AY, M. Ayabe, A. Ayers, T.A. Ayotte, C.
AyymmsA Azerad, R.
563
B
Author Index
180 504 410, 535 302 466 030 546 069,329 283 489 137 242 037 323 515 462,418 205 022.032 153,404 107 398 206, 312,491 511 337 21 1 394 133, 134 356 079, 389 217 228 294 348, 529 066 111 126, 150 050 03 1 517 528 156, 502 066 229 104,556 368 013, 233,254 037
Aziza, K.B. Aznar, F.
llizma&
lkd2aJ.
Baba, Y. Babdoub, M.J. Babu, S.D. Babudri, F. Bac, N.V. &KhL
FkxJdE l3ixldx
Backenstrass, F.
Bacos, D. Badaou, E. Badawi, M.M. Badawy, D.S. Badejo, I.
I3zhwD.
Baevsky, M.F. Baggaley, K.H. Bagheri, V. Bagno, A.
IhLQ.
Baikova, I.P. Bailey, P.L.
Bailey, W.J. Bain, A.C. Bains, S. m w a . J.S. Bak, D.A. Bakale, R.P. Baker, D.L.
l3akJm
Bakouetila, M.
515 141,419 031,072,076 041, 043, 123, 185, 193, 221, 336, 368, 437, 459,472,489, 502 512 249 009 311 515 293 187, 328 136, 176 555 483 318 043, 071, 151, 225, 370, 382, 395, 432, 448, 482, 524, 536, 548 149 114 123 374 101 524 532 053 050, 514 014 119, 127 416 530 035, 078,247, 359 482 087 007, 369 015, 049, 164, 338 20 1 180 026 047,090 102
564
Bakshi, R.K Bakthavatchalam, R. Balachkova, A.I. Balasubramanian, T. Balavoine, G. Balcerzak, P. Balducci, R.
Balenkova, E.S. 512, 517 Ballester, P. Balleslri, M. Balme, G. Balog, A. Balova, I.A. B a l m , M. Baltork, I.M. Ban, Y. Bandini, E. Bando, T. Baiddakar, B .S.
I5almLA Bang, S.H. Banno, H.
ilammLK Bao, J. Baraldi, D. Baran, R.C.
w
Barbaro, G. Barber, C. Barhero, A. Barhieri, G. Barcina, J.O. Barhadi, R. Barker, J.M.
Authors
Compendium of Organic Synthetic Methods, Vol8
040 322 406 220, 333, 374, 463,484 484 248 112 46 1 123, 309, 386, 449, 458, 474, 515,524 195, 384, 389, 060, 198, 213 25 1 210, 217 065, 218, 268, 548,553,557 280, 287, 446, 451,455 523 285 328 328, 301 496 120 132,460, 554 497 052, 080, 260, 477 408 030, 175, 372, 513 375 067 323 444
519 273 357 262,263 483 010, 058, 202 506 139
Banies, D. Barnes, J.L. Barney, C.L. Barnick, J.W.F.K. Barr, K.J. €iamt&
l?amuGx
Barrett, C. Barrett, S.D. Barringhaus, K.H.
l2acmA&
Barta, N.S. Bartels, B. Barlh, F. Barth, L. Bartholomew, D. Bartoli, D. Barton, D.H.R.
Barton, J.C. B,utra, M.
l2iuaAL liamhN% llaskd.
Baskaran. S. Bastos, M. Basu, M.K. Batbeaux, P Baley, R.A. Batra, M.S. Bats, J-P. Bats, J.W. BalrngIia, A.
077, 085. 141, 146, 206, 314, 316, 317, 337, 387, 416, 419, 423, 424, 491, 493, 494,497 159 388 155,496 320 472 223 252, 257, 258, 529, 558 370 073 459 203 225 420 332
432
413 143 283 220,425,461,471 410,411, 553 006, 068, 076, 081, 148, 194, 212, 213, 214, 424, 431,461, 508 250 161 198 161 019 289, 318 137,494 168, 169, 182, 302,443 163, 165
332 112 236 35 1 114 393 273
Author Index
Batty, D. Baudin, J.B. Bauermeister, S.
IlAukmL
Bauml, E. Baures, P.W. Baxter, G. Bay, E.
I.ulLIz
Bay6n. J.C. Bayston, D.J. Balczewski, P.
€&aka
Beattie, M.S. Beaudet, I. Beaudoin, S. Beaufire, D. Becker, S. Beckwith, A.L.J. Beddoes, R.L. Bedeschi, A. Beeley, L.J. Beels, C.M.D. Beerli, R. Behar, V. Behrend, S.J. Beirich, C. Be1 Rhlid, R. Belair, N. Belerskaya,I.P. Bell, S.I. Bellassoued, M. Bellesia, F. Bellew, D.R. Bellosta, V. Bellur, N.S. Belmont, S.E. Belter, R.K. Ben Alloum, A. Ben Ayed, T. Ben Rayana, E. Ben-Yaakov, E. Benalil, A. Benammar, Y.
B
450 260 130 390 499,535 123,428 41 1 20 1 008 368 485 08 1 306 032 287,484 26 1 201 198 114, 375 486 231,232 06 1 414 265 526 317. 339, 356 353 006 028 239 010 002 545 37 1 208,464,465 338 052 046, 235 122 034,088 272,481, 556 309 528 356 559 137 208
565
Benazza, M. Benbow, J.W. Bencheqroun, M. Bennetau, B.
I&3mGm. Benoit, S. Benson, S.C. Beppu, F. Berestova, S.S. Berglund, B.A. Bergman, R. Bergmeier, S.C. Berk, S.C. BemaM, P. Bernard, A.M. Bernardo, J.E. m a a s . RC, Bernocchi, E. Bemstein, M.A. Berrios-Peiia,N. Berrios-Pefia, N.G. Beny, M.B. Bersani, M.T.
lkmdQlJ Berthiaume, S. Berllio, J-N. Berti, F. Bertozzi, C.R. JkLhJ. Beuchet, P. Bewersdorf, M. B.C.B. Bhakuni. D.S. Bhalerao, U.T. Bhanumathi, N. Bhar, S. Bharathi, S.N. Bharathi, T.K. Bhaskar Ready, G. Bhaskar, K.V. Bhat, N.G. Bhat, S. Bhamah, P. Bhatia, B.
20 1 399 3 10 221 250 526 274 297, 342 085 347 227 159 016,030 169, 379 392 198 21 1 309 089,094,415,451 149, 163 133, 167, 368 476 257 131 339 208 330 290 252 06 1 404 423 077 328 104 513 144, 145 405,446 371 142,544 289 499
444
537 326 082 008,479
566
Compendium of Organic Synthetic Methods, Vo18
Bhatt, M.V. Bhatt, R.K. Bhattacharya, A.
Bhattacharvva.P. Bhawal, B.M. Bhuma, V. Bhuniya, D. Bhupathy, M. Bhushan, V. Bhuvaneswari, N. Bickelhaupt, F. Bida, G.T. Bied, C.
Bigi, F. Biktimirov, R.Kh. Billi, L. Bilodeau. M.T. v. R.W. Birchenougli, L.A. Birgersson, C. Bischoff, L. Biswas, G.K. Bit, R.A.
-
lik&cuL
Blagg, J. Blanchot-Courtois. V. Blanco, L. Blart, E. Blase, F.R. Blavzczyk, J.
ludlJL
!aQ!kL
Blom, H.P. Blum, C.A. Blumenkopf, T.A. Blundell, P. Do, Y. Bocoum, A. Bode, H.E. Boelens, M. Boese, W.T.
058 089 174 272,541 137,351, 386 053,233 495 03 1 294 463 320 203 044 351,386 307 302, 323,443 108 157 158, 343, 385 049 165 399 164 272,541 117 134, 174, 452, 453 131, 147,424 363 547 217 09 1 550 55 1 170, 292, 525 476 090 222 478 068 127 057 418 392,555 425 366 063
Boesten, W.H.J. Boeykens, M. Boga, C.
lhuUQL
EQbLL
Boisvert, L. Boivin, J. BojiC, V.D. Boldrini, G.P. Boleslawski, M.P. Bolin, G.
JhlrnL
Bolourchian, M. Bonadies, F. Bonar-Law, R.P. Bonete, P. Bonfand, E. Boni, M. Bonini, B.F.
Bonnert, R.V. Bonnet-Delpon, D. Bontemps, J. Boons, G.J.P.H. Booten, K. Borah, H.N. Borchers, V. Boncdon, M.E. Borsotti, G.P. Bortolini, 0. Borcolitti, M. Bortolussi, M. Bosch, E. Bosco, M. Bose, A.K. Bothwick, A.D. Botteghi, C. Bou, V. Bouchlel, E. Bouhlel, E. Boukouvalas, J.
Authors
436 366,415 418 149, 407, 424, 440,512 081, 194 216 004, 159, 222, 399 155 345 218 420 023, 106, 108 222 333,334,441 163 458 558 464,465 025,273 034, 295, 339 534 356, 317 352 048 422 216 508 134 346 526 011 055 345 292 010, 160, 216, 245 176 410,411 118 347 085 308,506 048 528 086 450 23 1,293
Author Index
Boulanger, R. Boumaiza, L. Bourguignon, J.J. Bousbaa, J. Bouyssi, D. Bouyssou, P. Bouzide, A.
.
.
O V l C U
Bovonsombat, P.
IhYLIuL
Bradshaw, C.
Brahma, R. Braisted, A.C. Bran, G.
Brandes, B.D.
l2rmduL li%mhuL Brandvold, T.A. Bratz, M. Braun, H. JbuJLm
Braun, M.P. Briiunlich, G. Braverman, S. Bravo, A.A. Breau, L. Breault, G.A. Bregar, 2.
.
.
Breitschuh, R. Brennan, J. m o w .R Brestensky, D.M. Breuilles, P. Brichard, M-H. Brieden, W. Briennc, M.J. Brieva, R. Brigaud, T. Brillet, C. Brimhle. M . 4 , Brisbois, R.G. Brocard, J.
B
521 518 367 186 280, 287 283 385 201,339 207 038 040 407 507 390 166 327 109 310,409 001, 192, 248, 276, 281,464 448 478 148 014 499,525 012 548 142 186 264 204 146, 239 292 370 215 091 507 43 I 459 279 382 492 170 121, 135 354 082 177
567
Bronk, B.S. Broody, M. Brooks, D.W. Brown, B.B. Brown, D.S. Brown, E.G. Brown, F.M. Brown, G.A. Brown. H.C. Brown, J.T. Brown, M.F. Brown, M.J. Brown, P.A. Brown, P.S. Jr. Brown, R.T.
JihmJx
Brubaker, C.J.Jr. Bruckner, R. Bruneau, C.
lhnelA
Brunet, P. -lie. W.H. Brunner, E.J. €!luuLL Brzezowski, C.M. BuBay, W.J. Buchholz, R.
Ihl&dc% Buckle, D.R. Buckman, B.O. Budries, N. Buenger, G.S. Bujons, J. Bulachkova, A.I. Bullock, W.H. Butnagin, N.A.
E!!m!LG
Bureau, R. Burgess, J.P.
Burgess, L.E. Burini, A.
llukM.L
447 41 1 137 497 116 050 270 452 014, 019, 074, 160, 260, 352, 450, 537 483 115,455 469 534 243 182 267 093 286,462 387,452,453 351 493 464 526 053, 317 557 488 384 016, 030, 152, 417,412, 523 488 504,552 104 040 46 1 429 552 002 435 084 06 1 435 047, 301,430 156 075,457 152
568
Compendium of Organic Synthetic Methods, Vol 8
iluk!Gm
Burkhardt, E.R. Burkholder, C.R. Bumell-Curly, C. Burnett, F.N. Bums, E.E. Burroff. J.A.
l3ummLL lihmDLu Bury, P. Busato, S. Bussolari, J.
I!luumL Buttke, K. By, A.W. Bye, M.R.
risLJJL
Bykov, V.V. Byslrom, S.E. Bzhezovski, V.V. Bzowej, E.I.
Cabal, M.P. Caballero, C. Cabral, J. Cabre, F. Cabrera, A. Cabrera, E.
sh!xi&
Caglioti, L. Cailhil, N. Cairon, P. Calabrese, J.C. Calkins, T.L.
-
044,075 Callinan, A. 044 Cabx 109, 110 Cameron, K.O. 42 I Campbell, M.G. 536 084 Campestrini, S. 027,415 158,204 Campopiano, 0. 089, 282, 338, Campos Neves, A S . 433,434,496-498campo~,J.L. 550 Campos, P.J. 357 120 Camps, F. 002 075, 327, 363, Canali, G. 515, 538 244 Canas, M. 206 Candiani, 1. 206 Canet, J-L. 196,427,444 Cano, A.C. 002 179 Cantrell, W.R. Jr. 535 Cao, Q. 259, 260, 478, Capdevielle, P. 485 Cap6 M. 026,419 440 127 28 1 094 037 215, 231, 232, 300 012, 075, 092, 094, 286, 415, 421, 451, 457 085 415 099,221 094 120, 157, 316, 402,407 20 1 047 067
Capperucci, A. Cardellicchio, C. Cardi, N. Cared&, M.C.
cilELL Carfagna, C.
CarlsrrOm, A-S. Carpenter, A.J. Carpentier, J-F. Carpita, A. Cam, R. Cameiio, M.C. Carrillo, J.R. Carroll, A.R. CZUTOII, M.K. Carroll, P.J.
Authors
509 444 470 077 052 055
149,366 507 224 450 085, 206, 337, 491, 497 183, 370, 458, 461, 524 443 228 313 23 1,232 479 243 521 113 313 037, 038, 059, 221 25 1 280 105,413,468,490 112, 137,413 275,557 210 29 1 198 092 176, 178 156
087 02 1 177 089,091 438 089 542, 557, 557 541, 542, 547, 522 127, 185 259 230 27 1
Author Index
Carry, J-C. Carson, K.G. Casares, A.M. Casarini, A.
GwJ!L
lkiQLM
Casnati, G. Cassidei, L. Cassidy, 3. Castagnani, R. Castail&. A. Castanet, Y. Castafio, A.M.
€asmhL Castro, J.
CasLGA Catteau, J-P.
€a&xLL
Cazes. B. Ceccherelli, P. Cecchi, R. Cederham, F.E. Cegla, M.T. Celentano, G. Celerier, J-P. Cervantes, H. Cha, D.D. Cha, H.T.
U
-
cllLu
Chahardes, P. Chahot, C. Chakraborti, R. Chakrahorty, R.
Chakravarty, A.K. ner. P.A. Chamberlin. A.R. Chamchaang, W. Champion, N. Chan, C. Chan, E.T.T. Chan, J.B.
C
251, 536 155 518 282 542 168, 304 302, 323,443 036,224 301 553,557 478 177 290, 523 07 1 368 487,510 289 105 058 041. 198, 310 455 442 524 247 142 396 210, 149 240 066 203 11s 054, 059, 060, 063 370, 371,483 216 37 1 018, 162, 297, 348 295, 314 543 021,022 213 128, 396 413 5 34 488 271
569
Chan, P.C-M. T.9 Chan, T.Y. Chan, Y-L. Chan, Y.N.C. Chandramouli, S. Chandrasekhar, S. Chandrasekharam, M. Chang, K.Y. Chang, M.H. Chang, 2-Y. Chaouk, H. Chapel, N. Chaptal, N.
ctlmaJL
Charlton, T.P.
Chnrpentier, P. Charreau, P. Chastanet, J. Chastrette, M. Chatani, N. Chatla, N. Chatla, N.
Chauhan, K. Chauvin, J. Chavant, P-Y. !2MYaE Chehli, S. Chemla, F. Chen, B-C. Chen, B. Chen, C-P. Chen, C-T. Chen, C. F-E. Chen, H. Chen, H.G. Chen, K.
K.Y.
292 026, 076, 263, 345,478, 536 264 488 110 147 539 016, 168, 169, 182, 302, 326,443 176 24 1 202 353 274 366 429 455 459 503 096 114 116,497 077 482 029, 347 088, 210, 217 007, 135 160 543 147 534 537 22 1 052 432 064 345 254 156 265 440,473 042 295 073 008, 230 165
570
Compendium of Organic Synthetic Methods, Vol8
Chen, L. 0-Y. Chen, S. Chen, S.Y. Chen, W.Q. Chen, Y-X. Chen, Y.
clumUL Chcng, C-Y. Cheng, H-C. Cheng, M. Cheng, X-M. Cheong, C.S. Chern, C-Y. Cherry, D. Chesney, A. Chesney, A. Cheung, A.W-H. Cheung, G.K. Chevalier, C.
l2hhbmL Chiacchio, U. Chianelli, D. Chiang, C-J. Chiang, M.Y. Chiara, J.L. Chiba, K.
CmCL
Chidambaram, N. Chieffi, A. Chikami, Y.
Chima, J. Chinchilla, R. Chini, M. Chinn, R.L. Chittari, P. Chiu, P. Chiusoli, G.P. Cho, C-G. Cho, I-S. Cho, J.R Cho, S. Cho, Y. Chockalingam, K. Choe, Y.H.
227 204 379 084 245 311 509,532 283 083 296 540 510 041,452 269 006 385 367 367 255 130 2n4 058 066 189,220 120 462 211,300 212 093,246 302,326 103 498 344 038 370,519 278, 311, 351 385 302 350 460 159 120 254 323 121 390 388
Choi, S-C. Choi, S. Choi, S.S-M. Choi, W-B. Choi. Y.R.
iJlQuJx Choo, G.L.P. Chopard, C. Chou. C-T. Chou, F-L. 9-S.P.
i2lQuJX cllQuL
Chou, W-N.
Chowdhury, R.L. Christensen, D. Chu, k-P. Chu, K.S. Chumg, T-H. Chuche, J. Chucholowski, A .w. Chung, H.S. Chung, J-F. Chung, K.H. Chung, Y.K. Church, K.M. Ciattini, P.G. Cibura, G. Cicchi, S. Ciga&& Cilloir, F. Cimarelli, C. Cimetitre, B. Cimprich, K.A. Cirillo, P.F. Clapp, G.E. Claramunl, R.M.
clauLL
Authors
442 428 425 345 234 033, 170, 173,292 176 515 095 248 411,553 274, 292,425, 540 274 357,477 019, 177, 222, 233, 288, 330, 372,427 043 130 321 290 450, 558 120 332,487 544 117 488 110 206,243 412 451, 554, 555 338, 352 089, 284,454 499 310 157, 267 06 1 283,410,411 112 018,041,452 131,308 028 063 175 033 377 181,385
Author Index
Clark, A.B. Clark, A.J. Clark, D.L. Clark, J.D. Clark, J.S. Clark, K.B.
l2akEa
Clark, T.J. Clasby, M.C. Claver, C. Clawson, D.K. Claxton, E.E. Clayton, T.W. Jr.
Clinet, J-C. Clive. D . U Cloux, R. Coates, A.J. Coates, B.
llmsJUL Coche, L.
Cogen, J.M. Cohen, B.I. Cohen, M.A.
CQmLC. Colard, N. Cole, D.C. Cole, S.J.
Coleman, M.J. Coleman,R.S. Coles, N. Collado, I.G.
Ix.ktA
Collin, J. Collington, E.W. Collins, J.L. Colobert, F. Colovray-Gotteland, V.
C
57 1
25 1 123 Conan, A. 357,477 Concell6n. J.M. Concepcion, A.B. 164,373 Concialini, V. 343 217 Conde, S. Condon, S. 120, 227, 377 456 Connell, R.D. Connet-Delpon, D. 540 368 Conrad, M. 069 Consolandi, E. 514 Constantieux, T. 429 Contreras, B. Cook, G.R. 539 158 Cook, J.D. 285 &&, M.P. 357,456, 533 09 1 Cooke, R.J. ner. G.F. 315 39 1 Cooper, J.P. 274 Cooper, M.A. 093 Copa, F. 447 Coppens, W. Corbett, W.L. 353 128 Corcocan. R.C. Cordero, F.M. 013 024, 031, 301, fQmLu. 46 1 463 357 216 046 Cornelis, J. 265 Corriu. R.J.P. 021,466 147,424 Corte, J.R. 05 1 cop. cossar, J. 208,435, 501 Cossi, P. 377 Cossio, F.P. 044, 308, 345 cossu, s. 546 176,437 171 CQSua. 044,511 Costa, P.R.R. 542, 557 Costanza, C. 455 ihEkJL 135 Courtemanche, G. 009, 089, 103, 463 Courtieu, J.
-
cmduL
w
123, 318, 383, 500 177 493,494 183 370 542 517 402 339 500 131 394 373 418,420 365,409 396 102 101 143 092, 250 382 403 3 70 149 408, 543 409 018, 020, 040, 041, 052, 157, 232, 277, 305, 323, 348, 394, 452, 554 366 117,420 049,495 001 447 289 089 056, 252,402 558 052, 382, 385 460 327 128 058 28 1 008
572
Compendium of Organic Synthetic Methods, Vol 8
C o ~ ~ t a rJ-M. d, Couturier, D. couty, r:. Cowen, K.A.
155,402 310 309 146 131,308 131 145 131, 362, 369, 446, 540, 549
CQZZIA
Cozzi, P.G. Cragg, J .E.
444
Craig, M.E. Craig, S.L. Crawford, S.D.
ikmLx. Cregg, C.
CLkhJL
T.
Criso. G.T.
llULaL
Crispino, G.A. H.-J. Cristofoli, W.A. Cros, P.
ihULL
Crouch, R.D. Crowe, W.E. Csfiky, A.G. Cuadrado, P. Cube, R.V. Cui, W. Culshaw, A.J. Culshaw, P.N. Cuiiat, A.C. 0. K.F,
LhmJ. . . mi. M.
m.D.P. Curran, P.P. Curtis, A.D.M. Curulli, A. Cusak, K.P. Cywin, C.L. Czeskis, B.A.
208 104,439,556 208 265 330 450,473,440 255,468, 512 393 457 303 414 333 084 278, 311, 351 536 so9 050 510,087 262,263 149, 163 168 304 549 283 104, 248,254 036, 241, 224 442 083. 100, 124, 218, 219, 335, 500, 523, 529, 531 103 378 322 092 274 348 34 1
DAccolti, L. DAndrea, S.V. d'Angelo, J.
D'Hondt, L. d'lncan, E. d'orchymont, 11. Da, Y-2. Dabdoub, V.B. Dabin, G. Daeuhle, J.F. Dahl, M.L. Dai, H. Dai, W. Daigneault, S . W.P, Dalko, P.I. Dalla, V. Dallemer, F. Dalpozzo, R.
QilhnJL
Dan-oh, N.
lhldaa
Dang, V.A. Dang, Y. Daniel, K.L. Daniel, T. Daniels, K. Dannecker-Doerig. 1. Daran, J-C. Daroszewski, J. Das, A.R. Das, J. Dasgupta, S.K. Dam, R. Date, T.
QilhmxG Daudon, M. Daus, K.A. David, S.
Davies, I.W.
Authors
241 036 037, 103, 327, 404,503 413, so5 177 119 169 011,089 089 168 091,248 340 25 1 435 456, 533 214, 556 43 1 463 345 410,411 038 065 349 172 25 1 066, 082, 180, 523 125 233,254 369 169, 385 265 309 216 018, 033, 034, 043, 348, 542 016 489 049 430 027, 109, 353 223 208 489 556 113, 379,456,457 540,546
Author Index
Davis. F A Davis, J.M. Davis, S. Davis, W.M. Dawson, B.T. Daynard, T.S. De Bemardinis, S. De Buck, K.
lmhvdu. De Corte, B.
De Cusati, P.F. . . e Giovani. W.F.
lX!exLE.
ne. N.
De la Rosa, M.A. De Nicola, A. De Sarlo, F.
lx3mu-R
de Carvalho, M. de Froidmont, Y. de la Hoz, A. de la Moya Cerero, S. de la P r a U
& -
de Mendoza, J. de Raadt, A. De, B. De, R.N. Deacon, G.B. Dean, D.W. Debacker, M. DeCusati, D.F. Depl’hlno_cend. A. Degueil, M. Dehaen, W. Dehghani, A.
Dehmlow.ti.
573
D
028, 163,489 Del Maslro, M. 132, 254, 271, Del Valle, L. 345, 383,494 del Campo. C. 423 del Grosso, M. 117 del Pozo Losada, C. 036 del Rosario-Chow, M. 417 del Veccio, G I - I . 222 Dekanghe, P.H.M. 299 Delaunay, J . 215 Delbecq, P. 366,422 Deleuze, H. 40 1 Delgado, A. 370,493 Dclgado, F. 445, 507 DeLima, C. Dellaria, J.F. Jr. 055,450 Dclmastro, M. 010, 130 141,192, 366, 369,Delogu, G. 370, 372, 409, DeLombacrt, S. 413, 41s. 422, Delonne, D. Deluca, M.E. 93, 505 001 Demailly, G. 290 310 I2aukhL Dembofsky, B.T. 430 Demchuk, D.V. 338 114 490 058 Dcncmnark, D. 030,558 Deng, L. 086, 217, 401, 445, 508, 519 DeNicola, A. 157, 379 DeNinno. M.P. 013,288 554 Dennehy, K.D. Denurra, T. 405 427 Deo, N. DeprCs, J-P. 550 310 DCrien, S. 172 Deroncic, L.O. 313 105, 263, 364, DeSarlo, F. 413, 417, 468, l x h u L L 490, 517 Deshpande, P.K. 216 Deshpande, S.M. 404 P, Deslon-ns. 500 Desmdle, D. 193 DcsMarteau, D.D.
-
286 07 1 013 393 423 378 010 114 559 149, 210 010,130 181 242 266 387 075,457 076 400 216 294 558 20 1 282, 517 138 185 179, 348 114,226 136 195 532 510 040 116, 255,265, 552 533 03 1,072 106, 140 170 285 385 434 409 05 1 03 1 007, 135 103,502 327,404,413 224
574
-
Compendium of Organic Synthetic Methods, Vol8
Detert, H. DeuBen, R. Devanne, D. Devasagayara, A. Devine, P.N. DeVita, R.J. Dhal, P.K. Dhaliwal, H.K. Dhar, R.K. D h m a Rao, P. Dhillon, R.S. Dhimane, H. Di Fabio, R. Di Zio, J.P. Dias, M. Dickinson, J.M. Dieter, J.W. Dfez-Bma, E. Dikic, B. Dimock, S.H.
l2uCi.
Ding, Z. Dinges, W. Discordia, R.P.
DiVerdi, M.J. P.H. Dixon, B.R. Djeghaba, Z. Do, Q.T. Dodge, J.A. Doh, C.H. Doi, Y. ier. W.R. Dole, M.P. Dombroski, M.A. Dominguez, E. Dominguez, C. Dominguez, E. Dornmerholt, F.J.
Dix&
-
488 237 453 505 300,457 531 302 399 069 318 182 46 1 295 202 132 490 144,421 106, 140 049,104,106, 140 127, 185,490 434,494 055 545 099, 100 028, 105, 326 415 423 186 353 353 358 387,452,453 523 130 190 171 140 262 109, 110 5 14 510 541 087,510 541,542 447 265
Donnelly, K.D. Dopico, M. Dorchak, J. Dorff, P. Dorgan, B.J. Dorrity, M.J. Dosen, M. Doty, B.J. Doubleday, M.D. Doucet, H. Doulut, S.
lAutkuA IlQELLE
QQJEdw.
J2QlkML
Doyle, T.J. Draagisich, V.
IlfamJA
Droescher, P. Drouin, J. Drozdetskii, A.G. Duan, J-X. Duan, J.J-W. Duan-Mu, J. Duann, Y .F.
l2llkL
Dubbert, R.A. Duchene, A. Dudek, C.M. Dudzihski, B . Dufour, C.
l2lmmdL
Dulckre, J-P. Dumas, D. Dumas, F. Dumas, J . Dumont, W. Dunn, T.J. Dunogues, J. Dupuy, C. Durandetti, S.
Authors
148,467 138 215 068 002 163 121 437 092 024 452 315 358 236,442, 527 536 050, 109, 111, 125,429,473 406 067 199,270 036 012 377 406,420 204 436 22 1 177 346 453 26 1 255 190 190 113, 370, 371, 373,483, 537 190, 196,496 409 103,404 539 114, 335 034, 215, 285, 504,506 420 221, 394 100 195
Author Index
Durga Prasad, A. Diirner, G.
IhfficL Durst, T.
lAJxmkL
IhEmLuL Dustman, J.A. Dutta, D.K. Dvorak, D . Dwivedi, S. Dyall, L.K. Dyszlewski, A.D. Eagle, C.T. Earle, M.J.
l2asmxL J2bzhkK
Eberspacher, T.A.
EbalL Ebina, Y. E&uamAK Ecker, J.R.
Eddarir, s.
libiLw.
Edmonds, M.K.
E4lwddL Edwards, J.P. Edwards, L.G.
Egashira, E. Egbertson, M.S. Eggleston, D.S. Eggleton, N. Eguchi, M.
l2mdliA
Ehui, B. Eibisch, H. Eid, C.N. Jr. Einhorn, C.
l3sdLLl
Eisenbeis, S.A.
E
222,288 393 186,307, 311 436 007 36 1 495 010 489 007 375 552 109 130, 384,431 381 025 406 252 086 074, 157, 290, 329 195 282,286 337 354 549 116 250 140, 549 288 477 165 123,428, 550 556 105, 107 397,424 093 012 083 096,470 237 118, 164 118, 164,290 218,059, 190 174
575
Ejjiyar, S. El Ah, B. El Gaied, M.M. El Gharbi, R. El Kaim, L. El Louzi, A. El-Subbagh, H. ry. M.F. Eke, E.
EluuLL
Elie, C.J.J. Elinson, M.N. Elkaim, L. Ellsworth, E.L. Ellwood, C.W. Elmaleh, D.R.
FilmuAL
Elworthy, T.R. Emonds, M.V.M. Emziane, M.
Enders.D. EMQJ'
l2lUWL EllhhJ3 Ennis, D.S. Epa, W.R. Erdmann, P. Ericsson, A.M. Erker, R. Esch, P.M. Escudier, J-M. Espanet, B. Etkin, N. Etter, J.B. Evans, A.
lhuL4UL JikaLsL Evrard, G. Ewald, M. Eyley, S.C. Ezell, E.F.
499 170 309 530 222 557 542 134 003 377 048 367 004 099,250 494 368 058,080, 120,374 095, 097, 532 102 314 228,440 064, 190,223 376,402 027, 326, 372, 397,415,440 222 517,538 034, 147, 241 258 5 24 198 523 398 328 034 311 322 524 047, 092, 158, 297, 320, 340, 343, 385 288 369 114 023, 106 130 128
576
379 Fabbri, D. Faber, K.
l3ddaJA
Fadel, A. Faggi, C. Fahrang, R. Fairhurst, R.A.
EtdcuJL
Eilkrdx
Falling, S.N. Fan, W-Q. FaiianSs, F.J. Fang, C.
l3muY.
Fariiia, F. Farmer, L. Famier, M. Farooq, 0. Fasseur, D. Fatmi, N. Fatykhov, A.A. Faul, M.M. Faure, B . Faure, R. Favaretto, L. Favero, L. Favorskaya, LA. Favret, G. Fay, J.G. Fazlur-Rahman, A.K. Feaster, J.E. Fedcnyhski, M. Feducovich, S.K. Feiring, A.E. Felder, M.
liemmJ& Feng, F. Fengl, R.W. Fenlon, E.E. Fenor, M.
Authors
Compendium of Organic Synthetic Methods, Vol 8
558 013,288 145 479 468 153 130, 384,431 089, 113, 176, 275,431 358 337 025,321 141 146,317 106 120 087, 257 074 368 389 068, 079, 259, 272 3 10 131 416 158 084 432 468 278,351 285 141 I38 177 I52 112 367 464 023, 108 437 337 512 503 246
Fensterbank,L. Femhdez, R. Femhdez, S. Femhdez, C. Fernhdez-Mayodas, A. Ferrahuschi, P. Ferraccioli, R. Ferreira, J.T.B. Ferro, P.G. Ferround, c. Fevig, T.L. Fiandanese, V. Fiaud, J-C.
Finet, J-P. Fiorani, T. Fiorentino, M. Fischer, R. Fisher, G. Fisher, G.B. Fisher, M.J. Heck, A.E. E l C u i B 2
Fleming, A.
I?lmiuJ Flbrez, J. Flygare, J.A.
€ikimaL
Foa', M. Folest, J-C. Fontaine, M. Fontana, F. Fontanel, M-L. Fontani, P. Fooks, C.J. Forbes, D.C. Forbes, I.T. Ford, K.L.
301 106,238 541, 543 129 256 542 3 19 337 328 104 102 004
088 218 275, 515, 557 070,071, 508 006 503 070 148,467 I78 036,224, 241 019, 222, 224, 233,270 012 495 043 367,414 122 528 428 439 071, 262, 263, 533 428 077 257,529 132, 136 01 1 174 226 403 358 112 311 397 275 374
Author Index
Ferster, S. Fort, Y. EQrtes. C1.C
l&tiJLL
Fossatelli, M. Fotiadu, F. Foubelo, F.
&lluJLu
Fouque, E. Fouquet, E. Fournet, G. Foumier, J. Fowler. F.W. Fowley, L.A. Fox, D.N.A. Fox, M.E. Foxman, B.M. Fraile, A.G. Fraiz, S. Jr. Francalanci, F. Francesch, C. Franciotti, M. Francisco, C.G. Franck, R.W. Franklin, P.J. Franklin, R.J. Franzini, L.
Etala&
IiIwuwi
EGWRULLS Fray, A.H. Freeman, J.P.
l3euL
French, L.G.
l?mwLR
Frey, H. Fried, C.A. Friedrich, D. Friesen, R.W. Frommer, J. Jr.
EfLLL EcYLLL Fu, C. Fu, G.C.
F
288 198 474 368 287 084 146 467 175 159, 399 446,451 387 386 085 328 275 552 058 141 215 282 360 38 1 514 526 427 542 021,022 360 368,410 535 404 036 087 403, 503 167 279 257,449 359 408,459,476 535 333, 529 467 121,211 274 141 047, 090,092
577
Fu, J-M.
J?udLLL Fugami, K.
EUUL
Fujihara, H. Fujii, H. Fujii, T. Fujirnori, T. Fujimoto, T. Fujimura, M. Fujimura, 0. Fujirnura, T. Fujinami, T. Fujino, S.
EUiioka. 13.
Fujisaki, S. Fujishima, H. Fujishita, Y. Fujita, H. Fujita, M. Fujita, T. Fujitsuka, H. Fujiwara, K. Fujiwara, M. Fujiwara, S. Fujiwara, T.
ara. Y,
Fukase, K. Fukuda, Y.
Fukuhara, T. Fukui, H. Fukumasa, M.
E!&umm&
Fukunishi, H. Fukushirna, M. Fukushima, T. Fukuyama, H.
E!AuauA
073 207,436,464 012, 177, 204, 263 028 114, 217, 379, 392, 460 302 406 043, 307, 308, 324, 335 435, 505, 551 204, 554 170, 315, 346 490 296 441 179, 189 070 474,529 205, 208, 515 041, 115, 256, 297, 305, 339 284 319 151,416 219, 255, 271, 545,554 072, 167, 325 472 315 185 142, 307,475 079, 236, 480, 483, 509, 538, 539 297, 342 048.051 139, 220, 278, 485, 516 001 038 01 1 165 083 056 084,491 480 113, 179, 189, 364
578
Compendium of Organic Synthetic Methods, Vol 8
Fuller, C.E. Fuller, J.C. Funabiki, K. Funaki, 1. Funakoshi, K. Funaro, J.M. Fung, A.P. Furata, K. Furlong, M.T.
l2lwmdL
Furuhashi, K. Furumori, K. Furusawa, A. Furuta, K. Furuta, T. Furuune, M. Furuya. M.
l?lmuwd Fusco, C.
l3mXQ.A FWU,S-L.
GilkLL
Gaboury, J.A. Gadamaserti, K.G. Gadgil, V.R. Gage, J.L. Gage, J.R. Gai, Y. Gajda, T. Gal, J. G a b , A.
liauhaL Gallardo, T.
Galle, J.E.
Galons, H. Gambaro, M. Ganboa, I.
LicmmE
Gangloff, A.R.
076 043 49 1 112 212 274 038 020 003 353,486, 486 180 011 406 285 527 226 010 002,485 280 060 036, 224, 241 314, 316, 424 250 307 426 159, 324 363 073 340 112 154,547 506 157 442 390, 443, 453, 513,546 354 190 337 191 007 252 064, 164, 254, 268,459 059
Ganguly, A.K. Gao, L. GLQL
Gaonac'h, 0. Garcia Navio, J. Garcia Ruano, J.C. Garcia Ruano, J.L. Garcia, A. Garcia, E. Garcia, J.M. Garcia, 0. Garcia-Martin, M.A. Garcia-Raso, A. Garcia-Ruano, J.L. Gardossi, L. Gareau, Y. Garg, C.P. Garlaschelli, L. Gasc, M.-B. Gasch, C. Gaspard-Iloughmane,11.
..
Gasparski, C.M. Gataullin, R.R.
GUi&
Gaudemar, M.
Gautam, R.K. Gavai, A.V. Gavaskar, K.V. Gavrishova, T.I.
LiWQLEL
Geary, P.J. Gelas-Mialhe, Y.
u Genet, J-P. Geng, L. Gengyo, K. Genicot, C.
LkxUGJ.
Georgiadia, T.M. Gerardin, P. Gerdes, P. Geri, R. Germani, R.
Authors
552 337 323 537 386 553 542 052 226 148, 252 243 206 077,215 557 252 545 47 1,495 135 064 414 54 1 346 269 314 416 011,466 37 1 374 102 448 078 . 517 366 298 42 1 09 1,094, 399
164
475 236 380,471 118, 386,403 365 365 165 440 280 333
Author Index
Gero, T.W. GCro, S.D. Gesson, J.P. Ghannam, A.
GhelfLE
Ghera.E.
Gherardini, E.
GlLuidu GbQxzJu chsluu. Ghosh, M.
GlmhA.
Ghouch, A.A.A. Giacomini, D. Giaroni, P. Gibson, F.S.
ciiaLE
Giesler, A, Gil, S. Gilchrist, T.L. Gilday, J.P. Giles, M. Gill, W. Gillard, J.W. Giordano, C. Giordano, O.S. Giorgianni, P. Giovannoli, M. Guard, C. Guard, J-P. Guard, S. Girard, Y. Girault, 3.P. Girdaukas, G. Giuliano, C. Giunta, N. Glaser, R. Gleason, R.W. Gleason, T.G.
G
131 43 1 127 018,101 208, 229,464, 465 553,559 133 493 227, 380,471 300 118 174,258 429 316,402,401 308 159 163,388 085, 088, 217, 258 25 1 004, 162 39 1 294 409 134 513 265 299,368 035,231 337 222 273 269 211 05 1 103 330 037 029 034 141 427 368 523 196 033
579
GlChLrL Glink, P.T. Gobeaux, B. Gobel, T. Godfrey, A.G. Godinez, R.
GsUAaL Gogoll, A.
siQmmAL Gombatz, K. Gbmez, A. G6mez. A.M. Gbmez, C. Gomez-Pardo, D.
Gong, L. Gong, W.H. Gonsalves, A.M.8A.R. Gonziilez, A. GonzSlez, A.M. GonzSlez, C. Gonzdez, F.J. GonzBlez, J.M. Gonziilez, R. Gonzdez, S.M. Gonzdez-NuRez, M.E. Goo, Y .M. Go0dkin.G. Goodman, C. Goodson, P.A.
siQmhd=
C.T. Gordeev, A.N. Gordeev, M.F. Gordeeva, G.N. Gore, J.
-1.
Gorobets, E.V Gorys, V. Gosselin, P. Goti, A. Goto, D.
GtuL
Goto, M.
284 393 47 1 258 064, 254,459 052 154 548 311 063, 128 428 256 173 519 503 54 1 179,319 189 409 171 262,263 382 314,424 206,491,497 146, 317 500 24 1 134 21 1 144 39 1 486 043, 260 062
005
062 280, 287, 409, 446, 451, 455, 48 1,455 249 328 330, 332 558 310,409 177 37 1 511
580
Compendium of Organic Synthetic Methods, Vol 8
Goto, 1’.
CbtQLX Goth, S.
Gottardo, C. Gottlieb, H.E. Gottlieb, L. Gouda, N. Goudarzian, N Goux,
c.
Gowriswari, V.V.L. Gows, I.D. Goyal, s. Grabowska, U Graham, A.E. Graillot, Y.
GlmlusA
Gramain, J-C. Granberg, K.L. Grandberg, K.L. Grande, M.
cicmLR
Grandjean, C. Grandjean, D. Granja, J.R. Grant, B. Grant, E.B.
i2wdL Grass, F.
l3aYclL
Gray, D.J. Gray, M. Grazini, M.V.A. Greck, C. Green, D.L.C. Green, J. Green, J.M
chlx5Jx Green, J.V.
GEwLuL
QBduWLm Greenhill, J.V.
Gluxem.
Gregoire, P.J.
Grese, T.A. Greyn, H.D. Gridnev, I.D.
042 129, 382 308 200,509 465 144 032 019 189 318 130 179,468 123,393 505 388 230 42 1 523 448 440 229,464 455 332,487 322,541 07 1 466 452 284 368, 526 038 079 463 164
544 007 543 230 25 1 170, 281, 510 27 1 187 045 420 429 541,555 243 384,389
Griedel, B.D.
ihxd-fi
Griesgraber, G. Griesser, H .
GckLR
Griller, D. G r i m , E.L. Grisenti, P.
Grondin, R. Grossman, R.B. Grote. C.W.
LkQYdm Grover, P.T.
siumLuL
Gruseck, LJ. Grushin, V.V. Grynkiewicz, G. Gu, J-H. Gu, J. Gu, Q.M. Gu, x-P. Gu, Y.G. Guagnano, V. Guan, L. Guan, X. Guama, A. Guehring, R.R.
ci.umaA Guertin, K.R. Gueugnot, S.
l3uiMA
Guithem, J. Guillemont, J. Guillot, C. Guingant. A. Guiry, P.J. Guitifin, E. Guittet, E. Gung, B.W. Gunterovfi, J.
Authors
020, 101, 164, 171,373 092 013, 180, 288 08 1 380 121,405 217 368 319 067,336 126 417, 523 552 001 354 090 45 1 012,054,287 546 321, 327 151 029 439, 502 359,536 374 465 118 310,409 383 370 345 277 248 332 380 356 370, 371,483 556 216,330 404 246 148,467 07 1 114 357 295
Author Index
Guntrum, E. Guo, C.
H
Gutsulyak, R.B. GWA. Guy, R.K. Guyot, B. F.S. Jr. GllmhA Guzzi, U. Gybini, A S . Gygax, P.
551 522,528 177 514 135, 396 040 070 289 166 132 433 388 186 147 213 001 524 262 360
Ha, C.
407
G u x
Gupta, R.B.
iibmJL
Gurjar, M.K. Gusmerol, M.
Gutierrez, E.
L3mlmAL
HaaL
Haaf, K. Ham, J.P. Jr. J Haarmann, H. Habaue, S. Hachisuka, C. Hachiya, I. Hadjimpglou, L. Hadley, M.S. Hagegawa, M. Hahn, C.S. Haiying, C.
JJaiCuL
Hajicek, J. Hale, J.J. Hall, D. Hall, H.K. Jr.
Hallett, P. Hama, M. Hamada, S . Hamaguchi, N. Hamaguchi, T. Hamamoto, M.
JlmmhA
544
246 349 025 025 157, 158 346 194,470, 543 513 33 1 269 364 208 164 163, 165 216 006, 110 084, 389, 533 443 465 524 224 171 197 093, 190, 192, 236
Hamann, L.G. Hrunasaki, T. Hamashima, €I. Hamdouch, C. Hamel, N. Hamill, T.G. Hammond, M. Hammoumi, A. Hamsen, A. Han, B-H. Han, D.S. Han, J.S. Han, L. Han, W.
I%im&U
Hanafusa, T. Hanjizi, J. Hanamoto, J. Hanamoto, T. Hanano, T.
HimfhAa Hanau, C.E. Handa, Y.
HalmLL
Hansen, J. Hanson, P. Hanss, I. Hansson, L. Hansson, S. Hansson, T. Hanzawa, Y. Hara, K. Hara, R. Hara, S . Hara, Y. Hmda, A. Harada, N.
IlaadcL
Haratake, M. Harden, D.B. Hareau. G. D.C.
w.
58 1
298, 335 390 313 542 169 350, 377,445 51 1 133, 271 037 028 086, 160 304 191, 211, 233, 244, 344,400 522 271, 383,494 010, 058, 204 49 1 329 067 3 12,426,499 383 282 309 094,426 211, 261, 300 363 232 271 40 1 156 178 116 278, 361, 363,449 477 342 026, 095, 182, 284,513 303 033 012 046, 075, 129, 191,225,373 12s 142 260 153
582
Compendium of Organic Synthetic Methods, Vol8
Harigaya, Y. Harirchian, B . Hark, R.R. Harmat, N.J.S. Harms, A.E. Harms, K. Haroutounian, S.A. Harp, J.J.
llixwLm
Harring, L.S. Harrington, R.E. Harris, G.D. Jr. Harris, K.J. Harris, P. Harris, P.A. Harrison, B. Harrison, J. Harrison, K.N. Harrison, T. Harrowven, D.C.
IhLJ2.L
Hartfiel, U. Hartgraves, G.A. Hartm'ann, B. Hartmann, M. Hartz, N. Haruna, S.
HxuLL JlawJX.
Harvey, I.W. Hasehe, K. Hasegawa, A. Hasegawa, E. Hasegawa, M.
Hasegawa, N. Hasegawa, S. Hasegawa, T. Masegawa, Y. Hasha, D.L Hashida, M. Hashimoto, A. Hashimoto, H. Hashimoto, S. Hashimoto, T.
229 Hashimoto, Y 390 188 352 HasswA Hata, E. 250 023 JhaJi 202 Hata, N. Hatajirna, T. 196 Hatakeyama, S. 035, 191, 235 Hatanaka, K. 066, 322, 329 196 €liuuh& 420 Hatanaka, T. Hatanaka, Y. 029 Hatanka, K. 146 420 Hatayama, A. Hatta, Y. 545 Hattori, S. 043 047 Hauck, B.J. Hauck, S.I. 469 357,486 lriului 124 Hauske.J.R. Haverty, S.M. 475 496 HaYdLL Hayakawa, A. 170 316 Hayakawa, S. 188 Hayakawa, T. 197,237 Hay'ama. Y. Hayase, K. 283 Hayashi, A. 111, 115,455 Hayashi, M. 555 07 1 380 240, 342 Iiwdlu 080, 180, 237, 301,415,436,487 240, 378, 441, Hayashi, Y. 460, 469, 473, 477,520 166 Hayden, M.R. Hayward, W.D. 170 234, 362 He, P. 130 €Icm&n Heard, N.E. 260 05 1 Jhuu&uL 447 Heaton, S.B. IIehel, D. 116 154. 195, 255,443 Hebri, H. 267, 362, 548, 559
Authors
080, 180, 240, 441, 460, 469, 473,477, 520 404, 465, 553, 559 197 319,441 048 338,358 359 412,419 378, 520, 533 022,023 086,532 I55 197 193,489 319 086 257 464 002 537 003,191, 228. 531 364 503 322 110 5 16 278,426 022, 175, 306, 314, 316, 349, 350,352 047, 192, 245, 086, 169, 358, 361, 363, 416, 489, 513, 551 361 533 386 130, 384,431 439 305 024 408,492 215, 504, 506 447
Author Index
Heckmann, B. Herding, J.M. Hegarty, S.C.
lksduAL
Hehemann, D.G. Heidbreder, A. Heidt, P.C. Heinis, D. Heintz, M. Heitz, A. Heitz, M.P. Hell, 2. Hellberg, L.H. Helle, M.A. Heller, E.
licmhmG
Henderson, I. Hendricks, R.T.
HcuhamL
Henke, S.L. Hennessy, M.J. Henry, K.J. Henry, K.J. Jr.
HcxlaAE
Herbert, R.W. Hermans, B. Hermawan, T. Hernhdez, A.E. HernAndez, R.
€tamhJK
Herr, R.J. Herrinton, P.M.
-
Hesse. C.
HssLIkL
Hettrick, C.M.
HelmmlA Heus, M.
llwaiJu
Hewkin, C.T. Hi&, M.
583
H
176,431 519 489 020, 071, 376, 400,468, 520 049 230 159 107 504,506 315 282 109 057 406 338 373 059, 372, 402, 536 430 027, 109 184 192 384 039 101 171 145 497 463 495 107 38 1 113, 196, 510, 527 420 469 518 418 156.384 516,519 178 248 45 1 463 492 377
Hidaka, S. Hideshima, C. Hiernstra._H,
Higashi, H. Higgins, D. High, K.G. Highuchi, T. Higuchi, K. Higuchi, T. Hiiro, T. Hikage, S. Hill, D.K. Hill, J.M.
BilLmL
Hillmyer, M. Hillon, M.J. Hilty, T.K. Himdi-Kabbab, S. Himeda, Y.
HimLL
Hirabayashi, A. Hirai, A. Hirai, K. Hirai, T. Hirano, M.
-
Hirashima, T. Hirata, K. Hirata, T. Hirofuji, H. Hirose, Y. Hitchcock, S.R. Hitomi, K.
094 068,221 225 126, 380, 392, 398, 402, 420, 429,436 07 1 07 1 050 42 1 03 8 24 1 017,057 307,343 135 05 1 252, 258,529 532 193 186 476 280,551 445 521,533 150,417 165 110,354 264 01 1 302,329 055, 171, 181, 223, 270,271 143 079, 083, 174, 194, 435, 470, 498, 505 017, 168 080 383 017,038,057 033,052 060 351 342 185 058
5 84
Compendium of Organic Synthetic Methods, Vol 8
Hizatale, S. Hlavacek, J. Ho, 0-C. Hobart, J.A. Hobe, M. Hoberg, J.O. Hodgson, A.
Hodson, H.F. Hoehner, M.C. Hoem, A.B. HBfer, J.
v Hoffmann, R.
HQmEu&E Hoffinann, IJ. Hogan, K.T. Hohlein, U.
HsiQLMa Holcomb, H.
IJQhkMx Holland, H.L. Hollis, T.K.
llQhaAL
IIolmquist, C.R. Holub, D.P. C.W.
lbLLL Honda, H.
J&mdcr. Honda, Y.
Hang, F-T. Hong, Y. Hongwen, H. HBnicke-Schmidt. P. Hoover, G.J. Hopkins, E. Hopkins, M.H. Hopkins, R.B. Hopkins, T.E. Horaguchi, T.
086, 125, 143, 189, 203, 491, 491,499, 532 402 432 202 528 114, 186 090 443 253,362 so1 40 1 243 452 227, 399, 425, 492 384,470, SO1 462 201,328 336 502 255 122, 331, 417, 426,446,487 467 376 270 347 275 438 397 050 321,449 238 516 381, 394 525 044, 326, 511 091, 154,409 013 044 507 469 448 438 065,342
Hori, K.
HmidL
Horiguchi, Y. Homback, W.J. Hornbuckle, S.F. Homer, G. HBrsch, B. Hoshi, M. Hoshino, K.
HQdiEaJ Hosoya, N. Hossain, M.A. Hosseini, S. Houchigai, H. Houk, K.N. Houlihan, W.J. Houri, A.F. Hoveyda. A.H. Hovorka, M.
lhYaaAL Hsu, J. Hu, B-F Hu, B.
HlLmL Hu, H. Hu,N-X. Hu, X.
HUL kiuaaL
Huang, L-J. Huang, W-S. Huang, W. Huang, X.
Huang, Y. Huang, 2-H. H ~ m gZ-Z. , Huber, E.W. Hubert, A.J.
Authors
548 475 430 083 414 385, 502 216 288 046, 047, 500, 530 473 393 33 1, 355, 408, 410,446,487 197 265 375 369 107, 520 517 428 452 046 047,297, 320 295 046 496 439 113,457 101,490 057,062 012 151 033,057, 062, 168 142,544 274 250 105 210, 287 019,024, 064, 186, 187, 221, 252, 278, 280, 445,450, 478 456 278,511 010 15s 114,226
Author Index
Huboux, A.H. Huby, N.J.S.
Hudrlik, A.M. P.F. Hudson, C.M. Huffman, J.C.
IiuslJM Huh, K-T. Hui, R.C.
HIhJL
Hull, K. Hulsdiinker, A. Humer, W. Hummer, W. Hung, M.H. Hung, S-H.
HiuLL
HlmLwL llJmLR
Hur, C.U. Hussoin, MdS. Husson, H-P. Hutchinson, K.D. Hiittmann, G-E. Hutzinger, M.W. Huval, C.C. Huyser, J.J. Hwang, H.J. Hwang, J-T. Hwang, J.P. Hwang, T.S.
u Hyuga, S .
ltmdL
Ibuka, T. Ichi, T. Ichihara, Y. Ichimura, Y.
I
031, 352 379 159, 252, 294, 324, 439, 467, 483 078 078 480 414 444 146 504 095,510 518 097 365 224 497 464 274 468 037 332, 526 452 184 546 299 469 231 536 45 1 050 269 353 229,238 462 095,367,554 095 154 108 122 49 1 410 500,524 214,498
585
Idou, Y. Ifill, A.D. Igarashi, T. Ignatenko, A.V Ihara, M. Ihmels, H. Ii, A. Iichama, K. Iihama, T. Ikari, K. Ikebe, M. Ikeda, I. Ikeda, K.
u Ikeda, S.
Ikematsu, Y. Ikuro, K.
€hJL
Ilovaisliii, A.I. hnada, Y. Imagawa, K. Imai, A.
bai& JJnaia.
Imajo, N.
LQummL
Iman, M. Imanaka, T. Imanishi, T. Imashev, U.B. Imazaki, H. Imbeaux, M. Imwinkelried, R. Imwinkelried, R. J Inagaki, H. Inagaki, M.
JIlaimA
Inamasu, T. Inamura, Y.
Illamwd
Inazu, T. Ince, F. Inesi, A. Inoguchi, K.
363 I58 362 293 165 346 114 344 079 138 234,522 439,502 126 122, 126, 127 347 255,443 072 383 241, 538 056 303 197,303 538 447 110, 336
094
058, 338, 358, 397 283 197,231 480 062 461 178 020 400 303 155, 384,412,419 149,430 240,477 100 067, 093, 094, 190, 249, 312, 360,426 269 130 092 082
586
Inoki, S . Inokuchi, T.
II-mmlL Inoue, F. Inoue. H. Inoue, I. Inoue, J. Inoue, K.
JnQueA
Inoue, T. Inubushi, A. Inubushi, T. h i , N.
IQUL IGlwulL
JLclmmE Irie, A. Irie, H. Irie, R. Irie, S.
Isaacs, R.C.A.
I.swuaL
Isaka, M. Isayama, S. Ishi, S.
Ishibashi, T. Ishibuchi, S. Ishichi, Y. Ishifune, M. Ishige, H. Ishige, 0. Ishihara, K. Ishihara, S. Ishii, K. Ishii, N. Ishii, T.
IshkX
Compendium of Organic Synthetic Methods, Vol 8
045, 181, 320,
331, 381 056, 212, 321, 341, 349 182 320 374 145 236 415 022, 023, 185, 198, 250, 251, 349,350 185, 343, 350, 356, 383,436 342 036 296 008, 119, 167, 465,479, 518 301,328 098 07 1 528 197, 198 330 074 526 257 045,320 259 122, 126, 127 545 072 052,226 098, 338, 355 5 16 098 394,433 492 025 270 055, 183 125 027, 197, 217, 304, 337, 346, 348,467,498
Ishikawa, A. Ishikawa, N. Ishikawa, T. Ishimoto, M. Ishiwawa, T. Ishiyama, K. Ishiyama, T. Ishizawa, S. Ishizuka, T. Islam, I. Isobe, K.
h k M & IsQtLL Isogami, Y. Isono, N. 110,H. Ito, K.
Ito, M.
Ito, T.
u 118, s. Itoh, A.
&&l
Itoh, M. Itoh, N. Itoh, S.
IIsunLL
Iuliano, A. Ivana, C. Ivanova, N.M. IvanoviC, M.D. Iwakura, K. Iwamoto, 14. Iwanami. K.
hLI!LJ
Iwaoka, M. Iwasa, S.
Authors
318 285 264 154 130 154 342 078, 232, 238, 516 449 023,072, 125 169, 182,443 186 503 28 1 052, 181, 226, 369,475 154, 398 346 278, 361, 363,449 023, 146, 157, 166,468 038, 160 004,282, 283, 358,446 149, 197,198, 296, 312, 313, 316, 415,539 009, 315, 387,394 196 042, 116, 125, 161, 224, 344, 432,458 181 236,253 379 146, 157, 158,468 022 489 34 1 155 552 100 498, 512 540 495 339,456,527 077
J
Author Index
IHaswLN Iwaski, M.
k&lL
Iwata, E. Iyanar, K. Iyer, L.G. Iyer, R.R. Iyoda, J.
IYQLku
Izatt, R.M.
I.ZmiJ IzuliL
Jachiet, D. Jackman, R.J. Jackson, J.T.
JA&mAEK Ji&mouL
Jacobsen, J.R.
J&aY4 Jagoe, C.T. James, D.M. Jan&, L. bnecki. T. Jang, D.G. Jang, D.O. Jang, S. Janousek, Z. Janowitz, A. Jansen, J.F.G.A. Jarmillo, L.M. Jarosinski, M.A. Jarstfer, M.B. Jarvi, E.T. Jarvis, B.B. Jash, S.S. Jaspars, M. Jasperse, C.P. Jaszberenyi, J.C.
587
503, 527 126 356,433,480 47 8 088 056 537 063 074 407 151 031, 137, 241, 349
Jaszberenvi. J.Cs.
329 003
Jc@wAL
444
492, 530 128, 149, 298, 366,427 195, 271, 281, 397 086 127, 155,402 391 131 224, 365, 551 020,373 206 142 392, 530, 555 160 068, 212-214 21 1 43 1 156,367 106 415 315 109 549 428 272 028 218 213
lhudLL Jaxa-Chamiec, A. Jebaramam, D.J.
k?mzdL limmLcx
Jeganathan, A.
J.GM&G Jensen, M.S. Jeon, Y.T. Jeong, I-H. Jeong, J.U. Jeong, K-S. Jeroncic, L.O.
LwLL
JcyamaB Jhingran, A.G. Ji, J.
JwLE Jiang, H-X.
Jiang, S. Jiao, X-Y. Jimenez, H.N. Jin, C.S. Jin, F. Jin, N. Jin, S-J.
JimL-Q. Jintoku. T. Jisheng, L. Joglar, J. Joh, T. Johar, P.S. John, J.A.
JilhmLL Johnson, E.J. Johnson, J.W. Johnson, S.A. Johnson, T.O. Jones, D. Jones, G. Jones.
a
Jlam&uL
006, 068, 076, 212,214 483 423 534 056, 277, 372, 538 231,293 348 534 045, 118 524 410 03 1 234 279 412 418 121 159,412 437 504 487,499 221 045, 326 439 380 304 487 490 075, 363 364 342 354 3 14,424 46 1 327 358 180.499, 525 073 272 387 522 112 186 308 024, 305 368
588
Compendium of Organic Synthetic Methods, Vol8
Jutateladze, T.G.
123 539 42 1 183 130 383,500 240 124 316 547 08 1 059 29 1 059 094,399 064, 112, 266, 479,497 260 516 002 088 486 153 229 424 096 418 241,538 524 189 078 502
Kabashima, T. Kabbara, J. Kabore, L. Kaczmarek, L Kadam, S.M. Kaddachi, M.T. Kadota, I. Kafka, C.M.
007, 011, 031, 039, 135, 158, 160, 161, 193, 229, 289, 292, 300, 325 192 531 432 060 052 088,414 003, 147, 360 250
JMC5-K.
Jones, K.D. Jones, T.H. Jordes, L.
Joseph, S.P. Joseph-Nathan, P. Josephy, P.D. Josey, J.A. Jouglet, B.
JiulldA Jroundi, R.
Judge, T.M. Juge, S.
JuaJL
Juliano, C.A. Julin, S. Julius, M. J Jumbam, D.N.
lun.J-G.
Jung, J.C. Jung, K.W.
JilLML Jung. Y-W.
Juntunen, S.K. Juroboshi, M.
JalkmdA
IGimlaE Kaino, M. Kaiwar, V. Kaji, S.
Kajii, K. Kajikawa, Y. Kajita, M. Kakeya, H. Kakikawa, T. Kakimelahi, G.H. Kakinami, T. Kalashnikov, S.M.
ih.uLsx Kalesse, M.
I%
Kaller, B.F. Kallweit, H. Kalsi, P.S.
KamaLA
lGlmu& KalIhLU Kainei, K. Kamezawa, M. K,amio, C. Kamiya, N. Kainiya, Y. Kamm, B. Kamphuis, J. Kanagawa, Y. Kanai, M.
lihaai&
Kanamori, F. Kanazawa, A.M. Kanbe, N. KantLi, 11. Kandeel, E.M. K'andil, A. Kandzia, C. Kane, R.R.
Authors
044,272, 308, 345 433 040 133 205, 208, 398, 495,515 547 347 083 014,245 150 095 205,208,495,515 062 27 1 441
413,466 48 1 253 058 059, 317 240 062, 142, 168, 237, 307, 343, 417, 423, 484, 489,522 356 320 084, 270,491 548 410 217,498 338 343 017,029 380,436 027, 304 108,463 294 483 170 234 297 120 124 063 042
Author Index
Kiln&&
Kaneko, I. Kaneko, M. Kaneko, T. Kaneko, Y. Kaneta, N. Kang, D.H.
IbnLL lQuusJL IkimLsL Kann, N. Kanno, Y.
KmLL Kant, J.
IsiumaL Kanth, J.V.B. Kanzaki, A.
I4!QmJL
Kapovits, I. Kaptein, B. Karabelas, K. Karaman, R. Karikomi, M. Karim, M.R. Karlsson, U. Karpa, A. Kashimura, S. Kasi Reddy, C.P.R. Kassir, J.M. Kataoka, H. Kataoka, M. Kataoka, T. Kataoka. Y. Katayama, H. Katayama, Y. Kates, S.A.
JGuLL
Kato, M. Kaio, S.
K
197, 237 478 310 022 021,327 400 087, 249, 346 304 353 234, 305 22 1, 525 458 462 372 435 195 386 053, 075, 177 016,040, 143 218 223,471 471,495, SO8 269 380,436 533 121.21 1 335 438 370,548 258 108,426 098, 338.355 161 066 372 51 1 475 069, 184, 247, 360, 395, 423, 485 106 348 510 045, 181, 320, 400,401. 544 430.484 148, 154, 157
589
Kato, Y. Katoh, Y. v. A.R.
Katsuhira, T. Kalsuki, J.
Katsumata, K. Katsuura, A.
KatLu
Kauffm;mn.T.
KauJwi
Kaur, B. Kaur, N.P. Kawahata, T. Kawada, M. Kawada, Y. Kawafuchi, H. chi. AT, Kawai, K. Kawai, T. Kawai, Y. Kawakami, T. Kawamoto, K. Kawamura, M. Kawamura, Y. Kawasaki, Y. Kawase, T. Kawashima, H. Kawashima, T. Kawate, T. Kazala, A.P. Kazi, A.B.
m!d%A.
lbkG.L Kee, I S . JkwmMA Keil, R.
Keiner. P. Keith, S. J
240,385 025 005, 141, 146, 169, 187, 272, 274, 311, 375, 419,420,480 075, 142 093, 360 023, 197, 198, 318 463 475 192 082, 113 202,435 024, 028, 097, 207, 253,428 219 228 314 125 170, 255, 279, 285,455 430 212,349 40 1 307 548 039, 217, 323 041,303 237 359,441 132 029 070 183,229 133 1so 109 428 034, 333,472, 535 324, 356 014, 048, 050, 072 192,464,485 250,263 006,239 462 462
590
Compendium of Organic Synthetic Methods, Vol8
Keller, T.H.
KcllGE Kdwx K.a&A&
Kennedy, M.
Kennedv.R.M. Kenny, C. Keogh, B.P. Kepler, K.D.
Keriomov, F.F.
IiwdLY. JhmiLL
Keusenkothen, P.F. Kgaphola, M.M. Khan, K.M.
JchanaA
Khanapure, S.P. Khanna, M.S. Khanna, V.V. Khanolkar, A.D. Khazanovich, N. Khetani, V. Khosrowshah. J.S. Khotinen, A.V.
lauumd& Kibayashi, S.
mQ&E
Kielbasinski, K. Kielty, J.M. Kiely, J.S. Kiers, N.H. Kielbasinski, P. Kihara, N.
rciuyL Kiji, S.
Kijima, A. Kikuchi, K. Kim, B.H. Kim, B.J. Kim, B.M.
532 47 1 294 162, 251, 531, 547 551 334 324 096 208 494 478 314 038, 050, 163, 233 125, 127, 138 145 048 465 351,386 495 014 035,078 459 518 179 273 012, 167, 257 160 140 428,430 396 532 467 097 238 551 080,240,477 012 083 144 384,412,419 128,243 248 099, 188 234 295,299
Kim, C.W.
Kuna
Kim, H - 0 . Kim, H.J. Kim, H.R. Kim, Kim, Kim, Kim, Kim, Kim, Kim,
H.S.
J.M. J.N. J.S. K. K.C. K.D. Kim, K.K. Kim, K.M. Kim, M. Kim, S-G.
KimA.
Kim, Kim, Kim, Kim, Kim, Kim,
S.S. S.W. T.J. W.J. Y.C. Y.G.
Kim, Y .S. Kimoto, H. Kimura, K. Kimura, M. Kimura, T.
Km!lLX
Kinder, F.R. Jr. Kinoshita, H. Kinoshita, K. Kinsella, M.A. Kinter, C.M. Kinter, K.S. Kipphardt, H.
Authors
117 100, 241, 390 304,305 227, 399, 492 206,493 010, 206, 436, 493,496, 549 140,390 059 243,436,496 304 009,305 083 084,496 496 496 229,269,270 514 458 014, 033, 034, 048, 050, 072, 099, 117, 187, 241, 254, 305. 470, 479, 481, 518, 522, 526 020, 520, 525 465 140 462 305,419 187, 241,470 009, 202, 229, 267, 270,493, 549 424,465 469 023, 125 379, 392, 392 27 1 023,205 315 182 350 141 536 440 440 024,417
K
Author Index
Kirby. G.W.
Kirchhoff, E.W. Kirio, Y. Kirito, Y. Kirollos, K.S. Kirshning, A. Kirwan, J.N. Kise, N. Kishi, K. Kishigami, S. Kishimura, K. Kissick, T.P.
Ki&L
Kitagaki, S. Kitagawa, K. Kitagawa, 0. Kitajima, H. Kitamura, M. Kitano, K. Kitoh, Y. Kiyoi, T. Kiyomiya, H. Klass, M.Rg. Klein, B. Klein, D.A. Klempier, N. Klicic, J. Klimko, P.G. Kling, J.K. Kluge, R.
JLnafkL
IwmJE.
Knight, K.S. Knoch, F.
ILIwbdL
Knoess, H.P.
425 514 342 502 408 182 214, 216 315, 325, 346, 439 415 019 182 073 155, 169, 238, 283, 384, 412, 419, 474, 529 238 062, 196 383,434,436 050, 163,233 038 174,323 192, 276, 280 157 253 416,511 083 021, 325, 327 299 377 537 013,288 543 442 519 269 343 163, 165, 388 156 086,090, 196 391 003, 073, 099, 103, 104, 278, 339, 355, 425, 460, 480, 533, 540,556 003
59 1
Knorr, R. Kobayashi, Kobayashi, Kobayashi, Kobayashi,
H. K. M. N.
Kobayashi, T. Kobayashi, Y. Kobbing, S. Kobertz, W.R. Kobs, U. Kodama, T. Kodama. Y. Koenig, T.M. Koerber, K. Koga, A. Koga, G. KQb=K. Koga, K. Koh, J.S.
KQ!LL
Kohlman, D.T. Kohlmann, A. Kohlstruk, S. Kohmoto, S. Kohmura, K.
KQhlJ
Kohno, M. Kohra, S. Koide, K. Koide, Y. Kojima, A.
-
Kol, M. Kolaczewska, A.E.
KQl!J&L
Kolbe, A. Koldobskii, G.I. Komatsu, H. Komatsu. N.
375 500,524 435,539 061 264 115, 191, 211, 229, 233, 280, 312, 319, 342-344, 346, 350, 373 122,206 358,434,449,473 472 061 137 357 129 414 547 206,477 091,351 48 1 098 214,498, 512 098, 108, 145, 235 295 033,034 436 21 1 193 519 330, 356,456, 527 314 128 183 355 191 058 121 016 194,268 459 264 55 1 406,429 547 149,430 270
592
Compendium of Organic Synthetic Methods, Vol8
Komiya, Y. Komura, M. Komuro, M. Konaklieva, M.I. Kondo, K. Kondo, M. Kondo, S. Kondo, T. Kondo, Y. Kong, K-C. Konigsberger, K. Konishi, H. Konishi, K. Konno, A. Konradi, A.W.
.
. I
Konusch, J. Konwar. D. Konyushkin, L.D. Koo, S. Koot, W-J. Kopola, N. Kopping, B. Korda, A.
Koreeda.M. Kort, M.E.
Koschinsky, R.
IQELLL
Kostikov, R.R. Kostitsyn, A.B.
J.cQ€wA Kotachi, S.
KQuLA Kotani, T. Kotani, Y. Kolha, S.
Kottirsch, G. Koul, V.K.
ihf&LL
KovBts, Ez.
136,478 02 1 017 340 077 042 323 162, 226, 403, 458,519 078,089, 178 083 180 030 198 436 538 096, 200,470 308, 312 432 440 160,245 185 475 126 399 088, 217 124 197, 296, 298, 335,475 01s 499 230,540 111 110 473 146 169, 398 287 075 404 068, 193 003, 126, 140, 147, 185, 312 285 122 283 09 1
Kowalczyk, J.J. Koyama, K. Koziara, A.
A.P.
Kpegba, K.
KmLML
Kr.mJx
Krakowiak, K.E. Kral, V. Krass, N.
KEluda Krause, J.
lsmua.
Krauze, A. Krebs, J.D. Krempp, M. Kreutzer, K.A.
KmA
Krishnamurlhy, V. Krishnamurti, R. ma,0. Krolikowski, D.A.
lcuQQd3 Krosley, K.W. Krueger, A.C. Kriiger, C. Kruglov, E.A. Kruse, C.G. Ku, W-S. Kubo, A. Kubo, Y. Kuchin, A.V. Kudo, H. Kudo, K.
KlKUL
Kudoh, E. Kuester, P.L.
U
Kukui, M. Kulak, A.N. Kulawiec, R.J. Kulicke, K.J.
Authors
082 176,447 032, 206, 381 154 148, 389 390,537 097 138,442,445,516 067 407 432 037 035, 097, 232, 4 10,466 550 45 1 370 161 22 1 016 112, 114, 186, 335 032, 361 338 016 396 073 208 033 394 3 14 062 317 13s 192,487 496 249 27 1 469,473, 520 017,029 490 013 404 305 108,426 518 085 111
Author Index
KULAs.
Kumanovic, S . Kumar, A.
IcluLE
Kumar, H. Kumar, H.M.S. Kumar, M.U.
IclmmLE
Kumar, P. Kumarathasan, R. Kume, K. Kume, Y. Kumohayashi, H.
lslukui
Kunimi, N. Kunishima, M. Kuniyasu, H.
IilwJL Kunz, T.
Kuo. D.L. KUO, M-Y. Kurasawa, Y. Kurata, T. Kure, S. Kurihara, T. Kurohoshi, M.
Kuroda, C.
Kurcxla, H. Kuroda, T. Kuroki, Y. Kurosawa K.
IwhJ!u
Kurumada, T. Kurusu. Y. Kusaka, H. Kusama, H. Kusama, Y. Kusano, K. Kusche, A. Kushko, A.D.
593
L
013,235 054 219 526 147, 345 168,228 168,228 403 406 065 065 031 327 230 378, 379,401 489 023,072, 125 315 283 489 056,239, 340 367 002,219 532 150.444
175 010 392 534 025, 143, 203, 40 1 122 055 077 393 469 032,454,414 480 028, 299, 300, 364, 454, 473, 534 320 358, 361 467 062, 237, 506 462 535
Kusomoto, M. Kusumoto, T. Kuwabara, T. Kuzmierkiewicz, W. Kwak, K.H. Kwon, H.B. Kwon, 0.0. Kwon, T. Kwon, T.W. Kwon, Y .G. Kwong, H-L. Kyrij, A.B. Kyushin, S. Ltlaridon, P. Laarmann, B. Lahar, D. LaBeau, D. Labiad, B . Lahrde. & Laboue, B. Lahoureur, J.L. Lahrecque, D. Lachaise, I. Lacour, J. Ladhar, F. Laffitte, J.A. Lafont, F. Lagu, B. Lalioti, R.J. Lai, E.K.Y.
R.W
Lakslimaiah, G. Lal, G.S. Lalloz, L. Lamatsch, B. Lamhert, C. Lamidey, A-M. Lamont, R.B. Lamothe, S. Landis, M.S. Lane, G.H.
321,341 048,051 38 1 40 1 096, 352, 419, 430,487 187,480 229,238 511 059 23 1 138, 395,490 140 295 535 080 164 024 335 369 501 097, 158 22 1 335 536 49 1 155, 525 530 094 052 106, 140 233 555 104 422 132 041 29 1 278 114 546 263 291, 336,416, 529 420 421
594
Compendium of Organic Synthetic Methods, Vol 8
LauJsx
Lang, R.W. Langadianou, E. Lange, C.
I2KusGL Langhals, E. Ialuhka Langlois, P. Lanneau, G.F. Lansky, A.
LmQsJ'
LarchevCque, M. Lardicci, L. Lardicci, L.
LamLRc
Larouche. D. Larsen, J. Larson, A.L. Larsson, E.M. Larsson, J. Larsson, U.
IaShJa ILlszhx
Lathburg, D. Latif, M. Latouche, R. Latrofa, A. Lattanzi, A. Laurent, A.
u Laurent, E.
Jdauma.
Lauterbach, E.H. Lawrence, N.J. Lawrence, R.M. Lazor, J. Lazzarini, E. Le Blanc, S.
520 Le Guillanton, G. 434,498 021,022 Le Marrec, N. 208 Le Nocher, A.M. 200,509 Le Roux, C. 234 le Rouillb, E. 234 ILtama& 293 Leathers, T. 424 Lebedev, M.Yu. 117 Lebedev, S.A. 086 LebhlLL 428 Lecea, B. 073,394 LeCIercq, M. 261 Lecoq, J.C. 280 l&LAJuL 087,150,189, Lee, c-P. 257,354,389, Lee, C.H. 417,444,449,Lee, D-H. 476,521 L&LE 250 Lee. F.L. 130 Lee, G.K. 026 Lee, G.M. 179 Lee, H.S. 084 Lee, IS. 156 Lee, J-S. 401 Lee, J-T. 201 Lee, J-Y. 543 Lee, J.B. 127,195,501 Lee, J.C. 453 520,525 146 LxLLG Lee, J.H. 350 166 Lee, J.I. 334 Lee, J.K. 464
236 432,492 031,034,088, 114,250,297, 352,359,534 324,471 216 071,534 437 074 403 385
Lee, J.M. Lee, J.W. Lee, K-S. Lee, K. Lee, K. Lee, M-S. Lee, N.H. Lee, P-c. Lee, S-B. Lee, S-J. Lee, S-Y. Lee, s.
Authors
SO8 190 423 273,362 346 467 366 467 195 085 126,133 252 279 038 488 410 202 277 424,452 307 269 492 054,059,060,063 493 458 006,210,262 110
060
054,059,221, 083,203,229,238 234,305 102 134 099,117,481 555 525 487,517 552 217 189,195,281,521 104
064 274 047 033,072,161, 234,518,522
L
Author Index
Lee, S.-H. Lee, S.E. Lee, S.J. L d L l x
Lee, W. Lee, W.K. Lee, Y.B. Lee, Y.Y. Lee. S.E. Leelavati, P. Leemhuis, F.M.C. Lefrancois, J-M. LeGallic, Y. Legido, M. Legros, J-Y. Lehmann, R. Lei, B. Lei, H. Lei, X-H. Leigh, A.J. Leijonmarck, H. Leite, M. Leitenberger, V. Lelandais, P. Lemieux, R. Lenarao, E.J. Lensen, N.
m
Leon, F.M. Le6n. E.I. Le6n-Col6n, G. Leonard, W.R. Leonard, W.R. Jr. Leone, C.L. Bav. Lequeux, T. LeRoux, J. Lesage, M. Lesheski, L.E. Lesirnple, P. LeRmann, K. Lessor, R.A. Leuck, D.J. Leung, W-Y. Leung-Toung, R.
095 059,063,412 412 289, 330, 340, 475,514 004 306 134 134 054 474 447 464,484 371 148,394 070,071, 508 263 32 1 412 133 517 327 072 380 23 1 216, 330, 332
009
397 128 522 381 249 407 107 213 201 339 508 462 097 307 236 076 128 146 354 179
595
Levart, M. Lew, G. Lew, W. Lewis, N. Lewis, P.J.
LedAx
Ldbamw&
Lhoste, P. Li, B. Li, C.J. Li, K. Li, L-H. Li, L. Li, M. Li, N-S. Li, Q. Li, S-W. Li, S-Y. Li, X-Y. Li, X. Li, Z-Q. Li, Z. Liang, S. . . . Liao, Y. Licini, G. LieberknechL A. Im. B. Light, J. Li-jewski,L
Lim, J.K. Lim, S.C. Limosin, D. Lin, J-H. Lin, K-C. Lin, P-Y. Lin, S-C. Lin, S-H. Jin. S-Y. Lin, X. Linde, R.G. I1
195 286 096 145 443 050 116 149,210 189, 314 374 026, 191, 235 335 076 060 399 532 294 252 449 200, 203,408 434 186 499, 542 090 521. 525 064,221,445 558 380 342, 387, 512, 521, 523 062 215 040 535 462 491,549 093 080 160 135 060 296, 357 280 354,412 38.5 008, 018, 092, 101,408
Compendium of Organic Synthetic Methods, Vol8
596
Link, J.O. Linstrurnelle, G. Liotta, L.J. Lipowska, M.
Lira,
s.
u Litvinov, V.P. Liu, C.
u Liu, H. Liu, L.
LiLw
Liu, Z-R.
lLhMJE
Llavona, L.
Llinares, M. Llinas-Brunet, M. Llorente, I. Lloyd, H.A. Lluch, A-M. Lobo, A.M. Locati, L. Lodaya, J.S. Lodge, B.A. Loffet, A. Ltiffler, A. Loh, T-P.
IAbasAE Lohse, P. Lolkema, L.D.M. Loner, H. Long, Q-H. Longley, K.L. Longmire, C.F. Longrnore, R.W. Look, G.C. Lopatina, V.S.
041, 157, 232 Lopez, C. 277, 286 Lopez, L. 345,431 Lbpez, C. 164 Lbpez, F. 142 Lbpez, J.C. 095, 097-100, 102, L d p ~M.C. , 108, 226, 250, Ldpez, M.P. 263,532 Lbpez-Alvmdo, P. 172 Lopez-Leonardo, C. 115 Lorente, A. 166 Lou.J-D. 096, 265,425, LOU,W-X. 507 185 Louey, J.P. 536 Lough, A. 214, 321, 351, Lough, A.J. 435,453 083, 124 Louvet, A. 082 Lovell, H. 296, 357 LQ!tdx& 218 LowenlhJ, R.E. 013 Lozanova, A.V. 493,494 Lu, G. 458,524 Lu, H. 315 LLL 216 Lu, L. 497 L U L 369 183 144 Lu, Y-w. 333 540 Lu, Y. 206 Lubbers, T. 290 Luce, P. 280 Lucero, M.J. T 310 275, 302, 304, Ludwig, C. 312,509 332 Ludwig, R. 429 Lue, P. 332 419 308 Luheshi, A-B.N. 288 Luis, F.R. 444 Luke, G.P. 478 Lukevics, E. 085 Luna, D.
u
u
Authors
256 444 252 497 173,204 348 105 126, 150 530 546 057 057 165 039 297 088 127, 166, 185, 191 42 1 289 252 109 262 460 498 289 321,449 287, 449, 456, 456, 459, 475, 491,499, 504, 522,528 174 087 428 384 554 105, 118, 100, 164, 290, 356 072 293 187, 311: 419 069, 080, 215, 260,534 400 208 357 311 052
Author Index
Lund, K.P. LlaEL
Luo, J. Luo, w. Lupattelli, P. Lupi, A. Lusinchi, X.
LwlYkJ
Lutsenko, A.1. Luzzio, M.J. Lyford, L. tyfwa, P. Ma, D. Ma, R. Ma. S. Ma, Y. Ma, 2.
Maas&
Mabon, G.
MacDougall, J.K. Machigashira, N. Machii, D. Macias, F A . MacKenzie, A.R. MacLeod, D. Macomber, D.W. Macor, J.E. Maddaluno, J. Maddock, J. Madero, J.G. Madge, D.J. Ma&, J. Maeda, M. Maekawa, €1. Maekawa, K. Maekawa, T. Maekawa, Y. Maeta, H. Maezaki, N. Magar, S.S.
-
M
111,115 248-250, 395,485 268 435 339 012 081, 194 216 185 307 109 045 270 148,450, 504 336 287, 456, 459, 491,499 423
051
112 559 213 278, 311, 351 046 127 036 501 369 486 274 403 537 540 208 501 320 160 012 534 226 441
267, 362, 538, 559 480 028
Maggi, R. Maggini, M.
-11s.
. .
P.4.
Maguire, A.R. Mahajan, A.R. Mahajan, M.P. Maliajan, S.W. Mahanty, .IS. Mahmmd, K. Mahon, M.F. Mahwald, R.
Maihara, A. Maikap, G.C. Maillard, M. Maiti, S.B. Ma.j!jdoub, M. Majid, T.N. mdar. Makarnura, 11. m c r i a . M. Mala~~da, J-C. Malik, S. Mallart, S. Mallo, A. Malone, J.F. Manage, A.C.
MalEMAL
Mandville, G. Manfredi, M.C. Mangeney, P. Mangold, R.
MmbaLMA
ManjunaUia, S.G. Manly, C.J. Mann, A. Mansell, H.L. Mansuy, D.
597
375 302 346 155, 316, 413, 473,525 335 084,483,496 55 1 010 425 182 489 048 540 373, 503 556,558 446 012, 167, 257 010, 130. 216 368 543 166 517, 518 073 405 33 1 06 1 358 261, 374 048 094 030 121, 315 168 170, 255, 279, 285,455 182,215 525 161 069, 397 380 118 543 448 360, 377 I S8 515
598
Compendium of Organic Synthetic Methods, Vol8
Mao, X.J. Mar, E.K. Mar, E.K. Maraval, M. Marble, L.K. Marcantoni, E.
Marchese, G. Marchetti, M. Marco, J.A. Marco-Contelles, J.L. Marcotullio, M.C. Marcucci, J.L. Marczak, S.
MaEu
Margot, C. Marian, L.
Marinas, J.M. Marinelli, F. Marini, F. Marion, P. Markandu, J.
McdsUJi
Markb, L. Markova, S.A.
MixkCIL
Marlin, J.E. Marotta, E.
MamkaA
Marquet, B . Marr, J. Marron, B.E. Marrs, C. Marschner, C. Marshall, J.
MlamuA Marshall, R.L.
245 170 173 346 255 268,553 094 515 308 312 256 442 152 513 047,090 360,464,484 356 176 129,410 052 075, 092, 094, 286, 415, 421, 45 1,457 47 1 102 404 405 008, 026, 055, 075, 075, 103, 119, 172, 188, 220, 367, 485, 40 1 444 249 047 552 553
053 432 107 044 141 468 443 249, 357, 476, 482,488 027
Martelli, G. Martin Castro, A.M. Martin, M.G.
Martin, V.A.
-
Martin-Cantalejo, Y. Martin-Lebn, N. Martha, D.P. Martinelli, G. Martinez, J.P. Martorell, G. Martre, A-M. Maruoka, K.
Maruyama, T. Maruyama, Y.
Marzabadi, M.R. Masaki, M.
Masa)ri..
Masawaki, T.
MaLLA
Mashava, P.M. Masiero, S. Masjededizadeh, M.R.
MmukAA
Massanet, G.M. Masters, J.J. Masuda, M. Masuch, R. Masuda, S. Masui, Y. Masumi, N. Masumizu, T.
Authors
123, 393 120, 157 553 143 348 111, 115, 171, 316, 550 342,465 009,271, 336,425 365 256 557 002 058 315 361 010,202,204,500 077,215 239 030, 061, 175. 183, 262, 306, 355, 372, 513 226 289 155,345 462,480 029 004, 196, 282, 283, 556 017, 109, 326 484 029 335 118 025 265 550 208,435, 501 520 483 122,417 298 046, 047, 080, 500,530 128 062 307
Author Index
Masumoto, K. Masunari, T.
Maswmhx Mata, E.G. Matasi, J.J. Mathew, F.
MaukXJ
Mathew, T.S. Mathvink, R.J.
rihmbm&
lkimbmx Matsubura, S. Matsuda, H.
Matsuda, S. Matsuda, T. Matsuda, Y. Matsuguchi, A. Matsui, T. Matsuka, T. Matsukuma, A. Matsumoto, H.
k%lmmLL Matsumoto, N. Matsumoto, S. Matsumoto, T. Matsumoto, Y. Matsumura, Y . Matsunaga, S . Matsuo, F. Matsuo, H. Matsuo, J. Matsuo, S. Matsuoka, S. Matsushita, H. Matsushita, K.
M
240 446 028,299. 300, 364, 454, 413, 534 029 510 179 433, 511, 519 054 440,512 139, 278, 350, 414,531 017 348 041, 043, 118, 123, 130, 193, 221, 336, 368, 437, 459, 412, 489, 502 34 1, 374, 392, 449 238,283 349 046 285 528 334 320 032 154, 185, 214, 229,299 197 056, 094, 321, 54 1 267, 343, 559 301 012, 325, 388 181, 226 368 02 1 010 026 001 045,056,239 080 397,424, 528
599
Matsusita, H. Makuura, H. Matsuyama,H. IaaEOu Matthews, D.P. Matthews, I. Matulenko, M.A. Matusiak, M Maugein, N. Maumy, M. Maumy, M. T Maury, C. Mauz6, B.
Ma!mJM.
Mayesky, B. Mayoral, J.A.
MaYdL MauJL
Mazurchik, A.A. Mazzanti, G. McCallum, J.S. McCamey, M.T. McCarthy, C. McCarthy, K.E. McCarthy, N. McCrea, W.R. McCubbiii, Q.J. McDemott, P.J. McDermott, T.S. McDonald, C.E. McDonough, C.S. McEachin, M.D. McGarry, D.G.
McGettigan, C. McKee, B.H. Mckee, S.P. McKennon, M.J.
lYmm&bm McKie, J.A. lop. A, McKinnis, B.R.
483 030, 112 270 230,412 496, 549 206 146 044
547 557 037,038,059 22 1 546 530 21 1 041 10s 499 535 203 025 387 473 315 123 140, 155,496, 549 143 473 552 441,552 537 366 067 174,452,453 461 243 516 188 020,235 248 511 300
422 370,473, 551 044, 301 443 464
600
McLaren, L. McLoughlin, J.I. McMullen, L.A. McNeill, A.H. McPhail, A.T. McSorely, K. Mecozzi, S. Medich, J. Meenakshi, R. Meguir, H. Mehandoust, M. Mehta, S. Mehta, V.D. Mei, N-W.
M&AL
Meier, I.K. Meier, M. MeirAs, D.P. Mekhalfia, A. Mello, R.
hkhAM.
Melnik, N.N. Melville, J.C. Menashe, N. Mendelson, W. Mendoza, J.S. MenCndez. E. MenCndez, J.C. Menezes, R.F. Meng, X-J. Menges, D. MerCny, R. Merger, R. Merino, I.
Merriman, G.D. Merritt, J.E. Mertin, A. Messadi, D.
M=awGA
-
Compendium of Organic Synthetic Methods, Vo18
443 507 527 353, 362 207,495 47 1 410 295 107 056 162,256 394 257 117 069,260 488 248 246 07 1 008, 026, 055, 119, 172, 188, 485 036, 224, 241 031, 072, 076, 308 420,431 535 41 1 220 428 162, 251, 547 129 126, 150 138 289, 300. 325 024,097 261,374 43 1 284 416 084, 183 419 520 401 059, 129,244 130 183,461
Messeri, T.
MesSLR
Metais, E. Mettemich, R.
bkxLL
Metz, W.A.
lYlWw2.
Meyer, A.G. Meyer, D. Meyer, E. Meyer, R.
MeYmAL Meyerson, S. Mezzina, E. Miao, S.W. Michael, J.P. Michelon, F. Michelotti, E.L. Michioka, T. Michoud, C. MiCoviC, I.V. Middleton, D.S. Midura, W.H. MihailoviC, M.Lj. Mihara, I. Mikami, S. Milczanowski, S.E. Millan, S.D. Miller, A. Miller, D.G. Miller, R.F. Milligan, G.L. F.D. MilosavljeviC, S. Min, S.J. Minato, M.
Authors
09 1 178, 282, 286 294 22 1 343 393 441 097, 273, 362 457 147 132 380 041, 107, 144, 150, 156, 404, 407,422 006 316 142 332, 526 293 526 408 190 155 099 430 147,530 284 432 280 264, 310, 327, 333,481 470 551, 270.430 138 442 306 237 314 082 134 182 432 059,060 071, 125, 175, 266, 278,400, 5i00 296
Author Index
Mincione, E. Mineta, H. Minniear, J.C. Miranda Moreno, M.J.S. Miranda, E.I. Miranda, R. Mishida, S. Mishra, P. Misiti, D. Miskevich, F. Mitchell, A.L.
Mitsuhashi, 11. Mitsui, H. Mitsui, K. ohu. Q. Mittakanti, M. Miura, A. Miura, K. Miura, T. Miwatashi, S . Miyachi, N. Miyagawa, N. Miyaguchi, N. Miyai, J. Miyai, T. Miyama, N. Miyamoto, H. Miyamoto, Y. Miyashita, K. Miyata, H. Miyata, 0. Miyata, S.
M
339 110 403 082 089, 113, 119, 176, 282,431 224 039 240 336 469 269 001 007 032, 206, 381 096 35 1 076,449 403,453,458 070 268 128 535 042 434 299, 433, 479 002, 116, 224, 458,485 196 025, 395,423 167 152 151 269 069,360 039 264 238 302 350 093, 133 433 156, 176, 502, 528 149 381,430,450 435
60 1
512 001, 045, 078, 085, 090, 232, 264,516 218 474, 529 255 192 551 433 526 168 173, 304 041 333
Miyauchi, Y Miyaura, N. Miyazaki, K. Miyazaki, M. Miyazaki, Y. Miyoshi, N. Mizu, Y. Mizuno, H. M1ochowski-L Mohele, B.I.
MQdGmA MiwLKa
Moens, L. Mogami, T. Mohammed, S. Mohamud, M.M. Mohri, K. Moiseenkov, A.M. Mokolajczk, M.
Molina, A. MolinaS. Molinillo, J.M.G. Miiller, T. Molloy, K.C. Moloney, M.G.
Il4amcL
Monette, M. Monflier, E. Montanari, V. Montaufier, M-T. Monteagudo, E.S. Monteiro, N. Monteith, M. Montgomery, D. Montserrat, J.M. Moorcroft, D.
MmlLJLx
Moore, J.S. Moorhoff, C.M.
055
309, 365,462,480 413 307 431 066
143 262,341 199 044,088, 090, 301, 322, 324, 329, 349,470 165, 386 530 501 028 540 123, 309 383 167 325 224 127, 501 334.441 455 135 39 1 077 486 519 242 403
602
Compendium of Organic Synthetic Methods, Vo18
Moran, J.R.
MQmLuL
MQuaLuA Morel, D. Morena, E. Morente, M. Morera, E. Morere, A.
MsmLLM. Morgan, B. Morgan, I.T. Morgan, J. Mori, A. Mori, H.
MQLM.
MQtiJ. Mori, T.
Moriarty, K.J. tv. v. R.M. Morikawa, S. Morikawa, Y. Morimoto, M. Morimoto, S.
Morin-Fox, M.L. Morinaka, Y. Moriiita, T. Morita, H. Morita, T. Morita, Y. Moritani, T. Moriwaki, M. Moriyama, K. Morizono, D. Morkcn, J.P. Morken, P.A.
440 338 105, 263, 356, 364, 413, 417, 490,517 420 284 089 558 089, 284.454 132 183,458, 524 171,319 533 234 023, 349, 350 243 079, 083, 087, 237, 249, 346, 41 1, 470, 496, 528 075 410
497 347, 438, 468, 507, 517, 538 179 166 297,515 353 439 055, 086, 171, 181, 223, 270, 27 1 172 257 441
346 050. 163 277, 343 26 1 030, 154, 297 205,208, 236 408 173 046 498
Morooka, M. Morreno, 1. Morrison, D.S.
b&lmLGK MQlsLKx
Morton, H.E.
l!!mEmA
Moskovkina, T.V. Mosleh, A. MLuLtlL Mossman, C.J. Motoyoshiya, J. Mottaghinejad, E. Moughamir, K. Mouri, M. Mouriilo, A. Moursounidis, T. Mouser, J.K.M.
MQuwJL t. J-C Movano..
Muci, A.R. Mudd, J. Mudryk, B . Mueller, B. Mueller, R.H. Mueller, T. Mues, C. Mukai, C. Mukai, I. Mukai, T. Mukaiyama. S.
Mukhopadhyay, A.
Authors
038 559 557 172 092, 509, 528 042 366 177,325 494 078 423 134 115, 207, 236, 253, 347 266 222 178 114 020 105,356 316 536 239 081,093 281, 313,487,510 120, 367,414 19s 386 031, 301,461 486 073 534 393 282 196 519 049 008, 129, 176, 181, 191, 195, 197, 211, 225, 233, 244, 280, 03. 310, 320, 331, 342-344,350, 373, 381,400,401, 474,544 513 131
N
Author Index
Muler, J. Muller, C.L. Muller, B. Miiller, J. Miiller, M.C. Miiller, P. Munakata, Y. Munson, H.R. Jr. Munster, I.
Morai.A. h!lmLL
193 551 246 108 052 111
320 131 462 151, 181, 268, 303, 379, 393 128, 129, 153, 327, 378, 389, 392,401 337,477 029, 110, 347,
354, 522
lxkacL
Murakami, K. Murakami, M. Murakami, T. Murakata, M. Muralidharan, K.R. Murashima, T. Murat, T. Murata, K. Murata, N. Murayama, H. Murayama, H. Murayama, K. Murphree, S.S.
Murphy, C.K. Murphy, E.
lwxb!JA MlJdudL
MllmbmL
Murry, J.A.
Murlhy, K.S.K. Musaeva, Kh.E.
MWQA
Musick, H. Mustafaeva, Z.G. Mustafin, A.G. Mustaphin, A.H. Muxherjee, I.
154, 157 356 316, 373,460 255 235 483,483, 555 272, 545 296 125 078 285 455 419 199, 273, 548, 551 353 473 144,421 168,247 268, 370 324 478 533 111 176, 178 43 1 111 416 273 542
603
Muxworthy, J.P.
bhimlJ.
Myers, P.L. Myoung, Y.C.
MYdddA U.Y. Nadzan, A.M.
NllmbaA
Nagai, M. Nagak, S.K. Nagano, Y. Nagao, K. Nagao, M. Nagao, Y. Nagaoka, H. Nagaoka, T. u w a . K. Nagasawa, S.
Nagashima, T. Nagata, S. Nagata, T. Nagatsu, Y.
Nageswar, Y.V.D. Nagumo, S. Nagy, M. Nahmed, E.M. Naidorf-Meir, S. Naiini, A.A.
MIA
Naito, K.
mJQJ siwaL
Najime, R.
IwaL
Nakada, M. Nakadaira, Y.
l3ahwLu Nakagawa, Y. Nakahira, H.
tbkaiJ
Nakajima, M.
053 223,288 428 486 179 122 376 262, 306 074 477 400 554 453 283 331 042 166 223 125, 374, 392, 432 180,460 408 197 017 497 403 320 415 118 465 093 049 516 381,430,450 032,458, 548 317 277 229 080 1 50
312,464 234, 522 264, 310, 321, 327, 333, 336, 362,481 235. 295
604
Compendium of Organic Synthetic Methods, Vo18
Nakajima, T. Nakamura, A.
k4ihmm&
Nakamura, N. Nakamura, S. Nakamura, T. Nakanishi, E. Nakanishi, K. Nakanishi, N. Nakano, K. Nakano, M. Nakano, T. Nakata, J. Nakata, S.
NimaJ.
Nakatani, S. Nakato, T. Nakayama, A. Nakayama, I. Nakayama, 0. Nakayasu, S. Nalhandy, M. Nam Kung, J-Y. Nam, G-S. Namavari, M. Namhu, Y. Namy, J.1,. Nanami, 11. Nanko, T. Nantermet, P.G. Naota, ‘S.
Narahu, S.
503, 513, 552 Narasimhan, N. Narayama, C. Narayana, C.
307 Narayanan, B.A. Nmyanan, K. 121,484 Nardi, A. 498 036, 076, 257, khxa& 441 Naruse, Y. Naslund, J. 039, 323, 336 122, 126 WiLL Natchus, M.G. 229 Natile, G . 218, 352,487 Nadvi, C . 384 Navarro, C. 388 Navarro, M. 537 Nayak, S.K. 512 02 1 Naylor, A. 118 Nayyar, N.K. Nazareno, D. 299 190 Nedugov, A.N. 285,304,455 369 kkfhka& 151, 153, 389 Il!umJL 019 398 296 Negoro, A. Negrete, G.R. 287 NCgri, S. 225 Nehry, K.J. Jr. 117 544 Neighhour, B. Neil, D.A. 203 190 Neiteler, G. 308,345 Nemoto, H. 24 1 Neshitt, S. Nestler, B. 278 Nestler, H.P. 512 Netz, D.F. 320 129, 151, 153, 181, 327, 378, 379, 389, 392, Neveux, M. 40 I 33s New, D.G. 086, 358, 361, 363, 371, 416, Newton, R.C. 460, 469, 489, Ng, D.K.P. Ng, H.P. 302 N&-u.A 039 Nguyen, T. 011, 031, 229, Ni, Z-J. Ni, 2. 202
-
Authors
464 396,476 298 525 149,433 022 215, 515, 557 467 269 136,482 216 055 052,080, 260 539, 546 119,479 441 174,491 192 110,341 066,088, 204, 247, 256, 286, 359, 520 192 290 078 020 21 1 111,llS 207 380
447
012, 194 393 393 137 420 137 453 462,480 406,407 032 534 109 193 359,511 215, 260, 534 400, 558
N
Author Index
Nicolini, M. Nienaher, H.
NwbLL
Niihata, S. Niimoto, Y . Nijasure, A.M.
Nikitenko, A.A. Nikolaides, N. Nilsson, B. Nilsson, K, Nilsson, Y. Nirnura, Y. Ning, C. Ninomiya, I. Nisato, N. Nishi, K. Nishibayaqhi, Y. Nishida, K. Nishida, S. Nishigaichi, Y. . . milchi. L JVishieu Nishihara, K. Nishikawa, T. Nishimura, A. Nishimura, IM. Nishirnura, S. Nishimura, T. Nishinda, M. Nishiuchi, M. Nishiwaki, K. Nishiyama, S. Nishiyama, T.
Nishizawa, €1. Nishizawa, K. Nisiyama, T.
177,423 244 188, 288 175 097 445 489, 513 113 215 056, 185,283, 293, 367 323 064, 268 227 389 149 364,454 332 430,450 074 283 270 098,469 198 110 loo, 344 017, 168 169 515 030 082
I15
Nitta, H. Nina, M. Niwa, N. Niwa, S. Niyazymhetov, M.E. Noble, G. Noda, K. Noels, A.F. Nogue, D. Nohair, K. Noheda, P. Nohira, H Noiret, N.
lYi&5LG
IhtUELK Nomura, M.
Nomura, N.
l!.bmaA
Nonomiya, I. Nonoshim, K. Noman, B.H. J-F. Norwood, B.K. Nosal, R. Nour, M.A. Novack, V.J. Novak, L. Nowick, J.S.
mQrLE. 303, 397 191, 211, 233, 49Nozaki. 11. 098 469 312 Nozaki, K. 052 Nugara, P.N. 042 rYumaA 466,s 12 Nuhrich, A. 056,320 Nuliez, M.T. 027,093, 190, Nunokawa, Y. 192, 197, 236, Nusshaurner, P. 304 126, 140, 185, 3lXysuiim, J-E. 234 056
605
350 151 154 022,277 185 146 197 114,226 398 422 49 1 074 029,093, 133 413 030, 170,446 410,411 133, 162 002, 1 16, 224, 458,485 116 118, 130, 315 381 372 544,545 281, 329, 360, 464,484 557 I36 120, 374 343 167 180 174, 277, 323 049, 065, 167, 259, 278, 480, 485,504 093,479 532 032, 317 114 009,336 046,047 083 211, 398 537
606
Compendium of Organic Synthetic Methods, Vol 8
OBannon, P.E. OConnor, K.J. OConnor, S. OHara, L.C. OMahony, R. ONeil, 1.A. OShea, D.M. OShea, M. J
QxWLc. QaLA
Oalmann, C.J. Obayashi, R. Obaza-Nuhitis, J. Oheyesekene, N.U. Obrist, H. Ochi, M. Oda, D. Oda, H. Oda, K.
QkiK Oda, T. QdaL Ode, J.M.
Odenkirk, W. Odriozola, J.M. Oehlschlager, A. Oeschger, T.R. Ofner, H. Ogasawara, K. Ogata, K.
QwaA-
Ogawa, M. Ogawa, Y. Ogawawm, M. Ogibin, Yu.N. Ogilvie, W. Ogilvie, W.W. Ogino, Y. Ogiso, A.
Q&xA
214,556 158,204 383 399,414 307 468 386,474 253 357 432 396 111,115 462,484 21 1 042 176 003, 147 004, 282, 283, 556 467 196 198 017, 070,074 128 026, 181, 327 27 1 347 056 319 171, 536 130 494 144 331, 355, 358 062, 142, 168, 192, 343, 417, 423,462,484, 489,522 285,455 183 095 056 332 186, 188 295 449 035
Ognyanov, V.I. Oguchi, Y.
Qum-N.
s&lm-H.
LwJLKOh, C.H. QhJu. QhLL
Oh-e, T. Ohara, M. Ohha, S. Ohe, K.
i2lmLX Qhidi
Ohkawa, S. Ohki, Y. Ohkuma, M. Ohkuma, T. Ohlmeyer, M.J. Ohm, S. Ohmizu, H. Ohno, A. Ohno, H.
QluIQJL Ohno, T. Ohiiuki, M. Ohrai, S.
Ohshila, J. Ohsubo, A. Ohsumi, K. Ohta, A.
Qhtaa
Ohta, K. Ohtake, H. Ohtake, T. Ohtsuka, T. Oi, R. Oida, T. Oikawa, H.
Authors
384 395 022, 175,306, 314, 349, 350, 352 238 219, 545, 554 25 1 487,488, 51, 555 300, 325, 57 085, 232 477 080 559 029, 110, 185, 347 388,400 259, 261 093 388 33 1 174,323 30 1
535 077, 507 039, 323 350 115, 149, 191, 194,229 191. 211, 233, 344 095
527 079, 083, 149, 174, 194, 435, 470,498, 505 285 280 487 349,5 I I, 547 014, 136, 138, 214, 229, 230, 245, 337, 478, 541 066 038,057 066 270 397 381 527
Author Index
shhia. QihaJ
Oka, H. Okabe, N. Okada, E. Okada, H.
l,xad&L Okada, M. Okada, S. Okada, T.
QlmaLM, Okai, K.
QlcmmLE
Okamoto, M. Okamoto, M.T. Okamoto, S. Okamoto, T. Okamura, K. W.HA Okano, H.
s&mQL
Okauchi, T.
Qku&
Okimoto, M. Okino, E.A.
CuLA
Oku, Y. Okubo, K. Okudo, M. Okuhara, T.
s?kmu.
Okumoto, H.
Okumura, T. Okura, K.
ilYahAu
Olah, J.A. Olano, B. Oliveira, A.R.M.
0
048, 302, 304 124,306 325 013 417 321 017 126 150 086,338 439,502 26 1 148 107 338 284, 358,446 205, 208,495 132,430 532 101 012,013,424 371, 460, 469, 552 188 246 474 075 522 017 107 439 136, 138,478 082, 287, 391, 412,023 509 002,485 013, 014, 037, 038, 068, 079, 133, 181, 188, 194, 198, 200, 203, 211, 218. 218, 221, 259, 269, 272, 408, 503, 504 038 316,423 102
607
Olivier, E. Olivo, H.F. Qllis. W.D. Ollivier, J. Olmstead, M.M.
QMuLRA QlsaJU Olson, A S . Olson, J.T. slll&& Onanaka, M. Onda, K. Onimura, K. Onishi, H. 0110, N. Ono, T. Ontoria, J.M. Ooi, T. Oose, M.
c&DabLx
Orena, M. Orgiku. T. Orita, A. Orita, H. Orivama. T. Orlek, B.S. Orliac, A. Ortaggi, G. QmLa Ortega, B.R. Ortlioland, J-Y. Osaka, M. Osborne, S.
Osowska-Pacewicka, K. Osterhout, M.H. Otani, S.
Otera.J.
Otogawa, H. Otsuho, K.
326 467 055, 172 217, 508 454,474 172, 445, 507 082, 149 375 134 03 1,349 24 1 253 398 348 548 150 056 061, 306, 355 181, 223 253, 291, 532 334 077 110 322 214,498, 512 136 559 339 089,284,454 006 420 350 147 466,469 043, 069, 093, 217, 247, 299, 307-309, 324, 335, 360,433,479, 556 498 154 232 154 049, 065, 167, 480, 504 240 426 526
608
Compendium of Organic Synthetic Methods, Vol 8
Otsuka, H. Otsuka, K. Otto, A. Ouazzani,J. Ouimet, N. Ouvisson, G. Ovaska, T.V. Overly, K.R.
f-wmaU2 Overton, W.M. Owczarczyk, 2. Owczarczyk, Z.R. Owens, W.H. Ozaki, H. Ozaki, N.
Qzaki& QzaYLE
Ozbalik, N.
Pace, R.D. Pachinger, W. Padmanabhan, S.
IMmLA.
Pages, L. Pagliai, L. Pagnoni, U.M. Pahuja, S. Pakusch, J. Pal, M. Palacios, F. Palaz6n, J.M.
PakE
IuLlLL Palio, G. Palmieri, G.
074 125 411 037 326 037 247 020 122, 421, 424, 469, 478, 522, 469 082 066 520 060 287 125,432 033, 052, 053 192,487 424 168 161 532 031 066, 084, 199, 273,385,490, 502,544, 545, 548, 551, 552, 558 506 505 524 263 007. 103 208, 229, 464,465 468 246 489 416 27 1 332,463,487 554,558 482 269,410,411, 283
Palucki, M. Pan, G. Pan, L-R. Panangadan, J.A.K. Panasenko, A.A. Panco, S. Pandey, B.
F?ukYAPandhi, S.B. Pandian, A. Pandolfi, E.
I-hldLw
Pankayatselvan, R. Pankowski, J. Panyachotipun, C. Papadatos, A. Papageorgiou, G. ou. V.P. Papahaatjis, D.
l2uuuJA Paratian, J.M. Paredes. M.C. Parish, S. Park, B.K. Park, C.Y. Park, H-J. Park, H.G. Park, J. Park, J.H.
I!ak&H.
Park, K.P. Park, M. Park, 0-S. Park, P. Park, Y.H. Park, Y.J. Pamar, A. Pannee, E.R. Parra, M.
Authors
056, 148, 252, 348, 394, 402,529 27 1 044
553 544 416 215 065 144, 145, 151, 422,462 118 037 467 063, 170, 187, 448,456 423 445 120, 157, 316, 402,407 34 1 473 384 398 318 090, 134, 359, 403,506 205 074 238 238 505 299 121 121 300,354 050,470, 518 060 544 121 378,514 389 014,050 009,261 168 326 294
P
Author Index
Parrain, J-L. Parrilla, A.
I2imoLu Parvez, M. Pasquato, L.
l?amLsB l?&mmL
FYimmLL Patil, P.A.
I!amLwL Patois, C. Patra D. Patra, R. Patragnoni, R. Patrick, T.B. Patro. B.
F?imahG
Paugam, R. Paugram, J-P. Paulson, K.L. Paventi, M. Pavlova, N.N. Paz, M.M.
Pearson, M.M.
F3ium&&
Pecchi, S. Pedchenko, V.V. Peddada, L. Pedersen, M.L. Pedregal, C.
F!edmaA
Pegram, J.J. Pei, Y. Pellegrini, S. Pellissier, H. Pellon, P.
€wcuL
Pence, S. Pendalwar, S.L. Peng, M-L.
261, 287,484 370 079,085, 539 545 558 404 466 469 124 051, 053, 235, 240 454 258 543 211 369 538 357,486,494 422 49 1 228 003, 228, 531 192 420 453 050 150, 159, 160, 422,523 364 085 181 319 300, 308, 312, 354 379 171 482 306 325 452 445 058, 080, 120, 374,539 232 091, 092, 250, 532 274
609
Penmasta, R.
FkIlnAL r!auLM
Peresa, S.A.R. Perez, D. Perez, F. Perez, M. Perez-Encabo, A. Perez-Flores,F.J. m v . M.
Perichon, J.
Perner, R.J. Perri, S.T. Pemier, H. Perron, F. Perrot-Petta, M. Perrotta, E.
EGaLRL
Perumal, S. Pesce, G. Peschard, 0.
M.J.
EktLLE
Peters, D. Peters, E-M. Peters, J.L. Peters, K. Peters, T.H.A.
l!&wmd&
Peterson, M.A.
Pelif&
Petit, Y. Petri, A. Petricek, V. Petrier, C.
-van. V.A Petrov, B.s.
347 060 291, 336,416, 529 022 239 008 523 171 050 016, 017, 040, 143, 207, 505 117, 276, 281, 313,487, 510 034, 105, 174, 177, 195, 205, 215, 285, 504, 506 298, 366,437 040 126 079 342,465 117 136 1 24 369 187 444 113 222 259-261,478,485 224, 385,459 486 401 042 407 192 514 31 1 177,325 073. 394 298 489 100 065, 218, 268, 548,553,557 185 085
6 10
Compendium of Organic Synthetic Methods, Vol 8
Petrov, V.A. Petterson, S.E.
LmLA&
Pfeifer, K-P. Pfrengle, W. Pham, K.M. Pham, V.C. Phelps, M.E. Philipp, C. Philippo, C.M.G. Philippon, N. Philippot, K. Phillips, E.D. Phillips, H.K. Pi, J-H. Pianese, G. Piatak, D.M. Picard, J.P. Etccolo. 0.
Pias&
Pieters, R.J. Pietroni, B. Pietroni, B.R. Pigeon, P. Pilard, J-F. Pilard, S. Pilarski, B. Pilcher, A S . Pinel. C. Pinetti, A. Pinetti, A.
A.R.
Pinho e Melo, T.M.V.D. Pini, D.
w,
Pinto, A.C.
J?iwLL
Pinzani, D. Pires, J. Piroddi, A.M. Pirrung, F.O.H.
Piscopio, A.D. Pifchumani. K,
224 142 332 55 1 539 146 459 203 028 359 191 453 555
447 219 403 155 394 076 172 448,535 050, 109, 111 075 457 191 377 317 146,272 05 1 094,290 208,464 465 128, 396 234 409 021,022,298 537 141 488 364,417 198,217 313 031,072 436 47 1 044,075 037
Pitt, M.J.
PiaQ
Pizzo, F. Plant, A. Ple, G. Plesek, J. Plobeck, N.A.
r?luuLL
Plummer, J.S.
Plzhk, z. Poch, M.
Poindexter, M.K. Poirier, J-M. Pokorski, U. Polezhaeva, N.A. Polizzi, C. Polo, A.
iwLR
Polzonetti, V. Ponomaryav, A.B. Ponomaryov, A.B. Pons, J-M. Popielarczyk, M. Popov, Yu.N. Pornet, J . Porter, J.R. Porzi. G.
Postich, M.J. Pouilhes, A.
Power, M.B. Pozzi, G.
m Prados, P. Prajapti, D.
l3ak&A l?lmLE
Prapansiri, V. Prasad Rao, K.R.K. Prasad, A.D. Prasad, A.S.B.
Authors
381 212, 224, 385,459 333 228 113,371, 373 016 524 030, 087, 365, 376,510 292 164 016 313,510 529 082 370, 371,483 415 273 280 122 368 273 311 548 466 413 33 1 270 062 147 5 14 334 159, 251, 511, 536 150
293 225 529 144 157 027 338 179,438,468, 507 382 455 033 233, 330, 372 143
R
Author Index
Prasad, C.V.V. Prasad, G.
I?twd&
I?rahmL htQ&L
Prechtl, F. Pregnolato, M. Price, J.D. Priestley, E.S. Prieto, P. Prieto, R.
Prince, B.
Pritchard, G.J. Pritytskaya, T.S. Procter, G. Protopopova, M.N.
PWhJJL l?csLiu Puchot, C. Pujol, M.D.
Punzalan, E.R. Purchase, C.F. 11.
li%LslL Pyo, s. Pyun, C.
Qabar, M. Qian, C-P. Qian, Z. Qing, F-L. Qiu, Y-L.
QllakE Querci, C.
Quesnelle, C. Quintana, D. d. J-P. RBbai, J. Racha, S.
188 372 156 428 346 344 224 055 159 546 45 1 490 486 309 307 111 247, 306 125,429 165 298 309 172 262, 263 035 154 239 545 115 234 376 336 205,337 490 101 486 205,409 072,079 393 29 1 26 1, 287, 484 269 069 542
61 1
Racherla, U.S. Rachwai, B. Rachwal, S. Radhakrishna, A S . Radinov, R.N. Raina, S.
Rajanarayanan, A.
RSkos, L. Ralbovsky, J.L. K.V.
IbulhJL I3mak.K
Ramaiah, P. Ramaswamy, S. Ramazanov, e.A. Ramhaud, D. Rambo, E. Ramcharilar, S.H. Ramesh, K. Ramesh, N.G. Rami, H.K. Ramfrez, C. Ramdn, D.J.
Ramondenc, Y. Ramos, M.T. Rancourt, J . Rand, C.G. Randad, R.S. R'andiiamahefa, S .L. Rane, R.A. Rangaishenvi, M.V. Rani, K.S. Ranu. B.C. Rao, A.B. Rao, Ch.S. Rao, E.S.
lxaaHsE IklLIa
014,019 274 146,274 033,228 253 318 323 495 369 032 412 137,543 333 141 223 040 403,446 162 269 319 478 127 439 458, 524 508 374 488 379 026, 027, 299, 302, 340 371 013 216 270 352 127, 501 055 074,260 422 018, 033, 034, 043, 162, 297, 332, 348, 371, 542 317 24 1 427 042, 134 405
Compendium of Organic Synthetic Methods, Vol8
612
IbQJm
lhXkM2.
065 059, 317 531 355,480, 533 427 010 072 137 450 105 221 445 129 159 290 300 032, 190, 339, 361 041 107 262 362,446 368 103 382 I28 161 207 347 145,151 094 295, 314 134 543 119 01 I , 039, 229, 292 177 176 065 27 1 137 203,259 135 291, 324, 328,
f3'wuAL
522
Rao, M.V. Rao, P.S. Rao, S.A. Rao, V.S. Rascle, M.-C. Raslan, D.S. Raiajczyk, J.D.
IiamLMx
Ratovelomanana, V Ratton, S. Rault, I. Raut, S.V. Ravindran, T. Raw, A.S.
LbXaLML Rawson, D. Rawson, D.J. RaYA Reader, J.C. Real, J. Rebikre, R. Rebolledo, F. Recht, J.
liiabu.
Reddy, Ch.K. Reddy, D.R. Reddy, G.D. Reddy, G.M. Reddy, G.V. Reddy, K.S. Reddy, K.V. Reddy, M.M. Reddy, N.K. Reddy, N.P. Reddy, R.E. Reddy, R.S. Reddy, R.T. Reddy, T.I.R. Reddy, V.P. Reed, K.L. 471, 529
Reginato, G. Reho, A. Reich, H.J.
JiulJG Reiher, T.
IiciRL
Reiser, 0.
Remizova, 1.. Reinuson, R.
IGaauda
Reny Runge, J.M. Repic, 0. Repke, D.B. Rescifina, A. Reshef, D. Retherford, C. Rethmeier, L. Reuter, D.C. Reuther, F. Revial, G. Reviere, F.
BsxiLA
Rheingold, A.L. Rhode, 0. Riheiro, C.M.R. Ricart, S.
hxiA
ltkLM.
Rice, M.J.
KislLx RidlJa
Richardson, P.F. Richter, M. Riedl, B. Rieger, D.L.
IIkElA
Authors
105, 282, 318, 364,413,417,490 166 239 23 1 244 178,372 037,038 086 068 367 428 285 42 1 545,548 23 1 156 120 066 220 224,434 540, 556 097 097,008 290 037 272 476 448 008, 197, 344 328 183 105, 136, 263, 282,318, 364, 413, 417, 468, 490,517 205 542 310 067 49 1 334 380 343 044, 222, 231, 263, 363,457, 536 281, 313,487
R
Author Index
Riesinger, S.W. Righi, G. Righi, P. Right, G. Riglaudy, J. Ril32.A Rigollier, P. Rim, J.G. Ringe, K. Rishton, G.M. Ritchie, B.M.
RiLaL
Riva, R. Rivera, I. Rivero, I.A.
396,521 376,394 034,339 553 295 414 310 085,473 305 531 469 447
444
070 039,074 057 132 Roan, B.L. 085 Robber, S. 097 214,216 I%QkkEE Roberts, L.R. 115, 253 Roberts, S .M. 298 Robertson, J. 449,515 Robichaud, A.J. 422 41 1 Robins, M.J. 205 Robinson, E.D. 476 Robinson, L A . 232 Robinson, N.P. 347 Robl, J.A. 367 Roby, P. 137 Rochigneux, I. 358 414 Roden, F.S. 340,475, 514 338 558 Rodriguez, D. 478 Rodriguez, J. 190,496 Rodriguez, J.H. 553 Rodriguez, M. 315 Rodriguez, M.J. 474 196 Rodrlguez, C.M. 271,425 Rodriguez. J.H. 546 Rodriguez, M.A. 085, 337, 497 Rodriguez-Camps, I.M. 424 Rodriguez-Lopez, J. 376
v
613
Rodrfquez, M.A. Rodrlquez-L6pez, J. Rcdriquez-Luis, F. Roelena Roffia, S. Rogers, C. Rogers, R.D. Rogic, M.M. Roh, K.R. Rojo, J.
IlQuJ.
Romain, I. Romanelli, A. Romea, P.
I.Qmmdx Romero, R.H. Romine, J.L. Roos, E.C. Roos, G.H.P. Roper, T.D. Rosa, A.M. Rosado, I. Rosati, 0. Rose, P.A. Rosini, C.
lbh.iA ROSS,J-C.
IbssLE'
Rossi, L.
RcmLR
l3maaaL
Rotello, V.M. Roth, F.
€wh&L
liLukH&
RQusau&
Rousset, C.J.
Roy, S.S. Royer, J. Rozema, M.J.
112 497 365 50 1 318 370 472 359 420 270 157, 547 178,282, 286 140 525 219 161 055,450 442 107,407 380, 392 55 1 348 144 101 442 453 021,022, 298 218,553 131, 374, 421, 438,488 05 1 396 034 089.091 105, 107 434 222 360 076,087, 178 354,497 175, 321, 547 088, 204,256 406 174 546 003,278
6 14
Compendium of Organic Synthetic Methods, Vol 8
w
Rubenstein, S.M. Rubiales, G. Rubina, K. Rubio, E. Rubio, R.
JukLuL
Ruder, H. Ruegg, G.M. Rucl, 0. Ruel, R. Ruiz, P. Ruiz-Hitzky, E. Ruiz-Montes, J. Runk, C.S. Russell, C.E.
I!aidAA
Rutjes. F.P.J.T. Ryback, G. Rybczynski, P.J. Ryoden, K. Rys, A.Z.
IiYLmL
u
Muri. N Sadakane, M.
Ls&M&aL saQwdL
Saffrich, J. Safi, M. Saha, G. Saha, S. Sahai, M. Sahasrabhuddhe, A.S. Sahli, A.
194, 268, 408, 464,492 351, 546, 547 325 402 311 387 263 246 347,557 243 434 260 502 542, 557 166 399 537 087 099, 235 420 298 430 08 1 279 202 206, 243, 436, 493,496 062, 110, 142, 234, 237, 343, 354, 423, 489, 506, 522 077, 215, 251 095,204 39 1 474 224 166,416, 511 373 153,518 174,258 405 006,239 493 007
S~*OO, P.K. Said, S.B. Saidi, M.R.
SakQJL
Saimoto, H.
Sain, B. Saito, E.
Saito, K. Saito, M.
siluQA Saito, T.
Saitoh, H. Saive, E.
SakaiX 3ahLM. Sakai, N. S'akai,
s.
s&iJ
S'akaibara, Y. S,akait,ani, M. Sakakibara, J. S,akakibara, M. Sdakakibara,Y. Sakakura, M. Sakakura, T. Sakamoto, J. Sakamoto, M. Scakmoto, T. Sakane, T. S&?ta, H. Srzkata, S. Sakata, Y. Sakaue, N. Sakdarat, S. sako, Y. Sakuraba, S.
Sakurai, Y.
sdah.L
Salazar.J.A. Salehi, P.
Authors
012, 167, 257 173 114 080, 180, 240, 331. 378, 380, 441, 460, 469. 473,477, 520 218,527 027 392 026,473 042 030, 154, 297 303, 378, 379, 401, 526 337 114 106, 212, 320 216, 217, 394 014,245 094, 113, 179, 189,364 055,094,451 216 400 374, 392 463 217,244 468 010,258 45 1 167 078, 089, 128, 178, 243,477 157 096 35 1 337, 346, 348,467 076 447 394 082 024,417 146 217,445, 479, 508 381 233
Author Index
Salem, S.M. Sallese, G. Salley, J.M. Sallin, K.J. Salomon, C.J. Salunkhe, A.M. Saluzzo, C. Samoniya, N.Sh.
sauumn2
v
Shnche-Cantelejo, Y.M. Shchez-Baeza, F. Sanders, W.M. Sandham, D.A.
sallmLU
Sandri, J. Sandri, S. Sanner, C. Sano, A. Sano, H. Sano, T. Sansano, J.M. Sansoulet, J. Santamarfa, J. Santaniello, E. Santelli-Rouvier, C.
SaIlLR
Santiago, B. Santinelli, F. Sanyal, B.J. Sarandeses, L.A.
Sardarian, A.R. Sardarov, I.K. Sarkar, A.K. sakaclx Sarma, J.C. Sarma, P.K.S. sarmah, P. Sarshar, S. Sartor, D.
sami&
Sasai, H.
S
400 176, 178 217 387 029 160,450 464,476 02 1,022, 298 502 438 258 376 183 300 347 010, 027, 160, 216,245 201 334 073 014 158 029 032 127, 185, 191 059,088,414 28 1 319 331,537 537 175, 176, 178, 215, 231, 232 074,256 333 406 100, 105, 356 233 111 421, 533 266 508 318 161 041 373 302, 323,443 087, 342
615
Sasaki, A. Sasaki, D.J. &&& Sasaki, 0. Sasano, S. Sasao, S. Sasaoka, S. Sasatani, H. Sashiwa, H. Sacake, N. Satchell, J. Satici, H.
SahX
Sato, H. Sato, J. Sato, J . Sato, K-I.
&uQ&
Sato, M. Sato, N. Sato, 0.
&uQ&
Sato, S. Sato. T.
SiltQJ. Satoh, H. Satoh, M. Satoh, S. Satoh, T. Satoh, Y. Sattsangi, P.D.
Sattur, P.B.
Satyanarayana,G. Satyanarayana, N. Sauer, G. Sauv&tre,R. Savchenko, A.I. Savelli, G. Savignac, M. Savignac, P. S v o i a . D. Sawa, E. Sawada, H. Sawamura, M.
43s 453 216, 217, 244 009, 387, 394 122 392 46 1 548 218, 527 403 130 372 284, 334, 358,446 525 030 06 1 489 024,074, 185 045,095 183 329 042 341,449 049, 122, 126, 127, 167, 434, 480, 504, 516, 520 25 1 167 084 087 236, 253, 551 137 422, 536 405 203 177 515 092,219 498 111 333 09 1 454 370,418 333 49 1 313
616
Compendium of Organic Synthetic Methods, Vol 8
Sawden, J. Sawhney, S.N. Sawicki, M. sEaelA3
ham-s.
Sayrac, T. l3aEAAScapecchi, S.
Scartozzi, M. Scettri, A.
SchaIk, C. Schaumann, E.
Schelkun, R.M. Scherbakova, I.V. Scherler, D.
2icuka.
Schionato, A. Schirlin, D. Schkeryanu, J.M. Schlingloff, G.
5!iuwLu Schmid, C.R.
Schmitt, A. Schmitt, M. Schmittling, E.A. Schneider, A.
3cb!uLA
Schoemaker, H.E. Schoenfelder, A. Scholz, G. Schoop, A. Schreer, M. Schreuder, I. Schrickel, J. Schroth, G. Schubert, S.
013 468 368 051 100 179 242 318 126 334,441 162,428 119 182 486 540 375 097 293, 373, 41 1, 503, 505 441,531 506 119 422, 523 023 291, 310, 356 01 1 308 380 148 068 367 0s 1 163 148 013 255 380,436 377 440 012 393 207 509 485 097 432 545
Schulte, G.
schuLm. Schullz, M.
3!alkmi ikhuhJa
Schumacher, B. Schurig, V. Schuster, E. Schwa, G.
&A!umJ 3ckakMA
Schwering, J.E. Schwinden, M.D. Schwindt, M.A. Scialdone, M.A. Scilimati, A. Scopes, D.I.C. Scorrano, G. Scott, I.L. Scott, M.E.
s!aLKL
sLlw&LG
slalu%h Sdassi, H. Sebastiano, R. Seconi, G. Seddighi, M.
iicchaa si%LMSeidel, B.
Seilz, C. Seitz, W.J. Seki, K. Seki, T. Sekiguchi, M. Sekihachi, J. Sekiyama, T. Selim, M.R. Sellen, M. Senanayake, C.B.W. Sengupta, S. Sennyey, G. Seoane, G. Seong, C.M.
Authors
384 196 340 390 343 393 418 483 418 519 054,248 151 388 466 400 180 275 546 346 442, 516 483 075, 516, 519 138 333 121 317 175 282,468, 517 222,233, 270 29 1,292 121,484 551 393 193 375 123,432 204 142,417,423,484 169 379 534 071,536 499, 525 072,296,448 290 159 219, 529, 531
S
Author Index
SaaA
Serguchev, Yu.A. Serra, E. Serratosa, F.
2hrXiAL
Seth, S. Seto, H. Setsune, J. Seyden-Penne, J.
s!afaLQ
Shah, J.H. Shah, K. Shah, P.M. Shah, V.G. Shambayati, S. Shankar, B.B.
slxuux
Sharifi, A. Sharma, G.V.M. Shanna, M.K. Sharma, N.D. Sharma, P.A. Sharma, R. Sharma, R.1. Shanna, S.
sllmdm Sharp, M.J.
sJmRkdm Shastin, A.V.
sllmJL Shaw, R.
Shay, W.R.
stulJu
Shekharam, T. Shen, G-J. Shen, H.B. Shen, W.
ShaLX
Sheng, H-Y. Sheppard, G.S. Sherbum, M.S. Sherick, J.M.
shm&&
Sheu, J-L.
161,477 433 198 117,276 043 002 205,337 477 175 504 059 201 048 046 509 441, 552 331, 332 224 03I 307 038 040 228, 304 122 098 118 124 279, 295, 299, 303, 397 517 036 390,453 124 438 048 363 040 245 504 358, 395, 454, 508, 530, 531 280 343 144 082 I10 138
617
Sheu, J. Sheu, K-W Shi, G. Shi, J.
ShLIZL Shi, X. Shi, Y.
Shibaa, K. Shibagaki, M.
Shibata, K. Shibata, T. Shibutani, T. Shibuya, K. Shigekawa, Y. Shih, Y-E. Shiina, I. Shim, S.B. S.C. Shima, H. Shima, T. Shimada, K. Shimada, M. Shirnada, S. 378, 380,441 Shimadzu, H. Shimamura, Y. Shimazaki, M. Shimizu, H. Shimizu, K. Shimizu, T. Shimoyama, I. Shimoyama, M. Shimpuku, T. Shimshock, S.J. Shin, D-S. Shin, H.H.
130 239 433 410 019, 024, 186, 187,252,450,478 260 119, 534 135 535 045, 056, 239 087, 167, 237, 249, 342, 346, 411,525 041, 043, 336, 368,437,472, 502 250 363,416 406 33 1 429 218,527 029 176, 319 123 140,353 053 377 135,490 050, 163, 233 086, 180, 331, 489 219 353, 511, 547 475,513 289 146, 272, 538 041, 322, 339 310 075, 342 445 171 320 05 1 089 267
Compendium of Organic Synthetic Methods, Vol 8
618
Shin, H.S. Shin, W.S. Shin, Y.S. Shinada, T. Shindo, M. Shinkai, I. Shinoda, T. Shinohara, K. Shinozaki, H. Shiono, H. Shiori, T. Shiozawa, S. Shiragami, 11. Shirai, F. Shiraishi, Y. Shiratani, T. Shiro, M. Shirouchi, M. Shitikova, O.V. Shoban, N. Shoda, H.
shQlLL
Shook, C.A. Shostakovsky, M.V. Shrier, A.M. Shuhkin, R.L. Shudo, K. Shuhaibar, K.F. Shulishov, E.V. Shulman-Roskes, E.M. Shundo, R. Shvily, R.
sbY!Lx.
Shymanska, M. Si, Z-X. . .
bIhl-
.
sim&.
A
Siddiqui, M.A. Sidduri, A.R. Siedlecka, R. Sielecki, T.M.
153 487 304 430,450 098, 145 40 1 255 259 39 1 535 184,268 378, 380 052 386 278,485 32 1 1so 528 132 325 426 420 487 072, 098, 315, 325, 338, 346, 355, 388,439 46 1 413,466 447 153 776,402 130 110 25 1 017 239 220 311 439 228,304,426 105, 177, 195, 205 120, 124 103, 104, 460 301 225,304 150
Sierra, M.A.
UlAX Silverberg, L.J. Simig, G. Simler, R.
3.iamld
Simoneau, B. Simonelli, F.
Singh, A.K. Singh, A.P. Singh, G.P. Singh, K.N. Singh, M. Singh, M.
0.K
Singh, P. Singh, S.P. Singh,. J.
Sinislema, J .V.
sjlUd2.
slsiL%
Sisko, .I. Sivaprakash, K.
Sivavamakrishnan. H. Siviai, L. Sjii, P. SkaIitzky, D.J. Skowrcx~,J.F. 111 Skrinjar, M. Sledeski, A.W.
slnahAL Smart, B.E. Smerz, A. Smit, V.A.
Authors
365,468 1.51 029 396 009 324 291,310 526 148 216, 332 102 190,559 099,479, 558 043, 160, 260 008 065 033,228 195 007, 314 007 268 427,471, 508 314 190 043,495 058 361, 442, 451, 554,555 013 153, 189, 314, 401,518
444 119, 140, 141, 523 033,228 177 526 343 279 08 1 173. 225. 304 115 398 23 1 400 464 470 262
S
Author Index
Smith, Smith, Smith, Smith,
A.B.
A.C.
A.L. A.M.
C.C.
Smith, D.G. Smith, H.D.
smith&
Smith, S.C. Smith, T.P. Smith. W.B, Smilrovich, J.H. Smushkevich, Y.I.
Snow, S.R.
Snvder.J.K.
SQLL
Sobolov, S.B. Sodeoka, M. Siiderberg, B.C. a
s
t
.
5.4.
Soga, T. Sohma, J. Sohmiya, H. Sojka, M. Sokoloski, E.B. Sol&,L. Solarz, T.L.
-
SolladiC-Cavallo, A. Somasekhar, B.B.V. Somers, P.K. Somers, T.C.
436 03 1 288 549 001
517 488 082 456 080, 186, 206, 307,539 125, 127, 130, 138, 395,490 099, 230 152 34 1 274 202 101 375 231, 391, 504, 510, 520, 552 072, 073, 077, 079, 120, 124, 227, 296,448 554 274 021, 022, 023, 107, 277, 351 050 087 376,468, 531 039, 074, 101, 249,256 244,474 143 27 1 299 369 487 135 326, 542, 557 310 057 462 188 385,437
Sommazzi, A. Son, Y.C.
s!2mda&
-
Sonoda, S. Sonoda. T. Sorato, C. Siirensen, 11. Sosnovskii, G.M. Sotgiu, G. Sotirious, C.
sr?llfiaOU
i. M,
Souma, Y. Southern, J.M. Sowell, C.G. Sowin, T.J. Sparks, M.A. Spears, G.W.
silcuLL
Spero, D.M. Spiliolis, V. Sprengeler, P.A. Springer, R. spunta, G. Sridhar, M. sfldharan,v. Srinivas, D. Srinivasan, K.V. Srinivasan, N. Srinivasan, T.N. Srivastava, A.
Staab, A.J. Stack, D.E. Stahnke, M. Stambouli, A. Stanescu, C.
619
143 210 138 013, 046, 235, 254 062, 110. 142, 168, 192, 234, 237, 307, 343, 354,417, 423, 462,484,489, 506,522 107 500,524 295 28 1 337 339 004 120, 227, 377 482,557 062,063 075,220 096,425 366 170,448 388 126, 380, 392, 398, 402, 420, 429,436 247 472 3 18 436 258 120, 157 145 121 363 233 162 405,446 423 007, 167,465, 518 438 222, 363 092, 219 482 352
620
Compendium of Organic Synthetic Methods, Vol8
Stang, P.J. Stanoeva, E. Siarostin, E.K.
s&xmmE Steel, P.J. 3&.eloA
-
Steeman, W.J.M. Steenkamp, J.A. Stefinovic, M.
Steigef, A. Stemerick, D.M. Stengel, P.J Stemfeld, F. Stevens, C.
Stevens, R.V.
sluLAL stiuLU Stinn, D.E. Stocks, M.J. Stokes, T.M. Stoll, D. Stolle, A, Stone, G.B. Storer, R. Storey, J.M.D.
SlQrka
Stowe, J.A. Stracker, E.C. Strada, A. Stradi, R.
stmLJuL
Straws, H.F. Strazzolini, P. Strecker, A.R. Streith, J.
Streith..J.
Strobel, E.D. Strologo, S.
sLlxhad Stucchi, E.
276, 280 505 293 063, 391 375 138 436 104 186 378 014 140,549 136 102 332 141, 192, 369, 370, 372,409 228 038, 315, 391 071, 511 085, 250, 418, 420 444 143 171 425 217,445 342 428 123 074,264,427 03s 276,286 396 396 026 I30 141 193 313 318 319 142 537 205 091, 111,248 105
bm.xGLL
Sturino, C.F. SU,D-B. Su, J. SuArez, E. Su&rez,J.L. SuArez-Sobrino, A. Suhha Rao, Y.V. Suhhas Bose, D. Subrammian, L.R. Subramanian, R.S. Suda, A.
ma& Suda, S.
Sudalai, A. Sudha Rani, K. Sudo, A. Suehiro, I. Suehiro, K. Suemune, H. Suenaga, €I. SllfkU Suga, S.
sllanmL
Sugahara, T. Sugai, T. Sugamoto, K. Sugawara, K. Sugimoto, J. Sugimoto, K. Sugimoto, Y.
Sugita, H. Sugita, K. Sugita, N. Sugita, T. Sugiyama, E. Sugiyama, K. Sugiyama, M. Su,jatha, K. Sukirthalingam, S. Sullivan, E.L. Sumathi, T. Sumimoto, N. Sun, C-J.
Authors
242 476 204 183 381 49 1 387 019 163 010, 058, 202, 204,500 220 236,480, 539 241,507 233,342 254 144 380 430 076 106, 320 140 286 121 167 128 014, 245, 541 528 359 433 167 067 429, 527 025,416,426,435 526 031,349 185 270 023 480 175 223 121 274 333 179 130
Author Index
Sun, C-M. Sun, U.J. Sun, Y-S. SunU, J. Surendrakumar, S. Suri, S.K.
w Suryawanshi, S.N. Suseela, Y. Suslick, K.S. Sutowardoyo,K.I.
suukiA
Suzuki, I.
Suzuki, M. Suzuki, N. Suzuki, S. Suzuki, T. Suzuki, Y. Sviridov, S.V. Swanson, D.R. Swapna, V.
sx!amdA
Swindell. C.S. Swiss, K.A.
w Szab6, G.T.
T
553 525 478 22 1 405 033 013, 014, 037, 068, 181, 188, 194, 203, 218, 221, 259, 269, 408 513 017 495 314,401 001, 026, 045, 078, 085, 090, 095, 182, 232, 238, 284, 513, 516 106, 112, 148, 150, 240, 272, 272, 354, 477, 545 387 189, 233, 267, 353, 362, 538, 559 144, 277 088, 229, 5 11 255 065, 329 516 111 256, 520 233 509 550 345 206 109 167 036
621
Tabata, M. D.F. Tabuchi, T. Tachibana, H. Tachibana, Y. Tachizawa, 0.
llu.h&
Taek, R.D. Tafesh, A.M. Tagat, J. Tagliavini, E. U Y c h i . TTahir, S.H. Tajima, T. Takacs, B.E.
lilkmJU T&da, E. Talrada, N.
JkkaiJL Takagi, Y.
Takahara, J.P. T,akahashi, A. Takahashi, H. Takahashi, K. Takahashi, M. Takahashi, N.
Jhk&mH'
lkki&
Takami, N. Takanami, T. Takano, H. Takano, M.
T.dmLs
Takanohashi, Y.
143 039,324 426 320 478 38 1 212 136, 360,482 375 356 441 345 278, 361, 363, 383,434,436,449 454 125 262 262,406,486, 507,539 284 469 216,244 079, 538 028,300 525 115,469 045, 056, 181, 239, 341 077, 233,419, 547 154 01 1 033,075,461 088, 095, 204 383 069, 184, 247, 296, 360, 395, 423,457,485 008, 045, 181, 195, 197, 303, 344,350, 381 297, 342 423 241, 507 538 393 144,359 142,201
622
Compendium of Organic Synthetic Methods, Vol8
Takaoka, Y. Takashima, T. Takasu, M. Takata, T. Takaya, H. m!&LL
3hkahx.
l2lkLx
Takeichi, E. Takeishi, Y. Takenoshita, H. Takeuchi, H. Takeuchi, K. Takeuchi, M. Takeuchi, T. Takeyama, T. Takeyama, Y. Takezoe, K. a. Y. Takiyama, N. Takizawa, M. Takusagawa, F.
lhkwLA
Talbot, A. Tam, W. Tamami, B.
JhmaaL
Tamareselvy, K. Tamariz, J.
lllmauL
Tam& J. Tamayo, N. Tame, S . Tamura, H. Tamura, M. Tamura, 0.
l2iamaA
Tamura, S. Tamura, Y. Tan, L.C.
282,283 320 373 064,223 093, 390,469 229,238 057, 079, 152, 225, 236. 480, 483,509, 538, 539 322 107 343 135 244,474 397 206 122, 195 183 337 338 217 520 135,490 338 243 133 100,344 338 250 019 296, 312, 539 088 s20
114, 132, 379, 392, 426, 460, 554 269 074 344 472 352 29 1 106,467,477 307 283 007, 193
Tanks, B. Tanaka, A. Tanaka, H.
TiuUbX
Tanaka, S. Tanaka, T. Tanaka, Y.
32lEmm&
Tang, Q. Tang, S. Tani. H. Tani, S. Tanier, S. Tanigawa, H. Taniguchi, M. Taniguchi, N. Taniguichi, M. Tanimoto, S. Tanino, K. Tanmatu, H.
xillwza Tao, W. Tao, X. Tapia I. IafLl.
Tarnus. C. Tarsi, L. Tasdelen, E.E. Tashika, H. Tashiro, M. Taricchi, A.
llusuuL Tau, S-I. Taya, J.
Tavlnt.R.J.K. TavlatS.K. Taylor, W.C. Tazawa, K. Tehhe, M. Tekawa, M.
Authors
269 433 415,461,442 019, 112, 302, 349, 350,460 019, 062, 063, 070,085, 245, 258 114, 297, 342, 379, 392,460 205, 276, 356, 396 263 065 293 334 240,477 283 399 379 192, 276, 280 217, 307, 308, 309 165 415 381 352,419,487 217 399 447 443 440 055 119 370 181 298, 366 505 076 520 049,066 265 169 403 265,443 035 259 102 402 289
T
Author Index
Tellier, F. Tempkin, 0. Teng, K. Teng, M. Teng, T-F. Tern& M. Terakawa, T. Terakawa, Y. Teranishi, K. Terauchi, J. Tereshchenko, G.F. Terrence, K.M. Terrett, N.K. Testaferri, L. Tezuka, M.
XzukaL
Tham, F.S. Thellend, A. Thenappan, A. Theohald, P.G.
Thiemann, T. Thijs, L. Thomas, A. Thomas, A.P.
Thomas, J.A. Thomas, P.J. Thompson, A.S. Thompson, M.
m2lwmJx Thorel, P-J. Tianhui, R.
Tim&, T. Timony, P.E.
498 326 296 386
080
310, 327, 333, 48 1 148 49 1 236 388 406,429 447 099 220, 425, 461, 47 1 350, 377 069, 184, 457, 485 447 196 382 433,497 532 161 401,519 447 302 07 1 353, 362 243 178 466 478 544 275 388 322 341, 347,455 163 331,332 058, 179 220, 425, 461, 47 1 47s 076 201
623
Tinao, L.V.
Tingue, P.S. Titouani, S.L. Titus, S.S. Tjaden, E.B. Tjepkema, M. Toba, T.
3XlaE.
Toda, S.
lJMaL
Todd, R.S. Togni, A.
lwlIHa
Tohma, H. Tohma, T. T6ke, L.
TQkuhM Tokumaru, Y.
Tokunaga, M. Tolstikov, G.A. Tomaru, J. Tomk, M. Tomasini, C. Tomesch, J.C. Tometzki, G.B . Tomilov, Yu.V. Tominaga, N.
Tomo, Y.
l32mdaA
Tomoi, M. Tomooka, K. Tomori, H. Tomoskozi. I Tonnard, F. Torii, K.
TsUiiLL
Torisu, K. TorLijada, A.
365 220,425,461,471 152 557 012 111 368 175 440 019, 259, 276 182 335 158 404 139, 152 155,412,419 296 109
553
025, 151,416,426 276 323 108, 249,416,426 236,270 387 29 1 428 48 I 110 346 355,408,410,446 264 098, 108, 145, 295 432 495 205 277,362 54s 294 445 238 056, 082, 212, 287, 321, 341, 349, 391, 412, 415,461 400 294
624
Compendium of Organic Synthetic Methods, Vo18
Toshima, K. Toske, S.G. Tbth, G. Totleben, M.J. Tottie, L. Tottleben, M.J. Toupet, L.
l3llLmL
Towne, R.W. Toy&, J. Toyosaki, T. Tozer, M.J. Trabsa, H. Trainor, R.W. Tramontini, M.
3lamuLL
Trivedi, N.J.
IkLlLL
3bLEM.
Trost, M.K.
liwxlAA
Troyanskii, E.I. Tsai, C-Y. Tsai, J-C. Tsay, S-C. Tsay, Y-H. Tschamber, 7 Tsubaki, Y. Tsubuki, M. Tsuchiya, Y. lhdLL
Tsuji, Y. Tsujimoto, A.
102, 463, 501, 509 049,066 38 1 126 109 218,335 333 103 164 091, 092, 250 026 154 130 114 542 427 414 166 181, 194 01 1 345 108, 141, 183, 285, 322, 341, 355, 459, 481, 518, 534, 539, 541, 555, 557, 558 534 504, 506 185 274 177 367 314 318 297, 342 055, 094, 451 516 350 166, 268, 416, 511 170, 255, 279, 285, 296, 432, 446,455 146, 147, 226
544
Tsukamoto, K.
Tsukamoto, Y. Tsukiyama, T.
l3llmhI Tsurya, S. Tsusaka, M. Tsushima, K. Tsuzuki. Y. Tu, C-L. Tubergen, M.W. Tucci, F.C. Tucker, C.E. Tucker, T.J. Turner, S.U. Tuncay, C.I. xlmblux
lilmeaL
Turner, S.C.M. Turner, S.R. 3luQSJi
Tyrrell, E. Tzeng, Y-L. Ubukah, Y. Uchibori, Y. Uchida, M. Uchida, 0. Uchida, S . Uchida, Y. Uchimura, J. Uchiro, H. Uchiyama, H. IJchiyama, M. Uda, H. IJdding, J.H. Ueda, A. Ueda, I. Ueda, N. Uematsu, M. Uematsu, N.
L!cmwLA IJcRQL
Authors
272,498, 545 175 28 1 009, 252, 315, 324, 387,394 512 102 477 238 129 208 103 099,533 388 415 113, 527 495 495 134 013 309 124 026,045, 340 539 069, 260, 534 263 205.337 025,071, 505 400 183 095,204 046 310, 343 318 282 473 402 307 378, 521, 533 471 429 439 185,270 298,396 102,463, 501, 509
Author Index
Uesaka, N.
IlmLn
Uguen, D. Uh, K.H. Uhlendorf, S. Ujikama, 0. Ujikawa, 0. Ukaji, Y. Ulivi. P. Umarani, R. Umehara, €1.
IJImmmL
Umeno, M. Umezama, J. Umpierrez, E.F.
3.Jwam&
Ung, C. UngvAry, F. Ungwitayatom, J.
LhQJr.
Uno, M. Unrau, C.M. Uozumi, Y. Urahe. H. Urabe, K. Urata, H. Urogdi, L. Urpi, F. Ushijima, Y. Ushio, Y. Ushizaka, K. UskokoviC, M.R. Usuki, Y. Ukaka, M.
IJakL&
IJtimoto.
K,
Uyama, H.
uY!wax
V
237 507 064,479 518, 526 544 360 190 115, 256, 297, 305 490 345,418 369 240 492 205,337 01 1 467 062, 196, 418, 463 097
625
UZW. R. VSgberg, J.O. Vaid, B.K. ValdCs, C. Valenti, E. Valli, V.L.K. Valoti, E.
201
537 438, SO, 438,507 419 117, 276, 510 222, 288, 330, 312 076 lhlYakA 173 Van Dort, P.C. 172 Van I Iemelryck, B. 446 Van Oeveren, A. 429 van Asten, P.F.T.M. 548 van Boom, J.H. 048 van den IIeuvel, H.G.M. 001 van den Nieuwendijk, A.M.C.H. 317 444 320 378 van der Donk, W.A. 047 148, 150 van der Gen, A. 053,317 033,461 van der Heiden, R. 248 077 vnn der Kerk, A.C.T.H.M. 287 047,411 van der Linden, J.B. 548 108, 334, 341, van der Marel, G.A. 048,053 355,539 van der Merwe, T.L. 050 137 yan He&n. F.lt 050 012, 177, 204 van Harden, P.S. 104 146 van Leeuwen, P.W.N.M. 238 064, 161, 246, 343 van Zanden, M.N.A. 402 158 Vandcr Roest, J.M. 101 041 147 Vanderesse, R. 447 Vruiderpl,z, B.C. 47 1 499 169,443 Vankar, P.S. yil&cfa 201 495 055 Vaquero, J.J. 386 094,451 310 Vara Prasad, J.V.N. 025, 043, 060, Varma, M. 459 093, 139, 184, 217, Vmna. R.S. 008,459 247, 278, 296, 299, Vasapollo, G. 08 1 220, 307, 308, 309, Vnsconcellos, M.L. 327 324, 335, 348, 350, Vasilevskii, D.A. 111 360, 390, 395, 395, Vasilcvsky, S.F. 287 414,423,433,457, Vasudevan, S. 5 14 479, 485, 516, 537 Vafcle, J-M. 409,481 098 h l t i e r . M. 112, 137, 317, 387,404 413.557
-
626
Compendium of Organic Synthetic Methods, Vol8
Vavrecka, M. Veale, C.A.
YAxkkJL
Veera Reddy, A. Vega, J.A. Veit, J.R. Velarde, E. Velasco, L. Venanzi, L.M.
Venkataraamam, R.V
l!ma&MN
Venugopal, M. Verardo, G. Verdageur, X. Verhoeven, T.R. Verkruijsse, H.D. Verma, P. Vernier, J-M. Verpeaux, J-N. Verteletskii, P.V. Veschambre. H. Veselovskii, V.V. Viado, A.L.
YiakL
Viana, L.H. Viaud, M.C. Vickers, D. Vidal, J.
l!i&&G
Vig, R. Vijayashree, N. Vilar, E.T. Vilarrasa, .I. ViIchez, J.E. Villeras, J. Vinczer, P. Violeau, B. Visger, D.C. Viski, P. Viso, A.
I56 188 158 290 386 044 001 243 263 463 53 I 130 007 369 141 3 13 167 001, 276 262 526 I 1 2, 266, 479, 497 512 239 262 316 20 1 01 1 140 107 377
064
43 1 057 258 058,204 048,064. 161, 246 54 1 201, 272, 481, 501, 556 309 167 155,402 197 270 030
Authors
Vitarius, J. Vivas, S. Vo, N.H. Voerckel, V. Vogl, K. Vogt, w. Vohra, R. Volanle, R.P. Volonterio, C. von Schnering, H.G. Vong, A.K.K. Vong, W-J. Vos, B.A. Vostell, M. Vu, C.B. VukiCevic, R. Vysotskii, V.I.
410 097 359 407 428 340 314 401 467 407 437 296 557 535 365,409,438 432 494
Waas, J.R. Wachter-Jurcsak, N. Wada, E. W a 4 I.
103
lb&LrL 3xak.M.
Wadgaonkar, P.P. Wagman, A S . Wagner, A.
-
llLUmJ3
Wakahara,Y. Wakamatsu, H. Walda, B.
Waldmiiller, D. Walgrove, T. Walizei, G.H.
!lwkeLu
Walker, K.A. Walker, M.A.
xahl&Q
Wallace, E.M. Wallace, I.H.
3!ahcdm
Wal Ihank, P.J . Wallis, C.J.
121
400 046 303 343 007, 135, 160, 161 550 282 313 298,396 504 125,432
070
276 340 014 123 146 275 549 305 042,465 258, 529 556 139 076 428
Author Index
Walsgrove, T. Walter, D.S. Waltermire, R.E.
YmaLMA JYim%lL !li&mJL Wan, B.Y-F. Wang, C-J.
lYuLLL
Wang, E-C. Wang, F. Wang, G-Z.
NilaLL
Wang, K. J?hlLKK Wang, L. Wang, M.C. Wang, M.D. Wang, Q-Z. Wang, Q.
Wang, R-T. Wang, S-L. Wang, S.L.B. Wang, T. Wang, W-B. Wang, w-L. Wang, W. Wang, X. Wang, Y-F. Wang, Y-X. Wang, Y. Wang, Z. Wang, Z.Y.
NaaLAa l3hrLQL lYarmIA
Warthow, R. Wartski, L.
llkuxsu
W
393 526 05 1 243 550 012 549 552 138 076 383 212 151,225 168 235 359,422, 536 303 260 131 133 013, 034, 037, 133, 181, 194, 218, 241, 272, 408 248, 249, 395, 485 296 183 358, 508,531 019, 024, 131, 186,488 504 036 227, 240, 482, 558 040 265 089,428 158, 289, 300, 325,395 191 382 48 1 352, 546 501 422 299
627
Watabe, K. Watruiabe, 1-1. Watanabe, J. WaLinabe, K. Watanabe, M. Watanabe, N. Wak?nahe, S. Wat'anabe, T.
Jl!mmkL
Watanuki, S. Watkins, L.M. Watson, B.T. Watson, J .V. Watson, R.J.
JwJLS.
Webb, K.S. Wedler, C. Wehineyer R.M. Wei, C-P. Wei, D. Wei, L.
NkLX
Weichert, A. Weidmann, H. Weining, P. Weinreh. S.M. Weinstein, R.M. Weismiller, M .C. Welch. C.J. Welch, J.
l3!cmJL
Wells, C. Wells, K.M. Welinaker, G.S.
l!!mbzA
Wenglowsky, S. Wermuth, C.G.
222, 365, 384, 409,438 106 418 24 1 372, 381 021, 023, 125, 64,277, 362 249,443,443 167,268 078 102, 146, 147, 162, 226, 322, 403, 453, 458, 463, 501, 519 528 109 412 36 1 443 179, 514 086,090 237,462 51 1 505 23 1 52 1 213 192 322 470 486 044
119, 140, 141, 420,492, 545 504 345 022 370 292, 383,493,497 362 428 357 336,448 067 189, 529 367
628
Compendium of Organic Synthetic Methods, Vol8
Wescott, S.A. Wessling, M. Westcott, S.A. Westrum, L.J. Wey, S-J. Whelm, J. Whipple, W.L. White, A.C.
..
-1
!xcb&!.
Wichtowski, J.A. Wiechert, R. Wieczorek, M.W. Wiedemann, J.
Wiest, 0. JVilcox. C& Wilkinson, J.A. Willems, H.M.G. Williams, G.M. Williams, J.M. R.M R.V. Willis, C.R. Willis, M.C. Willoughby, C.A. Wilson, A.L. Wilson, F.X. Wilson, L.J. Wilson, R.B. Jr. Wilson, T.E. Wilson, V.P. Winchester, W.R. Winders, J.A. Winghermiihle, D. Winf,.P. Wischmeyer, U. Wise, L.D.
090 162 047 429 158 347 239 147, 423, 533 158 354,357, 126,437, 136 555 322 513 383 227 501 092,219 551 011 552 39 1 074 207 053 232, 399 354 020 003,286 534 214,216 131 152 227,492 428 43 1 398 035 208 125 208 028,097 013, 098, 090 260
Witty, D.R.
JYlwLL
424, 477 524
Wizenbug, M.L. Wojtowicz, H. Wolher. E.K.A. Wolin, R.L. Wolowyk, M.W.
Wm, s. Wood, M.L. Woods, J.M. Woosley, J. Wovkulich, P.M. Wright, C. Wrohel, 2. Wu, A.
wu, c - c . wu, G. Wu, J.
NLML MLEL !&LILA
wu, S.C. wu, T - c .
WU,X-M.
llLdKxB m
w
. D.1.
Wydra, R.L.
XlauLL
Xiao, X. Xinhua, X. Xiong, H.
zh.Lz
101
Xu, D. Xu, J. Xu, L.H. XU, R-1-1. xu, S.L.
X L L
xu, 2.
Authors
072, 398 428 277 006 110 246 096, 100 156 040 034 139 550 193 499 516 325 014, 068, 079, 198, 211, 218, 259, 272, 503, 504 104 247,445 146,274 104 130 460 124 044 212 067, 183, 448 260 418 142 326 055 364 044, 263,457 245 084,303 379 391,412 024 066,084 433,487, 499 046
Y
Author Index
xa&tXL
Yadav, V. Yager, K.M. Yahata, N. Yakuma, K. Yakura, T.
Yamabe, S. Yamada, H. Yamada, J. Yamada, K. Yamada, M.
xEmah&
Yamada, Y. . . Yamaguchi, A. Yamaguchi, J. Yamaguchi, K.
Yamaguchi, S . Yamakawa, I.
xamahu&
J2ambwJ
Yamamoto, A. Yamamoto, A.
031, 363,427 025 437 554 474 155, 384, 412, 419 465,472 161, 319,477 086, 101, 137, 330,360 330, 356, 456, 527 244,474 171, 173, 344, 525 008, 045, 181, 195, 197, 303, 344, 381 118, 331 317 083 057, 079, 152, 225 175 217 071, 094, 175, 190, 223, 249, 278, 318, 360, 377, 400, 426, 498 390,537 042 358 236,253, 551 029 021,289 415 020, 025, 030, 061, 116, 175, 183, 226, 262, 294, 306, 355, 372, 373, 433, 513,529 173, 296, 297, 305,464
Yamamoto,
s.
Yamamura, K.
lkmlmm& Yamana, Y.
Yamanaka,H.
Yamanaka, T. Yamaoka, T . Yamaoki, H. Yamasaki, 11. Yamashita, H. Yamashila, K. ita. M, Ya~naslii~i, T.
xzumQL
Yamauchi, H. Yamazaki, 11. Yanazaki, T. Yarnazaki, Y.
LuLc.
YiuudLL
Yanada, R. Yanagawa, K. Yanagi, R. Yanagi, T. Yanagisawa, A. Yang, B. Yang, C-C. Yang, GX-Q.
xmLK
Yang, M. Yang, M. Yang, P-F.
YaJlLuL Yang, X. Yang, Y-J. Yang, z-Y.
629
154, 169, 330, 56,456, 527 225 068, 320,441 010,101,106, 108, 137, 153, 315, 330, 360, 380, 387,404 264 466 192 078,089, 178 474, 529 344 285,455 472 085 424 50s 023,441 076, 221 161 062, 506 152, 195, 242, 465,412 383 I%, 242 540 162,256 162, 256 049 473 355,446 025, 116, 294 082 120 113 374 187 456 069, 534 080 399 357 089, 282, 338, 434,434, 550
630
Compendium of Organic Synthetic Methods, Vo18
Yano, K. Yao, 2-P. Yaser, H.K. Yasuda, M. Yasue, K. Yasuhara, A. Yasui, K. Ye, T. Yechezkel, T. Yen, C-F. Yeoh, H.T-L. Yeske, P.E. Yi, K.Y. Yi, L. Yi, P. Yiannikouros, G. Yildirir, Y. Yin, C. Yoakim, C. Yohannes, D. Yokota, K. Yokota, T. Yokoyama, H. Yokoyama, K.
Yokovama.. Yokovama.. XQlUuL Yon&, T.
Yoo, B. Yoo, J.Y.
XQQAE.
XxLL
Yoon, D.C. Yoon, Y .B. Yorozu, K. Yoshida, A.
Yoshida, M . Yoshida, T.
193, 221, 459, 489,502 415 136 502 294 178 114 473 553,559 265 110
475 273,548 010,052 412 09 1 188 188 33 1 154,409 216, 330, 332 407 175 151 154,462,484 462,484 014, 139, 152 030, 094, 183, 249.426 001 102, 501 098, 143, 469 500 390 010
161,412 549 305 197 256,339 052, 181, 226, 369 061,527 093, 335, 491 041, 043, 286, 469
Yoshida, Y. Yoshida, 2. Yoshiga, T. Yoshimatsu, M. Yoshimura, N. Yoshbnura, T. Yoshino, T. Yoshitake, S. Yoshitomi, S. Yoshiyama, T. Yoshizawa, T. Yoshizumi, K.
lhLm.L JbiulaU
Young, J.R. Young, R.N. Youssofi, A. Yu, c-c.
Yu,C-M. Yu, D.
Yu, H.K.B. Yu, J. Yu, K.H. Yu, X.Y. Yu, Y. Yuan, K. Yuan, T-M. Yuan, W. Yue, X. Yulan, Z. Yulin, J. Yum, E.K. Yurnoto, M.
JhlEkul
hsJL
0.
A
rl
Yusyhov, M.S.
Authors
205 114, 132, 195, 379, 392, 426, 460,554 306 156, 428, 430, 502, 528 475 147.437 05 1 284 337 115, 234, 356 166 206,477 207 338 395.395 205 133 027 085 167 413 069 277 023 054 113, 275,431 396 138 530 075 069, 080.4 11 042 132 331, 332 168 389,417 137 168 535 026, 027, 102, 146, 299, 302, 340,493,494, 548 503
