Annual Reports in Organic Synthesis, Volume 2004 (Annual Reports in Organic Synthesis)

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Author: Philip M. Weintraub | Kenneth Turnbull | Jeffrey Sabol | Peter Norris

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annual reports in organic synthesis - 2004

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annual reports in organic synthesis - 2004 Philip M. Weintraub

Kenneth Turnbull

Aventis Pharmaceuticals Bridgewater, New Jersey

Wright State University Dayton, Ohio

Jeffrey Sabol

Peter Norris

Aventis Pharmaceuticals Bridgewater, New Jersey

Youngstown State University Youngstown, Ohio

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Contents PREFACE .................................................................................................... LIST OF JOURNALS ABSTRACTED ...................................................... GLOSSARY OF ABBREVIATIONS ....................................................... I

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CARBON-CARBON BOND FORMING REACTIONS A Carbon-Carbon Single Bonds (see also: I.E., I.F., I.G., I.H.) ........1 1 Alkylations of Aldehydes. Ketones. and their Derivatives .......1 2 Alkylations of Nitriles. Acids and Acid Derivatives ................2 3 Alkylations of p-Dicarbonyl. p-Cyanocarbonyl Systems. and Other Active Methylene Compounds ................................ 5 4 Alkylations O f N.. P.. S.. Se & Similar Stabilized Carbanions ....7 5 Alkylations of Organometallic and Related Reagents (see also: I.B.3., I.B.4., I.F., I.G.) .............................................. 9 6 Other Alkylation Procedures .................................................. 12 7 Nucleophilic Addition to Electrophilic Carbon ...................... 12 a 1.2.Additions .................................................................... 12 ( 1 ) Aldol-Type 1. 2 Additions .......................................... 12 (2) Add’n of N. P. S. Se & Similar Stabilized Carbanions ..19 (3) Addition of Organometallic and Related Species ......20 (4) Other 1 2-Additions .................................................... 31 b Conjugate Additions ......................................................... 33 (1) Enolate-Type Carbanions ........................................ 33 35 (2) Organometallic and Related Reagents ..................... (3) Other Conjugate Additions ...................................... 38 8 Other Carbon-Carbon Single Bond Forming Reactions .........40 B Carbon-Carbon Double Bonds (See also: I.E.l) ........................... 43 1 Wittig-Type Olefination Reactions ......................................... 43 2 Eliminations ............................................................................ 45 45 a Alcohols and Derivatives .................................................. b Halides .............................................................................. 46 c Other Eliminations ............................................................ 46 47 3 Olefin Metathesis .................................................................... 4 Other Carbon-Carbon Double Bond Forming Reactions .......50 5 Vinylations.............................................................................. 53 6 Allene Forming Reactions ...................................................... 5 5 C Carbon-Carbon Triple Bonds ....................................................... 57 D Cyclopropanations ........................................................................ 60 1 Carbene or Carbenoid Additions to a Multiple Bond .............60 2 Other Cyclopropanations ........................................................ 62 E Thermal and Photochemical Reactions ........................................ 64 1 Cycloadditions ........................................................................ 64 2 Other Thermal Reactions ........................................................ 72

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3 Photochemical Reactions ........................................................ 73 F Aromatic Substitutions Forming a New Carbon-Carbon Bond ....75 1 Friedel-Crafts Type Aromatic Substitution Reactions ...........75 2 Coupling Reactions to Form an Aromatic-Aromatic Bond ....78 3 Other Aromatic Substitutions and Preparations ..................... 82 G Synthesis via Organometallics ...................................................... 86 1 Synthesis via Organoboranes .................................................. 86 2 Carbonylation Reactions ......................................................... 88 3 Other Syntheses via Organometallics ..................................... 91 H Rearrangements ............................................................................ 95 1 Claisen. Cope and Similar Processes ...................................... 95 98 2 Other Rearrangements ............................................................ OXIDATIONS 102 A C-0 Oxidations .......................................................................... 1 Alcohol + Ketone. Aldehyde .............................................. 102 2 Alcohol. Aldehydes -+ Acids. Esters ................................... 104 B C-H Oxidations........................................................................... 105 1 C-H -+ C - 0 .......................................................................... 105 2 C-H + C-Hal ........................................................................ 107 C C-N Oxidations........................................................................... 107 D Amine Oxidations ....................................................................... 108 E Sulfur Oxidations ........................................................................ 109 F Oxidative Additions to C-C Multiple Bonds .............................. 110 1 Epoxidations ......................................................................... 110 2 Hydroxylations ..................................................................... 113 3 Other Oxidative Additions to C-C Multiple Bonds ..............114 G Phenol-Quinone Oxidation ......................................................... 115 H Dehydrogenation ......................................................................... 115 I Other Oxidations ........................................................................ 116 REDUCTIONS A C=O Reductions (see also 1II.F.1) .............................................. 118 1 Aldehydes, Ketones + Alcolols ........................................... 118 2 Acids. Esters, Amides + Aldehydes .................................... 120 3 Acids. Ester. Amides -+ Alcohols ........................................ 120 B C-N Multiple Bond Reductions .................................................. 121 1 Imine Reductions .................................................................. 121 123 2 Reductions of Heterocycles .................................................. C Reduction of Sulfur Compounds ................................................ 123 D N - 0 Reductions .......................................................................... 124 E C-C Multiple Bond Reductions .................................................. 125 1 C=C Reductions .................................................................... 125 2 C=C Reductions .................................................................... 127 F Hetero Bond Reductions ............................................................. 128

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V

VI

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128 1 C-0 -+ C-H .......................................................................... 2 C-Hal -+ C-H ........................................................................ 129 130 3 C-S + C-H ........................................................................... G Reductive Cleavages................................................................... 130 1 Oxiranes ................................................................................ 130 131 2 N-0 Cleavages ................................................................... 132 3 Other Reductive Cleavages................................................... H Reduction of Azides ................................................................... 132 I Other Reductions ........................................................................ 132 SYNTHESIS OF HETEROCYCLES A Oxiranes, Aziridines. and Thiiranes ........................................... 133 B Oxetanes. Azetidines. and Thietanes .......................................... 137 C Lactams ....................................................................................... 137 D Lactones ...................................................................................... 146 E Furans and Thiophenes ............................................................... 151 F Pyrroles. Indoles. etc ................................................................... 159 G Pyridines. Quinolines. etc ........................................................... 167 H Pyrans. Pyrones. and Sulfur Analogues ...................................... 174 I Other Heterocycles with One Heteroatom .................................. 179 J Heterocycles with a Bridgehead Heteroatom ............................. 180 K Heterocycles with Two or More Heteroatoms............................ 183 1 Heterocycles with 2 N’s ........................................................ 183 a 5-Membered.................................................................... 183 b 6-Membered.................................................................... 188 c 7-Membered.................................................................... 191 2 Heterocycles with 2 0’s or 2 S’s .......................................... 192 3 Heterocycles with 1 N and 1 0 ............................................. 193 199 4 Heterocycles with 1 N and 1 S ............................................. 5 Heterocycles with 1 0 and 1 S ............................................. 202 6 Heterocycles with 3 or more N’s .......................................... 203 7 Heterocycles with 2 N’s and 1 0 .......................................... 206 8 Heterocycles with 2 N’s and 1 S or 1 Se .............................. 206 L Other Heterocyles ....................................................................... 207 M . Reviews ....................................................................................... 209 PROTECTING GROUPS .................................................................. A Aldehyde and Ketone Protecting Groups ................................... 215 B Amino Acid Protection ............................................................... 217 C Amine Protecting Groups ........................................................... 217 D Carboxyl Protecting Groups ...................................................... 220 E Hydroxyl Protecting Groups ....................................................... 221 F Other Protecting Groups ............................................................. 224 USEFUL SYNTHETIC PREPARATIONS A Functional Group Preparations ................................................... 225 I Acetals and Ketals ............................................................... 225

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2 Acids and Anhydrides (see also: I.A.2, II.B.l, V.E) ............228 3 Alcohols& Related Species (see also: II.B.1, III.A., V.E., VI.A.ll) ...229 4 Aldehydes and Ketones (see also: I.A.l., I.G.2., II.A.l .......231 5 Amides and Related Species................................................ 233 6 Amines ................................................................................ 237 241 7 Amino Acid Derivatives ...................................................... 8 Azides .................................................................................. 246 9 Carbohydrates ...................................................................... 246 10 Esters (see also: I.G.2., IV.D., V.D., VI.A.3) ...................... 248 1 1 Ethers ................................................................................... 250 12 Halides (see also: II.B.2.) ..................................................... 253 13 Nitriles and Imines ............................................................... 256 14 Other N-Containing Functional Groups .............................. 257 B Additions to Alkenes and Alkynes ............................................. 259 260 C Boron Compounds ...................................................................... D Nucleosides, Nucleotides etc ...................................................... 261 E Phosphorus, Selenium and Tellurium Compounds .................... 263 F Silicon Compounds .................................................................... 267 G Sulfur Compounds ...................................................................... 269 H Tin Compounds .......................................................................... 272 VII REVIEWS (see also: IV.M, VIII.A.5; VIII.C.7) A Techniques ................................................................................. 274 B Asymmetric Synthesis and Molecular Recognition .................... 276 C Reactions .................................................................................... 281 D Reactive Intermediates................................................................ 284 E Organometallics and Metalloids ................................................. 287 F Halogen Compounds and Halogenation (see also: VI.A.lO) ......293 G Natural Products ......................................................................... 294 H Others (see also: IV.M, VIII.A.5, VIII.C.6, VIII.F.7) .................299 VIII SELECTED TOPICAL AREAS A Fullerene Chemistry .................................................................... 306 ......................................... 306 Diels-Alder Type Cycloadditions 1 2 Other Cycloadditions ............................................................ 306 3 Photochemical Reactions ...................................................... 307 4 Other Fullerene Chemistry ................................................... 308 5 Reviews ................................................................................ 311 B Taxol and Related Taxane Chemistry ......................................... 312 C Dendrimers, Calixarenes and Other Unnatural Products ............315 1 Dendrimers ........................................................................... 315 a Dendrimer Synthesis ....................................................... 315 b Dendrimer Catalysts ....................................................... 318 c Hetero-Containing & Miscellaneous Dendrimers ..........318 2 Calixarenes ........................................................................... 319 a Calixarene Receptors ...................................................... 319

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b Synthesis of Calixirene ................................................... 320 c Synthesis on Calixirenes ................................................. 322 d Calixirene Isolation. Conformation. etc ......................... 323 3 Rotaxanes ............................................................................. 324 4 Supramolecules ..................................................................... 326 5 Cyclophanes .......................................................................... 328 6 Other ..................................................................................... 328 7 Reviews ................................................................................ 329 D Total Syn. of Selected Natural Products (see also: VII1.B).................329 E Reactions in Polar Media ............................................................ 346 1 Reactions in Aqueous Media ................................................ 346 2 Reactions in Ionic Media ...................................................... 351 F Combinatorial Chemistry ........................................................... 362 1 Supports. Linkers & Protecting Groups ................................ 362 2 Supported Reagents. Catalysts Ligands & Scavengers.........364 3 Solid-Phase Heterocyclic Synthesis...................................... 368 4 Solid -Supported Organic Reactions .................................... 372 5 Targeted Library Synthesis ................................................... 375 6 Novel Techniques in Combinatorial Chemistry ................... 377 379 7 Reviews ................................................................................ AUTHOR TNDEX ....................................................................................... 38 1

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One of the more difficult problems facing chemists today is that of “keeping up with the literature.” For several reasons, the problem is particularly severe for the synthetic organic chemist. Bits of information of potential use are scattered throughout common chemistry journals and can be found in any paper, not just those dealing strictly with synthesis. Thus, synthetic chemists must read a large number of journals and must organize and index what they read to make the information available for future reference. Fewer chemists are doing this as electronic searching becomes more prevalent. The ability to leaf through a concise compendium of the recent literature still remains important. Thus, readers of such a collection can quickly see new developments in several areas of synthesis and, additionally, an abstract may catch their eye and catalyze a new research idea. The problem, however, is shared to some extent by all. Most organic chemists are at some time faced with the problem of synthesizing a desired material, and for many the problems are formidable. Nonspecialists faced with the synthetic problem are not likely to have kept pace with the developments in synthe tic chemistry that may well solve their problems, and they will not have the necessary information in their files, despite the capabilities of on-line searching Thus, we feel an organized annual review of synthetically useful information should prove beneficial to nearly all organic chemists, both specialists and nonspecialists in synthesis. It should help relieve some of the information storage burden of the specialist and should enable the nonspecialist who is seeking help with a specific problem to rapidly become aware of recent synthetic advances. Ideally also, it should appear as promptly as possible after the close of the abstracting period. As in the past years, we have placed particular emphasis on keeping the abstracts as concise as possible, while indicating the generality of the reactions involved. We have tried to combine similar publications into inclusive abstracts. This practice has allowed us to include a larger number of references without a substantial increase in the book’s length. It should be noted that where multiple references are included in the abstract, the first mentioned refers to the equation shown. The remaining references are related but not identical. To further aid the readers, we have separated related but less similar references from that represented by the graphic by the phrase “see also:”. We have allowed for two such separations per graphic. In a number of cases we xi

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PREFACE

have attempted to further elucidate the contents of these multiple references by including a statement below the graphic. If this statement is enclosed in square brackets [e.g. 1I.A. 1-2: “similar solvent free oxidation using CrO3” and 1V.D-1: “also with ally1 bromides”] then it pertains to data from the references following the lead reference. If round brackets are employed (e.g. I.E.3-4: “similarly for tetrhydrofurans and pyrrolidines” and 1I.A. 1-4; “also odorless Swern”) then further information about the lead reference is being provided. The year has been omitted from each reference as presumably all are from 2003. Any references from 2002 (journals received after our February 1 cutoff date) are noted appropriately. In an effort to be more space efficient, we have adopted letter abbreviations for the journal references from Katritzky’s Handbook of Heterocyclic Chemistry. See the List of Journals Abstracted for definitions of these letter abbreviations; they are alphabetized by the abbreviations rather than the journal name. Last year the Journal of the Chemical Society (Perkin I ) and (Perkin II) were combined into a new journal entitled Organic and Biomolecular Chemistv (OBC). In producing Annual Reports in Organic Chemistry2004 we have abstracted 43 primary chemistry journals, selecting useful synthetic advances. Only the common journals received by our libraries have been abstracted. We have also exercised selectivity in choosing which papers to abstract. Our general guidelines have been to include reactions and methods that are new, synthetically useful, or reasonably general. We have tried to present the information in an organized manner, emphasizing rapid visual retrieval. The purpose of this emphasis is to aid the reader in scanning the book. The mind is capable of absorbing a whole picture in an instant, but is considerably slowed by having to read sentences. If the pictures presented catch the reader’s interest, he or she should then seek details from the original paper. The author index is based on the name of the senior author(s) or sometimes the first author. No subject index is included because we feel the Table of Contents serves that fimction. Chapters 1-111 are organized by reaction type and, hopefully, the organization is self-explanatory; thus, there should be no difficulty in locating a new method of oxidation or a new cyclopropanation procedure. Chapter IV deals with methods of synthesizing heterocyclic systems. Where fused ring systems bearing multiple heterocyclic rings are shown, we have chosen to categorize the heterocyclic system by the ring formed in the reaction. Chapter V covers the use of protecting groups. Chapter VI deals with those synthetically useful transformations that do not fit easily into the first three chapters. In Chapter VII, the reviews have been divided into sections to help the reader to quickly find a review on a specific topic. Other area specific reviews may be found at the end of the section. Heterocyclic reviews may be found at the end of

PREFACE

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Chapter IV; Selected topical reviews are in VIII.C.7. Selected Topical Areas, consists of topical areas we felt are topics, and have collected titles of papers in these areas. While not an all inclusive listing, we hope it will prove useful. We organized the section on Total Syntheses of Selected Natural Products (V1II.D) so the synthesized target names (with associated author and reference) have been sorted and grouped alphabetically to help the reader locate a particular compound as quickly as possible. To keep the Annual to a reasonable size, only one author is listed in this section. We used our editorial prerogative to select from the many applicable syntheses. We maintain the section on Carbohydrates (VI.A.9) in the Useful Synthetic Preparations chapter, as well as the section divisions on Combinatorial Chemistry (V1II.F): 1 . Supports, Linkers & Protecting Groups; 2. Supported Reagents, Catalysts Ligands & Scavengers; 3. SolidPhase Heterocyclic Synthesis; 4. Solid-Supported Organic Reactions; 5 . Targeted Libraries Synthesis; 6. Novel Techniques in Combinatorial Chemistry; and 7. Reviews. Because of the increasing number of papers being published and the constraints placed on the number of pages we want AROS-2004 to be, we made further changes to the formating allowing more abstracts to be presented. We tightened the spaces between abstracts even further, and no longer use “and” when two or more authors are cited. Any undertaking of this type involves a series of compromises. We have chosen to emphasize reasonable cost and rapid visual retrieval of information at the admitted expense of detail and beauty. We would like to thank our readers over the past years for the wonderful reception they have given our endeavor. In passing on the editorship of AROS, two of us (KT, PMW) would like to acknowledge the excellent contributions made by our colleagues over the past 15 years as reflected in the high quality of AROS. It has been highly rewarding that scientists have communicated to us the usefulness of this series. We are proud of our speed to publication especially in the years before ChemDrawB. Comments (negative or preferably positive) or suggestions from the reader will be well received by the senior editor. Senior and Contributing Editor Philip M. Weintraub Contributing Editors Kenneth Turnbull Jeffrey S. Sabol Peter Norris

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LIST OF JOURNALS ABSTRACTED Aldrichimica Acta Accounts of Chemical Research Acta Chemica Scandinavia Angewandte Chemie International Edition in English Australian Journal of Chemistry AJC Bulletin of the Chemical Society of Japan BCJ BMCL Bioorganic and Medicinal Chemistry Letters Journal of the Chemical Society Chemical Communications cc ccc Collection of Czechoslovakian Chemical Communications European Journal of Chemistry CEJ Chemistry and Industry (London) CKL) Canadian Journal of Chemistry CJC Chemistry Letters CL Chemical and Pharmaceutical Bulletin CPB Chemical Reviews CRV Chemical Society Reviews CSR EJOC European Journal of Medicinal Chemistry EJOC European Journal of Organic Chemistry Heterocycles H Helvetica Chimica Acta HCA JACS Journal of the American Chemical Society JCR(S) Journal of the Chemical Research (S) Journal of Heterocyclic Chemistry JHC Journal of Medicinal Chemistry JMC Journal of Organic Chemistry JOC Journal of Organometallic Chemistry JOM Monatschefte fur Chemie M Organic and Biomolecular Chemistry OBC Organic Letters OL OM Organometallics Organic Preparations and Procedures International OPP Organic Synthesis 0s Pure and Applied Chemistry PAC Russian Chemical Reviews RCR Synthesis S Synthetic Communications sc

AA ACR ACS

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LIST OF JOURNALS ABSTRACTED

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SL ST T TA TCC TL Z

Synlett Steroids Tetrahedron Tetrahedron Asymmetry Topics in Current Chemistry Tetrahedron Letters Zeitschrift fur Naturforschung, Teil B

GLOSSARY OF ABBREVIATIONS 4-PP pyrrolidinopyridine 9-BBN 9-borabicyclo[3.3. I]nonane 18-Cr-6 = 8-C-6 18-crown-6 AA amino acid Ac acetyl acac acetonylacetone ad adamantanyl ADC 9,lO-anthracene dicarbonitrile ADDP I , 1 '-(azadicarbony1)dipiperidine AIBN azobisisobutyronitrile ALB aluminum lithium bis(binaphth0xide) All ally1 Alloc = ALOC allyloxycarbonyl An p-anisyl APC ally1 palladium dimer APSG aminopropylated silica gel aq aqueous Ar aryl ATD aluminum tris(2,6-di-tertbutyl-4-meth ylphenoxide) ATPH aluminum tris(2,6diphenylphenoxide) AZMB 2-(azidomethyl)benzoyl BAlB bis-acetoxyiodobenzene BARF tetrakis[3,5-bis(trifluoromethy I)phenyl]borate BCN N-benzyloxycarbonyloxy-S-norbomene-2,3dicarboximide BDMS bromodimethyl-sulfonium bromide BDPP (2R, 4R) or (2S, 4s) 2,4bis(dipheny1phosphino)pentane

BER

borohydride exchange resin BICP (R,R) 2(R)-2'(R)-bis(diphenylphosphin0)1(R), I'(R)-dicyclopentane BIH bis(symcollidine)iodine(l) hexafluorophosphate BINAL-H LiAlHq/ethanol/l, 1'bis-2-naphthol complex BINAP = DINAP 2,2'-bis(diphenylphosphin0)-1,l binaphthyl BINAS 6-fold sulfonated 2,2'bis(diphenylphosphin0methyl)- l,I'-binaphthyl Bip biphenyl-4-sulphonyl BLA Bronsted acid assisted chiral Lewis Acid bmin 1-butlyl-3-methylimidazolium cation Bn benzyl BNAH l-benzyl-l,4-dihydronicotinamide BOB 4-benzyloxybutryl Boc t-butyloxycarbonyl BOM benzyloxymethyl BPO benzoyl peroxide bpy bipyridyl BQ benzoquinone BSA bovine serum albumin BSA N,O-bis-silylacetamide = 0,N-bis-trimethylsilyl acetamide Bt 1- or 2-benzotriazolyl BTAC benzyl triethylammonium chloride BTF benzotrifluoride Bth benzothiazole I-

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BTI BTI

PhI(02CCF3)2 [bis(trifluoroacetoxy) iodo]benzene BTEAC benzyl triethylammonium chloride BTFP 2-bromotri fluoroisoprene BTMA benzyl trimethyl ammonium BTS bis(trimethylsily1)sulfate BTSA bis-trimethylsilyl chromate BTSP bis(trimethylsily1) peroxide butyl Bu Bus tert-butylsul fonyl Bz benzoyl CAN ceric ammonium nitrate cat. catalyst benzyloxycarbony1 Cbz CCE constant current electrolysis CHD cyclohexadiene CHP cumene hydroperoxide Chx2BI dicyclohexyl iodoborane C1 FeTPP meso-tetraphenylphyrin iron chloride CMHP cumene hydroperoxide CMMP cyanomethylenetrimethylp hosphorane cod 1,5-~yclooctadiene cot cyclooctatriene Cp cyclopentadienyl CPTS collidinium-p-toluenesulfonate Cr-PILC chromium-pillared clay catalyst CRA complex reducing agent CSA camphor sulfonic acid CTAB cetyl trimethylammonium bromide CTACl cetyl trimethylammonium chloride

GLOSSARY OF ABBREVIATIONS

CTAN ceric tetra-N-butylammonium nitrate CTMS = TMCS chlorotrimethylsilyl Cu MeSAl copper(1) 3-methylsalicylate Cu TC copper(1) thiophene-2carboxylate Cy cyclohexyl A heat D day DABCO 1,4-diazabicyclo[2.2.2]octane DAMFA (diethylaminoethylene) hexafluoroacetylacetone DAST diethylaminosulfurtrifluoride DATMP diethylaluminum 2,2,6,6-tetramethylpiperidide dba dibenzylidene acetone DBAD=DTBAD di-tertbutylazodi-carboxylate DBH di-tert-butyl hyponitrite DBI dibromoisocyanuric acid DBn p-dodecyloxybenzyl dbpp 1,3-bis(dibenzophospholy1)propane DBPO Di-tertbutyl peroxyoxalate DBS dibenzosuberyl DBSA dodecylbenzylsulfonic acid DBTA dibenzyl L-tartramide DBU I ,5-diazabicyclo[5.4.0]undec-5-ene DCA 9,lO-dicyanoanthracene DCB dichlorobenzene DCC dicyclohexylcarbodiimide DCE 1,2-dichIoroethane DCN 1,4-dicyanonaphthalene Dcpm dicyclopropylmethyl

GLOSSARY OF ABBREVIATIONS

2,3-dichloro-5,6-dicyanobenzoquinone de = d.e. diastereomeric excess DEAD diethyl azodicarboxylate DEPC diethyl cyanophosphor idate DEPO diethylphosphine oxide DET diethyl tartrate DHAP dihydroxyacetone phosphate DHP dihydropyran DHQD dihydroquinidine DIAD diisopropylazodicarboxylate DIB (diacetoxyiod0)benzene DIBAH = DIBAL diisobutylaluminum hydride DIM 2-(hydroxyethy1)- 1,3dithiane DIMCARB dimethylammonium dimet hy 1 carbamate DIOP 2,3-O-isopropylidene-2,3dihydroxy-l,4-bis(diphenylphosphin0)butane dippp 1,3-bis(diisopropylphosphino)propane DIPT diisopropyl tartrate DLP dilauroyl peroxide DMA N,N-dimethylacetamide DMAD dimethyl acetylene dicarboxylate DMAP 4-(N,N-dimethyl)aminopyridine DMB rn-dimethoxybenzene Dmb 2,4-dimethoxybenzyl DMB 2,3-dimethylbuta-l,3diene DMBQ 2,6-dimethyl-l,4benzoquinone DMD dimethyl dioxirane DME dimethoxyethane DDQ

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DMF dimethylformamide DMFDMA dimethylformamide dimethyl acetal DMG directed metalation group DMI 1,3-dimethylirnidazolidin2-one DMM dimethoxymethane DMN 1,5-dimethoxynaphthalene DMP Dess Martin Reagent DMP 2,6-dimethylphenol DMPS dimethylphenylsilyl DMPU N,N'-dimethylpropyleneurea DMSO dimethylsulfoxide DMT 4,4'-dimethoxytrityl DMTMM 4-(4,6-dimethoxy[ 1,3,5] triazin-2-yl)-4-methylmorpholinium chloride DMTr dimethyltrityl DNBA 2,4-dinitrobenzoic acid dpba 2-(dipheny1phosphino)benzoic acid dpma N,N,-di(pyrroly1-amethyl)-N-methylamine DPC diphenylphosphoro chloridate DPDC diisopropyl peroxydicarbonate DPDM diphenyl diazomethane DPEDA 1,2-diphenylethane- 1,2diamine DPM diphenylmethyl DPPA diphenylphosphorazidate dppb bis( 1,4-diphenylphosphino)butane dppe = DPPE bis(dipheny1phosphino)ethane dppf dichloro[ 1,l'-bis(diphenylphosphinoferrocene)]

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1,3-(dipheny1phosphino)propane DPS t-butyldiphenylsilyl DPTC O,O'-di(2-pyridyl) thiocarbonate dr diastereomeric ratio ds diastereoselectivity DTBAD = DBAD di-tertbutylazodi-carboxylate DTBB 4,4'-di-tert-butylbiphenyl DTBP 2,6-di-t-butylpyidine dfBPF 1,1'-bis(di-tertbuty1phosphino)ferrocene DTE dithioerythritol DTPM [ 1,3-dimethyl-2,4,6-(1 H, 3H,SH)-trioxopyrimidin5-ylidinelmethyl E general electrophile EDAC ethyldimethylaminopropylcarbodiimide EDC l-ethyl-3-(3-dimethylaminopropy1)carbodiimid e EDCP ethylene dicarboxylic diphosphonic acid EDTA ethylenediamine tetraacetic acid ee = e.e. enantiomeric excess en ethylene diamine EPHP N-ethylpiperidine hydrophosphorous acid Et ethyl EWG electron withdrawing W U P Fc ferrocenyl FDMA formaldehyde dimethyl acetal FDP fructose-l,6-diphosphate Fe(dbm)3 tris(dibenzoy1methido) iron(1I I) dppp

GLOSSARY OF ABBREVIATIONS

FePHEN tris( 1,lO-phenanthroline)iron(III)hexafluorophosphate Fe(Epp) iron(II1) tetraphenylporphyrin fl flavin FI 9-fluorenyl flosyl = Fs fluorosulfonate Fmoc 9-fluorenylmethoxycarbonyl fod 6,6,7,7,8,8,8-heptafluoro2,2-dimethyl-3,5-octanedione FSM mesoporous silica Fs = flosyl fluorosulfonate FTT 1-fluoro-2,4,6-trimethylpyridinium triflate FVP flash vapor pyrolysis GaSO chiral Ga heterometallic complex GEBC gel entrapped base catalyst Gr graphite GSNO nitrosoglutathione Gltco-PTS glycosyl phenylthiosulfonate h hours Hap hydroxyapatite HDNIB [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo] benzene hfacac hexafluoroacetylacetone HFIP hexafluoro-2-propanol HGK 4-hydroxy-2-ketoglutarate HLADH horse liver alcohol dehydrogenase HLE horse liver esterase Hmb 2-hydroxy-4-methoxybenzyl HMDS 1,1,1,3,3,3hexamethyldisilazane

GLOSSARY OF ABBREVIATIONS

HMPA = HMPT hexamethylphosphoramide HMS hexagonal mesoporous silica HMTAB hexamethylenetetramine bromide HNIB [hydroxyb-nitrobenzenesul fonyloxy)iodo] benzene hv irradiation with light HPA heteropoly acid 3-HQD 3-hydroxyquinuclidine HTIB [hydroxy(p-tolylsulfony loxy)iodo]benzene IBDA iodobenzene diacetate IBX o-iodoxybenzoic acid IDCP iodonium dicollidine perchlorate I MesH2 1,3-dirnesyl-4,5dihydroimidazole-2ylidene INOC Intramolecular Nitrile Oxide Cycloaddition Ipc2 diisopropylcamphyl IPr 1,3-bis(2,6-diisopropylphenyl)imidazol-2ylidene K- 10 a Montmorillonite clay KMBA potassium Nmethylbutyramide KSF a Montmorillonite clay LA Lewisacid L-selectride" lithium triSbutylborohydride L.R. Lawesson's reagent LAH lithium aluminum hydride LBDE lithium perchlorate in Et20 LDA lithium diisopropylamide LDBB lithium 4,4'-tbutylbiphenylide LDE lithium diethylamide

xxi

LDPE lithium perchloratediethyl ether LICKOR BuLiltBuOK liq. liquid LR Lawesson's reagent LTMP lithium 2,2,6,6-tetramethylpiperidide MABR methylaluminum bis(4brom0-2,6-di-~butylphenoxide) MAD methylaluminum bis-(2,6di-tbutyl-4-methylphenoxide) MAPh methylaluminumbis(2,6diphenoxide) MBDA magnesium bis(diisopropylamide) MBT 2-mercaptobenzothiazole MCPBA m-chloroperbenzoic acid MCM-4 1-TBD hybrid organic/ inorganic reusable catalyst Me methyl Mek methyl ethyl ketone MEM p-methoxyethoxymethyl MEPY methyl 2-pyrrolidone5 (S)-carboxylate Mes = mesityl 2,4,6-trimethylphenyl MMPP magnesium monoperoxyphthalate Mmt 4-methoxytrityl Mn(phox)3 tris(2-oxazoliny1)phenato manganese@) MOM methoxymethyl MPD 1-methylpyrrolidone MPM methoxy(phenylthi0)methyl Mpm = PMB p-methoxybenzyl MPPC N-methyl piperidine chlorochromate MS molecular sieves

xxii

methanesulfonyl methanesulfonic acid o-mesitylenesul fonyl hydroxylamine Mspoc 2-methylsulfonyl-3phenyl- 1-prop-2-enyloxycarbonyl MTO methyltrioxorhenium (MeRe03) MTPA methoxy-a-trifluoromethylphenylacetyl MV2+ methyl viologen MVK methyl vinyl ketone mw = pW microwave NaBMGS sodium butylmonoglycosulfate NAP naphthylmethyl Naph = Np naphthyl NBS N-bromosuccinimide NCS N-chlorosuccinimide NCP N-chloro-3-methyl-2,6diphenylpiperidin-4-one NDMS 2-norbornyldimethyl silyl neocuproine 2,9-dimethyl-l,10phenanthroline Nf nonaflate Nf nonafluorobutylsulfonyl NfF nonafluorobutane sulfonyl fluoride NFOBS N-fluoro-O-benzenedisulfonimide NHPI N-hydroxyphthalimide NIS N-iodosuccinimide NISac N-iodosaccharin NMM N-methyl morpholine NMO N-methylmorpholine-Noxide Nph neophyl NPM N-phenylmaleimide N-PSP N-phenylselenophthalimide NR no reaction Ms MSA MSH

GLOSSARY OF ABBREVIATIONS

Ns Nuc. [O] ODCB ONf

2-nitrobenzenesulfonyl general nucleophile general oxidation o-dichlorobenzene nonaflate= nonafluoro- 1butanesul fonyl Oxone potassium peroxymonosulfate PBP pyridinium bromide perbromide PCC pyridinium chlorochromate PDC pyridinium dichromate PEG polyethylene glycol Pf 9-phenylfluorenyl pfb perfluorobutyrate PFC pyridinium fluorochromate Ph phenyl Ph-H benzene Ph-Me toluene PHOX 2-[2-(dimethyl(phosphin0)-phenyll-4phenyl-4,Sdihydrooxazole Pht tetra-tert-butylphthalocyanine PhTRAP 2,2'-bis[ 1-(diphenylphosphino)ethyl]- 1,1'biferrocene pic 2-pyridinecarboxylate PIDA phenyliodonium diacetate PIFA phenyliodo bis(trifluoroacetate) PLAP porcine liver acetone powder PLEPIG LIVER ESTERASE PMHS polymethylhydrosiloxane PMB = Mpm p-methoxybenzyl PMP 1,2,2,6,6-pentamethylpiperidine PMP p-methoxyphenyl

xxiii

GLOSSARY OF ABBREVIATIONS

PNB p-nitrobenzyl PNP dimer cis, exo-2-phenylnorbornylpalladium CIp-nitrobenzyloxycarbon yl PNZ polyphosphoric acid PPA ethyl polyphosphate PPE PPHF pyridinium polyhydrogen fluoride 2-pheny1-2-(2-pyridyl) PPI imidazole pig pancreatic lipase PPL pol y(p-phenylene) PPP PPSE polyphosphoric acid trimethylsilyl ester PPTS pyridinium p-toluenesul fonate Pr P'OPYl propargy loxycarbony 1 Proc PSCBH poly supported cyanoborohydride PSDIB poly[4-(diacetoxy) iodostyrene] PSE phenylsulfonylethylidene psi pounds per square inch PTAB phenyltrimethylammonium perbromide PTC phase transfer catalysis PTMSE (2-phenyl-2-trimethylsily1)ethyl PTOC pyridine-2-thione-Noxycarbony 1 PTS p-tolylsulphonate PTSA p-toluenesulfonic acid PTT phenyltrimethylammonium tribromide pyr pyridine QFC quinolinium fluorochromate QxDC quinoxalinium dichromate rac racemic RaNi Raney nickel

Rf ROMP rt Salen

perfluorinated alkyl ring-opening metathesis room temperature N,"-ethylenebis(salicyl ideneim inato) SAMP (s)-1-amino-2methoxymethylpyrrolidine SBER sulfurated borohydride exchange resin SC C 0 2 super critical C02 SDS sodium dodecylsulfate SEM = TEOC p-trimethylsilylethoxymethy 1 SES 2-[(trimethylsilyl)ethyl]sulfonyl Sia Siamyl Si-BEZA 0-(trisubstituted sily1)benzamide Si-PTA silica-supported phosphotungstic acid SMEAH sodium bis(2-methoxyethoxy)aluminum hydride SPB sodium perborate SPC sodium percarbonate T3p@ propane phosphonic acid anhydride TABCO 2,4,4,6-tetrabromo-2,5cyclohexadienone TADDOL 2,2,-dimethyl-a,a,a1, a*-tetraaryl-I ,3-dioxolan4,5-dimethanol TASF tris(dimethy1amino)sulfur(trimethylsily1)difluoride TBAB tetrabutylammonium bromide TBAF tetrabutylammonium fluoride TBAHS tetra-n-butylammonium hydrogen sulfate

xxiv

TBAT tetrabutylammonium trifluorodi fluorosilicate TBATB tetrabutlyammonium tribromide TBATFA tetrabutylammonium tri fluoroacetate TBATFA tetrabutylammonium tri fluoroacetate TBCO tetrabromocyclohexadienone TBDMS = TBS t-butyldimethylsilyl TBDPS butyldiphenylsilyl TEAB tetraethyl ammonium bromide Tbfmoc Tetrabenzo[a,c,g,i] fluorenyl- 17-methyloxycarbonyl TBH di-tert-butyl hypochlorite TBHP tbutyl hydroperoxide TBME tbutyl methyl ether TBP tributylphosphine TBST triphenyl silanethiol Tbs 4-methoxy-3-t-butylbenzenesulphony1 TBSOP N-fbutylcarbonyl-2(tbutyldimethylsi1oxy)pyrrole TBTH tributyltin hydride TBTSP t-butyl trimethylsilyl peroxide TCAA trichloroacetyl anhydride TCCA trichloroisocyanuric acid TCEP tris(2-carboxyethy1)phosphine TCF trichloromethyl chloroformate TClCA trichlorocyanuric acid TCNE tetracyanoethylene TCNEO tetracyanoethylene oxide

GLOSSARY OF ABBREVIATIONS

TDTAP tetradecyl trimethylammonium permanganate TCPCTFE (tetrakis(2,2,2-trifluoroethoxycarbony1)palladium cyclopentadiene TDS dimethyl thexylsilyl TEA triethylamine TEAA tetraethylammonium acetate TEAF triethyl ammonium formate TEAP tetraethyl ammonium perchlorate TEBA Benzyl trimethylammonium chloride TEEDA N,N,N',N'-tetraethylethylenediamine TEOC = SEM p-trimethylsilylethoxymethyl TEP triethylphosphite TES triethylsilyl Tf trifluoromethanesulfonyl TFA trifluoroacetic acid TFAA trifluoroacetic anhydride TFE trifluoroethanol TFFH tetramethyl fluoroformamidinium hexafluorophosphate TFMSA trifluoromethanesulfonic acid TFO methyl(trifluor0methy1)dioxirane TFP 1,1,1-trifluoro-2-propanol TFP tris (2-fury1)phosphine TFPZ trifluoroisopropenyl zinc TFSA trifluoromethanesulfonic acid THAB tetrahexylammonium bromide THAH tetrahexylammonium hydrogen fluoride thexyl 2,3-dimethylbutly

xxv

GLOSSARY OF ABBREVIATIONS

THF tetrahydrofuran THFA tetrahydrofurfuryl alcohol THP tetrahydropyranyl TIBA tri(isobuty1)aluminum TIBAL tri-iso-buylaluminum TIPPSe-Br (2,4,6-triisopropylpheny1)selenium bromide TIPS tri-ipropylsilyl TMABr tetramethylammonium bromide TMACC trimethylammonium chlorochromate TMAF tetramethylammonium fluoride TMAO = TMANO trimethylamine N-oxide TMATB trimethylammonium tribromide TMEDA tetramethylethylenediamine TMG 1,1,3,3-tetramethyIguanidine TMHI 1, 1, l-trimethylhydrazinium iodide Tmob 2,4,6-trimethoxybenzyl TMP 2,2,6,6-tetramethylpiperidine TMS trimethylsilyl TMSA trimethylsilyl azide = azido trimethylsilane TMSDEA N,N-diethyltrimethylsilylamine TMU tetramethylurea TNM tetranitromethane t-OcNC 1,1,3,3-tetrarnethylbutyl isocyanide To1 tolyl Tos = Ts p-toluenesulfonyl

Tp trispyazole borate TPCD tetrapyridine cobalt(I1) dichromate TPP Tetraphenylporphyrin TPP triphenyl phosphine TPP triphenylphosphate TPPB tris(pentfluor0pheny1)borane tppts m-sulfonated triphenylphosphine = tris(psulfonatopheny1)phosphine tpy terpyridine Tr = trityl triphenylmethyl Tsc 4-trifluoromethylphenylsu1fonyl)ethoxycarbonyl Ts-MIC tosylmethyl isocyanide TSE 2-(trimethylsilyl)ethyl TTBP 2,4,6-tri-tertbutylpyridine TT Co(I1) Pc tetrabutylammonium cobalt(I1) phthalocyanine5,12,19,26-tetrasulfate TTMPP tris(2,4,6-trimethoxypheny1)phosphine TTMSS tris(trimethylsily1)silane UHP urea-hydrogen peroxide complex wk week Z benzyloxycarbonyI Zr BDC Zr (BH&C12(DABCO)*

@ - = Q polymeric support @*= US ultrasound *

Denotes asymmetric center

This Page Intentionally Left Blank

I CARBON-CARBON BOND FORMING REACTIONS

I.A. Carbon - Carbon Single Bonds (see also: I.E., I.F., I.G., I.H.) I.A.1. Alkylations of Aldehydes, Ketones and Their Derivatives I.A.I-1 Liu, X.; Hartwig, J.F., OL, 5, 1915; Zhang, H. et al., SL, 2228. R

.~% Ph

Pd(dba)2, (Ad)2PtBu O + Ar-Br

K2CO3,Ph-Me

Ar O

~ Ph

40-85% I.A.1-2 Cho, C.S.; Shim, S.C. et al., OM, 22, 3608. OH OH OH R~"~Me + LR1 RuCI2(PPh3)3'KOH .1~ R ~ , , . ~ R 1 1-dodecene, dioxane, 80~ 25-90% I.A.1-3 Posner, G.H. et al. JOC, 68, 3049.

o

~o,. ~,,,,,,~ 1. LDA, THF, -280C

+

2. BF3oEt2O, THF, -78~ 3. H2, Pd/C, EtOH 62-70% I.A.1-4 Tanyeli, C.; Ozdemirhan, D., TL, 44, 7311. O O R ~ n

Mn(OAc)3'Bn'Br Ph-H, 80~

R ~ P h n

38-65%

2

ORGANIC SYNTHESIS--2004

I.A.1-5 Hidai, M.; Uemura, S. et al., OM, 22, 873; Campos, K.R.; Journet, M.; Cai, D. et al., JOC, 68, 2338. R ~ [Cp*RuCI(rr~-SR*)]2 P~ + Y NH4BF4,60~C OH O O 41-95%

ee = 10-35% I.A.1-6 Nakamura, M.; Nakamura, E. et al., JACS, 125, 6362. R1

R3,tnR

0

Me

CH2=CH2 H3 O+

94-99% ee = 58-98 %

I.A.1.7 Evans, P.A.; Leahy, D.K., JACS, 125, 8974. R

O

~OCO2Me

+ LiaR1

R

P(OMe)3,THF, 0oC_~rt

O

~~~JLR1 66-85%

I.A.1-8 Ma, J.-A.; Cahard, D.; JOC, 68, 8726; Grainger, R.S. et al., JOC, 68, 7889. "Mild Eleetrophilie Trifluoromethylation of -Ketoesters and Silyl Enol Ethers with 5-Trifluoromethyl-dibenzo-thiophenium Tetrafluoroborate."

I.A.2. Alkylations of Nitriles, Acids and Acid Derivatives

I.A.2-1 Bauta, W.E. et al., JOC, 68, 5967. CO2Et ~

CO2Et TMG, TEA M e ( ~ ~ M e --~O CIOC~J~Me MeCN, 0oC Meu

U

86%

CARBON-CARBON BOND FORMING REACTIONS

3

I.A.2-2 Takeda, K. et al., JOC, 68, 9330. OTBDMS R-X, NaHMDS.-~ TBD CN THF, .800C TBD

OTBDMS ~ N

C

80-99%

I.A.2-3 You, J.; Verkade, J.G., AG(E), 42, 5051. 9

D

iBui"

.BU.N.~-~.'~6/~"Bu

S1

Cl

R1

~"~N~

CN +

112 Pd(OAc)2or Pd2(dba)3 base, Ph-Me, 90~

10-96%

I.A.2-4 Maruoka, K. et al., AG(E), 42, 579 and TA, 14, 1599; Castle, S.L.; Srikanth, G.S.C., OL 5, 3611; Kumar, S.; Ramachandran, U., TA, 14, 2539. Ph2C .L-AA-OtBu R-X, chiral PTC Ph2C L-AA-OtBu ~"~O

50% aq KOH, Ph.Me, 0*C"~

~"'~O R 80-95% de = 90-98 %

I.A.2-5 Hruby, V.J. et al., TL, 44, 5863; Soloshonok, V.A. et al., TL, 44, 1063; Kawabata, T. et al. T, 59, 965. Ph Ph

~O I

Ph

. . . .

Br"J~"~

~ L ~ ~

H

N a O H , D M F , -30oc

96% i ~ H : a - H = 12:1

I.A.2-6 Wanner, T. et al. EJOC, 2233. MeO MeO

k___

BU

o -~,--,

~__~

,O T i S

80.C, 2hPtBu4 Me ~ ~" DME/THFl~tBi~X o

"

OTBS M e O

X---r~

, e - - ~" +tMe BtiX o

72% 9:7:3:1

O OTBS

4

ORGANIC SYNTHESISm2004

I.A.2-7 Chen, Y.; Yudin, A.K., TL, 44, 4865; Takemoto, Y. et al. AG(E), 42, 2054. Ph2C ].OAc Pd(OAc)2,BINAP Ph2~'~CO2 R ~.~CO2 R -I- Ph2C~--,.CO2R Nail, MeCN, rt Ph2C~N,~,,.CO2R

84% d,hmeso = 2:1 I.A.2-8 Trost, B.M. et al., JACS, 125, 4438.

g

/OBh

eh'~oNo~o "1" ~,~ OBn

Pd(O2CCF3)2'CH2CI2~ ph.~NoN~'oH ~NH~~~

67-87% dr = 13-20:1 ee =85-94%

~.....~PPl~ P h 2 P ~

I.A.2-9 Ley, S.V. et al., CC, 468; Munoz-Munoz, O.; Juaristi, E., T, 68, 4223; Shih, N.-Y. et al., OL, 5, 4249. MeO MeO R X

OMe

O LDA,HMPA/THF, -78~-550C

I.A.2-10 Cossy, J. et al., SL, 2171. 1. SBuLi,ZnCI2, -200C ~ 0 2. Ar-Br, NMez Pd(dba)2 ~

Bn cy2e

J,-

R OMe "-" 72-92% dr = 2-22:1

~,~~r

Bn 70-98%

I.A.2-11 Thebtaranonth, Y. et al., JMC, 46, 2397; Paintner, F.F. et al., SL, 627. C ~ EtO2C./----~ g-x EtO2 Ph Nail, DMF/THF, rt 65-76%

CARBON-CARBON BOND FORMING REACTIONS

5

I.A.2-12 Kawabata, T. et al., CC, 162. DMe Me-I P hN/ Y RRI~ O

MeO .Me 1 ph~ NRR

LTMP,TBME,-78*C

0 17-72% ee = 0-64%

I.A.2-13 Jubault, P.; Pannecoucke, X. et al., TA, 14, 1637. E OH OH E-X Ph2__~~~ '] BuLi, additive, -78-~-20~ ~H 3 0 Ph BH3 0 Ph

P er LrJ

v

32-90% de = 15-98% I.A.2-14 Chang, N.-C. et al., JOC, 68, 5688. R1

R1 s

R-X Nail, THF Re

81-88%

I.A.3. Alkylations of 13-Dicarbonyl, 13-Cyanocarbonyl Sy.stems and Other Active Methylene Compounds I.A.3-1 Kuwano, R. et al., JACS, 125, 12104; Kuwano, R.; Uchida, K.; Ito, Y., OL, 5, 2177. 2Et BSA, KOAc, DPPF Ar~OCO2Me + R CO2Et pd(rl3.C3H5)(cod)BF4

Av

'C.~RO2Et CO2Et 61-99%

I.A.3-2 Nakamura, M.; Endo, K.; Nakamura, E., JACS, 125, 13002. O O R1

R2 neat,100-1400C 76-99%

6

ORGANIC SYNTHESISm2004

I.A.3-3 Carretero, J.C. et al., JOC, 68, 3679; Brunner, H. et al., TA, 14, 1115; Bolm, C. et al., OBC, 1, 145; Ohta, T. et al., TA, 14, 537; Hou, X.L. et al., TA, 14, 107; Mino, T. et al., JOM, 665, 122; Douthwaite, R.E. et al., OM, 22, 4187; Kim, T.-J. et al., OM, 22, 1475; Moberg, C. et al., OL, 5, 2275; Tamaru, Y. et al., T, 59, 7767; Knochel, P. et al., TA, 14, 255; Wallner, O.A.; Szabo, K.J., JOC, 68, 2934; Moberg, C. et al., JOC, 68, 3258; Kurita, J. et al., TL, 44, 6217; Nakano, H. et al., TA, 14, 2361. Nut-H, [Pd(h3-C3Hs)CI]2 OAc ~uc THF or CH2CI~ rt Ph Ph Ph'/~""~Ph ~ . , ~ ~ 50-97% Fe PR,2 SR ee = 40-99 % I.A.3-40kano, T. et al., JOM, 676, 43. OCO2Et Pd cat., PPh3, tBuONa ph,,~l~ ph 4- CH2(CO2Et)2 ~

CH(CO2Et)2 ph~,~,,~ph 31-77%

I.A.3-5 Malacria, M. et al., JOC, 68, 5588. ___(SIR3 Pal(OAt)2, PPh3 ,SIR3 + CH2(CO2Me)2 ~AcO__~ / CO2Me AcO----/ ~-- OAc THF, rt ~\~O2Me 64-99% e:z= 1-100:1 I.A.3-6 Mori, M. et al., OL, 5, 31. CI"

O 4- CH2(CO2Me)2

_CH(CO2Me)2

1. CsCO3, RI~NR Pd2(dba)3"CHCl3 ~ 2. CH2N2,Et20

r

CO2Me 63%

I.A.3-7 Yang, D. et al. OL, 5, 2869; Krafft, M.E.; Lucas, M.C., CC, 1232; Fukuyama, Y. et al., TL, 44, 6235. O O O O O O Ln(OTf)3, dioxane

~'~-='~R 1 H

or

I

31-97%

_~,,,R 1 iI

CARBON-CARBON BOND FORMING REACTIONS

7

I.A.3-8 Maruoka, K. et al., AG(E), 42, 3796; Covarrubias-Zuniga, A. et al., SC, 33, 3165. O R-X, CsOH'H20, Ph-Me,-40~ ~~CRO2tBu

o2t u

Ar Br"

90-99%

e.e. = 87-96%

I.A.3-9 Trost, B.M.; Jiang, C., OL, 5, 1563. O EtO2C~~,,

SPh j 4- ~ ~ ' ~ O

OH Pdz(dba)3.CHCl3, lig EtO2C-~~ N , , / S P h CH2C12,rt 71% ee = 94 %

I.A.3-10 Hadjiarapoglou, L.P. et al., T, 59, 7929. O r + Phi +'~" SO2Ph MeCN,rt

O

SO2Ph

~(Y'~r 42-66%

I.A.4. Alkylations of N-, P-, S-, Se and Similar Stabilized Carbanions

I.A.4-1 Katritzky, A.R. et al., JOC, 68, 1443" Koo, S. et al., HCA, 86, 2620.

R1 R2 RSOf,,,J + B t ~ O

R1 BuLi 2~R2 TItF, .78C~ RSO O 73-96%

I.A.4-2 Uneyama, K. et al., TL, 44, 6319; Shipman, M. et al., CC, 1344; Mural, T. et al., JOC, 68, 8514. Tsh~ E+' BuLi TsIN~'E w" CF3 THF, .102oc ~" "CF3 13-95%

8

ORGANIC SYNTHESISm2004

I.A.4-3 Smith, III, A.B. et al., JACS, 125, 14435. R1 R ~ ~ O 1" tBuLi, Et20, "78-"25~ ~S

+

TBSO ~ S

2. E + HMPA, -78--,00C

TBS 56-74% I.A.4-4 Afarinkia, K. et al., S, 357.

+ R-X

LDA TI

,

.~'-

(EtO)2P~O

(EtO) O

34-81% I.A.4-5 Afarinkia, K. Jones, C.L., S, 509; Afarinkia, K. et al., SL, 513; Lequeux, T. et al., OBC, 1, 2486. E +, LDA ,..._ ~ . _ . Ph BnN,,.LT-O | Ph-Me,-78~ 6~~Me e E 40-64% d.r. = 1-15:1 I.A.4-6 Hodgson, D.M. et al., OBC, 1, 4293. ~~

O + EtCONMe2

_O•__Et

BuLi, sparteine Et20, -900C

57%

ee = 74% I.A.4-7 Falck, J.R. et al., OL, 5, 4759; Rychnovsky, S.D.; Takaoka, L.R., AG(E), 42, 818. PC~_x PC.,,x

SnBu3 R/~OyNR12 S

E+, CuI THF, 50~ "~ R ~

E OyNR12 S

45-96%

CARBON-CARBON BOND FORMING REACTIONS

9

I.A.4-8 Naud, S.; Cintrat, J.-C., S, 1391; Fleming, I.; Russell, M.G., CC, 198.

+

Bu3Sn,~ ~ "~ Bn

R ~ I O BuLi ~- ~ R O ~ ~ 1 , -100~

n

26-57%

I.A.5. Alkylations of OrganometaUic and Related Reagents (see also: I.B.3., I.B.4., I.F., I.G.) I.A.5-1 Zhou, J.; Fu, G.C.; JACS, 125, 12527. RCH2-X + R1.ZnX, Pd2(dba)2,PCyp3,NMI NMP/THF, 80~ I.A.5-2 Kambe, N. et al., JACS, 125, 5646. NiC!2 or CuCl2 R-F + R1-MgX

R~R 1 52-90%

R.R1 38-98%

I.A.5-3 Murphy, K.E.; Hoveyda, A.H., JACS, 125, 4690. iprO2C~ Et2Zn,(CuOTf)2.PhH,TI-IF i p r O 2 C ~ (EtO)211P-'O

~

r

0

~on

n o

H Et

o eu

ee=94%

I.A.5-4 Marek, I. et al., OL, 5, 5087. R --

~ Nipr2

R•R1

R-Cu, MgBr2,Et20 then E-X

~~'-Sier2

40-78%

I.A.5-5 Arrayas, R.G.; Cabrera, S.; Carretero, J.C., OL, 5, 1333; Nakamura, M.; Nakamura, E. et al., OL, 5, 1373. OH R-MgX, CuCI,PPh3

~

-OR

Ph-Me, rt 47-94% anti:syn = 9-49:1

10

ORGANIC SYNTHESISm2004

I.A.5-6 Shinokubo, H.; Oshima, K. et al., OL, 5, 4623. R

\

/

R1

E

CH2=CHCH2MgCi,MnCI2,THF

\R 2

R~ . ~

~

~

then E+ 0~ 34-78%

I.A.5-7 Brion, J.-D.; Ardisson, J. et al., S, 2530 and SL, 955. R

~-~

Li

1" E R2CuCNLi2 E-X 2 . H~~-~--~ 57-95%

I.A.5-8 Martynov, A.V. et al., JOM, 674, 101. NiClz(dppe) or NiCl2(dppp) EtSe~-~SeEt + R-MgBr

R

R

78-85% I.A.5-9 Tenenbaum, J.M.; Woerpel, K.A., OL, 5, 4325. BnO

BnOPh2Sj--0 ipr

1. CH2=CHCH2TMS,SnCI4, Ph-Me 2. H202, KF, KHCO3,MeOH/THF

~- ipr

OH

OH

I~,~ ~,~ ~ , ~ Me

Me

56%

I.A.5-10 Yoshida, H.; Kunai, A. et al., CC, 1510. Pal(OAt)2, dppp R.SiMen(OR1)m DMSO or DMSO/H20/O2

R-R 11-94%

I.A.5-11 Hodgson, D.M. et al., OBC, 1, 1139; Zhao, H.; Pagenkopf, B.L., CC, 2592; Smith, III, A.B. et al., OL, 5, 2751. ( ~

BuLi,Ph'Me, "780C~_ o ~ B U ip~

ipr

' N

H

N

~~

~O

OH

49% ee=49%

Et Et

I.A.5-12 Luzzio, F.A.; Mayorov, A.V., SL, 532. Phth~,,],_,~Cl

Pd(0),Nuc/NuC-HTHF, 0oc _~ P h t h N ~ . , ~ u c 34-99%

iq

CARBON-CARBON BOND FORMING REACTIONS

11

I.A.5-13 Gansauer, A. et al., CEJ, 9, 531; Lu, Y.; Li, C.-J. et al., CC, 2318. OH Rr + ~'~ "CO2tBu Cp*2TiCI,Zn ~..- R ~ c o 2 t B u 2,4,6-coludine.HCl R

R 68-90%

dr = 1.1-9:1 I.A.5-14 Smith, K. et al., S, 2345; Wu, G.G. et al., JOC, 68, 4984. H

~

~

H

E+BuLi ~~ R THF,-78*C

~

R 70-80% E

I.A.5-15 Kraus, G.A.; Choudhury, P.K., S, 659; Harmata, M.; Kirchhoefer, P., SL, 497; Harmata, M.; Wacharasindhu, S. CC, 2492. Br E Br _ _ ~ ~ ~

Me

E+' B u L i ~

THF, -78~

Br _ ~ ~

one/..._ Me 85-98%

I.A.5-16 Yus, M. et al., TL, 44, 5025 and T, 59, 8525. E+, Li, DTBB CaH17.F .~.- C8H17-E 53-98% I.A.5-17 Theberge, C.R.; Zercher, C.K., T, 59, 1521. O O PGH~~CO2Me CH212'EI2Zn ~ P G H ~ c o 2 M -

R

R

25-68%

I.A.5-18 Khwana, J.M. et al., OBC, 1, 1737. R

iron(II) oxalate

R

Ar

Ar~'---X HMPA/DMF,155-160~ 37-85%

e

12

ORGANIC SYNTHESISm2004

I.A.6. Other Alkylation Procedures I.A.6-1 Flynn, B.L. et al., CC, 1380. O R

/

frO XR1

1. Bu3SnH, Pd(PPh3)4 2. R-X, CuCI

R

48-93%

I.A.6-2 Kern, O.T.; Motherwell, W.B., CC, 2988. tBu--N~ + p h , ~ O +

R-CO2H

O O LiOTf .~ N~,,,.~O ~ THF, reflux tBuH R Ph 64-77%

I.A.7. Nucleophilic Addition to Electrophilic Carbon

l.A.7.a.1. Aldol-Type 1,2-Additions l.A.7.a.l-1 Evans, D.A. et al., JACS, 125, 8706; Crimmins, M.T.; Mc Dougall, P.J., OL, 5, 591; Romea, P.; Urpi, F. et al., SL, 1109; Hitchcock, S.R. et al., TA, 14, 3233; Casper, D.M.; Hitchcock, S.R., TA, 14, 517; Spanu, P. et al., TL, 44, 671; Hein, J.E.; Hultin, P.G., SL, 635. S O TMS-OTf, 2,6-Me2Pyr S O OH ~ ~ M CH2CI2/Ph'Me' "78-~'20~ ~ s ~ N ~ + R-CHO TrO OTf R e ~~o~~~ ~ Me 46-86% syn:anti = 6-49:1 syn ee = 91-97 % I.A.7.a.l-2 Yadav, V.K.; Balamurugan, R., OL, 5, 4281. TMS OH O R ~ + O TiCi4 R~H R Me R1AR2 CH2C12,-780C 45-79% a-H:I~-H= 2-12:1

CARBON-CARBON BOND FORMING REACTIONS

13

I.A.7.a.l-3 Shibasaki, M. et al., JACS, 125, 2169; Enders, D.; Burkamp, F., CCC, 68, 975; Adam, W.; Zhang, A., EJOC, 587. O OMe OH O OMe

o /'6 t2ZnliedlNO,

81-95% syn:anti = 2.57-32.3:1 syn ee = 87-99 %

I.A.7.a.1-4 Kobayashi, S. et al., JACS, 125, 2989; Denmark, S.E.; Pham, S.M., JOC, 68, 5045; Denmark, S.E.; Heemstra, Jr., J.R., OL, 5, 2303; Romea, P. et al., OL, 5, 519; Rychnovsky, S.D.; Cossrow, J., OL, 5, 2367; Juaristi, E. et al., JOC, 68, 1622; Calter, M.A.; Orr, R.K., TL, 44, 5699; Yamamoto, H. et al., SL, 2219; Gree, R. et al., JOC, 68, 6392; Jha, A.; Dimmock, J.R., CJC, 81, 293; Evans, D.A. et al., JACS, 125, 10893; s e e a l s o : Shibasaki, M. et al., JACS, 125, 5644; Kobayashi, S. et al., CC, 2016; Imashiro, R.; Kuroda, T., JOC, 68, 974; Lang, F. et al., TL, 44, 5285; Mukaiyama, T. et al., CL, 696; Chart, K.-F.; Wong, H.N.C.; EJOC, 83; Yu, C.-M. et al., CC, 2036; Shair, M.D. et al., JACS, 125, 2852; Yanagisawa, A.; Sekiguchi, T., TL, 44, 7163. R~OTMS Pr(OTf)3 OH 0 R-CHO +

R 2~

.L.L

R3

chiral b i s - p y r i d i n o - 1 8 - C r - 6

~ R_ nl.~n2

R3

1 s

53-99% syn:anti = 19-22.4 syn ee = 47-85%

I.A.7.a.1-5 Kwon, O. et al., OL, 5, 1923. TMSO MeO CO2Me

O Me9

~O2Me

CH2C12,-78~ 79% l.A.7.a.l-6 Knight, D.W. et al., CC, 2550. R1

OEt

THF, -78-'20~

1~2,,JDH

60-91% anti:syn = 2-100:1

14

ORGANIC SYNTHESIS--2004

I.A.7.a.l-7 Little, R.D. et al., OL, 5, 3615; Lee, Y.J.; Chan, T.H., CJC, 81, 1406; Mukaiyama, T. et al., BCJ, 76, 813. RO2C CP2TiCI2, Mn RO2O q } a ~---X + R2.CHO R1 THF, rt 2 64-95% I.A.7.a.l-7 Gona, L.-Z.; Wu, Y,-D. et al., JACS, 125, 5262; Martin, H.J.; List, B., SL, 1901; List, B. et al.,AG(E), 42, 2785; Jorgensen, K.A. et al., SL, 1915; Kotsuki, H. et al., SL, 1655; Tanaka, F.; Barbas, III, C.F. et al., OL, 5, 4369; 1685; see also: Ohsawa, A. et al., OL, 5, 4301; Barbas, III, C.F. et al., JOC, 68, 9624; Cordova, A. et al., SL, 1651; Hayashi, Y. et al., JACS, 125, 11208. O OH O e~ "25~ I,~ R~, ~ R-CHO + M Me o Ph Me ~ N H N~"~dIPh H ]OH

12-93% ee = 81-99%

I.A.7.a.l-9 Denmark, S.E.; Beutner, G.L., JACS, 125, 7800. R3 0 T B S OH R3 SiCl4, CH2CI2,-78~ Rj ~ / Y ~ 1 .~ CO2R1 R-CHO + R ~ R 2 OR1 MeO R4 R2 ~ ~ ~ e ~ :

CH2)5

68-97% ee = 10-100:1

l.A.7.a.l-10 Chen, K. et al., JOC, 68, 915; Corma, A.; Garcia, H.; Leyva, A., CC, 2806; Roy, A.K.; Batra, S., S, 2325; Fe!trin, M.P.; Almeida, W.P., SC, 33, 1141; Kataoka, T. et al., JOC, 68, 7532; Krishna, P.R. et al., TL, 44, 4973; Miller, S.J. et al., OL, 5, 3741; Aggarwal, V.K. et al., JOC, 68, 692; Kataoka, T. et al., CEJ, 9, 1496; Basavaiah, D. et al., JOC, 68, 5983; Shi, M. et al., T, 59, 1181; Shi, M., Jiang, Y., JCR(S), 564; Nemoto, H. et al., JACS, 125, 646. OH CO2R1 DARCO,MeCN, rt n~,~_ICO2R1 R-CHO + ~ II " ~ no2c ~,~,,~/-"XN~]..~ / 25-97% n62C -N ~ \ ee = 7-95%

CARBON-CARBON BOND FORMING REACTIONS

15

I.A.7.a.l-ll Satoh, T. et al., H, 59, 137. TMS~ 1. R-CHO,TBAF,THF, 4AMS~ Ph,,,

2. KOH, M e O H

HO_"!'R ~ _ ~,~

Ph,,,

36-69% l.A.7.a.1-12 Pare, P.W. et al., TA, 14, 971 and TL, 44, 949; Deng, G.-H. et al., HCA, 86, 3510; Li, G.; Headley, A.D. et al., OL, 5, 329; see also; Subburaj, K.; Montgomery, J., JACS, 125, 11210; Huddleston, R.R.; Krische, M.J., OL, 5, 1143. Me

+ R-CHO ~

O

~

Me

Mgl2 OH O . 0~ )b. R ~ I O" CH2C12'

0" tPr

~'I

~Pr 8O-87% de

= 37-58%

l.A.7.a.l-13 Ya, O.W.; Wang, J., OL, 5, 1527. OH Ph-CHO + r CO2Et Zr(OtBu)4,Br2BINOL~ p h ~ C O 2 E t N2 H20/DME, -35~ N2 65% ee = 87%

I.A.7.a.l-14 Mermerian, A.H.; Fu, G.C., JACS, 125, 4050; Long, Y.-Q. et al., JOC, 68, 7555; Ryu, Y.; Scott, AT, TL, 44, 7499. O O OTMS Et20/CH2CI2,rt Me'~~_ )w " RiCo + Ac20 Ph

R R

-'Fe

N

Ph

R,O

Ph

Ph Ph

R

R

73-92% ee = 76-99%

l.A.7.a.1-15 Adrian, Jr., J.C.; Snapper, M.L., JOC, 68, 2143. O R1 O R.NH2 + R1.CHO + ~ R 2 Me2Zn'NiCI(PPh3)3 R ~ N J ~ ~R2 Br CH2C12,rt H 58-97%

16

ORGANIC SYNTHESIS--2004

I.A.7.a.l-16 Donohoe, T.J. et al., OBC, 1, 3749. R

1. LiDBB, BMEA, THF, -78~ 2. Br(CH2)2Br CO2Et ~" I 3. MgBr2.Et2~ Boc 4. R-CHO

COzEt I Boc

68-76% anti:syn = 1.5-20:1 I.A.7.a.l-17 Amii, H.; Uneyama, K. et al., OL, 5, 4297; Ellman, J.A. et al., JACS, 125, 11276; Funabiki, K.; Matsui, M. et al., OL, 5, 2059 and JOC, 68, 2853. TMS~NsPMP BF3oEt20 OH N"PMP ~ + ~TMS CH2C12 "~ R1 F ~ ~ F [ TMS F 40-88% I.A.7.a.l-18 Jacobsen, M.F.; Skrydstrup, T., JOC, 68, 7112. O O ! ! R~OTMS tBu"S~l~ .i. __ EtO2C~ R OR1

Lewisacid ~

tBuIS~lH _ ~A ,,CO2R1 CH2C12,-78"C EtO2C- R ~ R 17-95% dr = 1-32.3:1

I.A.7.a.1-19 Shi, M.; Xu, Y.-M., JOC, 68, 4784. TS~NH O O N"Ts Ar.,J]

i~Ph +

DABCO THF, rt

Ar . ~ ~ P h -

Ph

)Z- o 54-85%

I.A.7.a.1-20 Liotta, D.C. et al., JACS, 125, 3690. O N.,OMe

R"

Jl

+

Ph~NH

S

O

1. TiCI4, sparteine

/e~"

2. Ph-COCI p r ~~

11-51%

S

CARBON-CARBON BOND FORMING REACTIONS

17

l.A.7.a.1-21 Trost, B.M.; Terrell, L.R., JACS, 125, 338" Jacobsen, E.N. et al., SL, 1919; Jorgensen, K.A. et al., CEJ, 9, 2359; Iqbal, J. et al., JOC, 68, 5735. O R,,N O R"NH A r ~ L A+ O Hu ,,• 4A-MS'THF-"-5~C '~ O ~ ~ ~ 1] "7 chiraldinuclear Zn species Ar x,,~XR1 R1 61-90% dr = 1.7-15:1 ee = 98-99% I.A.7.a.1-22 Ishimaru, K.; Kajima, T., TL, 44, 5441. CO2Me TMSO R1 ipr R O R1 N~ipr T f O H M e O- 2 ~ ~ R-~ 2 + /~~R 2 Et20 H 62-74% de = 70-92%

R.,JI

I.A.7.a.l-23 Jorgensen, K.A. et al., JOC, 68, 2583. R~N,,,.,,.CO2Me R / P G CuCIO, TEA, THF R ~ ~ C O 2 M e "l"

R1

I

~ I~

.~xNz / ~ a9

~

Ar2P

R1R,,~NHPG 61-99% syn:anti = 1.17-19:1 syn ee = 60-97%

I.A.7.a.l-24 Maruoka, K. et al., JACS, 125, 2054. OTMS ~O2 "O'~ + R1-CI-IO "~ g ~ gl chiral quaternary R ammonium bifluoride OH 45-94% anti:syn = 1.32-15.7:1 ee = 11-97% I.A.7.a.1-25 Kobayashi, S. et al., JACS, 125, 2507, 2481. O

O N'~C11H23 R102C,~]

R~__~OSiR3 Cu(OTf)2' CH2C12C11H23" ~ q~,~ H R2

~R3

chiral diamine

O

R102C- R2~R2xR3 77-96% ee = 6-94%

18

ORGANIC SYNTHESIS--2004

I.A.7.a.l-26 Andrews, D.M. et al., S, 1722; Suh, Y.-G. et al., OL, 5, 3635. /Cbz /Cbz Me e ~ : E t 1. BFa.Et20, CH2C12 ~ . ~ Me OEt + ~ ..... Me M TMS 2. K2CO~ EtOH O2Et NHCOCF3 NH2 90%

I.A.7.a.l-27 Estevez, R.J. et al., OL, 5, 4457. OBn BnO 02

aq NaHCO3

BnO"

OH MeOH,rt

O

BnO,

OH

HO"

"~OH OBn

"

53%

I.A.7.a.1-28 Satoh, T., Wakasugi, D., TL, 44, 7517. R2 ]---CN Li,~CN RI~s~ 0 + R CI

Tol

LDA

CN 1 ~

NH2

R 1- X ~ R 55-91%

I.A.7.a.1-29 Kanai, M., Shibasaki, M. et al., OL, 5, 3147. R-CHO+ [,~,CN CuOtBu,dppe H~CN R1 DMSO, rt ~ 1~ "R1 71-95% I.A.7.a.l-30 Katritzky, A.R., et al., JOC, 68, 4932. O R1 CN BuLi,THF,.78oc R'~Bt + p2 or tBuOK, DMSO, rt

O RR~IR~ N 2 71-95%

CARBON-CARBON BOND FORMING REACTIONS

19

I.A.7.a.2.Addition of N-, P-, S-, Se and Similar Stabilized Carbanions

l.A.7.a.2-1 Norrby, P.-O.; Tanner, D. et al., CCC, 68, 885. N,,R1 RIHN 0 r R.,Jl + "/81"Tol LDA ~ R.~,.., S...Tol Me O 75-98% conversion dr = 1-99:1 l.A.7.a.2-2 Rodrigues, A. et al., S, 1248. O II CI ~P(OEt)2 1. BuLi

O ~_

2. LDA, THF, -780C--,rt I(g./..~

SMe

O P(OEt)2

SMe 55-74%

l.A.7.a.2-3 Ruano, J.L.G.; Aleman, J., OL, 5, 4513. O O II [O II ~STol [,~N- ~'Tol LDA,.78oc ~STolH /O + R ~ fI[ ~ ~ R l ~ " ~ T ~

OTIPS

OTIPS 68-81% de = 98 %

l.A.7.a.2-4 Burger, K. et al., S, 915. O li BuLi N-PG ..P(OEt)2

F3

R

NMe2

PGHN O F 3 R C ~ I I P(OEt)2

THF, -78~

"NMe2 60-75%

l.A.7.a.2.5 Evans, D.A. et al., JACS, 125, 12692; Jorgensen, K.A. et al., OBC, 1, 153. i iOH EtOH, rt R-CHO + Me-NO2 R.~~... NO2

~"r I ~ 1

~

l" .,~"N~ "OAc~ q ~AcO

70-95% ee = 87-94%

20

ORGANIC SYNTHESISm2004

I.A.7.a.2-6 Huang, P.-Q. et al., OL, 5, 4341.

Et~..r

tBuLi, E +

MeO

%'1~ O

HMPA/THF,-78~

I

O I

PMB

PMB 45-87% de = 4-100%

I.A.7.a.3. Addition of Organometallic and Related Species

l.A.7.a.3-1 Joshi, S.N.; Malhotra, S.V., TA, 14, 1763; Yus, M. et al., TA, 14, 1103; Sprout, C.M.; Seto, C.T., JOC, 68, 7788; Richmond, M.L.; Seto, C.T., JOC, 68, 7505; Bringmann, G. et al, JOC, 68, 6859; Zheng, Z.; Chen, H. et al., TA, 14, 1285; Zheng, Z. et al., TA, 14, 297; Pericas, M.A. et al., JOC, 68, 3110; Wang, R. et al., TA, 14, 659; Braga, A.L. et al., OL, 5, 2635; Pelinski, L. et al., TA, 14, 1701; Ha, D.-C. et al., OL, 5, 4517; Munoz-Muniz, O.; Juaristi, E., JOC, 68, 3781; Soai, K. et al., OBC, 1, 244; Wu, K.-H.; Gau, H.-M., OM, 22, 5193. OH Ph-Me, rt R-CHO + Et2Zn ~ R~Et /oi-i Co

55-77% ee = 72-98%

I.A.7.a.3-2 Shibasaki, M. et al., AG(E), 42, 5489; Garcia, C.; Walsh, P.J., OL, 5, 3641. O iprOH/Ph-Me/Hex, -20~ H ~ . , Me R~'~CO2Me + EteZn 1-19 ~ R" ~"CO2Me 9

Ph

~Bn "/O~HPh

42-95%

ee = 59-96%

I.A.7.a.3-3 Walsh, P.J. et al., JACS, 125, 3210. 120H HO ol

sR Cy2B

~R1 R~

Et2Zn,0~ RV\ /"R 52-86% dr = 1-20:1

CARBON-CARBONBONDFORMINGREACTIONS

21

I.A.7.a.3-4 Ross, N.A.; Bartsch, R.A., JOC, 68, 360; Durandetti, M. et al., OL, 5, 317; Hong, Z.; Xu, X., TL, 44, 489; Colobert, F. et al., OL, 5, 629.

~R

(((.

Br. CO2Et Zn,I 2 0 p I

Ph +

R2

C(R O2Et

Dioxane

1R2 93-99%

I.A.7.a.3-5 Xue, S. et al., SL, 870; Shuto, S. et al.,AG(E), 42, 1021; Yu, M.; Pagenkopf, B.L., OL, 5, 4639; Rayner, C.M. et al., OBC, 1, 834. -

_L

BnO" y

j,,,,o

+

R2Zn

TFA/CH2CI2,0~

BnO'"y"OH

BnO

BnO 45-82%

I.A.7.a.3-6 Joseph, B. et al., SL, 1533; Tobrman, T.; Dvorak, D., OL, 5, 4289; Sugimoto, O.; Yamada, S.; Tanji, K.; JOC, 68, 2054; see also: Hilmersson, G. et al., TA, 14, 439; Chemla, F. et al., JOC, 68, 9747; Hoffmann, R.W. et al., JOC 44, 4546; Liu, Y.; McWhorter, Jr., W.W.; JOC, 68, 2618; Hakansson, M. et al., CEJ, 9, 4678; Nakada, M. et al., JACS, 125, 1140; Evans, W.J. et al. OL, 5, 2041; Sakamoto, M. et al., JOC, 68, 942; see also: Oi, S.; Inoue, Y. et al., T, 59, 4351. OHC ~ ~ ~ + I BuLi ~ ~ O ~ THF, -78C EtJ

Boc

Et2

~N~~ Boc 73%

I.A.7.a.3-7 North, M. et al., OL, 5, 4505; North, M., TA, 14, 147; Najera, C.; Saa, J.M. et al.,AG(E), 42, 3143; Deng, L. et al., JACS, 125, 9900; Feng, X. et al., SL, 558; Azizi, N.; Saidi, M.R., JOM, 688, 283; Fossey, J.S.; Richards, C.J., TL, 44, 8773; Cordoba, R.; Plumet, J., TL, 44, 6157. [(salen)TiO]2, -400C EtO2C~../CN R-CHO + EtO2C-CN ~ [

R 23-95% ee = 76-99%

22

ORGANIC SYNTHESISm2004

l.A.7.a.3-8 Mangeney, P. et al., OL, 5, 2567. NBn2 1. SBuLi,THF, -80--+-40"C TMS ~ / 2. CuCN, LiCI, -800C 3. R-CHO

TMS

..... pNBn2 I-I0 65-88%

l.A.7.a.3.9 Billard, T.; Langlois, B.R. et al., AG(E), 42, 3133 and SL, 230, 233; Langlois, B.R. et al., TL, 44, 1055; Prakash, G.K.S. et al., OL, 5, 3253; Caron, S. et al., S, 1693. Mg. JPh 1. CsF, DME OH or TBAT, THF ~ 1 - ~RR/- CF3 ~ § S 2. Bu4NF Fa~ 0 ee

30-93%

I.A.7.a.3-10 Prakash, G.K.S. et al., AG(E), 42, 5216. OH OH ~,R-CHO

+ PhSO2CF2H

tBuOK

DMF, -50~

RF~~~

R

52-82% de - 86-94 %

l.A.7.a.3-11 Kubota, K.; Leighton, J.L., AG(E), 42, 946; Hayashi, T. et al., JOC, 68, 6329; Malkov, A.V.; Kocovsky, P. et al., AG(E), 42, 3564; Maruoka, K. et al., CEJ, 9, 4380; Huckins, J.R.; Rychnovsky, S.D.; JOC, 68, 10135; Hsung, R.P. et al., SL, 791; Massa, A. et al., TL, 44, 7179; Zheng, X., Zhang, Y., JCR(S), 472; Oriyama, T. et al., OL, 5, 3045; Rowlands, G.J.; Barnes, W.K., CC, 2712; Denmark, S.E.; Fu, J., CC, 167; see also: Lloyd-Jones, G.C. et al., CCC 68, 865; La Ronde, F.J.; Brook, M.A., CJC, 81, 1206; Inanaga, J. et al., TL, 44, 8765; Leitch, S.K.; McCluskey, A., SL, 699; Zhang, Y. et al., JCR(S), 438. /---4-BrPh OH R-CHO + ~ .~~~~ K,,,,,,~,.,o~ "CI CH2C12,-10oc K

~-- 4-BrPh

~

61-93% ee = 95-98 %

I.A.7.a.3-12 Ollevier, T.; Ba, T., TL, 44, 9003. 1. R1-NH2, Bi(OTf)3.nH20 R-CHO

2. CH2=CHCH2-TMS

HN..R 1

27-86%

CARBON-CARBON BOND FORMING REACTIONS

23

I.A.7.a.3-13 Fernandez-Zertuche, M.; Ordonez, M. et al., TA, 14, 2693; Goti, A.; Merino, P. et al., OL, 5, 4235. R

~

O . .. ~p~

Nc~OH ~ ~0 Et2AICN,ZnBr2 ~- R'- _.~1 " , ~ O Ph-Me, -780C ~p~ 27-82% dr = 15.7-49:1

l.A.7.a.3-14 Morgan, J.B.; Morken, J.P., OL, 5, 2573; Yoshimitsu, T.; Arano, Y.; Nagaoka, H., JOC, 68, 625. R~ Me + [ EtO2G., 2 jO, r~_2 1. Pt(dba)2,PCy Hqk 1~. /Me EtO2C

tJB

2. R1-CHO "~ 3. H202,NaOH

I.A.7.a.3-15 Krische, M.J. et al., JOC, 68, 11. O o R ~ R1 THF,25~ R& n

~oO, n

R((

OH 58-72% ee = 33-74%

H~,,,R1

L~,,~J )n 5-91% syn:anti = 99:1

I.A.7.a.3-16 Gosmini, C. et al., S, 1909; Durandetti, M. et al., JOC, 68, 3121; Inomata, K. et al., H, 60, 2743; Auge, J. et al., JOM, 679, 79; Nair, V. et al., S, 2542. OH R~R10 + ~,,,,~OAc Zn'CoBr2 ~ R~ TFA/MeCN,rt 40-96% I.A.7.a.3-17 Malkov, A.V.; Kocovsky, P. et al., JOC, 68, 9659; Yamamoto, H. et al., JOC, 68, 5593; Chemler, S.R.; Roush, W.R., JOC, 68, 1319. OH MeCN, -40~ r ~ A Ar-CHO + R ~ S n C I 3 RR -'_ 27-88% ee = 87-99%

24

ORGANIC SYNTHESISm2004

I.A.7.a.3-18 Thomas, E.J. et al., CC, 1460. BuSn / ~ ~ BiI3 R-CHO + OBn

R

OH ~

Me

OBn

Me 45-92% 9-15:1

I.A.7.a.3-19 Lombardo, M.; Morganti, S.; Trombini, C., JOC, 68, 997; Lombardo, M.; Trombini, C., et al., CC, 1762; Berkessel, A. et al., AG(E), 42, 1032; Suzuki, H. et al., OBC, 1, 2160. O Br OH

1 ~ . o ~ ~ " ' 1 in TH~ or Zn ~H~, H~O. R~~'*'r~

R-CHO +

R

2. K2CO3

OH 60-94% syn:anti = 4-5.7:1

I.A.7.a.3-20 Thadani, A.N.; Batey, R.A., TL, 44, 8051; see also: Hall, D.G., JACS, 125, 10160; Yakelis, N.A.; Roush, W.R., JOC, 68, 3838; Szabo, K.J. et al., OL, 5, 3065. TBSO OH W ! TBSO

R2

Bu4NI

R

~ .I.

R~ C H O

+

R ~ . B F 3K+ CH2CI2/H20

TBSO

A~

OH

94-97% 1:1.86-3 I.A.7.a.3-21 Grigg, R. et al., TL, 44, 7969. II Ar-I + ~

+ R1-CHO

Pd(OAc)2, In, Cul TFP

A

R1 R

R

50-78% I.A.7.a.3-22 Nokami, J. et al., AG(E), 42, 1273. R1 ipr Ts-OH.H20

R-CHO + Me

R1 61-96% ee = 99%

CARBON-CARBON BOND FORMING REACTIONS

25

I.A.7.a.3-23 Parsons, P.J. et al., SL, 861" Gallagher, E.T.; Grayson, D.H., OBC, 1, 1374. Br OH TMS TMS tBuLi,ZnCI2 R ~ R-CHO + .78~

~

41-90%

dr = 1.5-9:1 l.A.7.a.3-24 Miller, M.J. et al., JOC, 68, 139. R1 O R-CHO,Pd(OAc)2,PPh~ I n I H20/TI-IF

oR1 O 39-73% cis:trans = 1:13-100

I.A.7.a.3-25 Yu, C.-M. et al., TL, 44, 5487; Loh, T.-P. et al., TL, 44, 507. BINOL-Ti[(OCH(CF3)2 FG~R-'CHO + ~ FG,, H R ~ tBuSBEt2,Ph-CF3, "20~ SnBu4 54-83% ee = 84-96% I.A.7.a.3-26 Urabe, H.; Sato, F. et al., JACS, 125, 6074. TMS tBuO2~

-l- R-CHO Ti(Oipr)4,..iprMgCI ~ I~,"~-~"R~r ~co2tBu ..... Et20' "20~ C6H13

HOTM~ ~-C6H13 61-77% ds = 7.33-13.3:1

I.A.7.a.3-27 Ramachandran, P.V. et al., JOC, 68, 9310; Concellon, J.M. et al., CEJ, 9, 5343; see also: Roy, A.K.; Batra, S., S, 1347; Verkade, J.G. et al., AG(E), 42, 5054; Almeida, W.P.; Coelho, F., TL, 44, 937; Krishna, P.R. et al., SL, 888; McDougal, N.T.; Schaus, S.E., JACS, 125, 12094. R2 OH iBu2AI- .,CO2Et R~~,ICO2Et CO2Et DIBALH,NMO "~ + R~OR. rt L R ~ ] THF, 0~ ~R THF, R 70-96%

26

ORGANIC SYNTHESIS--2004

I.A.7.a.3-28 Jeong, I.H. et al., TL, 44, 7213.

F3%

R1

TM~O (OMe F3C ~

Q~R 1 +

Ph Me

TBAF

R

Et20,-15~ 72-99%

I.A.7.a.3-29 Novikov, Y.Y.; Sampson, P., OL, 5, 2263; Shen, Y.; Wang, G., S 209. J Br

BuLi + O~R 1 .~- \ \ R TI-IF, -110~ B/

x( OH R1 R

20-85%

I.A.7.a.3-30 Jamison, T.F. et al., JACS, 125, 3442; Colby, E.A.; Jamison, T.F., JOC, 68, 156. R - ' - - R1 + R2.CHO

Ni(cod)~ Et3B, DMI/EtOAc iPrli, (

~,a Me

Ph2~'

OH Z. R2

R_ R1

35"97%

ee - 42-96%

I.A.7.a.3-31 Toru, T. et al., JOC, 68, 5766; Johnson, II, D.C.; Widlanski, T.S., JOC, 68, 5300. Tol

+ R1.CO2Et 1. LDA, THF,-780C ~ 2. DIBAL, TItF, -78~ ~TMS

O.. % 9 H T~ R1 ~TMS 30-83% dr = __.98:0:0:0

I.A.7.a.3-32 Shibasaki, M. et al., JACS, 125, 5634; Seki, M. et al., S, 2311; Bernardi, L.; Ricci, A. et al., SL, 1778; Heydari, A. et al., S, 1962; Hou, X.-L. et al., JOC, 68, 6264; ~ R N,,O TMS-CN,Gd(Oipr)3, EtCN Ph2 ~ r ~.. Ph2P~.O "OH

o ~ OH

~

Ns ~i~pph2 R~ R1 0 58-99% ee = 51-98%

CARBON-CARBON BOND FORMING REACTIONS

27

I.A.7.a.3-33 Wipf, P.; Stephenson, C.R.J., OL, 5, 2449; Chan, A.S.C. et al., JOC, 68, 1589. 1. Cp2ZrHCI, CH2C12,rt Nil 2. Me2Zn, Ph-Me, -78-,0~ ~fCO2 R1

R

~ R,,,~.,,,,-~ R1

3. o~,,co~1

75-93%

R1

LA.7.a.3-34 Marshall, J.A.; Bourbeau, M.P., OL, 5, 3197; Wang, R. et al., AG(E), 42, 5747; Kamble, R.M.; Singh, V.K., TL, 44, 5347; Cozzi, P.G.; AG(E), 42, 2895; Chan, A.S.C. et al., AG(E), 42, 5057; Chan, W.L.; Chan, A.S.C. et al., TA, 14, 449; Gong, L.-Z.; Jiang, Y.-G. et al., JOC, 68, 7921; Ishikawa, T.; Saito, S. et al., JOC, 68, 3702; Garcia-Tellado, F. et al., CEJ, 9, 3122; Bittman, R. et al., JOC, 68, 348,355.

Me

TMS 67% syn:anti = 19:1

l.A.7.a.3-35 Isobe, M. et al., OL, 5, 4883; Saeeng, R.; Isobe, M. et al., TL, 44, 6211; Yadav, J.S. et al., S, 247.

A~A~.~

+ [

SnCl4 MeCN, 0~

TMS

AcO

AcO" 78%

I.A.7.a.3-36 Florjancic, A.S.; Sheppard, G.S., S, 1653. H O Boc~N,,,jCO2H 1. Ar-Li, Et20 ~ H C I . H 2 ~ ~ A

R

2. HCl/dioxane

r 12-63%

ee = 99% l.A.7.a.3-37 Wang, X.; Zhang, Y., T, 59, 4201; Zhang, Y. et al., TL, 44, 1667.

R~O Bt

SmI2 ~

~_~

THF,rt 0-96%

28

ORGANIC SYNTHESIS--2004

l.A.7.a.3.38 Dieter, R.K. et al., T, 59, 1083; Frey, L.F. et al., T, 59, 6363. R R 1. SBuLi, CuX'2LiCI R R

I

2. R1-COCI

Boc

Boc

O

18-99%

LA.7.a.3-39 Gosmini, C. et al., T, 59, 8199; Wang, D.; Zhang, Z., OL, 5, 4645; s e e also: Kawakami, J. et al., S, 677; Vaquero, J.J.; Ezquerra, J. et al., OL, 5, 3791. /~___ CoBr2 /~_._~~ Z n B r + R-COCI F F 47-67% l.A.7.a.3-40 Zhang, Z. et al., JOC, 68, 10172; MaGee, D.I. et al., TA, 14, 3177; s e e also: Koutek, B. et al., SL, 937. O O R ~ + C I ' ~ ""I~Z CuI, TEA ~ _ ~ , ~ . . Z THF, rt O 43-95%

R rO

I.A.7.a.3-41 Boezio, A.A.; Charette, A.B., JACS, 125, 1692; Tomioka, K. et al., JOC, 68, 9723; Wang, C.-J.; Shi, M., JOC, 68, 6229; Gong, L.Z.; Mi, A.-Q. et al., JOC, 68, 4322; see also: Palmieri, C. et al., JOC, 68, 1200; Alexakis, A. et al., TL, 44, 8893; Martelli, G.; Savoia, D., CCC, 68, 1531; Charette, A.B. et al., JOC, 68, 3241; Trehan, S. et al., CC, 1420; s e e also: Galvez, J.A. et al., EJOC, 2268; Leault, C.; Charette, A.B., JACS, 125, 6360.

l~N",PPh2 II O

+ R12Zn

c.,o,02 =e OuP-OS~ R; Ph-Me, 0*C

H

,o Ph2

51-98% ee = 8 5 - 9 6 %

I.A.7.a.3-42 Motoyama, Y.; Nishiyama, H., SL, 1883; Maruoka, K. et al., TA, 14, 1603; Szabo, K.J. et al., AG(E), 42, 3656; Masuyama, Y. et al., TL, 44, 2845; Dias, L.C. et al., TL, 44, 6861. R1 ~HR~ R1 (ipr-Phebox)RhCl2(H20) R-CHO + ,~ ~'SnBu3 4A MS, CH2CI~ rt 82-97% ee = 9 0 - 9 9 %

CARBON-CARBON BOND FORMING REACTIONS

29

l.A.7.a.3-43 Evans, J.W.; Ellman, J.A., JOC, 68, 9948; Garcia Ruano, T.L. et al., OL, 5, 677. tBu tBu I

I

~o

H~'O

Me.

Ph-Me or THF, -78~ OPG

Me

R

OPG 72-98% syn:anti = 1:49-11.5:1

I.A.7.a.3-44 Wipf, P. et al., JACS, 125, 761; Minami, T. et al., JOC, 68, 4947. R2 N

Cp2ZrHCl, Me2Zn

R2~NH R1 35-90%

l.A.7.a.3-45 Kobayashi, S. et al., JACS, 125, 6610 and SL, 1749 and AG(E), 42, 3927; Takemoto, Y. et al., JOC, 68, 6745; Leighton, J.L. et al., JACS, 125, 9596; Niwa, Y.; Shimizu, M., JACS, 125, 3720; see also: Ricci, A. et al., JOC, 68, 3348; Crousse, B.; Bonnet-Delpon, D. et al., JOC, 68, 6444. H N'N"Bz

I1

+

CH2C12, -78~ SiCI3 ' ToI,~s,,Me t O

~

RI

H HN,,N,,B z 61-95% ee = 70-98 %

l.A.7.a.3.46 Hirashita, T. et al., JOC, 68, 1309. N,,R2 __~J

-I- B r ~ I

R1

R

HN,'R2 1. In, DMI _~ R l ~ R 3 2. R3-X, Pd(PPh3)4, LiC! R

22-77%

I.A.7.a.3-47 Trost, B.M.; Jonasson, C., AG(E), 42, 2063. OH P h ~

~e

MeO2C~N +

VO(OSiPh3)3 ~

LA r CH2CI2' 35.45~ -

O HN"CO2Me P h ~ A r Me 40-85% anti:syn = 1.5-9:1

30

ORGANIC SYNTHESIS--2004

l.A.7.a.3-48 Hoveyda, A.H.; Snapper, M.L. et al., OL, 5, 3273 and AG(E), 42, 4244; Knochel, P. et al., AG(E), 42, 5763; see also: Jiang, B.; Si, Y.-G., TL, 44, 6767; Vallee, Y. et al., TA, 14, 525; Wei, C.; Li, C.-J., JACS, 125, 9584; Li, C.-J. et al., OL, 5, 4473. Zn(CEC-TMS)2,Zr(Oipr)4

Me~

Zn(CH2TMS)2'Ph-Me' Ort/p'~ r MH~

RJ '

III1~ 2

~ ~ph TM

R ~ TMS 69-90% ee = 69-86%

I.A.7.a.3-49 Dransfield, P.J.; Shipman, M. et al., OBC, 1, 2723; Andrade, Z. et al., SL, 1189; Amat, M.; Bosch, J. et al. TA, 14, 1679; Dondoni, A.; Perrone, D., T, 59, 4261. OAe OAc Nuc, BF3.Et20 ~.,,,OAc OAc CH2C12,rt Nuc~A~N~k~I OAc I

I

Fmoc

Fmoc 63-80%

I.A.7.a.3-50 Shibasaki, M. et al., JACS, 125, 4712. O

O

N"PPh2 Ar'~[

+

OMe

0.,55

O

Et2Zn, THF, 3A MS ~

m

I

o ~

e Ar~

~

~ N ~ - - ~ 1 7 6

. A'~H [ ~ ~

96-99% anti:syn = 3-49:1 ee = 98-99%

I.A.7.a.3-51 Hatakeyama, S. et al., OL, 5, 3103; Shi, M.; Chen, L.-H., CC, 1310. N,,R ~ , ~ .CF3 DMF,-55~ ~ H~f" R O CF3

OH

CF3

Ar

- 1] ~~,~~E D'-t~'_ o

32-57% ee

= 93-100%

CARBON-CARBON BOND FORMING REACTIONS

31

I.A.7.a.3-52 Nakagawa, M. et al., JOC, 68, 3112. N,,R

R1 Yb(OTf)3,TMS.CI R2

THF/CH2CI2,rt

R"NH i11R1 111 A r ~ R 2 24-92%

l.A.7.a.4 Other 1,2-Additions I.A.7.a.4-1 Rick, R.T.; Jacobsen, E.N.,AG(E), 42, 4771; Ding, K. et al., AG(E), 42, 5478; Aikawa, K.; Mikami, K., AG(E), 42, 5458; Yang, D. et al., OL, 5, 3749; Yamada, T. et al., BCJ, 76, 49; Sasai, H. et al., OL, 5, 2647. OTMS DIPEA,4A MS, 40C OH OTMS R-CHO + ~ .1~ R ~ Me ~ 47-90% OTIPS 'tN~'~ ee = 87-93% "o-C%~

cl ~ "T tBu

l.A.7.a.4-2 Uneyama, K. et al., CC, 1752; see also: Namy, J.-L. et al. TL, 44, 5507. N"Ar CO, Pd2(dba)3.CHCI~K2CO3 Ar--~~___~--Ar

I

DMF/Ph-Me, 70~

Rf

Rf

0-82% I.A.7.a.4-3 Yamago, S.; Yoshida, J. et al., AG(E), 42, 117. R2

N"R2

(EtO)3Si-TePh

R,~R1 + R3--~

~

HN'

/TePh

R)

~__R3

R1 43-93%

I.A.7.a.4-4 Xu, B.; Shi, M., SL, 1639; Li, C.-Q.; Shi, M., OL, 5, 4273; Krische, M.J. et al., JACS, 125, 11488; Yu, C.-M. et al., OL, 5, 2813. Ph t

.

O~CO2Et CO2Et

Yb(OTf)3 ~ AcCI, rt

Phil OAc ~ICO2E CI CO2Et 85%

t

32

ORGANIC SYNTHESISm2004

I.A.7.a.4-5 Denmark, S.E.; Fan, Y., JACS, 125, 7825; Chen, J.; Cunico, R.F., TL, 44, 8025. OH R-NfC + R1-CHO + SiCl4

~

q

~

R"

R1

er = 2-99:1 ~,a,'J~

Me .J 2

I.A.7.a.4-6 Demir, A.S. et al., OL, 5, 2047. O Benzaldehyde lyase ._ l [ MgSO4,KH2PO4 buffer A r ~ O M e OH 70-94% ee = 91-98%

Ar-CHO + O H C ~ O M e

I.A.7.a.4-7 Procter, D.J. et al., OL, 5, 4811; Py, S.; Vallee, Y. et al., SL, 1527; Holemann, A.; Reissig, H.-U., OL, 5, 1463; Mukaiyama, T. et al., BCJ, 76, 413.

Mg

Me"~ O

Sml2 71% O ~MeOIt/THF

Sml2

,.e

~..

O tBuOH/THF

\OH O

64% I.A.7.a.4-8 Mead, K.T. et al., TL, 44, 6351, 6355. Ph TiCl4 Ph-OTIPS +

Ph n

CH2C12, -780C

H TIPSO" ~ "

82%

I.A.7.a.4-9 Najera, C.; Saa, J.M. et al., TA, 14, 197. CN aminomethyl BINOL R ~ o ~ C O 2 M e R-CHO + NC-CO2Me ~'95-98% ee = 1-10:1

CARBON-CARBON BOND FORMING REACTIONS

33

I.A.7.a.4-10 Kalbalka, G.W. et al., TL, 44, 1187. OH CI Ar-CHO +

R

PhBCI2 Ar ~ CH2CI2

R 36-96% anti = 64-98%

I.A.7.a.4-11 Wei, X.; Taylor, R.J.K., TL, 44, 7143. "~R 1

R-Li ~. ~ Et20, rt "-

Ph2

R1 R

Ph2 62-81%

I.A.7.a.4-12 Freistad, G.K. et al., AG(E), 42, 4982; Naito, T. et al., CC, 426. ~ ~ R-I,Cu(OTf)3,Et3B, 0 2 ~ ~ ~

~u

~.~ R~j

H

~o-~~o

R'~R 1 44-88% ee = 81-95%

l.A.7.a.4-13 Suzuki, K. et al., JACS, 125, 8432. O--N .-- R I ~ O R ~ ~~. ~

~O"N! RQ

R

DBU, tBuOH, 40~ OH Me

~S

~Et

~Br"

R2 / ~ , r ~

HO O 79-96%

I.A.7.b Conjugate Additions

I.A.7.b.1 Enolate-Type Carbanions I.A.7.b.l-1 Kaneda, K. et al., JACS, 125, 10486; Narasimhan, S. et al., TA, 14, 113; Akiyama, T. et al., CC, 1734; Shimizu, K. et al., TL, 44, 7421; Kozlowski, M.C. et al., JOC, 68, 1973. "A Novel Montmorillonite-Enwrapped Scandium as a Heterogeneous Catalyst for Michael Reaction"

34

ORGANIC SYNTHESISm2004

I.A.7.b.l-2 Shibasaki, M. et al., JACS, 125, 2582; Alexakis, A. et al., OL, 5, 2559; Maruoka, K. et al., JACS, 125, 9022; Keller, L.; Dumas, F.; d'Angelo, J., EJOC, 2488; Melchiorre, P.; Jorgensen, K.A., JOC, 68, 4151; Miura, K.; Hosomi, A. et al., SL, 2068; Sivaram, S. et al., TL, 44, 6047; Verkade, J.G. et al., T, 59, 561; Harada, T. et al., JOC, 68, 10046; Hagiwara, H. et al., OS, 80, 195; Willis, C.L. et al., TL, 44, 8153. O OMe O R1 O OMe

o. t2zn , s THF, -20~

linked BINOL

39-99% 1.56-13.3:1

I.A.7.b.l-3 Takemoto, Y. et al., JACS, 125, 12672; Taylor, M.S.; Jacobsen, E.N., JACS, 125, 11204; Ikariya, T. et al., JACS, 125, 7508; Jorgensen, K.A. et al., JOC, 68, 5067; Kanemasa, S. et al., TA, 14, 635; Grossman, R.B. et al., JOC, 68, 871; Labadie, G.R. et al., HCA, 86, 2741; Nakajima, M. et al., T, 59, 7307. R1

R1 ~g20 2C ~ v

Ph-Me, rt

R202C.~CO2R2 "1" R ~ N O 2

H

v3~N~s

H

~Me2

~

R~-,

CO2R2 "NO2

74-95%

ee = 81-93%

cv3

I.A.7.b.l-4 MacMillan, D.W.C. et al., JACS, 125, 1192; see also: Langer, P. et al., TL, 44, 7921. TMSO~~R

+ M~CHO

DNBA ~ o @ R o

-

P

"7"

"CliO

q~

n

73-87% 24-1:1-7 syn:anti = 90-98%

l.A.7.b.l-5 Beak, P. et al., OL, 5, 4155. I~ .,R 1

NC~R1 CN

BuLi, sparteine ~

+ ArtN"B~

Ph-Me, -78~

N

~

CN R Ar~N..Boc 86-96%

dr = 1.2-4:1 er = 6.7-19:1

CARBON-CARBON BOND FORMING REACTIONS

35

I.A.7.b.l-6 Kerr, M.S.; Rovis, T., SL, 1934. o EWG ~

/

OH EWG

KHMDS,Ph-Me '"

~l~

N ~S~ BE'4

58-90% ee = 75-95%

Ph

I.A.7.b.l-7 Satoh, T. et al., T, 59, 4327; Loughlin, W.A.; McCleary, M.A.,OBC, l, 1347. ( ~ ~ S TIo l D ~...R 1

+ LiCH2CO2R2

TI-IFI~

:-'~"STol

O

~.R

1

O 0-99%

I.A.7.b.l-8 Cao, S. et al., M, 134, 529. R102C~

O2~S~._CO2R+

~CO2

!.A.7.b.20rganometallic and Related Reeagents I.A.7.b.2-1 Hird, A.W.; Hoveyda, A.H., AG(E), 42, 1276. O 1 O R12Zn, (CuOTf)2Ph Meti: ~,OtBu ii

i

t~ppb2

N H

ii

NHBu

R•oO

61-95% ee = 76-98%

O ~Pr

I.A.7.b.2-2 Sosnovskikh, V.Y. et al., JOC, 68, 7747. O R1

R1

K2CO3'TEBA 02 N--~-'/~--"~ CO2R1 DMF ~"~CO2R 70-84%

N

+ TMS-CF3

THF, -10~

~"

O R1

R

50-86%

36

ORGANIC SYNTHESISm2004

I.A.7.b.2-3 Krauss, I.J.; Leighton, J.L., OL, 5, 3201; Feringa, B.L. et al., JACS, 125, 3700; Fraser, P.K.; Woodward, S., CEJ, 9, 776; Zhou, Q.-L. et al., JOC, 68, 1582; Hu, X. et al., JOC, 68, 4542, 8277; see also: Casamitjana, N. et al., JOC, 68, 9541; Zhu, N.; Hall, D.G., JOC, 68, 6066; Suarez, R.M.; Sestelo, J.P.; Sarandeses, L.A., CEJ, 9, 4179; Fleming, F.F. et al., JOC, 68, 4235; Chan, A.S.C. et al., TL, 44, 7217; Dambacher, J.; Bergdahl, M., CC, 144; Fleming, F.F. et al., T, 59, 5585; de Oliveira, A.R.M. et al., SL, 975; Lee, P.H. et al., S, 2189; Bergbreiter, D.E.; Li, C., OL, 5, 2445; Ma, S. et al., JOC, 68, 8996; Pearson, A.J.; Kim, J.B., OL, 5, 2457; Wendisch, V. et al., TA, 14, 3095; Tsantali, G.G.; Takakis, I.M., JOC, 68, 6455; Quntar, A.A.A.; Srebnik, M., CC, 58; Ohe, T.; Uemura, S., BCJ, 76, 1423. Cu(OTf)2, CH2C12,rt R12Zn +

IY~

)n

Ph2

)n

_,"

R F'

9u

R R 58-90% ee = 84-97 %

I.A.7.b.2-4 Dambacher, J.; Bergdahl, M., OL, 5, 3539; Williams, D.R. et al., CC, 2220; Arai, Y. et al., S, 1511; Murthy, K.S.K.; Rey, A.W. et al., TL, 44, 5355. .Bu

Me~

M

/~)

Li(BuCul) ,Ph 9 ~ Et20, -78~

\

O~~"

~

Li(BuCuI)

O~~

,Ph TMS-I ~ e THF,-780C

90% 15.7:1

\ O~~"

,Ph

I d r 83% 49:1

I.A.7.b.2-5 Knopfel, T.F.; Carreira, E.M., JACS, 125, 6054; Carreira, E.M. et al., OL, 5, 4557. Ar

+

Cu(OAc)2, Na-ascorbate H20[BuOH, rt A

55-98%

l.A.7.b.2-6 Ogle, C.A. et al., TA, 14, 3281; Iuliano, A.; Scafato, P., TA, 14, 611. "Chiral Lithiothiophenes as Non-Transferable Ligands in Organocuprate Conjugate Addition Reactions."

CARBON-CARBON BOND FORMING REACTIONS

37

I.A.7.b.2-7 Xie, M.; Huang, X., SL, 477. 1. PhMgBr, CuCN, THF/CH2CI2, -20~ R .SO2R1 R SO2R1 ~" h/~ - ( E, 2. E + p 56-82% I.A.7.b.2-8 Miyaura, N. et al., SL, 1040 and AG(E), 42, 2768; Andrus, M.B. et al.,AG(E), 42, 5871; Li, X.; Chan, A.S.C. et al., TL, 44, 6505; Boiteau, J.-G.; Minnaard, A.J.; Feringa, B.L., JOC, 68, 9481; Feringa, B.L. et al., OL, 5, 681; Adapa, S.R. et al., TL, 44, 5115; see also: Oi, S.; Inoue, Y. et al., OL, 5, 97. Rh(acac)(C2H4)2, KOH H20/dioxane, 50~ ~ ArR ~ ~ O R2 Ar-B(OH)2 4- R R ~ O R2 P--NR2

38-97% ee = 31-99%

I.A.7.b.2-9 Fleming, F.F. et al., JOC, 68, 7646. CN

M

CI

CN tBuMgCI

R 54-75%

I.A.7.b.2-10 Chemla, F. et al., AG(E), 42, 4043.

//

BnN/ _~CO2Me + Bu2Zn

\\

I2 ~

Bn~ C OI1 2_

Me

~Bu 48%

I.A.7.b.2-11 Krische, M.J. et al., JACS, 125, 1110; Procter, D.J. et al.,

JOC, 68, 3190. M

,o

e--Ci e O

[Rh(cod)Cl]2, BINAP "~F--~,,OH + Ph-B(OH)2 ~" p h ~ ~ ) n 69-88%

dr = 19:1 ee = 94-95%

38

ORGANIC SYNTHESISm2004

l.A.7.b.2-12 Py, S.; Vallee, Y. et al., AG(E), 42, 2265; Lassaletta, J.M. et al., JOC, 68, 2698. R1 R1 "O'N+~'~,~R2 SmI2 HO'N~R2 R[~ + ~ I C O 2 Et ~ R~,1, ~ H20/THF, -78~ CO2Et 36-96% dr = 1.3-19:1 I.A.7.b.2-13 Lee, P.H. et al., JOC, 68, 2510. o EtO2~y

R~~]

o

'~R1 In, TMS-CI~

EtO2C

THF, rt

~

R1

EtO2y~~

R2

r

t

~

80-97% I.A.7.b.3. Other Conjugate Additions I.A.7.b.3-1 Jorgensen, K.A. et al., AG(E), 42, 661, 4955. BnO2.C O R O BnO2C~ + R ~ R 1 neat, rt ~ B n O 2 ~ R 1 Bn~__.~ BnO2C 33-99% r~NMe ee = 59-99% COzH I.A.7.b.3-2 Furman, B.; Dziedzic, M., TL, 44, 6629.

o

TM

- C I:1U

THF, 30~ R

k

56-84% l.A.7.b.3-3 Iwasawa, N.; Lee, P.H. et al., JACS, 125, 9682. O OTBS + R-X

Me2S, TBS-OTf, In THF, -780C

~"

R 60-74%

CARBON-CARBON BOND FORMING REACTIONS

39

I.A.7.b.3-4 Venkateswarlu, Y. et al., TL, 44, 6257; Ji, S.-J.; Loh, T.-P. et al., SL, 2377; Bandini, M.; Umani-Ronchi, A. et al., S, 397 and TL, 44, 5843; Marcantoni, E. et al., JOC, 68, 4594. ~_~RIR~R3

O ~2/~R3 + R

H

Bi(OTf)3 MeCN.rt-

H 80-95%

I.A.7.b.3-5 Sammis, G.M.; Jacobsen, E.N., JACS, 125, 4442. O O BZ'H~

+ TMS-CN

iPrOH/Ph-Me,rt I. B z , ~

~R

tBu

~u

-u~OxClo-~ ~___

'~

___j

R 70-96% ee = 87-98 %

I.A.7.b.3-6 Sibi, M.P. et al.,AG(E), 42, 4521; Takasu, K.; Ihara, M. et al., OL, 5, 3017. O O O. O R1 ( ~ ~ O R + RI-x _______~__~Et3B/O2'Bu3SnH-78C ~ N'~~~'~ THF/CH~Cb,, ~ OR 70-92% ~lN~Ni ~~ ee = 50-92% tBu

O MeO2C--'~H~~~-Me TBSp.=

CO2Me TBS(~L ~ I ~ A Me,.,~.~~j.~H v TBSd ~/'~ -Me

tBu

"r

PMe3 H20/THF TBSO FI 84%

dr = 6:1

-Me

40

ORGANIC SYNTHESISm2004

I.A.7.b.3-8 Skrydstrup, T. et al., JACS, 125, 4030; Riber, D.; Skrydstrup, T., OL, 5, 229; Fuchibe, K.; Iwasawa, N., CEJ, 9, 905; see also: Pan, X. et al., JCR(S), 559; Yadav, J.S. et al., TL, 44, 8959. R1 R1 O N~S~~N ~ SmIz ~ RH + X THF,-78~ RH X O ~{2 O R~ 28-90% I.A.7.b.3-9 Fadini, L.; Togni, A., CC, 30.

X

NH +

lWO

R R1 ~-( [Ni(ppp)(THF)]CIO4 ~. EWG THF, rt

62-99% I.A.7.b.3-10 Kataoka, T. et al., AG(E), 42, 2889.

CHO

S N ~/

LO_~ / ph/

Ph

~Me

+

~

ff.....~ / O ? . ~ p h ~ _ ~ _ R _ ~ N ~ Me

BF3~t 2 0 CH2C12

R

Ph u 27-93% dr = 2.2-100:1

I.A.8. Other Carbon-Carbon Single Bond Forming Reactions

I.A.8-1 Murahashi, S. et al., JACS, 125, 15312.

Ar-NMe2

RuCI3onH20,NaCN,02 AcOH/MeOH

ME

Ar--~C N 81-88%

I.A.8-20uvry, G.; Zard, S.Z., SL, 1627; Gagosz, F.; Zard, S.E., OL, 5, 2655; Zard, S.Z. et al., CC, 204 and SL, 382; Nagano, H. et al., TL, 44, 7027; Naito, T. et al., OBC, 1,381; Yao, C.-F. et al., CEJ, 9, 2123; see also: Parsons, A.F. et al., OBC, 1, 373.

Ar

laurel peroxide

R,,

OEt +

R1 Ar

DCE,reflux ~

R1 33-64%

CARBON-CARBON BOND FORMING REACTIONS

41

I.A.8-3 Joshi, N.N. et al., JOC, 68, 5668; Li, Y. et al., JOM, 687, 12; Nishino, T.; Nishiyama, Y.; Sonoda, N. BCJ, 76, 536; Shimizu, M. et al., SL, 1535. OH Zn, TMS-CI,MeCN, -10~ 1 . Ar Ar-CHO '~ A

o,,k/.o-

o-

~.~"N--__~

65-94% dl:meso = 8-100:1 ee = 50-96%

I.A.8-4 Kim, S. et al., JACS, 125, 9574; Oltra, J.E. et al., OL, 5, 1935; Curran, D.P. et al., OL, 5, 419; Kozikowski, A.R. et al., JMC, 46, 921. l

~CO2Et

.CO2Et /~ ~CO2Et EtO2C~~-'-~ EtO2C d

(Me3Sn)2 Ph-H ~ (~P(OEt)2

EtO2C~co2Et

(other examples given)

79%

I.A.8-5 Renaud, P. et al., AG(E), 42, 4230; Landais, Y.; Renaud, P. et al., T, 59, 8543. OMe DMe O ~ I R

Bu3SnH,NaBH3CN ~ tBuOH' 80oc

H ~ R

R

Me R

44-81% dr = 5.25-15.7:1

I.A.8-6 Aggarwal, V.K. et al., OL, 5, 5075; Trauner, D. et al., OL, 5, 4931; Tius, M.A. et al., OL, 5, 4927; Fernandez-Mateos, SA. et al., JOC, 68, 3585. O O O O

R 1~

'l~r

'Pr

",R z

24-98% ee = 42-87%

42

ORGANIC SYNTHESISm2004

I.A.8-7 Cowden, C.J., OL, 5, 4497. Cl

R"

H

.. CO2H R1

+ ~N

N

Cl $208"2Ag+~

H

[~N

N

R"3~~ Cl

R1 Cl 27-88%

I.A.8-8 Davies, H.M.L. et al., JACS, 125, 6462; Sengupta, S. et al., A G(E), 42, 6405. BOC .CO2Me Boc CO2Me R~~) + N2~Ar Rh2(S'DOSP)4~ s n R L__~)n 58-94% ee = 77-94% de = 76-94% I.A.8-9 Lu, X. et al., AG(E), 42, 1035; Kraus, G.A. et al., TL, 44, 659. ~O n O -~ ~ PPh3 EtO2C + NPh ~ EtO2C NPh

X

O

H i~) 74-88%

I.A.8-10 Shanmugan, P.; Miyashita, M., OL, 5, 3265; Yadav, J.S. et al., TL, 44, 6501. OSiRa3 Raasi'OTf ~ R @ ~ R1 R" ''~?" "" R1 .[. AIR23 CH2C12'"50~ R2

90-95% anti from trans-epoxide syn from cis-epoxide I.A.8-11 Urabe, H.; Sato, F. et al., JACS, 125, 4036; Makino, T.; Itoh, K., TL, 44, 6335.

(

R iprMgCI, Ti(Oipr)4 ~ .78-,00C OCOR1

.R1 OH 62-76%

CARBON-CARBON BOND FORMING REACTIONS

43

I.A.8-12 Lee, H.-Y.; Kim, Y., JACS, 125, 10156.

~ R

2N " N~ph R1

-_R1R " 2 Ph-Me, ll0~

R

35-68%

"OH

I.B. Carbon-Carbon Double Bonds

(see also: I.E. 1) I.B.1. Wittig-Type Olefination Reactions

I.B.I.1 Ley, S.V. et al., TL, 44, 7779; Taylor, R.J.K. et al., CC, 2284. R A O H 1. TPAP, NMO, CH2C!2,4A M S R ~ R1 2. PhaP+CH2R1X', BaLi, THF (one pot)

13-94%

I.B.1-2 Moorhoff, C.M., M, 134, 429; Kulkarni, M.G. et al., TL, 44, 4913; Katsumura, S. et al., T, 59, 4945; Hoffmann, H.M.R. et al., S, 1844.

R1-CHO-I-

Ph3I~~~ O

R

LDA

~

O

R O O 29-70% Z:E = 1-5:1

I.B.1-3 Taylor, R.J.K. et al., TL, 44, 7735; Sano, S.; Takemoto, Y.; Nagao, Y., TL, 44, 8853. O CO2Me KHMDS ~ fCO2Me Bu3Sn/-~--NCHO + (CF3CH20)2P--"/ THF,-780C ~Ba3Sff "--" 82% 16-Cr-6 E:Z = 3.3:1 I.B.1-4 Reichwein, J.F.; Pagenkopf, B.L., JOC, 68, 1459; Augustyns, K. et al., TL, 44, 6231; see also: Cacatian, S.T.; Fuch, P.L., T, 59, 7177. O R 34 1. BaLi, THF,-78"C O~'OR4 O~~ I~,,,OR i~'OR3

1. saponify

R"

2.

1 R" 2 R

R2 61%

44

ORGANIC SYNTHESISm2004

I.B.1-5 Taylor, R.J.K. et al., TL, 44, 7209. O

O

t uo 18 r6 Ph-Me, 700C (EtO)2P~O

14-25%

I.B.1-6 Pihko, P.M.; Salo, T.M., TL, 44, 4361. R

%

NaI MeO2CII (OT~ + R-CHO THF,-780C~ Nail,

/~/ MeO2C 88-99% Z:E = 2.33-13.3:1

I.B.1-7 Reuter, D.C. et al., S, 2321. U~PPh2 1. Nail, DMF S" -I- R-CHO BocHNO 2. DMSO, A or TFA, CH2CI2

H2NO2S/~-~R 26-79%

I.B.1-8 Albrecht, B.K.; Williams, R.M., OL, 5, 197; Berthelette, C. et al., OL, 5, 4851; Lequeux, T.; Pazenok, S. et al., TL, 44, 8127; Kittaka, A. et al., JOC, 68, 7407.

o

c

O + I

~/N~ LHMDS,DMPU ,,, H DMF. 0oc Cbz L-.SO2Bt

O I

79% E:Z =5:1 I.B.1-9 Taylor, R.J.K. et al., OL, 5, 4441 and AG(E), 42, 1387; Pasetto, P.; Franck, R.W., JOC, 68, 8042. M I ~ I~

M ~eBon2 O2

KOH, CC14 tBuOH/H20' 80~

Me OBn 50%

E:Z = 1:8

CARBON-CARBON BOND FORMING REACTIONS

45

I.B.I-10 Nenajdenko, V.G. et al., OBC, 1, 1906. Br R1

Br

2. CBr4, CuCI 43-97%

I.B.I-ll Murai, T. et al., JOC, 68, 7979. Se Se . ~,~,~.CHO ~.~ BuLi ~ ~ ~ n , ArL N"On + NR2 THF,0~ A NR 2 TMS 44-99% I.B.I-12 Aggarwal, V.K. et al., JACS, 125, 6034. H 1. tBuOK, Ph-Me, 0~ R,,"~ N,,N~Ts 2. R1-CHO, CIFeTPP, PTC, P(OMe)3

R ~

R1

79-95% E:Z = 5.25-49:1 CIFeTPP = meso-tetraphenylporphryn iron chloride

I.B.2. E l i m i n a t i o n s

I.B.2.a. E l i m i n a t i o n s of A l c o h o l s and Derivatives

l.B.2.a-1 Sai, H. et al., S, 201; Bull, S.D. et al., CC, 2184; Bettadaiah, B.K.; Srinivas, P., SC, 33, 3615; Kraus, G.A.; Cui, W., SL, 95; Whitehead, R.C. et al., T, 59, 4827; Firouzabadi, H.; Iranpoor, N. et al., SC, 33, 3653; Maier, M.E. et al., S, 1324; Aramini, A.; Allegretti, M. et al., JOC, 68, 7911. HOk /CO2Me EDC,CuCl2 R~__/CO2Me H' "'~---~'"H R1 NHR

...... ~

Ph-Me,80~

threo

\

NHR 48-99% (E)

I.B.2.a-2 Nishiyama, K. et al., TL, 44, 4027; Kotera, M. et al., SC, 33, 3727. TBDMSO~B (TMS)aSiH,ph.H, . . . . 80~ _TBDMSO-~o~B PhH~O S

~ 1 NHPh S

49.82%

46

ORGANIC SYNTHESISm2004

l.B.2.a-3 Mangaleswaran, S.; Argade, N.P., S, 343. O ArN~ O

1. R-CHO, TPP,_THF, reflux _~ H O 2 C , ~ - R 2. HCI, AcOH, reflux HO2C" 82-88%

l.B.2.b. Eliminations of Halides

I.B.2.b-1 Ichikawa, J. et al., JOC, 68, 7800. F3C~ Nuc-M _~ F2C~Nuc SiMe2Ph THF,-78~

SiMe2Ph 51-99%

I.B.2.c. Other Eliminations

I.B.2.c-1 Mioskowski, C.; Falck, J.R. et al., JACS, 125, 3218; Kim, Y. et al., JOC, 68, 180; Ranu, B.C. et al., S, 1012. CrCI2 CO2R1 R.CHO + X3CCO2R1 -~" R ' ~ THF, rt X 91-99%

I.B.2.c-2 Concellon, J.M.; Bardales, E., JOC, 68, 9492. O O SmI2 Ar Ar NR2 "~ R1 MeOH NR 2 67-95% Z selectivity = 98% I.B.2.c-3 Zard, S.Z. et al., OL, 5, 2907. EtO~'~S R~R

1 lauroylperoxide NO2

DCE, reflux

R ~

R1

53-82%

CARBON-CARBON BOND FORMING REACTIONS

47

I.B.2.c-4 Malhotra, S.V., TA, 14, 645. BuLi, ipr2NH, chiral amines o THF 50-82%

ee = 39-95% I.B.2.c-5 Sinay, P. et al., EJOC, 2678. SePh OOe t, uOO.,i Oi r>4 B n O , . . y . ~ , OBn BnO

~

BOnn~.~~,, OBn BnO 60%

I.B.2.c-6 Zhang, Y. et al., TL, 44, 9349. OR~

OH

Sml2 ._ R~J%CCI2 CC13 THF,rt 70-96% v

I.B.3. Olefin M e t a t h e s i s

I.B.3-1 Grubbs, R.H. et al., JACS, 125, 10103, 11360. "Synthesis, Structure, and Activity of Enhanced Initiators for Olefin Metathesis." I.B.3-2 Blechert, S. et al., T, 59, 6545; Choi, T.-L.; Grubbs, R.H., AG(E), 42, 1743; Buchmeiser, M.R. et al., CC, 2742; Grela, K.; Kim, M., EJOC, 963; Lamaty, F. et al., OM, 22, 2426; Fogg, D.E. et al., OM, 22, 3634; Basset, J.-M. et al., CEJ, 9, 971; Taber, D.F.; Frankowski, K.J., JOC, 68, 6047. "Ruthenium Olefin Metathesis Catalysts with Modified Styrene Ethers: Influence of Steric and Electronic Effects." I.B.3-3 Cho, J.H.; Kim, B.M., OL, 5, 531. "An Efficient Method for Removal of Ruthenium Byproducts from Olefin Metathesis Reactions." I.B.3-4 Lavastre, O.; Kappe, C.O. et al., JOC, 68, 9136. "Microwave-Assisted Ring-Closing Metathesis Revisited. On the Question of the Nonthermal Microwave Effect."

48

ORGANIC SYNTHESISm2004

I.B.3-5 Neipp, C.E.; Martin, S.F., JOC, 68, 8867; Yang, Y.-K.; Tae, J., SL, 1043; Murphy, J.A. et al., OL, 5, 2785; Ibrahim, Y.A. et al., T, 59, 7273; de Fays, L.; Ghosez, L. et al., TL, 44, 7197; Beaulieu, P.; Ogilvie, W.W., TL, 44, 8883; Thanh, G.V.; Loupy, A., TL, 44, 9091; Florent, J.C. et al., TL, 44, 2579; Krafft, M.E. et al., TL, 44, 839; Lovely, C.J. et al., TL, 44, 1379; Gennari, C. et al., TL, 44, 7913 and T, 59, 8803; Manzoni, L.; Scolastico, C. et al., S, 2363; Nantermet, P.G.; Selnick, H.G., TL, 44, 2401; Vederas, J.C. et al., OL, 5, 47; Kaliappan, K.P.; Kumar, N., TL, 44, 379; Karama, U.; Hofle, G., EJOC, 1042; Chaikof, E.L. et al., TL, 44, 89; Landais, Y. et al., JOC, 68, 2779; Mol, J.C. et al., OM, 22, 5291; Werner, H. et al., OM, 22, 1558; Bohmer, V. et al., CEJ, 9, 3375; Dutton, C.J. et al., BMCL, 13, 321; Srikrishna, A. et al., TL, 44, 7817; Fischer, H. et al., TL, 44, 7121; Chao, W.; Weinreb, S.M., OL, 5, 2505; Miller, S.J. et al., JOC, 68, 2728; Iqbal, J. et al., JOC, 68, 5006; Postema, M.H.D. et al., JOC, 68, 4748; Chen, X.; Wiemer, D.F., JOC, 68, 6597; Danishefsky, S.J. et al., AG(E), 42, 1280; Evans, P.A. et al., AG(E), 42, 1734; Snieckus, V. et al., OL, 5, 3519; Zhu, L.; Mootoo, D.R., OL, 5, 3475; van Koten, G. et al., AG(E), 42, 228; Gurjar, M.K. et al., OBC, 1, 1366. O O N~R

PhCH=Ru(PCy3)CI2X~

~[~'n

N~R ~ } n

CH2C!2, rt

75-97% JACS, 125, 9582; Yang, Y.-K.; Tae, J., SL, 2017; Lievre, C. et al., EJOC, 2336.

I. B .3 - 6 Hansen, E.C.; Lee, D.,

MeO

O X\ , p , ~ ~ R

o.L x

CH2Ci2,reflux ~

Ze,~l-_ (~~Y _ ~ MeO

~

~ ~ MesN~INMes

n

PhCH"l~h"Cl I -CI PCy3

MeO \\ Me MeO

~'P

n

35-92%

I.B.3-7 Lee, H.-Y. et al., OL, 5, 3439; see also" White, B.H.; Snapper, M.L., JACS, 125, 14901. X \

+

~'R

CH2CI2 MesN.

NMes

HYCI PhC "I~CI PCy3

63-93%

CARBON-CARBON BOND FORMING REACTIONS

49

I.B.3-8 Sibi, M.P., OL, 5, 2883; Clark, J.S. et al., OL, 5, 89; Grigg, R. et al., TL, 44, 4899; Kim, D. et al., TL, 44, 7043; Martin, S.F. et al., OL, 5, 3523; Nemoto, H. et al., OL, 5, 2939; Nishida, A. et al., SL, 1207; Brown, R.C.D. et al., OL, 5, 3403; Fogg, D.E. et al., OM, 22, 1986. "~ O R1 R2 CH2Cl2,~reflux ~- C ~ ~

kJ

MesI~NMes P hCH::I~h"CI I "CI

PCy3

II-

19-88%

I.B.3-9 Lee, H.-Y.; Kim, B.G.; Snapper, M.L., OL, 5, 1855; Kulkarni, A.A.; Diver, S.T., OL, 5, 3463; Diver, S.T. et al., OL, 5, 3819. ~ R

MesN_ NMes

Phem

i -CI PCY3

II1 44-89% E:Z = 1.3-100:1

I.B.3-10 Morill, C.; Grubbs, R.H., JOC, 68, 6031; see also: Bisaro, F.; Gouverneur, V., TL, 44, 7133.

efB~ ~

+

M

I

RI

I

CH2C12,reflux M~sS,~NMes PhCIt:IRIk"cCII

R~B~~ 31-99% E:Z = 7-20:1

PCY3

I.B.3-11 Lazarova, T. et al., OL, 5, 443. X .a'

~

, ,Me

f'

F

Me~"~'~CHO CH2CI2,40~

'o"

M d'''~ O" ~ ' ~ ~'OR1

MesNN~,NMes p hCH: l{h"CI I "CI PCY3

,Me

''CHO f-'OR

O~'~,OR 1 42-78%

50

ORGANIC SYNTHESISn2004

I.B.3-12 Rivard, M.; Blechert, S., EJOC, 2225; Compain, P.; Martin, O.R. et al., OL, 5, 3269; Chang, S. et al., OL, 5, 3041; Pietrusiewicz, K.M.; Grela, K. et al., OL, 5, 3217. CuCl, CH2Ci2~400C R,,~~CN 1~~ + ~'~CN MesN_yNMes 27-74% PhCH:1~CI (10"52% W/outCu)

~y~

I.B.4. Other Carbon-Carbon Double Bond Formin~ Reactions

I.B.4-1 Zhang, X.P. et al., OL, 5, 2493 and JOC, 68, 3714, 5925 and OM, 5, 4905; Wang, J. et al., OL, 5, 2243; Woo, L.K. et al., OM, 22, 1468; Trauner, D. et al., OL, 5, 4113; Mete, A. et al., TL, 44, 6621; Taber, D.F.; Storck, P.H., JOC, 68, 7768. Fe(TPP)CI' PPh3 ~. R ~ C O 2 R 2 ~ R 10 + N2~'CO2R2 Ph-CO2H,Ph-Me, 80~ R1 42-93%

E:Z = 2.7-6.38:1 I.B.4-2 Takeda, T. et al., TL, 44, 7897. 0 + Cp2Ti[P(OEt)3]2 CI~OR 2

R1 49-85%

I.B.4-3 Kreher, U.P.; Strauss, C.R. et al., OL, 5, 3107; Trenkle, W.C. et al., OL, 5, 3333; Sevenard, D.V., TL, 44, 7119; Cardillo, G. et al., SC, 33, 1587; Ballini, R. et al., TL, 44, 9033; Kiyooka, S. et al., TL, 44, 927. O O ~CHO ~R2 DIMCARB,~ ~ R 2

I.B.4-4 Zhdankin, V.V. et al., JOC, 68, 1018. Ph-CHO +

TsO" Ph3I~ "l+Ph

Nue ~ Nuc Ph 40%

CARBON-CARBON BOND FORMING REACTIONS

51

I.B.4-5 Wicha, J. et al., OL, 5, 2789. Si3RI~O R2 N~N R + L s~N'N 02 Ph

R•R

LHMDS THF, -78~

2

78-84% E:Z = 1.63-2.12:1

I.B.4-6 Mukai, C. et al., TL, 44, 1583.

PhO

~

~ CO2R

tBuOK tBuOH, rt

CO2R

PhOtON,/

CO2R

72-98%

I.B.4-7 Ronsheim, M.D.; Zercher, C.K., JOC, 68, 4535. O O 1. Et2Zn, CH212,CH2CI2 O R,~J ~ 2.12 ~ L ~ .,R1 R1 3. aq Na2S203 R" " ~ y 4. DBU O (one pot) 59-86% I.B.4-8 Jung, M.E.; Wasserman, J.I., TL, 44, 7273. Me Me Ac WCI6 Me I /OAc CH2C12,450C~ C1 ~ ~ ~ 7 .... H

H

94%

I.B.4-9 Hon, Y.-S. et al., T, 59, 1509. rrlv O O 1~ CH2Br2,Et2NH Ar R ~ CH2C12or MeCN Ar

R

0-85%

I.B.4-10 Urabe, H.; Sato, F. et al., OL, 5, 67. R

TSXNBn /

TS~NBn

I!§ II 1

Ti(Oipr)4,iprMgCI ~Et20, -50~

R'~

(also with BZ in place of Ts)

R1 56-93%

52

ORGANICSYNTHESISm2004

I.B.4-11 Etzkorn, F.A. et al., JOC, 68, 2343. "Serine-cis-proline and Serine-trans-proline Isosteres: Stereoselective Synthesis of (Z)- and (E)-Alkene Mimics by StillWittig and Ireland-Claisen Rearrangements." I.B.4-12 Wong, K.-T.; Hung, Y.-Y., TL, 44, 8033. R ~ O + [~>---MgBr I'0~ R1 2. AcCI, 50~ R~

40-90%

I.B.4-13 Yoshida, K.; Hayashi, T., JACS, 125, 2872. PhO2S',~~ph

4- ArTi(Oipr)3

kr

[Rh(OH)(BINAP)]2~. THF, 40~

Ph 97-99%

I.B.4-14 Liu, R.-S. et al., JACS, 125, 9294. OH TpRu(PPha)(MeCN)2PF6,LiOTf v

Ph-Me, ll0~

52-91%

I.B.4-15 Luh, T.-Y. et al., OL, 5, 4489. IL

R1 + R2MgX

Ni(acac)2, va33 ~

~

R2 R

1

48-73% I.B.4-16 Komatsu, M. et al., JOC, 68, 6164. R3Me2Si~1

O

R" ~ ~ R 2 Ph-H, 180~

R1 R~OSiMe2R3 R2 44-93% Z:E = 3-24.5:1

I.B.4-17 Dhal, R. et al., S, 2269. Me Me"~OMe13(" +

N~ H O R._~-/_. k1k2

TMS-OTf,CSA, TEA CH2C12,55~

~

LN~

O R_.~~.. k1k2

73-90% ee = 99 %

CARBON-CARBON BOND FORMING REACTIONS

53

I.B.4-18 Murakami, M. et al., JACS, 125, 4720. R

R

CN~~ Ph

TMS +

CpRu(PPh3)2CI NaPF6, 150~ 66-76%

I.B.4-19 Fallis, A.G. et al., OL, 5, 2989. R

OH

R1

1. R1MgX, THF/Ph-Me, reflux

R

2. R2-X, Pd(PPh3)4, reflux

R2~-~_OH 10-73%

\

I.B.4-20 Dixneuf, P.H. Eisenstein, O. et al., JACS, 125, 11964. R

R

+ HO~C.R 1

dioxane, r t

.....

1

30-98%

I.B.4-21 Curini, M. Epifano, F. et al., SL, 552. Ph

R 1 + R-CHO

O

Yb(OTf)3 y

90~

Ph

R R1 50-84%

I.B.5. Vinylations

I.B.5-1 Ishii, Y. et al., JACS, 125, 1476; Kita, Y. et al., OL, 5, 3703; Roglans, A. et al., OL, 5, 1559; Xu, J.-H. et al., SC, 33, 773; Kondolff, I.; Doucet, H.; Santelli, M., TL, 44, 8487; Doucet, H.; Santelli, M. et al., SL, 841; Whiting, A. et al., TL, 44, 7645; de Meijere, A. et al., EJOC, 2375; Tobe, Y. et al., OL, 5, 341 l; Hou, X.-L.; Dai, L.-X. et al., OL, 5, 3651; Jacobs, P.A. et al.,AG(E), 42, 3512; Oh, C.H.; Lim, Y.M., TL, 44, 267; Iqbal, J. et al., TL, 44, 353; see also: Tanaka, T. et al., JOC, 68, 5550; Yao, C.-F. et al., JOC, 68, 4030. Ar-H +

~,,,,CO2R

Pd(OAc)2, 02, H7PMo8V4040 AcOH, 90~

Ar~CO2 62-75%

R

54

ORGANIC SYNTHESISn2004

I.B.5-2 Miura, M. et al., AG(E), 42, 4672; Inoue, A.; Shinokubo, H.; Oshima, K., JACS, 125, 1484. Ar-COCI + ~ R [RhCI(C2H4)2]2~ A r ~ R Ph-Me2, reflux 51-98%

og:

I.B.5-3 Grigg, R. et al., TL, 44, 7969. Pd(OAc)2,In, TFP Ar-I + ~ \ + R1.CHO R additives

Ar

R1 R

0-88% I.B.5-4 Zeni, G. et al., SL, 579, 1880; Hou, Z. et al., JACS, 125, 1184; Uemura, A. et al., OL, 5, 2997; Braga, A.L. et al., JOM, 682, 35; Cai, M. et al., JOM, 681, 14, 98 R1 R1 R + B u T e ~ Y R 2 PdCI2,CuI, TEA ./~~yR2

MeOH

R~

71-88%

LB.5-5 Peyrat, J.-F. et al., TL, 44, 6703; Betzer, J.-F. et al., TL, 44, 7553; Knochel, P. et al., OL, 5, 1059. R-M + CI~ R 1 PdCl2(dppf) _ R~R 1 THF, 68"C 60-96% I.B.5-6 Menzel, K.; Fu, G.C., JACS, 125, 3718; Fu, G.C. et al., AG(E), 42, 5079; Duchene, A. et al., TL, 44, 1647 and S, 448; Mazur, A.W. et al., OL, 5, 1163; Moloney, M.G. et al., OBC, 1, 3726; Li, H. et al., SC, 33, 3761; Guanti, G.; Riva, R., OBC, 1. 3967. I L ~ B r + Bu3Sn.~ [(~-allyl)PdCll2'Mep(tBu)2~ H H t ~ " HH R1 ~ R1 55-96% (for 13-hydrogencontainingalkyl bromides) I.B.5-7 Franzen, J.; Backvall, J.-E., JACS, 125, 6056. M ~ 2 ~ CO2Me _ ~ ~ _ RCO2Me CO2Me (~/ L Pd(O2CCF3)2,BQ " ( THF, reflux tI x~

73-94%

CARBON-CARBON BOND FORMING REACTIONS

55

I.B.5-8 Marson, C.M. et al., T, 59, 4377; Lando, V.R." Monteiro, A.L., OL, 5, 2891; Sato, F. et al., OL, 5, 523. O O

~

B(OH)2 + r ~ R 1

R" ~

B

)n

Pd(PPh3)4,aq Na2CO3 EtOH/Ph-Me, reflux

R 92-98%

I.B.5-9 Zhang, X." Larock, R.C., OL, 5, 2993, 1579; see also: Bhat, N.G. et al., TL, 44, 7175. R

+ R ~

R + Ar-B(OH)2 PdCI~KF ~ H20/DMF, 100~ R1

R1

56-93%

I.B.5-10 Luo, F.-T. et al., TL, 44, 7249. O

1. Me2S.BHCy2, THF 0*C~ rt

R

R~~NMe2 47-73%

2. BrCI-I2CONMe2,Pd(dba)2 PCy3, K3PO4~THF, 70"C

I.B.5-11 Buchwald, S.L. et al., OL, 5, 3667. O

O

MeHNCH2CH2NHMe

R,,'~ NH ~1

4-

~"X

K2CO3or Cs2CO 3 (62-95%)

I.B.6. Ailene Forming Reactions

I.B.6-1 Huang, X.; Xiong, Z.-C., TL, 44, 5913 and CC, 1714. O R

PPh2 4- R1S-Li + R2-CHO

R

THF, rt

~

R2

RIs/ 61-87%

56

ORGANIC SYNTHESIS--2004

I.B.6-2 Sato, F. et al., OL, 5, 2145; see also: Hsung, R.P. et al., OL, 5, 2663. _OMe _OMe N~ Ph -I- R ( Ti(Oipr)4,iprMgCI H Ph Ar~J 1_ X Et20,-35~ AP'" R1 -

R

45-74% dr = 13.3-49:1 I.B.6-3 van Vranken, D.L. et al., JOC, 68, 4955. Uoc

RS~ ~

dppe, FeCI2 R1 + BocN3 DCE, 0~

RS--~ = R1

31-73% I.B.6-4 Furstner. A.; Mendez, M., AG(E), 42, 5355. R

/ ~ ~

RIMgBr,Fe(acac)3 Et20 or Ph-Me,-5~

R1 'OH 54-98% syn:anti = 1.2-49:1

I.B.6-5 Leclerc, E.; Tius, M.A., OL, 5, 1171. MeO~O TMS H BuLi .~ Me 6 +Ph ~r__~O--" tBu Md~' LN--'X ~2 THF' "78-~"400C

O

74% tBu I.B.6-6 Evans, C.A.; Miller, S.J., JACS, 125, 12394. O O R~RI + ~CO2Et ~ ' ~ R ~

CO2Et

50-98%

CARBON-CARBON BOND FORMING REACTIONS

57

I.B.6-7 Sato, T. et al., CPB, 51,966. 1. tBuMgCi ~~)( ~_~CI 2. EtMgCi, THF, .78oc 6IS--Tol 3. PhSO2C(Li)RR1 THF, THF, -78~ ~ rt

0-65 %

I.C. Carbon-Carbon Triple Bonds I.C-I Leadbeater, N.E. et al., OL, 5, 3919.

R~~ff.._X +

R1 ~tW,NaOH~

R~~..._

R1

~

PEG/H20 10-99%

I.C-2 Gelman, D.; Buchwald, S.L., AG(E), 42, 5993; Leadbeater, N.E.; Tominack, B.J., TL, 44, 8653; Soheili, A. et al., OL, 5, 4191; Andrus, M.B. et al., OL, 5, 3317; Heuze, K. et al., CC, 2274; Doucet, H.; Santelli, M. et al., OBC, 1, 2235; see also: Mori, Y.; Seki, M., JOC, 68, 1571; Spivey, A.C. et al., JOC, 68, 1843; Nolan, J.M.; Gmins, D.L., JOC, 68, 3736; Walker, I.V.; Rokita, S.E., JOC, 68, 1563; Vargas-Berenguel, A. et al., OL, 5, 2389; Chanteau, S.H.; Tour, J.M., JOC, 68, 8750; Erdelyi, M.; Gogoll, A., JOC, 68, 6431; Utesch, N.F.; Diederich, F., OBC, 1,237. R~/~C!

+ ~R

1 PdCI2(MeCN)2,Cs2CO3 MeCN, 70-95~ ipr P.CY2

R~//-~___ 77"95%

i p r ~ ipr I.C-3 Zou, G. et al., TL, 44, 8709. R

--

-I- R1-B(OH)2

PdCl2(dppf),Ag20,K2CO3

R

- -

R 1

0-90%

I.C-4 Shirakawa, E.; Hiyama, T. et al., JOM, 670, 132. [PdClffl3-CaHs)]2 R ~ SnBu3 ~ R ~

~ p p N~Ph~.OA c

~ R 84-93%

R1

58

ORGANIC SYNTHESIS--2004

I.C-5 Plenio, H. et al., AG(E), 42, 1056 andOM, 22, 4098; Kollhofer, A.; Plenio, H., CEJ, 9, 1416; Hillerich, J.; Plenio, H., CC, 3024; Beletskaya, I.P. et al., TL, 44, 5011; Gallagher, W.P.; Maleczka, Jr., R.E., SL, 537 and JOC, 68, 6775; Eckhardt, M.; Fu, G.C., JACS, 125, 13642; Ravina, E. et al., T, 59, 2477; Fairlamb, I.J.S. et al., S, 2564; see also: Brimble, M.A. et al., OL, 5, 4425; Prasad, K. et al., OPRD, 7, 733; Kotschy, A. et al., JOC, 68, 3327; Novak, Z.; Kotschy, A., OL, 5, 3495; Ho, T.-I. et al., CC, 2146; Muller, T.J.J. et al., JOC, 68, 1503. 1~~/C.+

__

RI Na2PdCI, Cu,, (1-ad)2PBn.HBr R , ~ / : ~ DMSO, 100~

~

....R1

~ - ' -

62-96% I.C-6 Low, P.J. et al., JOM, 670, 178; Braga, A.L. et al., TL, 44, 1779; Zeni, G.; Braga, A.L. et al., TL, 44, 685; Forsyth, C.J. et al., BMCL, 13, 2127. R

CI,~CI R~

Pd(PPh3)4,CuI, ipr2NH

+

R

~

]

/

-

CI~

"CI

Rj ~

~'~R 30-60%

I.C-7 Negishi, E. et al., OL, 5, 1825. X X + XZn - -

TMS

PdCI2(DPEphOS)THF~ 65-99%

TMS

I.C-80tera, J. et al., T, 59, 5635. F F

tBuOK

Ph---~

~=/ SO2Ph

"~ Ph "-'O--P(OEt)2 TI-IF O

O

R 92%

I.C-9 Shinokubo, H.; Oshima, K. et al.,AG(E), 42, 5613. N,.OMe TsO,,~ N,,OMe LDA R ~ R1 40-74%

ct

CARBON-CARBON BOND FORMING REACTIONS

59

I.C-10 Dunetz, J.R.; Danheiser, R.L., OL, 5, 4011. 17,,,NH + I EWG

Bt ~

R1 KHMDS,CuI pyr, rt

/N --- R1 EWG 42-78%

I.C-II Miljanic, O.S.; Vollhardt, K.P.C.; Whitener, G., SL, 29; Gleiter, R. et al., S, 2535; Konig, B. et al., JOC, 68, 9379; Cummins, C.C. et al., OM, 22, 3351; Lipton, M.A. et al., JOC, 68, 8471; Young, D.G.J. et al., JOC, 68, 3494; Tykwinski, R.R. et al., CEJ, 9, 2542. R R

~

~

(Me3CO)W-CCMe3~ Ph-Me, 80~

~/~

27-54% R R

I.C-12 Poloukhtine, A.; Popik, V.V., JOC, 68, 7833. o hv ~.- R "'-"~ R1 R

R1

MeOH

50-90%

I.C-13 Kurita, J. et al., TL, 44, 8589. Me I

~b

+ R-COCI

PdCI2(PPh3)2 DCE

Ar R 63-86%

Ar I.C-14 Cheng, C.-H. et al., OL, 5, 881.

- - . - - - .

~ +N ~ [

Bu3Sn"

+ R I ~ CI

CN

Pd(PPh3)4 ~ R 2 Ph-Me, rt, 8h

i~3

74-80%

60

ORGANIC SYNTHESIS--2004

I.C-15 Abele, E. et al., TL, 44, 3911.

Ar-Br + CI~ B r

Pd(OAc)2,dppb,KOH 18-Cr-6,Ph-Me

Ar

Ar 29-61%

I.C-16 Shun, A.L.K.S.; Tykwinski, R.R. JOC, 68, 6810; Tykwinski, R.R. et al., JOC, 68, 1339. "Synthesis of Naturally Occurring Acetyenes v/a an Alkylidene Carbenoid Rearrangement."

I.D. Cyclopropanations

I.D.1. Carbene or Carbenoid Additions to a Multiple Bond

I.D.I-1 Katsuki, T. et al., TA, 14, 823; Sugimura, T. et al., TA, 14, 881; Perez-Prieto, J.; Stiriba, S.-E.; Moreno, E.; Lahuerta, P., TA, 14, 787; Nakada, M. et al., JACS, 125, 2860; Kwong, H.-L.; Che, C.-M. et al., TA, 14, 837.

N2

O Co(II)-salen~ R1 10-93% ee = 3 8 - 9 8 %

I.D.1-2 Aggarwal, V.K. et al., OL, 5, 4417.

Ph~OH

R2

Me'~~ I N ' R 1 Me R

Zn(CH2I)2

Phi_ IOH

R2

CH2C12,0~ ~ Met" I ~ ~ R 1 Me R 93-96% dr = 8-49:1

I.D.1-3 Wurz, R.P.; Charette, A.B., OL, 5, 2327; Muller, P.; Ghanem, A., SL, 1830; Muller, P. et al., TA, 14, 779. R

R~ + NO2~n IR1 O

PhI(OAC)2neat rt ~,

~NO2 "O~r'-R1 75-91%

CARBON-CARBON BOND FORMING REACTIONS

61

I.D.1-4 Zhang, X.P. et al., JOC, 68, 8179; Salvadori, P. et al., CC, 2466; Reiser, O. et al., TA, 14, 765; Muthusamy, S. et al., SL, 1599; see also:, Charette, A.B.; Janes, M.K.; Lebel, H., TA, 14, 867; Iwasa, S.; Nishiyama, H. et al., TA, 14, 855; France, M.B. et al., TL, 44, 9287; Che, C.-M. et al., TL, 44, 8733; Edulji, S.K; Nguyen, S.T., OM, 22, 3374; Moore, J.D.; Hanson, P.R., TA, 14, 873; Berkessel, A. et al., CEJ, 9, 4746; Mezzetti, A. et al., TA, 14, 845; Mizuno, K. et al., JOC, 68, 7700; Mayoral, J.A. et al., TA, 14, 773. R1 R

+ N2CHCO2Et

Co(Ph4Porphyran) -~ Ph.Me, 80~

~,A R CO2Et 89-99% cis:trans = 1:2.3-3.3

I.D.1-5 Miki, K.; Ohe, K.; Uemura, S., JOC, 68, 8505; Donaldson, W.A. et al., JOC, 68, 901. R

OCOR2

[RuCI2(CO)~2

R ~

OCOR2

DCE, 50"C 24-97% cis:trans = 1-1.63:15.7-1

I.D.1-6 Dolbier, Jr., W.R. et al., OS, 80, 172; Xu, W.; Chen, Q.-Y., OBC, 1, 1151; Yang, Z.-Y., JOC, 68, 4410. ~"~co2tBu

F F %

NaF + FSO2CF2CO2TMS Ph-Me, reflux

CO2tBu 55%

I.D.1-7 Shi, Y. et al., JACS, 125, 13632. R1 R~ R 2

CH2I~ ZnEt2, CH2C12 n

o

.COzMe

R1 R,~ ee

'~r

R2

43-84% = 72-91%

I.D.1-8 Takai, K. et al., JACS, 125, 12990; Paugam, J.P. et al., SL, 485. CHI3, CrCI2, TEEDA R/'~

THF, 25~

~

R ~ I 37-97% trans:cis = 10-49:1

62

ORGANIC SYNTHESISm2004

I.D.1-9 Motherwell, W.B. et al., CC, 2656. R1

EtQ~___

Zn(Hg), ZnCI2, TMS-CI Et20, reflux

R3 9-88% trans:cis = 1-19:1

I.D.2. Other Cyclopropanations

I.D.2-1 Gaunt, M.J. et al., AG(E), 42, 828; Florio, S. et al., JOC, 68, 1394; de Meijere, A. eta., S, 956; Ballini, R. et al., SL, 1704. O O ph~Cl + ~.~,,.EWG Na2CO3,MeCN, 800C ~ ~ . ~>% - Ph "' EWG 63-82% trans:cis = >19:1

I.D.2-2 Diez, D. et al., S, 53 and OL, 5, 3687. OR S02Ph LDA ._ THF, .78~

S02Ph

,,,....-

68-99%

I

I.D.2-3 Tang, T. et al., JACS, 125, 13030. i~ R21

~ BPh4" S3 + ~/~+Te~~"~R 1 ~....i.,. R 9e e

O LiTMP HMPA

R2,--

R1 R

1-99% 7.3-99:1 ee = 93-99% I.D.2-4 Szymoniak, J. et al., TL, 44, 4827; Bertus, P.; Szymoniak, J., SL, 265 and JOC, 68, 7133; Laroche, C.; Bertus, P.; Szymoniak, J., TL, 44, 2485; de Meijere, A. et al., OL, 5, 753. OR R1 R1R @ , ~ BuLi,ZrClzCI~ THF ~ R2~Me 50-85% trans:cis = 1-3.2:1

CARBON-CARBON BOND FORMING REACTIONS

63

I.D.2-5 Taylor, R.E. et al., OL, 5, 1377. OH Tf20 R

~

OTES

pyr-Me2, -78~

~

R~ I C H O 84-89% trans:cis = 2.1-6:1

I.D.2-60uhamou, N.; Six, Y., OBC, 1, 3007. Ti(Oipr)*THFC'C5H9MgCI"~ ~

~

93% I.D.2-7 Cha, J.K. et al., OS, 80, 111. ~,,~Ph

CITi(Oipr)3' c'CsH9MgCI + MeCO2Et THF ~

H(~,Me " ~",/Ph " 80%

I.D.2-8 Dixneuf, P.H. et al., AG(E), 42, 5474; Ohno, H.; Tanaka, T. et al., OL, 5, 4763. / m RuCICp*(cod) R~ r X R1 X\ / R + N2CHCO2Et dioxane, 100oc CO2Et 60-75% I.D.2-9 Miki, K.; Ohe, K.; Uemura, S., TL, 44, 2019. OAc R2 R~R"1l ' O~ A c

~"~R 2

[RuCI2(CO)3]2 ~ Ph-Me, 60~ 18h 1-91%

I.D.2-10 Concellon, J.M. et al., JOC, 68, 1132. OH O

R~R3 R Cl

1. SmI2, THF, -25~ NR2 2. Sm, CH2I~ -30~

O

R

NR2

80-96%

64

ORGANIC SYNTHESISm2004

I.D.2-11 Wessig, P.; Muhling, O., HCA, 86, 865. ~ ~NR hn, TsOH O\ , I-I"-.~~NR Ph" " ~ v OTs

NMI. CH2CI2~ phY"H~ 69-78%

I.E. T h e r m a l and P h o t o c h e m i c a l Reactions

I.E.1. Cycloadditions I.E.I-1 Brand, S. et al., OL, 5, 2343; Ito, H.; Iguchi, K. et al., TL, 44, 1259; Scheeren, H.W. et al., EJOC, 894; Uneyama, K. et al., CC, 2902. OR 1

Me t,~R1

TEA

OCl

+ II

Me I / v

Et ou R 45-75%

R

I.E.1-2 Mislin, G.L.; Miesch, M., JOC, 68, 433.

F E

71-82% I.E.1-3 Suzuki, K. et al., OL, 5, 3551; Durst, T. et al., CJC, 81,997. ~.OTf+EIO~ }n

OTBDMS

I

BuLi

THF, -78~ ~

I.E.1-4 Komatsu, M. et al., S, 1398. O TMS

'n~ OTBDMS I OEt I 43-75%

EK

Ph-Me, 180oc E

59-89%

/E

CARBON-CARBON BOND FORMING REACTIONS

65

I.E.1-5 Padwa, A. et al., JOC, 68, 6238.

~

SO2Ph

SO2Ph

TEA ~ , ~ ~ ~H RI Ph-H, 800C R2 82-92%

I.E.1-6 Bashiardes, G. et al., OL, 5, 4915. Me,,N~CO2Me CI~CHO

Mf"N~

~',,,~'~~

R1

Ph-Me,reflux C

l

~

R1

CO2Me or l.tW

R

70-98%

I.E.1-7 Ishikawa, T.; Saito, S. et al., OL, 5, 3875, 3879. MeH OD~~,~NO2 "~ TEA,DMAP ~ Me"si'L'XO~ I ~O MeCN,0~ -~ rt ~R-~-N R O~iMe 2 75-95% /~ dr = 5-99:1 "~

+CIMe2Si

I.E.1-8 Rigby, J.H.; Wang, Z., OL, 5, 263. O X Ph-H, reflux

O X 55-88%

I.E.1-9 Jao, E. et al., TL, 44, 5033.

r +

Ph-Me, reflux .|'

Ph"

.

PIf

80%

66

ORGANIC SYNTHESIS--2004

I.E.I-10 Evans, D.A.; Wu, J., JACS, 124, 10162; Sprott, K.T.; Corey, E.J., OL, 5, 2465. CO2Me O Me f ~ ;"" II II + `% THF/Ph-Me,-78~ .~ i"~':" "\"" R1 ~ R1 O

R

R31,. _

R2

"ffO'l'OTf

OTf

II

R3

o

I

O

H-

R

84-99%

~._

Rz

ee = 9 1 - 9 9 %

I.E.I-ll Shindo, M. et al., S, 1441; Kouklovsky, C.; Langlois, Y. et al., S, 1419; Yamada, T. et al., S, 1462; Tadano, K. et al., SL, 1865. O

9

OLi

i

II

R~N,~

..~--N~B +

n

_

R

n

;o 48-93%

13-H:cx-H= 5.25-19:1 I.E.I-12 Krische, M.J. et al., JACS, 125, 3682; see also: Takacs, J.M.; Lesnov, A.P., OL, 5, 4317. O R1 O

EtOAc, ll0~ 71-86% de = 19:1 I.E.I-13 Sibi, M.P. et al., JACS, 125, 9306. O+R~~ Zn(OTf)%CH2C12,rt

O

RI . ~ H ~ O , ~ . ~ M e Ph

O 82-94% endo:exo = 1.3-17 ee (endo) - 89-96%

CARBON-CARBON BOND FORMING REACTIONS

67

I.E.l-14 Pinho e Melo, T.M.v.D. et al., TL, 44, 6313.

CO2R 0*C~rt

O2R

N3

38-49% I.E.I-15 Ellman, J.A. et al., JOC, 68, 3; Armstrong, A. et al., TL, 44, 3915; Khrimian, A. et al., T, 59, 5475; Keay, B.A. et al., TA, 14, 749; Marchand-Brynaert, J. et al., JOC, 68, 9809; Hawkins, J.M. et al., OL, 5, 4293; see also: Paquette, L.A. et al., OL, 5, 2639; Klimova, E.I. et al., OBC, 1, 1210; Ruzziconi, R. et al., JOC, 68, 736; Timen, A.S.; Somfai, P., JOC, 68, 9958; Fringuelli, F.; Pizzo, F. et al., JOC, 68, 9263; Yang, Z.-Q.; Danishefsky, S.J., JACS, 125, 9602; Mohri, K. et al., CPB, 51, 502; Pedrosa, R.; Andres, C. et al., S, 1457; Dunach, E. et al., TL, 44, 8841; Thunberg, L.; Allenmark, S., TA, 14, 1317; Aly, A.A., OBC, 1, 756; He, Y.; Junk, C.P.; Lemal, D.M., OL, 5, 2135; Singh, V.; Kane, V.V. et al., OL, 5, 2199; Sarkar, T.K. et al., JOC, 68, 6919; Nakayama, J. et al., JACS, 125, 8255; Desimoni, G. et al., JOC, 68, 7862; Carreno, M.C. et al., CEJ, 9, 4118; Knappwost-Gieseke, C.; Winterfeldt, E. et al., CEJ, 9, 3849; Stoermer, M.J. et al., CEJ, 9, 2068; Barriault, L. et al., JOC, 68, 2317; Piettre, S.R. et al., JOC, 68, 7990; de la Pradilla, R.F. et al., CC, 2476; Livinghouse, T. et al., OBC, 1, 2038; Asao, N.; Yamamoto, Y. et al., JACS, 125, 10921. R<

+

RI[~

r~o

Cu(SbF6)2,cn2c12 ,.

R - - ~ ~ ~-~RI [ ~ 0

tBw, $I N ~ . ~ , , # , N.~s.'Bu II II

O

o

o

18-96% dr = 15.7-99:1 ee 41-93%

I.E.I-16 Boger, D.L. et al., JOC, 68, 3593; Afarinkia, K. et al., SL, 2341; Chittimalla, S.K.; Liao, C.-C., T, 59, 4039; see also: Hoornaert, G.J. et al., T, 59, 5481. O~ ~ OMe fK ~ OMe

~

-'~ .

.~N~

+ OMe "OMe

.

.

"OMe

.

.lb- O ~ OMe ~ "OMe 60-99%

68

ORGANIC SYNTHESISm2004

I.E.l-17 Hilt, G.; Smolko, K.I., AG(E), 42, 2795. MeMe Me M e ) ~Me MeMe'~.-O . ~Nc~,,B~~ ~ R ~R12 CoBr2(dppe),ZnI2

o.~.o

Ill §

1

2 R2

CH2C12

N" v 61-91%

R I.E.l-18 Barbas, III, C.F. et al., AG(E), 42, 4112.

Ar~q~O~~.~

O Me Arl-CHO i ~ O ~ O ~ ~'~Ar + +

chiral AA MeOH, rt Ar 1 80-99% ee = 84-99%

I.E.I-19 Barluenga, J. et al., AG(E), 42, 231. OR*

(CO)5Cr ~ R

1 +

1. BHT, Ph-Me, 80~ 2. aq HCI, THF, rt 85-90% ee = 79-99%

I.E.1-20 Young, I.S.; Kerr, M.A., AG(E), 42, 3023. RI~N+'O" ~ R2 Yb(OTf)3 R 1 ,N"O~R2 RI

CH2C12,rt R302C''~C O2R3

R302C CO2R3 50-96%

I.E.1-21 Asao, N.; Yamamoto, Y. et al., AG(E), 42, 3504; Dyker, G. et al., AG(E), 42, 4399. O R1 u'O'02

1+ "~" ~'~"~R

~ R3 TI-IF'800C

Re . R3 ~R4

26-90%

CARBON-CARBON BOND FORMING REACTIONS

69

I.E.1-22 Graetz, B.R.; Rychnovsky, S.D., OL, 5, 3357; Sulikowski, G.A. et al., OL, 5, 2777; Paintner, F.F. et al., TL, 44, 2549; Deslongchamps, P. et al., T, 59, 2781; Lepage, O.; Deslongchamps, P., JOC, 68, 2183; see also: Honda, T. et al., H, 59, 169; Coelho, P.J.; Blanco, L., T, 59, 2451; Cho, C.-G. et al., JOC, 68, 10191; Theodorakis, E.A. et al., OL, 5, 1491; Dineen, T.A.; Roush, W.R., OL, 5, 4725; Shing, T.K.M. et al., CEJ, 9, 5489; Jarosz, S. et al., TA, 14, 1709, 1715; Sherburn, M.S. et al., CC, 1610.

"r o

~/"

DDQ

,

Br ~9

O

Ph-Me, 90~ TMS

TMS

OR

~,~

78%

bR I.E.1-23 Nemoto, H. et al., EJOC, 2221; Crawley, S.L.; Funk, R.L., OL, 5, 3169; Martin, S.F. et al., JACS, 125, 12994. O

Me

Ph-CI2, reflux

MeO"

"~" 99%

I.E.1-24 Eckenberg, P.; Groth, U., SL, 2188; Kalogerakis, A.; Groth, U., OL, 5, 843; Slowinski, F.; Aubert, C.; Malacria, M., JOC, 68, 378; Yamamoto, Y. et al., JACS, 125, 12143; Deaton, K.R.; Gin, M.S., OL, 5, 2477; Mohamed, A.B.; Green, J.R., CC, 2936.

R

TMS/__~

(

A-
TMS R1 1. CpCO(CO)2 ..

~

R1

2. FeCIy6H20

i-O 53-81%

70

ORGANIC SYNTHESISm2004

I.E.1-25 Corey, E.J. et al., OL, 5, 3979. MeO2.Cl~I

CH2CI2,Tf:pI~o~ N ' 5'to0 -20~C

Me O 2 C ~ OTBS

~,. ~ ' ~ a,~..~,+.~

OTBS 93% de = 99% ee = 96%

Me

I.E.1-26 Padwa, A. et al., OL, 5, 3337; Hashmi, A.S.K. et al., CEJ, 9, 4339; Winkler, J.D. et al., OL, 5, 1805. B r @ .~../l~Bn Me

B r ~

Ph-Me,80~

O

Me'~NBn

82%

I.E.1-27 Shea, K.J. et al., JOC, 68, 5274 and OL, 5, 1613; Lovely, C.J. et al., OL, 5, 3623; Saa, C. et al., SL, 1524. O~ ,~OEt 4A.MS CHCI3,60~

HI,Bn

Bn~OMOM

OMOM 95% dr = 8:1

I.E.1-28 Denmark, S.E.; Gomez, L., JOC, 68, 8015. COX

NO2

~l

1. SnCI4,Ph-Me,-78~ ~XOC O ~ R 2. NaHCO3,Ph-Me,80~ 40-82%

I.E.1-29 Baldwin, J.E. et al., TL, 44, 4543. TBSO~,~~O~ OAc

+ ~'CN

Ph-Me, 120~ ,~ TBS ." NC

42%

CARBON-CARBON BOND FORMING REACTIONS

71

I.E.1-30 Trost, B.M. et al., OL, 44, 4149; Trivedi, G.K.; Deodhar, K.D. et al., SL, 2383. R3 R3 R4 R~'"~

R4 CpRu (MeCN)+3PF'6 R2~~ "~/~~~

R ~, .~..~\

Me2CO, rt

R 1,' 38-92% dr = 5-20:1

I.E.1-31 West, F.G. et al., OL, 5, 2747; Domingo, L.R. et al., OL, 5, 4117. O Me Me

DCE, 40~

""Me

t.j~ (other example are given) 67%

I.E.1-32 Hadjiarapoglou, L.P. et al., JOC, 68, 9155.

s..C~so2Ph 02

In

MeCN SO2Ph 27-46%

I.E.1-33 Herndon, J.W. et al., JACS, 125, 12720. .CO2Me

Ph

§ IllCO2Me

CO2Me CO2Me 64%

I.E.1-34 Werner, S.; Curran, D.P., OL, 5, 3293; Bourque, E,; Deslongchamps, P.; Dory, Y.L., JOC, 68, 2390. "Fluorous Dienophiles are Powerful Diene Scavengers in DielsAlder Reactions."

72

ORGANIC SYNTHESIS--2004

I.E.1-35 Constantino, M.G. et al., TL, 44, 2641. Ph-H, 90~

O 84%

I.E.1-36 A. Garcia-Mera, X. et al., TL, 44, 431; B. Braddock, D.C. et al., SL, 1121. Pr

02

HO

OH

O2~ N ~ p r O H

Chiral Auxiliary A

Catalyst

I.E.1-37 Wittkopp, A.; Schreiner, P.R., CEJ, 9, 407; see also: Barbas, III, C.F., et al., SL, 1910. "Metal-Free, Non-Covalent Catalysis of Diels-Alder Reactions by Neutral Hydrogen Bond Donors in Organic Solvents and in Water." I.E.1-38 Aversa, M.C.; Bonaccorsi, P. et al., S, 2241; Banwell, M.G. et al., AJC, 56, 861. "Sulfinyl Homo- and Hetero-Dienes from Sulfenic Acids: An Approach Towards Six-Membered Nitrogen Heterocycles in Enantiomerically Pure Form."

I.E.2. Other T h e r m a l Reactions

I.E.2-1 Pearson, A.J.; Wang, X.; JACS, 125, 13326. 2

R2 N"~R ffl

R3

Fe(CO)5,CO 3

Bu20,1420C

~ (CO)3Fe

1 a 20-92%

CARBON-CARBON BOND FORMING REACTIONS

73

I.E.2-2 Tokuda, M. et al., TL, 44, 3329. R

R1

~- n ~ n~lN

R1

Ph-Me2,A 85-99%

I.E.3. P h o t o c h e m i c a l Reactions

I.E.3-1 Kemmler, M.; Bach, T., AG(E), 42, 4824; Bach, T. et al., JOC, 68, 1994; Banerjee, S.; Ghosh, S., JOC, 68, 3981; Hiemstra, H. et al., OBC, 1, 4364; Krische, M.J. et al., JOC, 68, 15; Wrobel, M.N.; Margaretha, P., HCA, 86, 515; see also: Margaretha, P. et al., CJC, 81,417; Font, J. et al.,JOC, 68, 1283; Pedrosa, R.; Andres, C. et al., JOC, 68, 4923; Clayden, J. et al., JACS, 125, 9278.

CsO

hv ~ Et20

" O

70% I.E.3-2 Singh, R.; Ishar, M.P.S., TL, 44, 1943.

O

r

.

Me

85-90% Ar I.E.3-3 Booker-Milburn, K.I. et al., AG(E), 42, 1642. :o

rt~

~

R

hv MeCN

E t ~

O

R R

R

11-65%

74

ORGANIC SYNTHESISm2004

I.E.3-4 Jain, R.P.; Vederas, J.C., OL, 5, 4669. R1HN O

R1HN

O

52-58%

I.E.3-5 Uang, B.-J. et al., S, 497. H

H

o R

H

hv, I 2

R

R1 THF/MeCN R ~ N / ~ - " ~ ~ ~ - , ~ R H H

H

1

84-90% I.E.3-6 Steinmetz, M.G. et al., OL, 5, 71. o I~O~NEt2 hv O

O

R-CO2H 70-90%

H20

I.E.3-7 Kobayashi, K. et al., TL, 44, 751.

~~-S,9o~ C~~ 4~% I

h~

!

MeCN, 95% I.E.3-8 Aube, J. et al., OL, 5, 4999. OTIPS O-

hv

MeCN/Ph-Me

H

.~

,ooPs 0 68%

cx-H:~H = 1313:1

CARBON-CARBON BOND FORMING REACTIONS

75

I.E.3-9 Bach, T. et al., AG(E), 42, 3693. OH CHO

fCO2Me

Me02C

by, Ph_Me,.60C.~. ~Nn

o

~

CO2Me CO2Me

"Sd o 78% ee = 96%

I.E.3-10 Weissleder, R. et al., AG(E), 42, 1378. "Antibody-Catalyzed Enantioselective Norrish Type II Cyclization." I.E.3-11 McClure, C.K. et al., OL, 5, 3811. "Oxa-di-n-Methane Photochemical Rearrangement of Quinuclidinones. Synthesis of Pyrrolizidinones." !.F. Aromatic Substitutions Forming a New Carbon-Carbon Bond I.F.I. Friedel-Crafts Type Aromatic Substitution Reactions I.F.I-I Fillion, E.; Fishlock, D., OL, 5, 4653; Fillion, E.; Beingessner, R.L., JOC, 68, 9485; Brun, P. et al., S, 598; see also: Taylor, S.K. et al., TA, 14, 743; Balme, G. et al., OL, 5, 2055; Levacher, V. et al., T, 59, 8049; Ma, S.; Zhang, J., T, 59, 6273. O Sc(OTf)3 " ~ R MeNO2, reflux'~ X-"~ 1

13-83% I.F.1-2 Sefkow, M.; Buch, J., OL, 5, 193. R1 O

R1 Ar-H ~ R ~ R 2 A r 110.125~ -

82 H

0-88%

76

ORGANIC SYNTHESIS--2004

I.F.1-3 Williams, C.M.; Mander, L.N., OL, 5, 3499; Hu, H.; Zhai, H., SL, 2129; Snieckus, V. et al., JOC, 68, 5992. OMe

~

SO3Ag Me

~

OMe

~

"OAe

1

A~ ~

OH

OH

NO2 A~'

53%

I.F.1-4 Katritzky, A.R. et al., JOC, 68, 5720; Aygun, A.; Pindur, U., JHC, 40, 41 l; Bensari, A.; Zaveri, N.T., S, 267; Shimada, S. et al., TL, 44, 7715; LeRoux, C. et al., TL, 44, 2037; Zhang, G. et al., SL, 1447; Karam, O.; Zunino, F. et al., TL, 44, 1511. ,I., -~.

TiCl4 + R1-COBt R

,~. ~

]F-~,~COR ..

CH2CI2, reflux

R 15-94%

I.F.1-5 Petrini, M. et al., TA, 14, 1171; Pal, M.; Yeleswarapu, K.R. et al., JOC, 68, 6806. Ra

-

62-98% dr = 2.33-19:1

,~R4

I.F.1-6 Periasamy, M. et al., TL, 44, 8939; Torisawa, Y. et al., BMCL, 13, 65. CH2C12, 0-25~

O2R2 65-90%

I.F.I-7 Prakash, G.K.S.; Olah, G.A. et al., SL, 527; Tsuboi, S. et al., T, 59, 1781. J~O CF31-,CO2Et

.CF3SO3H or Ga(OTf) 3~ + Ar-H

HO Ar CF 3

CO2Et

40-99%

CARBON-CARBON BOND FORMING REACTIONS

77

I.F.1-8 Evans, D.A. et al., JACS, 125, 10780; Jorgensen, K.A., S, 1117.

R1

R1 R4

R+4~//~ O

CH2C12"78~~-~R ~ C O 2 (OMe)2 ~ ' / ~ I . . ~

d f

o

"-i~

~...N Sc N MeO~ I ~OMe ~..~ OMe ~r

Me

R3

51-88% ee = 80-99%

I.F.1-9 Hidai, M.; Uemura, S. et al., AG(E), 42, 1495; Ishii, K. et al., JOC, 68, 9340; see also: Huang, J.-W.; Shi, M., TL, 44, 9343; Koo, S. et al., JOC, 68, 7925. R1 R ~ + ~ _ _ ~ R 2 [Cp*RuCI(luSMe)2Cp*Ru(H20)]OTf~_ ~ "R1 OH

DCE, 60~

2 20-91% I.F.I-10 Jurczak, J. et al., TA, 14, 3643; Smith, K. et al., OBC, 1, 1552, 1560, 2321; Yamaguchi, M. et al., JOC, 68, 6752. -

""

bH 4-76% e e = __.78 %

I.F.I-ll Saidi, M.R.; Azizi, N., TA, 14, 389; Chen, Y.-J.; Wang, D. et al., 7', 59, 7609. Ph~Me Ar

~

OH + Ar-CHO +

Ph Me LiCIO4 "~__ NH2

.NH

~ O H

/

55-78% dr = 3-99:1

78

ORGANIC SYNTHESIS--2004

I.F.2. Coupling Reactions to Form an Aromatic Carbon-Aromatic Carbon Bond

I.F.2-1 Schultz, P.G.; Ding, S. et al., OL, 5, 3587; Bryce, M.R. et al., .S, 1035; Koutentis, P.A. et al., OBC, 1, 2900; Pie, N. et al., T, 59, 6375; Schmitt, M. et al., SL, 1482; Yang, W. et al., OL, 5, 3131; Meier, P. et al., S, 551; Ban, H. et al., TL, 44, 6021; Tagata, T.; Nishida, M., JOC, 68, 9412; Shaughnessy, K.H. et al., JOC, 68, 6767; Sutherland, A.; Gallagher, T., JOC, 68, 3352; Wagenknecht, H.-A. et al., S, 2335; Hollis, T.K. et al., OL, 5, 4847.

C!

Br 1"R'NH~ AcOH/di~ H

I~NH

R1

gW' 1501C~ ~ ' ~ ~

N

2. R1-B(OH)2,Pd(dppf)CI2-CH2CI2 K3PO4,dioxane,~tW,180~ (one pot)

H 56-98%

I.F.2-2 Buchwald, S.L. et al., JACS, 125, 11818; Kamino, T.; Kobayashi, S. et al., TL, 44, 7349.

Ar-OTs + Arl-B(OH)2

Pd(OAc)2,K3PO4, iBuOH,80~ -"-- Ar.Ar1 q~. 80-94 %

IPr

PCy 2

I.F.2-3 Kakiuchi, F. et al., JACS, 125, 1698.

O ~'J~tBu R" "o"

O ~ Ph--~t/ O O ~ B RuH2(CO)(PuPh3)3 + Ph-Me, A

R" ",o" "Ph 78-95%

I.F.2-4 Liebeskind, L.S.; Neumann, W.L. et al., OL, 5, 4349.

Br

Br

~~.N~ ~.SMe 1.3-BrPh-B(OH)2,Pd(PPh3)4 CuTC, THF, 53~ 2. 4-AcPh-B(OH)2,Pd(PPh3)4 Na2CO3,H20/dioxane,80C ~ O CO2tBu

[~ O Me

59%

co2tBu

CARBON-CARBON BOND FORMING REACTIONS

79

I.F.2-5 Zhang, M. et al., JOC, 68, 3729; Yoshida, H. et al., TL, 44, 1541; Zhang, Z. et al., TL, 44, 7095; Nolan, S.P. et al., JACS, 125, 16194; Queiroz, M.-J.R.P. et al., TL, 44, 4327; Gong, L.; Mi, A.-Q. et al., S, 337; Mino, T. et al., SL, 882; Kabalka, G.W. et al., S, 217; Jensen, J.F.; Johannsen, M., OL, 5, 3025; Broutin, P.-E.; Colobert, F., OL, 5, 3281; Baudoin, O. et al., SL, 2009 and JOC, 68, 4897; de Meijere, A. et al., JOC, 68, 883; Demir, A.S. et al., JOC, 68, 578, 10130; Parlow, J.J. et al., JOC, 68, 9678; Roca, F.X.; Richards, C.J., CC, 3002; Richards, C.J. et al., JOC, 68, 2592; Stockland, Jr., R.A. et al., OM, 22, 523; Hierso, J.C.; Doucet, H. et al., OM, 22, 4490; Tao, B.; Boykin, D.W., TL, 44, 7993; Boykin, D.W. et al., TL, 44, 7993; Duchene, A. et al., TL, 44, 9255; Datta, A.; Plenio, H., CC, 1504; Kim, Y.M.; Yu, S., JACS, 125, 1696; Yoburn, J.C.; van Vranken, D.L., OL, 5, 2003; Moroder, L. et al., OL, 5, 3435; Dupont, J.; Monteiro, A.L. et al., S, 2894; Bedford, R.B.; Butts, C.P. et al., CC, 466; Bedford, R.B. et al., OM, 22, 987, 1364 and CEJ, 9, 3216; Zhang, H. et al., OBC, 1, 1643; O'Shea, P. et al., JOC, 68, 2633; Tsubaki, K.; Fuji, K. et al., TA, 14, 1393; Uemura, M. et al., OM, 22, 1038; Hu, X. et al., TA, 14, 1267; Narayanan, R.; E1-Sayed, M.A., JACS, 125, 8340; Ikegami, S. et al., JOC, 68, 7733; Muller, T.J.J. et al., JOC, 68, 7509; Johannsen, M. et al., JOC, 68, 1258; Gagne, M.R. et al., CC, 3040.

Ar-X + - ~ ~ B _ B ' ~

1. Pd(OAc)2,KOAc,DMF,800C~ Ar.Ar1 2. ArlX, Pd(PPh3)4,CS2CO3,80"C 10-98%

-To" ,oS

I.F.2-6 Paintner, F.F. et al., SL, 522; Wolf, C.; Lerebours, R., JOC, 68, 7551. BnO

~ e

Bn

S

LiCI,NMP,90~

+

nnu3

Bn

I- II Vd

Vc~ || -| Bn NHBoc

73%

I.F.2-7 Leadbeater, N.E.; Marco, M.,AG(E), 42, 1407 and JOC, 68, 5660.

Ph--B(OH)2 +

X ~

TBAB,Na2CO3,~tW __~ ~ Ph H20 R

R

3-99%

80

ORGANIC SYNTHESISm2004

I.F.2-8 Blakey, S.B.; MacMillan, D.W.C., JACS, 125, 6046. N+Me~"OTf ~ Ni(cod)2,CsF, dioxane, 80~ + B/

(HO)2B/

Mes..N~ooN..Mes

R

B/

79-98%

I.F.2-9 Ley, S.V. et al., CC, 2652. "Palladium-Containing Perovskites: Recoverable and Reusable

Catalysts for Suzuki Couplings." I.F.2-10 Sezen, B.; Sames, D., JACS, 125, 5274, 10580 and OL, 5, 3607; Mori, A. et al., JACS, 125, 1700; Miura, M. et al., T, 59, 5685; Li, W. et al., OL, 5, 4835. Ph ]~--N~ H

Ph'I, Pd(OAc)2 PPh3, MgO

CN~ H

Ph'l, Pd(OAc)2 PPh3, MgO, CuI ~

]~---N~

Ph

H

72%

83%

I.F.2-11 Waldvogel, S.R. et al., S, 91; Kozlowski, M.C. et al., JOC, 68, 5500; Palmisano, G.; Sisti, M. et al., TA, 14, 1451; Chu, C.-Y.; Uang, B.J., TA, 14, 53; Schmittel, M.; Haeuseler, A., ZN(B), 58b, 211; Tanaka, H. et al., JOC, 68, 3938; Pezzella, A. et al., TA, 14, 1133; Gao, J. et al., AG(E), 42, 6008. MoCls CH2C12

RO

RO--~'

\Me

-

x

~

OR

~Me \OR 1 62-99%

I.F.2-12 Roy, A.H.; Hartwig, J.F., JACS, 125, 8704; Park, K. et al., JOC, 68, 3017; see also:, Mongin, F. et al., TL, 44, 3877; Knochel, P. et al., SL, 1892; Vidal, J. et al., JOC, 68, 9835; Lipshutz, B.H.; Tesche, B. et al., JOC, 68, 1177, 1190. Pd(dba)2, Ph-Me, 25-80~ Ar-OTs + ArlMgX ~- Ar-Ar1 PPI~ p(tBu) 2 Me

40-86 %

CARBON-CARBON BOND FORMING REACTIONS

81

I.F.2-13 Stanetty, P. et al., SL, 1862; Reeder, M.R. et al., OPRD, 7, 696; Gosmini, C. et al., JACS, 125, 3867; Fang, Y.-Q.; Hanan, G.S., SL, 852; Adamczyk, M. et al., T, 59, 8129. ~~---I + C ~ - ~ ~ N 1"BuLi' znI2' THF 2. Pd(PPh3)4, A or ~tW'~" N F

C!

F

~

N

90%

C!

I.F.2-14 Molander, G.A.; Biolatto, B., JOC, 68, 4302; Molander, G.A. et al., JOC, 68, 5534; Ito, T. et al., SL, 1435. Pd(OAc)2, or PdCl2(dppf).CH2Cl2, K2CO3 Ar-BF3K + Arl-X ~ Ar-Ar1 MeOH or EtOH, reflux 50-99% I.F.2-15 Wolf, C. et al., S, 2069; Denmark, S.E.; Ober, M.H., OL, 5, 1357; McElroy, W.T.; Deshong, P., OL, 5, 4779; Riggleman, S.; Deshong, P., JOC, 68, 8106. Pd-phosphinic acid Ar-Si(OMe)3 + Arl-X ~ Ar.Ar 1 MeCN, 80~ 58-92% I.F.2-16 Li, J.-H. et al., JOC, 68, 9867; Mukhopadhyay, S.; Sasson, Y. et al., OPRD, 7, 641. Zn, Pd/C Ar-X ~ Ar-Ar CO2 in H20 56-99%

I.F.2.17 Bedford, R.B. et al., AG(E), 42, 112; Bedford, R.B.; Limmert, M.E., JOC, 68, 8669; Oi, S.; Inoue, Y. et al., TL, 44, 8665. - ~ RhCI(PPh3)3'P/Pr2(OAr) - ~ Ar-X + HO ~ HO R Cs2CO3,Ph-Me A/ R 15-99%

I.F.2-18 Zhu, G. et al., BMCL, 13, 1231. ~ X

O~---NH ~ O

NH DDQ, Ts-OH

~Ph-H, Ph-Me or dioxane, reflux

J 68-88%

82

ORGANIC SYNTHESISm2004

I.F.2-19 Shimada, S.; Tanaka, M. et al., AG(E), 42, 1845. "5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly Reactive and Recoverable Organobismuth Reagents for CrossCoupling Reactions with Aryl Bromides."

I.F.3. Other Aromatic Substitutions and Preparations

I.F.3-1 Yao, Q. et al., JOC, 68, 7528; Chung, Y.K. et al., OM, 22, 415; Jung, K.W. et al., OL, 5, 2231; Catellani, M. et al., S, 2671; Cai, M. et al., JOM, 682, 20; Gushchin, A.V. et al., JOM, 667, 176; Cacchi, S. et al., SL, 1133; Venturello, P. et al., OL, 5, 3815; Gibson, S.E. et al., TA, 14, 1455; Larhed, M.; Curran, D.P. et al., JOC, 68, 6639; Itami, K.; Yamazaki, D.; Yoshida, J., OL, 5, 2161; Sjoberg, S. et al., JOC, 68, 3568; Yang, Y.-C.; Luh, T.-Y., JOC, 68, 9870; Carretero, J.C. et al., CEJ, 9, 1511; Diez-Barra, E.; Tejeda, J. et al., OM, 22, 4610; Hou, X.-L.; Dai, L.-X. et al., CEJ, 9, 3073; Zou, G. et al., CC, 2438; Molnar, A. et al., CC, 2626. Pd(OAc)2, K3PO4 A r ~ R Ar-Br + ~"~R DMA, 140~ 9-98% (no phosphine) I.F.3-2 Arvela, R.K.; Leadbeater, N.E., JOC, 68, 9122 and OBC, 1, 1119; Beller, M. et al., JOM, 684, 50 and CEJ, 9, 1828. R _ ~ x Ni(CN)2or NiBr2/NaCN~ R _ ~ CN NMP, lxW 19-99%

I.F.3-3 Blum, J. et al., S, 302 and TL, 44, 8593; see also: Lee, P.H. et al., OL, 5, 4963; Mineham, T. et al., OL, 5, 2405. ~--X + R2MLig [Fe(CO)4(~t-PPh2)Pd(~-Cl)]2 ~ _ _ R pR13, 78-120~ 21-98% I.F.3-4 Gallardo, I. et al., JOC, 68, 7334; Hoz, S., JOC, 68, 4388; Harrowven, D.C. et al., CC, 2658. x X 02

~ .,NO2 Me4N+.BBu4 02 MeCN, rt NO2

NO2 ~

"Bu

NO2 45-85%

CARBON-CARBON BOND FORMING REACTIONS

83

I.F.3-5 Miyaura, N. et al., JOC, 68, 6000. R 1 R2 R1 R2 [Rh(BINAP)(nbd)]BF4, TEA '~ Ar /~-, / ~-~ + Ar-B(OH)2 R ~---R3 H20/dioxane, 25~ S O~--R3 ,

B

6'

56-99% ee = 83-99% I.F.3-6 Lautens, M.; Yoshida, M., JOC, 68, 762; Queiroz, M.-J.R.P. et al., TL, 44, 6007. + Ar-B(OH)2

[Rh(cod)Cl]2, SDS, Na2CO3, H20 SO3K

R

"N"--,,p-sw

~

A

15-86%

"2

I.F.3-7 Lee, J.-Y.; Fu, G.C., JACS, 125, 5616; Denmark, S.E.; Amishiro, N., JOC, 68, 6997; Denmark, S.E.; Tymonko, S.A., JOC, 68, 9151; Hanamoto, T.; Kobayashi, T., JOC, 68, 6354. PdBr2, RMe(tBu)2,Bu4NF R-X + ArSi(OMe)3 .~- R-Ar THF, rt

36-84%

I.F.3-8 Gosmini, C. et al., OL, 5, 1043 and JOC, 68, 1142; Takagi, K. et al., JOC, 68, 2195; Jackson, R.F.W. et al., OBC, 1, 4254; Huo, S., OL, 5, 423.

R__~

Br

~,~,.,OAc +

CoBr2.Zn

R

~

MeCN, rt ~ 31-75%

I.F.3-9 Cai, M. et al., JCR(S), 465; Cheng, C.-H. et al., T, 59, 3635; Wolf, C.; Lerebours, R., JOC, 68, 7077. Bu3Sn R1 Pd(PPh3)4.CuI A~ R1 Ar-I + \m/ .~. / DMF, rt

R

R

65-74% I.F.3-10 Huang, J. et al., SL, 1716 and CC, 1444. Ar-Br+ ( C N NaH, PdCI~PR3 ,~ A r y C N WG

pyr, 850C

WG

67-88%

84

ORGANIC SYNTHESISm2004

I.F.3-11 Naskar, D. et al., TL, 44, 5819; Mahadevan, A.; McKew, J.C. et al., TL, 44, 4589.

R3

(~'CO2H4" R2-B(OH)2 dioxane,reflu~R2N ~ ~ + ~R2

R2

OR1

(RCO2H OR1 12-54%

I.F.3-12 Knochel, P. et al., S, 233 and CC, 396; Dobler, M.R., TL, 44, 7115; Li, L.; Martins, A., TL, 44, 5987; Sato, N.; Yue, Q., T, 59, 5831; Mongin, F. et al., OBC, 1, 3064; Marino, J.P.; Nguyen, H.N., TL, 44, 7395; Schlosser, M. et al., EJOC, 453; Fort, Y.; Rodriquez, A.L., JOC, 68, 4918; Gohier, F.; Mortier, J., JOC, 68, 2030; Enders, D. et al., SL, 1198; Mongin, F. et al., T, 59, 8629.

Me F

Me

~

1. iprMgCI,THF,.30~C~.- F OTf 2. E+ 3. Nuc',Pd cat.

I

~ E

Nuc

53-74% I.F.3-13 Hartwig, J.F. et al., JACS, 125, 11176; You, J.; Verkade, J.G., JOC, 68, 8003; Fagnoni, M. et al., JOC, 68, 4886; Cossy, J. et al., OL, 5, 3037; Byers, J.H. et al., TL, 44, 6853; Nolan, S.P. et al., S, 2590; Miranda, L.D. et al., CC, 2316; Maruoka, K. et al., JACS, 125, 10494; Liu, P. et al., TL, 44, 8869. O O

Ar'Br + R ~

~ R ~ XR1

xR1 Pd(dba)2'THF~176

ZnBr.THF

Ar 66-97%

Ph~v~ ~

v

Phe i~Bu2

I.F.3-14 Evans, G.B. et al., OL, 5, 3639; Sakai, N.; Konakahara, T. et al., JOC, 68, 483; see also: Tellitu, I.; Dominguez, E. et al., T, 59, 7103; Nishizawa, M. et al., OL, 5, 4563. Rz

+ H R

H

aq" "O R1 NaOAc, H20, 95~

~ R

H 47-78%

R1

CARBON-CARBON BOND FORMING REACTIONS

85

I.F.3-15 Correia, C.R.D. et al., OL, 5, 305; Wood, J.L. et al., TL, 44, 4919; Ray, J.K. et al., TL, 44, 7433; Schmidt, B., CC, 1656; Frejd, T. et al., JOC, 68, 1911. .~"N2+BF~" ~ Pd(OAc)2,tBu2pyrMe ~ R1 .~ R1 Me(Y ~ CO2R EtOH, 550C M e O ~ q ~ CO2R 67-98%

I.F.3-16 Langer, P.; Bose, G., AG(E), 42, 4033; see also: Yamamoto, Y. et al., CC, 1290; Stara, I.G.; Stary, I. et al., CCC, 68, 917; Cheng, C.-H. et al., CC, 718. OH

/ TMSO

~R-~~

OTMS

Om=~

R1 4- O==~i

TiX4

O

~

gl

CH2CI2

40-82%

I.F.3-17 Imahori, T.; Kondo, Y., JACS, 125, 8082. R ~ O ZnI2,Ph-Me or THF, -78~ rt ArR~RIOH Ar-H 4~ R1 q~u Me2NI N II ,NMe2 Me2N---oP=N-- P- N'-P- NMez Me2N N NMe2 II P Me2N" [ "NMe2 NMez

48- 92 %

I.F.3-18 Hallberg, A. et al., JACS, 125, 3430. ~ o ~ 1. Pd(OAc)2,H20/DMF, , 70-100~ Ar-X + M 2. H3O+ Me

~

M~ ' 0 . , ~ At: O 47-78% ee = 91-98%

I.F.3-19 Rovis, T. et al., JACS, 125, 10498; Ohno, K. et al., CL, 32, 828; see also: Vorndran, K.; Linker, T., AG(E), 42, 2489; Miller, J.A.; Dankwardt, J.W., TL, 44, 1907. O ~O 1. Ni(cod)~ dppb, neocuproine, THF /--CO2H ( )n O '~" ( Q . 2. Ph2Zn, fluorostyrene, THF, 660C N~__ph 50-58%

86

ORGANIC SYNTHESIS--2004

I.F.3-20 Cacchi, S. et al., OL, 5, 289. Pd2(dba)2, EtNipr2, LiCI . Ar-I + Ac20 DMF, 100~

Me. O Ar 25-94%

I.F.3-21 Iesce, R. et al., TL, 44, 5781; Wagner, A.; Mioskowski, C. et al., CEJ, 9, 3209. O O

Et20, rt 12-80% LF.3-22 Medio-Simon, M.; Asensio, G. et al., OL, 5, 1705; Luo, F.-T. et al., TL, 44, 1587. O O II Pd(PPh3) 4 ii p h t S ~ B r + Ar-B(OH)2 ~ p h t S ~ Ar R

R 0-87 %

I.G. S y n t h e s i s via O r g a n o m e t a l l i c s

I.G.1. Synthesis

via O r g a n o b o r a n e s

I.G.I-1 Hayashi, T. et al., JOC, 68, 1901; Renaud, P. et al., JOC, 68, 5769 and S, 2740; see also" Oh, C.H. et al., CC, 2622. (

~ o

+

Ar--B

~

[Rh(OMe)(cod)]2,BINAP ( ~ O - . ~ Ph-Me, 80~ Ar 95-98%

I.G.1-2 Rolando, C. et al., TL, 44, 5359.

Ph

R2

(Ph R" 0 68-93%

CARBON-CARBON BOND FORMING REACTIONS

87

I.G.1-3 Nadin, A. et al., JOC, 68, 2844; Occhiato, E.G. et al., JOC, 68, 6360; Cho, C.-G. et al., TL, 44, 4439; Organ, M.G.; Wang, J., JOC, 68, 5568; Sato, F. et al., JOC, 68, 9767; Ma, S. et al., CEJ, 9, 6049.

O+ R'B(OH)2 Pd(OAc)2,Cs2CO3 ,~ N DMF, 100oc

~O N R

66-99% I.G.1-4 Doucet, H.; Santelli, M. et al., SL, 1668.

y

X+

~

[Pd(C3Hs)CI]2,Ph-Me2,130*C

(HO)2B~'~R1 41-95%

Ph3v'r J L'~PPha Ph3P..'-- -~PPh3

l.G.1-5 Lam, P.Y.S. et al., TL, 44, 4927.

~~SS~

0

Bu

+

i['~ (HO)2BI

Cu(OAc)2 ,air pyr, rt

Bu

96% I.G.1-60rtar, G., TL, 44, 4311; Kabalka, G.W. et al., OL, 5, 3803; Schaffner, A.-P.; Renaud, P., AG(E), 42, 2658; Lautens, M.; Dockendorff, C., OL, 5, 3695.

R~~OA R2c , 1 + R 3 - - B x ~

PdCl2~ R R ~ R 2 R 3 58-91%

I.G.1-7 Patel, S.J.; Jamison, T.F., AG(E), 42, 1364; see also: Naskar, D. et al., TL, 44, 8861, 8865.

Ph

R HN,,Me N,.Me Ni(cod)2,P(c-C5H9)3 ,,... I I Me + R-B(OH)2+ _Lph MeOH/MeOAc,50*C- P h " ~ ~ P h Me 68-72% 11.5:1

88

ORGANIC SYNTHESISm2004

I.G.I-8 Snieckus, V. et al., AG(E), 42, 3399; Qing, F.-L. et al., T, 59, 7879. "Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids." I.G.2. Carbonylations Reactions I.G.2-1 Mukai, C. et al., JOC, 68, 1376; Brummond, K.M.; Gao, D., OL, 5, 3491; Austin, D.J. et al., OL, 5, 2203; Wender, P.A. et al.,AG(E), 42, 1853; Ishizaki, M.; Hoshino, O. et al., H, 60, 2259; Shibata, T. et al., SL, 573; Verdaguer, X.; Riera, A. et al., OM, 22, 1868; Cook, J.M. et al., JACS, 125, 3230; Krafft, M.E. et al., JOC, 68, 6039; Rivero, M.R.; Carretero, J.C., JOC, 68, 2975. R4 SO2Ph R

[RhCl(CO)2]2,CO Ph-Me ~SO2Ph

~

R 3 - ~ O R2 ~R1 15-96%

I.G.2-2 Carretero, J.C. et al., JACS, 125, 14992. R1 O NMe2 (co).co

_--41

+

R

f ~

O

NMO, MeCN 0"C-- R I ~ ~ : / R 0-68%12.5-49:1

'

I.G.2-3 Denmark, S.E.; Kobayashi, T., JOC, 68, 5153; Salvadori, P. et al., JOC, 68, 9292. R ~ CO, Rh(acac)(CO)2or [Rh(BuCN)]4[Co(CO)4]~ ~ R ~ ~ ~ O iPr2HSi

r

Ph-Me, 70~

)si:

OHC il/r~Pr 8-72%

I.G.2-4 Merlic, C.A.; Doroh, B.C.; JOC, 68, 6056. +MeO~Cr(CO)5 CO,hn DMAP R-CHO

Ph

THF

~

O~,.O MeO~ R ,OMe or Ph R Ph 43-61% 33-55%

CARBON-CARBON BOND FORMING REACTIONS

89

I.G.2-5 Chatani, N. et al., JOC, 68, 7538, 1591 and OL, 5, 4329; Castanet, Y. et al., SL, 1874.

~/~

~~N

CO, CH2=CH2,Ru3(CO)12 v DMA, 1600C O 40-94%

I.G.2-6 Gagnier, S.V.; Larock, R.C., JACS, 125, 4804; Studer, M. et al., JOC, 68, 3725. CO, Pd(OAc)2,Bu4NCI pyr/DMF, 1000C

C ~

R

R 45-99%

I.G.2-7 Chung, Y.K. et al., OL, 5, 4967; Aggarwal, V.K. et al., CC, 1046. / 'CO, R3SiH,Co2Rh2 X / ~ ~I S i R 3 X .1~ dioxane, 1050C ~a.~....-CHO 23-98% I.G.2-8 Larhed, M. et al., OL, 5, 4875; Sestelo, J.P.; Sarandeses, L.A. et al., S, 780; Sugi, Y. et al., S, 501; Ogawa, A. et al., T, 59, 3521. O R_~

I Co2(CO)&~tW MeCN

R

~

R

57-97% I.G.2-9 Nelson, A. et al., JOC, 68, 747. O,,

~

Me

O

tt

O,,

Me

IJ

H20, MeCN/MeCN ~ ~ . ~ L ~

,r-o@,o-r OAc

~

~

~[~

~,"~ u

ee = 95 %

-p

90

ORGANIC SYNTHESIS--2004

LG.2-10 Mori, A. et al., OL, 5, 3057. CO, PdCI2(PPh3)2,CuI R-CfC + Ar-X aq NH3, rt

g

n~

\r 15-87%

I.G.2-11 Chang, S. et al., JOC, 68, 1607. R-X

PdCl:~ Ru3(CO)12~NaHCO3 ~ O ~ DMF, 135~

+

63-97% I.G.2-12 Yoshida, M.; Ihara, M. et al., JACS, 125, 4874; Xia, C. et al., CC, 2042. O I~O~ /OCO2Me CO2, Pd2(dba)a.CHCl3, 4~ MS O& + HO-Ar ~ 0

R

(~PPh~

R~-,,~ OAr

48-94%

PPh'z

ee = 23-93% I.G.2-13 Cacchi, S. et al., OL, 5, 4269. Pd2(dba)3 or PdCl2(dppp) Ac20, EtNipr2, LiCl R-X + HCO2Li DMF, 800C I.G.2-14 Mori, M. et al., OL, 5, 2599. 1. CO, Ni(cod)~,DBU, TI-IF,O~ Ri

~

2. Ar-CHO

R-CO2H 43-92%

Ar~OH "~ ~ ~ 1 C O 2 H >46-73%

I.G.2-15 Nozaki, K. et al., JACS, 125, 8555; Gusevskaya, E.V.; dos Santos, E.N. et al., JOM, 671, 150; Breit, B. et al., CEJ, 9, 425; Suades, J. et al., JOM, 669, 172. "Solvent-Free Asymmetric Hydroformylation Catalyzed by Highly Cross-Linked Polystyrene-Supported (R,S)-Binaphos-Rh(l) Complex."

CARBON-CARBON BOND FORMING REACTIONS

91

I.G.3. Other Synthesis via Organometallics I.G.3-1 Ozaki, S. et al., JOC, 68, 4586; Liu, H.-J. et al., CC, 2490; Snider, B.B. et al., JOC, 68, 6451. O

~

~~,,.,CN

~

~,R1

O

De60oR'O .

------'~--n

ClO 4"

I.G.3-2 Hashimoto, S. et al., TA, 14, 817; Perez, P.J. et al., OM, 22, 4145.

CH2C12 It o

C02Me

~;~

O~-1-~

64-98%

X

I.G.3-3 Cai, M. et al., JCR(S), 485; Xie, M.; Huang, X., JCR(S), 584; Silveira, C.C.; Zeni, G. et al., JOC, 68, 662; Gevorgyan, V. et al., JOC, 68, 6251; Casey, C.P.; Dzwiniel, T.L., OM, 22, 5285. iBuMgBr, CP2TiCI2 R __/TMS I ' R1 R fTMS R

TMS Et20,

rt

~

-

\MgBr Pd(PPh3)4,THF

-

-

,\ R1

62-76% I.G.3-4 Kabalka, G.W. et al., JOC, 68, 7915; Miura, M. et al., JOC, 68, 6836; Larock, R.C. et al., JOC, 68, 339; Rayabarapu, D.K.; Cheng, C.H., CEJ, 9, 3164; Cheng, C.-H. et al., OL, 5, 3963 and JOC, 68, 6726; Xi, Z.; Takahashi, T. et al., JOC, 68, 1252. R4

R

R1 +

R4

oR'

3 CH2C12,rt

R1 R

65-90%

92

ORGANIC SYNTHESISm2004

I.G.3-5 Molinaro, C.; Jamison, T.F., JACS, 125, 8076; Tsuchimoto, T.; Shirakawa, E. et al., CC, 2454.

R ~

R I + O~ ~

R2 Ni(eod,2,PBu3, Et3B

R,~,~~R

2

R~ OH 25-68% 19:1 I.G.3-6 Mascarenas, J.L. et al., JACS, 125, 9282. ~~> X \

R

Pd2(dba)3,p(Oipr)3 dioxane,100~

X ~ R 65-96%

I.G.3-7 Ajamian, A.; Gleason, J.L., OL, 5, 2409; Mori, M. et al., OM, 22, 30.

TBSO~ M~~ -M

TBS(~ TMS Co2(CO)&P(OMe)3,~ MI~

~

Ph-Me, reflux

M

TMS 93%

I.G.3-8 Zhu, G.; Zhang, Z., OL, 5, 3645; Krische, M.J. et al., JACS, 125, 7758; Widenhoefer, R.A. et al., OL, 5, 2699; Tanaka, K.; Fu, G.C., JACS, 125, 8078" Echavarren, A.M. et al., CEJ, 9, 2627. X~ ~ R / X

\

~

R

+ Ar-B(OH)2

Pd(PPh3)4,KF y . ~ A i Ph'Me'60~

~

r

21-90% I.G.3-9 Sato, F. et al., JOC, 68, 4980; Cha, J.K. et al., OL, 5, 2137; Tsukada, N. et al., JOC, 68, 5961; Yamamoto, Y. et al., CEJ, 9, 2469.

R1 Ts

+

RI - R --

>

....OTBS

iprMgCI' Ti(Oipr)4 ~ Et20, -780C

'"IOTBS R 63-88%

CARBON-CARBON BOND FORMING REACTIONS

93

I.G.3-10 Knochel, P. et al., S, 1797 and CEJ, 9, 2789, 2797; Wu, J.; Yang, Z. et al., JOC, 68, 670; Fairlamb, I.J.S.; Taylor, R.J.K. et al., CC, 2194; Jackson, R.F.W. et al., OBC, 1, 140; Bailey, W.F. et al., JOC, 68, 1334; Li, S.; Dieter, R.K., JOC, 68, 969; Crotti, P. et al., OL, 5, 2173. Br,~Brh "!" P

1. RMgCI, Et20, -78--*0~

h~ E

CO2Et 2. E +

P

CO2Et 56-82%

I.G.3-11 Barluenga, J. et al., JOC, 68, 537 and CEJ, 9, 5725; Wulff, W.D. et al., JACS, 125, 8980; Katayama, H.; Nagao, M.; Ozawa, F., OM, 22, 586. RO M(CO)5 RO OMe R1 I ~ O M e ~ R1 -- I [ ~ ~ OH R2 R3]11~~4 R5 THF,reflux

R2 ~3

R4

R5

46-95%

I.G.3-12 Togo, H. et al., JOC, 68, 7629; Tsukade, N. et al., CC, 2404. O (.__ _

ZnorIn R

,._ (

H20/tAm-OH,A

CO2R 15-93%

I.G.3-13 Davies, H.M.L. et al., JOC, 68, 6126. Ar Rh2( DOSP)4 ~.~ A s ~,~q~j MeO2C,~N2 + T B S ~ tBuEt, 50~ - MeO2C .r ~--- R TBSO 33-98% de = 92-98 % ee = 62-92%

I.G.3-14 Oshima, K. et al., OL, 5, 3959; Reimelt, O.; Heck, J., OM, 22, 2097. ~,TMS TMS'CH2MgCI' C~ r R-Br + ~ ~ ~ ' R 1 Ph2P(CH2)6PPh2 R1 60-93%

94

ORGANIC SYNTHESISm2004

I.G.3-15 Ishii, Y. et al., JOC, 68, 5974; Tanaka, T. et al., JOC, 68, 5909, 7722; Wang, K.K. et al., JOC, 68, 5832, 8545; see also: Chang, S. et al., OL, 5, 2687. R\1

R"~

-I-

,/~O

R1

\O Mn(OAc)2,Co(OAc)2, 0 2 .1~ R A ~ C O 2 RI~o

130~

H

8-91%

I.G.3-16 Knochel, P. et al., OL, 5, 2111; Rodriquez, D.; Selesto, J.P.; Sarandeses, L.A., JOC, 68, 2518. R1

R2Zn 4-

OCOC6F5

Bu

R1

CuCN.2LiCI ~ R~,,,,~, ~ THF, .10~ Bu 68-90% ee = 89-95 %

I.G.3-17 Isakov, V.E.; Kulinkovich, O.G., SL, 967; Lee, P.H. et al., JOC, 68, 7085; Sato, Y.; Oonishi, Y.; Mori, M., JOC, 68, 9858; Rajanbabu, T.V. et al., JAC, 68, 8431. OH OH iprMgBr,Ti(Oipr)4 Et20, rt OH 63% I.G.3-18 Yamamoto, Y. et al., JOC, 68, 2297. hex ~ hex

Pd(PPh3)4, dppf + Nuc-H

EtOH, 100~

~

hex x ~ he

Nuc 52-86%

I.G.3-19 Sanchez-Martinez, C.; Faul, M.M. et al., JOC, 68, 8008; Ferreira, E.M.; Stoltz, B.M., JACS, 125, 9578; Suffert, J. et al., OL, 5, 2307; Occhiato, E.G.; Prandi, C. et al., JOC, 68, 9728. H

H

O Pd(PPh3)4, KOAr DMA, reflux H

H 5-63%

CARBON-CARBON BOND FORMING REACTIONS

95

I.G.3-20 Harada, T.; Kutsuwa, E., JOC, 68, 6716.

R'~

1. R23ZnLi, THF,-85~

R I ~

R2

2. ZnCI2, 02, TMS-CI "-

R'~O H 54-63%

I.G.3-21 Xi, Z. et al., JOC, 68, 4355; Oshima, K., JOC, 68, 6627. R

R ~

R

AICI3

ZrCp2 + R1-CHO

~--

R1

THF/Ph-Me,-78~ ~ rt

O 65-81%

I.G.3-22 Backvall, J.-E. et al., CEJ, 9, 3445 and JOC, 68, 7243. "Ailenes as Carbon Nucleophiles in Intramolecular Attack on (n-l,3Diene)-Palladium Complexes" Evidemce for trans Carbopalladation of the 1,3-Diene."

I.H.

Rearrangements v

I.H.1. Claisen, Cope and Similar Processes

I.H.I-1 Armstrong, A. et al., OBC, 1, 3142; Wang, J. et al., TA, 14, 891; Wee, A.G.H. et al., TA, 14, 897; Rainier, J.D. et al., TA, 14, 911. SX BocN~SX R ~ CH2C12,-40~-~ rt Boc "~ R1 R' EtO2C "CO2Et R 13-88% I.H.1-2 Blid, J.; Somfai, P., TL, 68, 3159; Tomooka, K. et al., TL, 44, 1239. 1-- R1 0 I

~

~

.n

O

NHBu

BBr3 ~

@

NHBu

NHBu 56-71%

96

ORGANIC SYNTHESISI2004

I.It.l-3 Anderson, C.E.; Overman, L.E., JACS, 125, 12412; Overkleeft, H.S. et al., EJOC, 2418. R2 R2 R['~~O

CH2C12,18h

k .Co " ~ ~

Ph~ph

b.~

R1N~ O

ipr

7-99% ee = 71-98%

Ph I.H.1-4 McComas, C.C.; van Vranken, D.L., TL, 44, 8203.

r.s+.j M e ,

Me

R*2NLi ~ M e @

THF, -78~ Me

Me 33-84% de = 20:1 ee - ___50%

I.H.1-5 Bio, M.M.; Leighton, J.L., JOC, 68, 1693; Karikomi, M. et al., TL, 44, 2167; Hana, I. et al., OL, 5, 1139; Cha, J.K. et al., AG(E), 42, 5044. T E S ~ 2 R~ TES R ~ ~ CO, pd(PPh3)4,EtNiPr2 OTf HO~ "~O Ph-CN, 80-100~ 1~2 R1

46-95%

I.H.1-6 Nelson, S.G. et al., JACS, 125, 13000; Motherwell, W.B. et al., SL, 805; Zhang, L. et al., TA, 14, 2195; Godage, H.Y.; Fairbanks, A.J., TL, 44, 3631; Florent, J.-C. et al., TL, 44, 4125; Eberlin, M.N.; Marsaioli, A.J. et al., JOC, 68, 5493. 1. [Ir(PCy3)2]+ CH2CI2/Me2CO OHL~~'~R2R~,,~'~R 1

2. 390C

R~~176 62-93% syn:anti = 11.5-49:1

CARBON-CARBON BOND FORMING REACTIONS

97

I.H.1-5 Stoltz, B.M. et al., JACS, 125, 13624. O " ~

H

1

R

C,,"

I

AgOAc,TEA 2 THF,450C ~

R2 80-98%

I.H.1-6 Vogelsang, T.; Borschberg, H.-J., HCA, 86, 3583; Suzuki, H.; Kuroda, C., T, 59, 3157. q ' ~ N

Pd(PPh3)4'PPh3~

I.H.1-9 Cheng, H.-S.; Loh, T.-P., JACS, 125, 4990. O ~ l -~I "'~ "" In(OTf)3 or TfOH R-CHO + CH2CI2or hex

U/x

OH R~~'~

""

53-95% ee = 40-98%

I.H.I-10 Pietruszka, J.; Schone, N., AG(E), 42, 5638. Ph Ph BO~o h MeC(OEt):~EtCO2H~. ~ B ' O~ O j''Ph Me HO%, / / / . . . - - ~ , O ~ . . o M : 135~C , -.( .....XO"a-"~'OMe Ph ~ ]~hPh Y 64-76% I . H . I - l l Hong, J.H. et al., T, 59, 6103. O~ O B n TB S

~

~

1. TMS-CI,TEA,LHMDS,-78~ r t MeO2C,~OBn 2. Me-I, Triton-B, MeOH, rt

OBn

~l""~"~'l

OTBS OBn 82%

98

ORGANIC SYNTHESISm2004

I.H.l-12 Nordman, G.; Buchwald, S.L., JACS, 125, 4978. R2

~4R3

O PhOe212o~ g~ ul se%__C-~~e

l~.,,~OH + R"

R4

g

Me- - ~ N~-'~N~----~Me

2

~

55-77%

I.H.I-13 Toyota, M.; Ihara, M. et al., H, 61, 133; Thomas, E.J. et al., TL, 44, 2713; Tsubuki, M.; Takahashi, K.; Honda, T.,JOC, 68, 10183.

~

~ 0 "

R

HO R R1 H

~

R1 BuLlor LDA THF, -78~

39-91% 1.7-7.3:1 I.H.I-14 Rainier, J.D. et al., JOC, 68, 993.

:- C~ SR

X

N2

SheOAc'4 CH2C12,rt

- 02R2

~:---~N&~ SR

H

75-98%

I.H.I-15 Davies, S.G. et al., CC, 2134.

"DoubleDiastereoselective[3.3]-SigmatropicAza-Claisen Rearrangement." !,H.2. Other Rearrangements I.H.2-1 Zard, S.Z. et al., OL, 5, 325. CO2H 1. (COCI)~CH2C12,rt

r

O~.o--CO2Et 2. c-C6HI:~reflux, h l ~ ~ ~ s ~

~C;

ONa

62%

O2Et

CARBON-CARBON BOND FORMING REACTIONS

99

I.H.2-2 Maruoka, K. et al., JACS, 125, 3220. H

a-Np~~,~CHO /N RR

O

Ph-Me,-78 to -40~

~

I

.,L,I. R

f

~

OH

NIMe f

I.H.2-3 Shionhara, T.; Suzuki, K., S, 141. OH M , H ~ Ms-CI,TEA, AIEt3~ Ph CH2C12

62-94% ee = 78-97%

M

O ~

e k-

Ph

86-92%

ee = 99 % I.H.2-4 Bernard, A.M.; Piras, P.P. et al., OL, 5, 2923. O,

HH

OHH~.~~ CH2C12 81%

(R,S):(S,S) = 19:1 I.H.2-5 Tu, Y.Q. et al., OL, 5, 2319 and SL, 623, 1497 and CC, 798 and TA, 14, 2189. OH

X-

v

CH2C12, rt

X" v

i~ NHTs

96-98% syn:anti = 99:1

I.H.2-6 Hills, I.D.; Fu, G.C., AG(E), 42, 3921; Ruchirawat, S. et al., TL, 44, 1019.

1 O2R

Izt:

CH2C12, 35*C Ph

~~~h CN ~

oo

Ph =

88-98 % ee72-95%

100

ORGANIC SYNTHESISm2004

I.H.2-7 Hurley, P.B.; Dake, G.R., SL, 2131. NBS iprOH,-78~

OH

Et

,Br r

rt

Et Ts

96% I.H.2-8 Jung, M.E. et al., OL, 5, 3159. OR OTES TMS.OTf,EtNiPr2 P r ~ Me Me

QTMS pr~~,_ CHO OR

CH2C12' .50~

Me Me 85-88%

I.H.2-9 Paquette, UA. et al., S, 1872. (

~OoBn KHMDS'18"Cr'6~" P h T H- F( , ~r t 41%

I.H.2-10 Pulido, F.J. et al., OL, 5, 4045.

ehoeeSi

R" v ~r~

CH2C12,0~

R1 68-82%

I.H.2-11 Shimizu, M.; Yamada, S. et al., BMCL, 13, 809. OMe OTBS ~ .

1. PdCI~ H20/dioxane . OBn 2. TBS-CI,DMF bBn

OBn OBn 84%

I.H.2-12 O'Brien, P. et al., TL, 44, 6613. NTs

SBuLi, sparteine

~- ~ N H T s

Et20, -780C ee

67% = 38%

CARBON-CARBON BOND FORMING REACTIONS

101

I.H.2-13 Marson, C.M. et al., TL, 44, 141. Et SnBr4 ~

CH2C12 OH 65%

I.H.2-14 de la Moya Cerero, S. et al., JOC, 68, 1451; Martinez, A.G.; de la Moya Cerero, S. et al., TA, 14, 1607; see also: Ruedi, G. et al., OL, 5, 2691. o.

~ O

E+ rt '~ CH2C12, E 67-98%

I.H.2-15 McWhorter, Jr., W.W. et al., OL, 5, 333. HCO2H Ph-Me, reflux d / ~

r

NH Br

65%

I.H.2-16 Tius, M.A. et al., OL, 5, 4069. O Me(Y~'-

+ Ph

O

O 2. R-X, SiO2 46-89%

R

!1 OXIDATIONS II.A. C-O Oxidations

II.A.1. Alcohols-->Ketones , Aldehydes

II.A.I-1 Zhdankin, V.V.; Tykwinski, R.R. et al.,AG(E), 42, 2194; Quideau, S. et al., OL, 5, 2903; Natale, N.R. et al., SL, 2213; Rao, K.D. et al., JOC, 68, 2058.

q,,o R1

CDCI3, rt

R1 26-99%

NHR

II.A.1-2 Kim, S.S.; Borisova, G., SC, 33, 3961; Kim, S.S.; Kim, D.W., SL, 1391. R,,],.OH + PhlO -l- Mn(III)(salen)Cl ~ %0 Ar MeCN, 4~ MS, rt Ar 11-99% II.A.1-3 Bagherzadeh, M., TL, 44, 8943. IL~OH + Oxone Bu4NBr, H20/CH2CI2, rt R1 o ~ '~ /-~ CN"k o~,,, I,,o-~

I~O

R1 60-99%

II.A.1-4 Uozumi, Y.; Nakao, R., AG(E), 42, 194; Nagao, Y. et al., H, 61, 449; Guram, A.S.; Bei, X.; Turner, H.W., OL, 5, 2485; Sigman, M.S. et al., JOC, 68, 4600. IL~OH nano Pd eat., O2 1~O R1 H20, reflux R1 83-99%

102

OXIDATIONS

103

II.A.1-5 Sheldon, R.A. et al., CC, 2414; Miller, R.A.; Hoerrner, R.S.; OL, 5, 285; Kim, S.S.; Jung, H.C.; S, 2135. TEMPO, tBuOK R-CHO R,~R,,OH1 + CuBr2(2,2'-bipyridine) H20/MeCN,rt ~ 61-99%

II.A.1-6 Xu, L.; Trudell, M.L., TL, 44, 2553; Hajipour, A.R.; Ruoho, A.E., SC, 33, 871; Fernandes, R.A.; Kumar, P., TL, 44, 1275. R~OHR 1 +H5iO6+Cr(acac)3

,MeCN~ R~R10 20-96%

II.A.1-7 Yamaguchi, K.; Mizuno, N., CEJ, 9, 4353; Ciriminna, R.; Pagliaro, M., CEJ, 9, 5067; Katsuki, T. et al., SL, 1868; Springer, D.M. et al., BMCL, 13, 1751; Matsubara, S. et al., TL, 44, 9201; Uemura, S. et al., JOC, 68, 5875. 02 R~OH + Ru/AI203 ~ R~O R1 Ph-CF3 R1 71-99% II.A.1-8 Martin, S.E.; Garrone, A., TL, 44, 549; Ferguson, G.; Ajjou, A.N., TL, 44, 9139. ~OH R1

+ H202 4- FeBr3

MeCN or neat, 25~

R1 84.91%

II.A.1-90hsugi, S.; Node, M. et al., T, 59, 8398; Srinivas, P. et al., JOC, 68, 2460. "New Odorless Method for the Corey-Kim and Swern Oxidations Utilizing Dodeeyl Sulfoxide (Dod.S-Me)" II.A.I-10 Neumann, R. et al., JACS, 125, 5280. "A Water-Soluble and 'Self-Assembled' Polyoxometalate as a Recyclable Catalyst for Oxidation of Alcohols in Water with Hydrogen Peroxide" II.A.I-ll Bogdal, D. et al., T, 59, 649. I~OH R1

jaw

+ Mag treiveTu - - - - - - ~

R•RO1 41-99%

104

ORGANIC SYNTHESIS--2004

II.A.I-12 Ghorbani-Vaghei, R.; Khazaei, A., TL, 44, 7525. R1

~

CH2C12,-15~

TEA

R~R10 89-95%

II.A.I-13 Strazzolini, P.; Runicio, A., EJOC, 526.

R1--2~

II + HNO3 ~ ' ~ CH2C12

R1 0-94%

H.A.1-14 Hiroi, K. et al., JOC, 68, 1601. Ph H ~ R,,~OH +

/

Ph~o~ir ~

R-CHO

Me2CO or EtCOMe, rt~80~

33-96%

II.A.1-15 Kroutil, W. et al., JOC, 68, 402. R~OH R1

Rhodococcusruber Me2CO

R~O R1

-I-

R~,,,OH R1

conversion = 52-94 % ee = 10-99%

II.A.2. Alcohols, Aldehydes-->Acids, Esters II.A.2-1 Zanka, A., CPB, 51, 888; Giacomelli, G. et al., JOC, 68, 4999; Desai, R.N.; Blackwell, L.F., SL, 1981; Punniyamurthy, T. et al., TL, 44, 6033. R,,/OH

+ NaCIO + TEMPO

KBr H20/MeCN or EtOAr

~

R-CO2H 16-99%

II.A.2-2 Kita, Y. et al., SL, 723; Hiegel, G.A.; Gilley, C.B.; SC, 33, 2003; Forsyth, C.J. et al., TL, 44, 57; Taylor, R.J.K. et al., S, 1055. R,,./OH

+ PhlO or PDAIS

PDAIS = ~-I(OAc)2

' ~ MeOH/aq HCi, rt

R-CO2H 52-90%

OXIDATIONS

105

II.A.2-3 Borhan, B. et al., OL, 5, 1031; Patel, B.K. et al., JOC, 68, 2944. R-CO2R1 O x o n e R-CHO ~Oxone ~ R-CO2H 9-98% RLOH DMF 19-99% [similarly with V2Os] II.A.2-4 Karimi, B.; Rajabi, J., S, 2373. R1 + 02 + Co(OAe)2 OR 1

NHPI MeCN, rt

R-CO 2R 1 82-95%

II.A.2-5 Fang, X. et al., SL, 489. R

I~

CHO + NaCIO2 S~ 2

NaH2PO4

I ~RC O 2 H

H20/DMSO

S~ 2 52-96%

II.B.

II.B.1

C-H Oxidations

C-H--->C-O

II.B.I-I Yu, J.-Q.; Corey, E.J., JACS, 125, 3232; Nikolaropoulos, S.S. et al., ST, 68, 407; Velusamy, S.; Punniyamurthy, T., TL, 44, 8955. /---5 PO(OH)2/C, K2CO3 -I- tBuOOH ~ )n n CH2C12 ~

79-80% II.B.1-2 Kiuru, P.S.; Wahala, K., ST, 68, 373. OTHP LIDAKOR .~ THe

H

~

B(OMe)3, H202 THe t LIDAKOR = BuLl, tAmOKJiPreNtt/THF/Hex

99%

106

ORGANIC SYNTHESISm2004

II.B.1-3 Momiyama, N.; Yamamoto, H., JACS, 125, 6038; MacMillan, D.W.C. et al., JACS, 125, 10808. R3SnO~.(R 3 BINAP.AgX O. R3 + Ph-NO ~ ~O-N-Ph Ri "R2 TI-IF, -78~ R1 R2 H 78-97% ee = 82-97 %

II.B.1-4 Lee, J.C.; Lee, Y.C., SC, 33, 3943; Curci, R. et al., JOC, 68, 7806; Demir, A.S. et al., TA, 14, 1489; Togo, H. et al., JOC, 68, 6424; Tanyeli, C.; Iyigun, C., T, 59, 7135. O O R ~ , , R 1 + TI(OTf)3

CH2Cl2,reflux ~

R~R 1 OTf 57-83%

II.B.1-5 Ishii, Y. et al., JOC, 68, 6587; Itoh, A. et al., S, 2289. x~.~ 02, AcOH, 25-100~ X . ~ ~ _ _ Me + Co(OAc)2 oi4 ~ CO2H O~,.N.~O

9-99%

HO"N"~N"oH O

II.B.1-6 Le Bras, J.; Muzart, J., TA, 14, 1911; Malkov, A.V." Kocovsky, P. et al., JOC, 68, 4727; Khan, K.M. et al., T, 59, 5549. Q CuI ~ Cull' cat" ~.~ + BzOOtBu

H20/(HOCH2CH2)20 ~

H

co2n

OBz

51-70%

ee = 34-42%

II.B.1-7 Schobert, R. et al., JOC, 68, 9827. CO2H 0

+ TBHP

0 2, hv CH2CI2, rt

O 60-72%

OXIDATIONS

107

II.B.2 C-H'C-Hal II.B.2-1 Montoro, R.; Wirth, T., OL, 5, 4729. "Direct lodination of Alkanes"

II.B.2-2 Massanet, G.M. et al., TL, 44, 6691. Me CeCIy7H20 + NaCIO H20/CH2CI2 R~ ...

~,,tC 1 60-98%

II.B.2-3 Togo, H.; Hirai, T., SL, 702. (BzO)2or AIBN Ar-Me + NBS ..... ionic liquid or neat

Ar~Br 21-89%

II.B.2-4 Stavber, S. et al., S, 853. O n_.~~Me (NO)

O

MeOH, rt

+ I2

(RO)n___~~ ''~''sl

F-N+ L.JN+-CHeCI03F4)2 II.B.2-5 Ghorbani-Vaghei, R., TL, 44, 7529. [TS'N__~ TFAA ~ Rx'--l"-~

+

1"

"~2 MeCN-

70-91%

R(3--1 90-93%

II.B.2-6 Corelli, F.; Botta, M. et al., S, 1039. "Microwave-Assisted C-5 Iodination of Substituted Pyrimidinones and Pyrimidine Nucleosides"

II.C C-N Oxidations

II.C-1 An, G.; Rhee, H., SL, 876; Rhee, H. et al., SL, 112. O B n . ~ BF3"Et20 B n . ~ + MCPBA CH2CI2, rt X

62-83%

X

108

ORGANIC SYNTHESIS--2004

II.C-2 Nicolaou, K.C. et al., AG(E), 42, 4077; Kocevar, M. et al., S, 2349. R,,N..,~R1 + IBx ,~ R,,I~R1 H DMSO, 450C 49-98% II.C-3 Zolfigol, M.A. et al., SL, 933. R"I~R1

+ UHP

maleic anhydride

MeOH, 0~

R-'R1 80-95%

II.D. A m i n e O x i d a t i o n s

II.D-1 Wang, Y. et al., SC, 33, 1781. H Ph""~"~N"N'Ar + NaBrO3

Ph N Ar H2SO4

n

O 74.86%

II.D-2 Licini, G. et al., TL, 44, 49. R1 R3.OOH Ti(Oipr)* CHP' 4A MS R,J'~ N-.R2 4H CHCI3, 60~

R~IN+R 2 O" 45-98%

II.D-3 Phanstiel, IV, O. et al., T, 59, 4315. R-NH2 + BPO

R,.N.OBz CH2Cl2/buffer

H

74-90% II.D-4 Jain, S.L.; Sain, B., AG(E), 42, 1265. RI~ CoII Sehiff base complex, 02 R,,N,,R2 DCE, 5A MS, 20~

R1 i ,,O

50-92%

II.D-5 Sain, B. et al., TL, 44, 3235. R/~---NH2

+ MeRuO3

MeCN, reflux

R/x~--NO2 89-92%

OXIDATIONS

109

II.D-6 Rassat, A.; Rey, P. et al., CC, 2722. "A Versatile Synthesis of N e w P y r i m i d i n y l Nitronyl Nitroxides"

II.D-7 Doris, E.; Mioskowski, C. et al., TL, 44, 6591. "Ph3BiCO3: A Mild Reagent for in situ Oxidation of Urazoles to Triazolinediones" II.D-8 Chen, F.-E. et al., S, 2629. RANH2

+ TCCA

TEMPO

R-CN

CH2CIz, 10*C

80-91%

II.E. S u l f u r O x i d a t i o n s

II.E-1 Akamanchi, K.G. et al., JOC, 68, 5422. R.. TEAB S + IBX ~1 H20/CH2CI2, rt 90-98% II.E-2 Aggarwal, V.K. et al., JOC, 68, 4087.

,o

1

+ Ph%oOHMe Ti(Oipr).DET . C~_ ]R1 Me

CH2C12,-40 to -20~

"o 60-75% ee = 98-99 %

I.E.3 Kim, S.S.; Rajagopal, G., S, 2461; Miyazaki, T.; Katsuki, T., SL, 1046; Saikia, A.K.; Chaudhuri, M.K. et al., TL:, 44, 4503; Begue, J.-P. et al., OS, 80, 184. Crmsalen R,, S,,,,O R'S + Ph-IO ~ ~1 CH2C12, rt ~1 64-99%

II.E-4 Weix, D.J.; Ellman, J.A., OL, 5, 1317. tBu~S~ S,'tBu + H202

VO(acac)

Me2CO, 0~

O II tB~,-S~ StBu 98% ee = 86 %

110

ORGANIC SYNTHESISm2004

II.E-5 Zen J.-M. et al., AG(E)i 42, 577. "An Efficient and Selective Photocatalytic System for the O x i d a t i o n of Sulfides to Sulfoxides"

II.E-6 Legros, J.; Bolm, C., AG(E), 42, 5487; Bradley, M. et al., OL, 5, 235; Thakur, V.V.; Sudalai, A., TA, 14, 407; Linden, A.A.; Kruger, L.; Backvall, J.-E., JOC, 68, 5890. CH2C12, rt ,O R.,.S -i- H202 ~ R., S .... 21-44 %

H

ee = 27-90%

II.E-7 Choudary, B.M. et al., CC, 754; Trudell, M.L. et al., JOC, 68, 5388; Finley, K.T. et al., JOC, 68, 4988. O2 R" s + LDH-OsO4 .1~ R~SO2 ~1 tBuOH, burrer R1 95-99%

LDH = layered double hydroxide II.E-8 Mohammadpoor-Baltork, I. et al., SC, 33, 953; MohammadpoorBaltork, I.; Khodaei, M.M.; Nikoofar, K., TL, 44, 591. R1 S R1 .O R.%2

+Oxone

neat ~

I~N'-~R2 73-99%

II.F. Oxidative Additions to C-C Multiple B o n d s

II.F.1 E p o x i d a t i o n s

II.F.I-1 Kuhn, F.E.; Romao, C.C. et al., OM, 22, 2112. "A Simple Entry to ( s-CsRs)chlorodioxomolybdenum (Vl) Complexes (R = H, CH3, CHzPh) and their Use as Olefin Epoxidation Catalysts" II.F.1-2 Stack, T.D.P. et al., OL, 5, 2469. I((phen)2(H20)FeIII)2(~t-O)lCIO4 R

AcOH/MeCN, 0~ 85-96%

OXIDATIONS

111

II.F.1-3 Rozen, S.; Golan, E., EJOC, 1915.

R1

R2

R

R3

R)LQ~RI HOF, MeCN

R

R"

70-95%

F2, H2O, MeCN II.F.1-4 Sartori, G.; Armstrong, A. et al., JOC, 68, 3232. R1 R2 KG-60-FT, Oxone R~ R

Na2EDTA, NaHCO3, H20/MeCN

R2

R 93-99% ee = 48-80%

KG-60-FT= (x-fluorotropinoneon SiO2

II.F.1-5 O'Neill, P.M. et al., TL, 44, 8135; Iqbal, J. et al.,JOC, 68, 1679. R1 R2 C(Tthd)2,02 R~L~R2 / \, R tBu-CHO R R~ 70-95% II.F.1-6 Chandrasekaran, S. et al., T, 59, 7761; Beller, M. et al., TL, 44, 7479. ipr-CHO, 02, NaHCO3, CH2C12 )n

'

)n f--~

o "~

56-80%

~

,~ 9 ,~ I N ~ O

I I . F . 1 - 7 0 n a k a , M. et al., OL, 5, 85; see also: Shibasaki, M. et al., AG(E), 42, 4680; Sasai, H. et al., TA, 14, 1587; de la Pradilla, R.F. et al., JOC, 68, 4797; Yamamoto, H. et al.,AG(E), 42, 941; Zhang, R. et al., JOC, 68, 1721, 8222; Lattanzi, A. et al., CC, 1440 R R 1 CHP, Zr(OtBu), OBTA ,R , g1 H (~~R --

2

Ph-CI

~

H ~(~/~o

R2

55-98% ee = 47-87%

112

ORGANIC SYNTHESIS--2004

I.F.1-8 Shi, Y. et al., OS, 80, 9; Bez, G.; Zhao, C.-G., TL, 44, 7403; Shing, T.K.M. et al., TL, 44, 9225. R1

R2

Oxone, KOH, DME/MeCN

R~

9

R2

71-93%

ee = 90-98% I I . F . 1 - 9 0 ' B r i e n , P. et al., OL, 5, 4955; Curci, R. et al., SC, 33, 3009; Sun, Y.-C.; Chen, K. et al., JOC, 68, 9816; Solladie-Cavallo, A.; Bovicelli, P. et al., TL, 44, 6523. "cis- and trans-Stereoselective Epoxidation of N-Protected 2Cyclohexen-l-ylamines" II.F.I-10 Zhang, R. et al., OL, 5, 725; Vogl, N. et al., TA, 14, 1355. R 1 R2 [ZnW(VO)2(ZnW9034)2] "12 R1 R2 \m/ k___/

R / ' ' ' ~ OH

~

Rf"~ ~ OH

TADOOH TADDOL N~..~

82-96% er = 19:1

I I . F . I - l l Liang, X. et al., CC, 2714; see also: Murphy, P.J. et al., TL, 44, 8677.

9

o

R

aq KOH, Ph-Me

R1 + cU " ( I!

o

p..-

OO

R2

74-97% ee = 64-96%

II.F.I-12 Stack, T.D.P. et al., JACS, 125, 5250. "Efficient Epoxidation of Electron-Deficient Olefins with a Cationic Manganese Complex" II.F.I-13 Kumaraswamy, G. et al., TA, 14, 3797. "Enantioenriched (s)-6,6'-DiphenylBinol-Ca: A Novel and Efficient Chirally Modified Metal Complex for Asymmetric Epoxidation of ~,13-Unsaturated Enones"

OXIDATIONS

113

II.F.l-14 Taylor, D.K. et al., JOC, 68, 5205. R~._R1

MCPBA CH2C12,rt

R - ~

R1

O 51-93% de = 26-100% II.F.2 Hydroxylations II.F.2-1 Choudary, B.M. et al., JOC, 68, 1736; Chandrasekhar, S. et al., CC, 1716; Percy, J.M. et al., OL, 5, 337; Beller, M. et al., S, 295; Jonsson, S.Y.; Adolfsson, H.; Backvall, J.-E., CEJ, 9, 2783; Hattori, K. et al., BMCL, 13, 4277; Ghosh, A.K.; Kim, J.-H., TL, 5, 3967; Hartung, J. et al., SL, 51; Marcune, B.F. et al., JOC, 68, 8088. DH 1. LDH-PdOsW, TEA Ar~R Ar-X + ~ R , ~.2. (DHQD)2PHAL,NMM, H202 ()H iBuOH/H20

82-93% ee = 47-99%

II.F.2-2 Morken, J.P. et al., JACS, 125, 8702; Plietker, B.; Niggemann, M., OL, 5, 3353; Huang, J.; Corey, E.J., OL, 5, 3455; Evans, P.; Leffray, M., T, 59, 7973; Friedrich, H.B., et al., CC, 2922; Muniz, K.; Nieger, M. et al., OM, 22, 4616. R1

R2

R

R3

( n o r b o r n a d i e n e ) R h ( a c a c ) , TttF, rt

OH 17-76%

R

ee = 3 3 - 9 8 % PPh~

II.F.2-3 Sato, K. et al., AG(E), 42, 5623. "Catalytic Dihydroxylation of Olefins with Hydrogen Peroxide: An Organic-Solvent- and Metal-Free System" II.F.2-4 Li, Z. et al., JOC, 68, 8599; Muller, M. et al., CEJ, 9, 4188. Enantioselective trans Dihydroxylation of Nonactivated CmC Double Bonds of Aliphatic Heterocycles with sphingomonas sp. HXN-200"

114

ORGANIC SYNTHESISm2004

II.F.2-5 Lohman, G.J.S.; Seeberger, P.H., JOC, 68, 7541; Knochel, P. et al., CEJ, 9, 5259. ~ , _.~ (RO)3

DMDO, ZnCI 2 ~ CH2CI2, 0IJC

<3~O~ (RO) 18-78%

II.F.3 Other Oxidative Additions to C-C Multiple Bonds

II.F.3-1 Hergenrother, P.J. et al., OL, 5, 281. NHCbz

OH

R.HO, O,~. ~

CbzNH 2, tBuOCi, K2OsO2(OH)4 NaOH, (DHQ)2AQN, MeCN, buffer ~

R-'-=~

+

B = 47-85% A:B = 1:3.5-21 er (B) = 3-5.7:1

II.F.3-2 Ackerman, L., OM, 22, 4367. R m

NHR2 R 1 + R2.NH2 TiCI4,tBu-NH2 ,~ -'/_...~ ~R2 + / - ~ Ph-Me, 105I,C R R1 R R1 22-95%

II.F.3-3 Muniz, K. et al., CEJ, 9, 5581. "Diamination of Olefins: Synthesis, Structures and Reactivity of Osmaimidazolidines" II.F.3-4 Ananikov, V.P.; Beletskaya, I.P. et al., OM, 22, 1414. "Mechanistic Investigation and New Catalyst Design in Palladiumand Platinum-Catalyzed Se---Se Bond Addition to Alkynes" II.F.3-5 Plietker, B., JOC, 68, 7123; Nepveu, F. et al., JCR(S), 507; Peris, E. et al., OM, 22, 1110. R1

RuCI3, NaHCO:~ Oxone ~

O R ~

H20/EtOAc/MeCN, rt

A-

R1 IOH

51-94%

OXIDATIONS

115

II.F.3-6 Barluenga, J. et al., JOC, 68, 6583; Lee, Y.-S.; Yoon, J. et al., JOC, 68, 9140; Ma, S. et al., JACS, 125, 4817. IPyrBF4, Nuc CH2Ci2,rt

Ph

P 66-84% de = 100%

II.G. Phenol-Quinone Oxidations II.G-1 Menendez, J.C. et al., TL, 44, 6003. H2N~

OMe CoF3 H20/dioxane, rt

0 95%

OMe

II.H. Dehydrogenations II.H-1 Hayashi, M. et al., JOC, 68, 8272. R

~

R1

]~~

R

R1

O2, activatedC~ ~ [ ~ ' ~ ~ Ph-Me2, 120bC 79-90%

II.H-2 Hashemi, M.M. et al., M, 134, 107, 411. R

EtO2C~

R

CO2Et H202,Co(OAc)2~ E t O 2 C ~

Me- "N Me H

MeOH, rt

CO2Et

Me- "N Me 92-98%

II.H-3 Kaneda, K. et al., TL, 68, 6207. "Highly Efficient Dehydrogenation of Indolines to Indoles Using Hydroxyapatitie-Bound Pd Catalyst"

116

ORGANIC SYNTHESIS--2004

II.H-4 Sabitha, G. et al., S, 1267.

zr

03,4

R1 ,

~

R1

A c O H , rt

Ph

Ph 80-82%

II.H-5 Sheng, S.-R. et al., JCR(S), 552. O _ ~ n 'CHO R--+ + ~SeNEt2

~

CHO

R--~nl

CH2Cl2,reflux

85-91%

II.I Other Oxidations

II.I-1 Jiang, W. et al., OL, 5, 43. O KO~ 18-Cr-6 ~r~

NR1

R H

H

R

0-75% II.I-2 Hasegawa, E. et al., TL, 44, 9317. O

~~

IH

1. CAN, MeCN 2. SiO2

~

H

38-47%

R

II.I-3 Levason, W. et al., JOM, 688, 280; Sanghvi, Y.S. et al., BMCL, 13, 3537. 02, SnI4 RaP ~ RaP=O 99% II.I-4 Cossy, J. et al., TL, 44, 3613. R1R2 OsO4, NMM, NMO, NaIO4 ~ R I ~ 2 R ~ , ~ CHO R" "CHO H20/Me2CO 50-68%

OXIDATIONS

117

II.I-5 Das, S. et al., TL, 44, 1375; Suhana, H.; Srinivasan, P.C., SC, 33, 3097. NalO4 RAX ~ R-CHO DMF, 1500C 80-90% 1I.I-6 Sain, B. et al., SC, 33, 3875. OH MTO, MgSO4 R~R MeCN,reflux 0

R-CO2H 94-97%

(unsymmetrical hydroxyketonessimilarlyoxidized) II.I-7 Ferraz, H.M.C.; Longo, Jr., L.S., OL, 5, 1337; Adapa, S.R. et al., SC, 33, 3035.

l l~,,~~,~..O

RuO4~ 1~', ~ 1 O

55-82% 11.1-8 Mehta, G.; Sreenivas, K., T, 59, 3475. OH H CH2C12, CF3CO3H 0.5~ ~

OH

H C ~

~ + Ill,. 82%

II.I-9 Bose, D.S.; Reddy, A.V.N., TL, 44, 3543. AcO OAe R_~CHO + ~iO~ A"l~OAc NaN3

O

~ R_~N

O

CH2C12,0*C

II.I-10 de Meijer A. et al., S, 1916. O RXN,,R Ca(OCI)2,moist A1203 H CHC!3 or CH2C12,35-40~

82-95%

O R~N~R 1 I CI

90-99%

3

III REDUCTIONS III.A. C=O Reductions (see akso III.F.1) III.A.1 Aldehydes, Ketones --~ Alcohols III.A.I-1 Yamada, T. et al., CEJ, 9, 4485; Lee, W.K.; Ha, H.-J. et al., JOC, 68, 7675; Tamami, B.; Mahdavi, H.; T, 59, 821; Singh, J. et al., SC, 33, 191; Padhi, S.K.; Chadha, A., SL, 639; Benhida, R. et al., TL, 44, 2199; Zeynizadeh, B., BCJ, 76, 317; Lichtenthaler, F.W. et al., TA, 14, 727. I~X NaBH4 ~ ,R~RIXH R1 R2OH/THFA Ar~_~r 81_97O/o N,,c,,r~k

/R ee=62-99~

~ Me

o Me

III.A.1-2 Kawanami, Y. et al., T, 59, 8471; Tang, C. et al., TA, 14, 95; Shin, C. et al., BCJ, 76, 643; Xu, J. et al., TA, 14, 1781 and JOC, 68, 10146; Periasamy, M. et al., S, 2507; Nakada, M. et al., TL, 44, 7239; Locatelli, M.; Cozzi, P.G.; AG(E), 42, 4928; Gilmore, N.J.; Jones, S., TA, 14, 2115. BH3"THF ~ l ~ O H ,,, H

OH

80-97%

ee = 50-97% III.A.1-3 Lipshutz, B.H. et al., OL, 5, 3085 and JACS, 125, 8779; Finn, M.G. et al., JOC, 68, 2540. 1 ~ o Et3SiH,CuCI, tBuONa,Ph-Me, rt .~.. l~OSiR23 R1

O ~

pA(Ph.Me3)2 PA(Ph-Me3)2

118

R1 83-91%

REDUCTIONS

119

III.A.1-4 Node, M. et al.,AG(E), 42, 4515; Jaenicke, S. et al., CC, 2734. OH Ph~O ~O Ph~ ..OH ~ S H Me2AICI~. ~ .~ + ~ " R 1 CH2C12,rt~ S, R1 R 37-92% a-H:b-H = 11.5-100:1

III.A.1-5 Nadkarni, D. et al., JOC, 68, 594; Shi, M. et al., CC, 2916. M~O PMHS'TBAF~ Me~DH + R~O'H'" R1

R1

MeC'~R 1

71-95% syn:anti = 1:3-100:1 IILA.1-6 Deng, J. et al., OL, 5, 2103; Kira, M. et al., OM, 22, 2199; Cadierno, V.; Gimeno, J. et al., OM, 22, 5226; Mathey, F.; Le Floch, P. et al., OM, 22, 1580; Andersson, P.G. et al., OBC, 1,358; Lindner, E. et al., TA, 14, 1045; Chen, H.; Zheng, Z. et al., TA, 14, 1467; Yeung, C.-H.; Chan, A.S.C. et al., CEJ, 9, 2963; Adolfsson, H. et al., CEJ, 9, 4031; Rautenstrauch, V.; Morris, R.H. et al., CEJ, 9, 4954; Chen, C. et al., OL, 5, 5039; Wender, P.A. et al., OL, 5, 277; Ratovelomanana-Vidal, V.; Genet, J.-P. et al., S, 2405; Kanger, T. et al., TA, 14, 2271; Zhou, Q.-L. et al., JACS, 125, 4404; Ramsden, J.A. et al., OPRD, 7, 89; Cossy, J. et al., JOC, 68, 9994. R ~ X [RuCl2(p-cymene)]2,SDS,HCO2Na,H20 ~ ,R~XH Ar

~ s NaO3

I-IzN

Ar O3Na NHTr

HI.A.1-7 Hirao, T. et al., T, 59, 10147. Zn, Ac20, imidazole Ar-CHO or Yb(OTf)3,Zn then Ac20

19-99%

ee = 80-98%

Ap--/ Acr 22-89%

III.A.1-80ltra, J.E. et al., TL, 44, 1079. O OH ph~,~CO2Me Zn, Cp2TiCI2 ~9 p h ~ i C O 2 M e H20/THF, Me3Pyr.HCI 66%

120

ORGANIC SYNTHESIS--2004

III.A.1-9 Radivoy, G.; Yus, M. et al., S, 443. R~X CuCI2~ O, Li-DTBB R1

~ I~XH

THF, 20I~C

R1 57-93%

III.A.I-10 Yadav, A.K. et al., TA, 14, 1079. "Enatioselective Cathodic Reduction of some Prochiral Ketones in the Presence of (-)-N,N'Dimethylquininium Tetrafluoroborate at Mercury Cathode." III.A.I-11 Patel, R.N. et al., TA, 14, 3105; Porto, A.L.M., TA, 14, 711; Irimie, F.-D.; Poppe, L. et al., TA, 14, 1495; Chang, C.-Y.; Yang, T.-K., TA, 14, 2239; Mahmoodi, N.O.; Mohammadi, H.G.; M, 134, 1283; Matsuda, T. et al., CC, 1198. "Diastereoselective Microbial Reduction of (S)-[3-Chloro-2-oxo-l(phenylmethyl)propyl]carbamic Acid 1,1-Dimethylethyl Ester."

III.A.2 Acids, Esters, Amides ---> Aldehydes

III.A.2-1 Hagiya, K. et al., S, 823. SMEAH, N-methylpiperazine RO2C-Ar-CO2R Ph-Me

OHC-Ar-CHO 30-94%

III.A.2-2 Davies, S.G. et al., OBC, 1, 2886. ~1 B n ~ e M e o

DIBAL

o

~[~1 ~"~CHO 74-95% ee = 87-94%

III.A.3 Acids, Esters, Amides ---> Alcohols

III.A.3-1 Batra, S. et al., SL, 1611. OH NaBH4 OH R~~]ICO2 R1 ~ R @ ' , . OH Me 79-91%

REDUCTIONS

121

III.A.3-2 Katti, S.B. et al., JCR(S), 516; Tale, R.H. et al., TL, 44, 3427; Zeynizadeh, B.; Zahmatkesh, K., JCR(S), 522. R ~ . CO2H Na2BH4'THF' rt b-

R1

OH

r

N PF6"

55-93%

Me2N~+NMe2

III.A.3-3 Ragnarsson, U. et al., SL, 2386; Chang, M.-Y.; Chang, N.-C. et al., T, 59, 9383. NH2 1. Boc20, DMAP R'-~O ~ RAOH 2. NaBH4 51-77%

III.B. C-N Multiple Bond Reductions

IH.B.1. Imine Reductions

III.B.I-1 Kadyrov, R.; Borner, A. et al., JOC, 68, 4067; Zhang, X. et al., JOC, 68, 4120; Yoon, C.M. et al., SC, 33, 3387. HO2C~O + Bn-NH2 H2, [Rh(deguphos)(cod)lBF4.~ HO2C~NHBn R MeOH/CH2CI2,rt R ~ ' ~ Pph2 19-99% (R,R)-deguphos Bm'~l'/ephz~ ' ee = 9-98% (similar reductions with Ir catalyst) III.B.1-2 Krzeminski, M.P.; Zaidlewicz, M., TA, 14, 1463. R~R~N'R2

H

THF'rtph~w R~N~R2 R3~..Vh R1 R2"~B'O H3B" H

12"92% ee = 40-94 %

III.B.1-3 Kuhl, S.; Schneider, R.; Fort, Y., OM, 22, 4184. O

R~~N~

BH

Bu3SnH'BF3~ CH2C12,-78~

O

.-- R~IN~ N~ R B~,,,t---.J 76-94%

122

ORGANIC SYNTHESIS--2004

III.B.1-4 Qin, J.; Friestad, G.K., T, 59, 6393. O

R~N~N~

H

O

Bu3SnH'BF3"Et20 ._ % ~ N ~ CH2C12,.780C

R1BI~r

"-

,

76-94% IH.B.1-5 Perdicchia, D.; Licandro, E. et al., T, 59, 7733.

R R~1N~NR2 I'Me3N'BH3, HCI, Ph'Me2~ R~IN"NR2 2. R2-CO2H, 140~ 25-95% III.B.1-6 Waldvogel, S.R. et al., S, 2689.

Me 9

Me N/OH

Ph-Me,reflux

.

NH2

59-93% IH.B.1-7 Yamada, T. et al., OL, 5, 3555.

cN~p(ph.Me) 2 NaBD4,TFA'd, , ' 4 0CHCI3 ~ Ar O A~._.~Ar Ar~ f--__N,,N~------~ Ar o~o~C%o/~o Me

~ I~H,,NH2 Ar 85-99% ee = 88-94%

Me

IH.B.1-8 Mebane, R.C. et al., SC, 33, 3373.

R-CN

RaNi, NaOH iPrOH, reflux

~

Me 1. aq HCI N~ .... ~ Ph~NH3+CI" Ph~ Me 2. KOH 3. HCI, Et20 88-97%

REDUCTIONS

123

III.B.2. Reduction of Heterocycles

III.B.2-1 Zhou, Y.-G. et al., JACS, 125, 10536. R

~

R

R1 H2,12,[Ir(cod)Ci]2, Ph-Me, r t Ph2P Ph2P,~

PPI~ PPh2

R1

~ 83-95%

ee = 72-96%

III.B.2-2 Faigl, F. et al., T, 59, 7897. OH R--~

1. H2, Pd/C, AcOH 2. HCI 61-91%

H-HCI

III.C. Reduction of Sulfur Compounds

III.C-1 Karimi, B.; Zareyee, D., S, 335.

R,.g,.,O NaBH4~12 ~1

R~ s

THF, rt 57-98%

III.C-2 Karimi, B.; Zareyee, D., S, 1875. 1~ s~O NBS, I2, HSCH2CH2CO2H ~IL ]~1 MeCN, rt

S

55-98% III.C-3 Yoo, B.W. et al., SC, 33, 53. R. g,.O TiCl4, In ~l

THF, rt

g'S 87-95%

III.C-4 Solladie, G. et al., TA, 14, 1291. "New Insights into the Reduction of 13,8-Diketosulfoxides."

124

ORGANIC SYNTHESIS--2004

III.D. N-O Reduction

III.O-1 Yoo, B.W. et al., SC, 33, 4185; Balicki, R. et al., SC, 33, 4137. 0 + TiCh'In ~N O" THF,rt 85-95%

III.D-2 Camps, P. et al., T, 59, 4143.

OH

~-

OH

H2

I

78% 1.1:1

OH

III.D-3 Goti, A. et al., OL, 5, 1773. R.N, OH In R. NH ~1 aq NH4CI/EtOH ~1 51-99%

III.D-4 Wang, L. et al., S, 2001; Bhaumik, K.; Akamanchi, K.G., CJC, 81, 197; Kim, B.H. et al., TL, 44, 77; Yoo, B.W. et al., SC, 33, 2985; Yoon, C.M. et al., T, 59, 10331; Wu, G. et al., S, 1657. j ~ Fe powder /<~__ NO2 H20,210~ ~NH2 37-96% III.D-5 Gowda, D.C. et al., SS, 33, 4221. AcNH~ Pb Ar-NO2 ~ Ar.,I~N,Ar MeOH, rt

82-91%

REDUCTIONS

125

IH.E. C-C M u l t i p l e B o n d R e d u c t i o n s

III.E.1. C = C R e d u c t i o n s

III.E.I-1 Paryzek, Z. et al., S, 2023; Yoon, C.M. et al., OBC, 1, 1099. R ~ R2 .HCO2NH4'Pd/C _'...- R I " ~ ~ R 2 R

X

MeOH, reflux

R

X

71-99% III.E.1-2 Czekelius, C.; Carreira, E.M:; AG(E), 42, 4793; Lipshutz, B.H.; Servesko, J.M., AG(E), 42, 4789; Jurkauskas, V.; Sadighi, J.P.; Buchwald, S.L., OL, 5, 2417. R1 NO2 R1 NO2 PMHS,Ph3SiH, tBuOCu, josiphos

>=/

R

),,,t/

H20/Ph-Me, rt

R

55-94% ee = 66-94 % josiphos = 1-[(2-diphenylphosphanyl)-

ferrocenyl]ethyldicyclohexylphosphine III.E.1.3 Rampf, F.A. et al., CC, 2210; Hoge, G., JACS, 125, 10219; Bakos, J. et al., TA, 14, 1087; Kissel, W.S. et al., JOC, 68, 5731; Zhang, M. et al., OL, 5, 1587 and AG(E), 42, 943; Imamoto, T. et al., TA, 14, 2171; Nakano, D.; Yamaguchi, M., TL, 44, 4969; Bakos, J. et al., TL, 44, 9025. R1 HN-Ac H2,[Rh(cod)2]OTf,CH2CI2,rt R1 HN-Ac 64-99% ee = 8-96 %

III.E.1-4 Beletskaya, I.P.; Pfaltz, A. et al., TA, 14, 1397; Knochel, P. et al., AG(E), 42, 3941; Cozzi, P.G. et al., SL, 833; Burgess, K. et al., JACS, 125, 113; H2, [Ir(cod)(lig)]+(BAr4)", CI-12C12,rt Me AAP(OEt)2 ~ Ar'~P(OEt)2 o

o (Me'Ph)2P

82-99%

ee = 70-94 %

126

ORGANIC SYNTHESIS--2004

III.E.1-5 Li, X.; Chan, A.S.C. et al., JOC, 68, 4539; yeung, C.H.; Chan, A.S.C. et al., TA, 14, 987; Weberskirch, R. et al., CEJ, 9, 3228; Mikolajczyk, M.; Chauvin, R. et al., OM, 22, 4810; Sajiki, H.; Ikawa, T.; Hirota, K., TL, 44, 8437; Beller, M. et al., JOM, 675, 91; Evans, D.A. et al., JACS, 125, 3534; Doherty, S. et al., TA, 44, 1517; Ward, T.R. et al.,JACS, 125, 9030 A ~ C O 2 M e H2, [Rh(cod)2BV4l,Tar, r t Aff~,CO2M e NHR

~

NHR 100% conversion ee = 96-99%

Op_NEtz o

III.E.1-6 Zhang, X. et al., AG(E), 42, 3509 and JACS, 125, 9570; Yeung, C.; Chan, A.S.C. et al., JOC, 68, 2490; Minnaard, A.J.; Feringa, B.L. et al., OBC, 1, 1087; Holz, J.; Borner, A. et al., JOC, 68, 1701 MeO2C~HN-Ac H2, Rh-binapine ~,- MeO2Cx,,,,~N'Ac Ar

THF, rt

Ar 99% ee = 96-99%

III.E.1-7 Giri, V.S. et al., S, 1549; Buchwald, S.L. et al., JACS, 125, 11253. O ~ O R

PPh3

MeOH ~ O ~ ~

R

O

55-75% III.E.1-8 Firouzabadi, H.; Iranpoor, N.; Alinezhad, H., BCJ, 76, 143. {[~.-CX Zr(BH4)2CI2(DABCO)2'Na(BH3CN).-- ( ~ ~ - C X ZnCI2, MeOH, A 82-91% (similarly for imines, reductive aminations) III.E.1-9 Ranu, B.C.; Samanta, S., JOC, 68, 7130 and T, 59, 7901; see also: Yamada, T. et al., TA, 14, 967. Rl NaBH4,InO3 ~. R,.,.~,,,,,,~R 1 MeCN, rt 77-97% [also with tx,~unsaturated ketones]

REDUCTIONS

127

III.E.I-10 Lee, H.-Y.; An, M., TL, 44, 2775. R1

O

R~3

R1 R2

C~ H20 ~ DME. reflux

O

RR ~ ~ 3

R2

0-99% III.E.I-ll Reetz, M.T.; Goosen, L.J. et al., OL, 5, 3099; Boulton, L.E. et al., OBC, 1, 1094; Vankelecom, I.F.J. et al., CEJ, 9, 334; Zheng, Z.; Chen, H. et al., OL, 5, 4137; Ojima, I. et al., OL, 5, 3831; see also: Lennon, I.C.; Pilkington, C.J., S, 1639. "Enantioselective Rh-Catalyzed Hydrogenation of Vinyl Carboxylates with Monodentate Phosphite Ligands." III.E.I-12 Ager, D.J.; Prakash, I., OPRD, 7, 164. ~ ~ ~ "CO2H H2, R h / C ~~b~ NH2 ~ ~

cO2H NH2

81-97%

III.E.2 C-C Reductions

III.E.2-1 Tsuji, Y. et al., CC, 2820. 1. Ti(Oipr)4, BuLl, THF, -78~ R

~

R

2. H3O+

90-99%

III.E.2-2 Huang, X. et al., JOC, 68, 1958. 1. Cp2Zr(H)CI, THF, rt R ~ Ts 2. E +

III.E.2-3 Wu, M.-J. et al., TL, 44, 1979. Pd(OAc)2, NaOMe R

~

R1

R1

R1

MeOH

R r

,_/ R

0-92%

E Ts 40-72% E:Z = 9.2-99:1

R1

R

R1

+ 0-50%

128

III.F.

ORGANIC SYNTHESIS--2004

Hetero Bond

Reductions

III.F.1. C-O --->C-H

III.F.I-1 Merschaert, A. et al., TL, 44, 4531; Kolis, S.P. et al., TL, 44, 5707. Me Ar Me OH Me Boc,, -~ Boc,, r Boc,, r EtOH Ph-Me, 100~ 52% 4.5:1 85% 24:1 III.F.1.2 Lautens, M.; Paquin, J.-F.; OL, 5, 3391. O OPG O OPG ~ O C O 2 R 3 Pd(OAc)2'Bu3PHBF4 ~._ HCO2H/TEA,MeCN,40*C- R ~ 60-89% dr = 1.4-20:1 III.F.1-3 Crich, D.; Yao, Q.; OL, 5, 2189; Dang, H.-S. et al., OBC, 1, 1330. I BnO

Bu3SnH, AIBN .~ B z O . ~ O ~ o R Ph-Me, reflux BnO--x~ -

~

74-80%

III.F.1-4 Deniau, E. et al., TA, 14, 2253. O ~ R

~MN-

O

Et3SiH,TFA ~ ~ I N . _ ~ CH2C12,-78~ -' rt e

III.F.1-5 Haldar, P.; Ray, J.K., TL, 44, 8229. EtO2 NaBH, I2 ~ EtO2 EtO2C~ ~ O THF - EtO2C~N/ Ar Ar 77-84%

'OMe 62-92%

REDUCTIONS

129

I I I . F . 1 - 6 0 h t a , T. et al., CC, 1192. 3 2 1. PhSiH3, RhCI(PPh3)3 R ~OR OR R1

2. aq

NaOH

R ~ O R2 R1 64-91%

III.F.2. C-Hal --> C-H

III.F.2-1 Nishiyama, Y.; Sonoda, N. et al., T, 59, 6609. "Dehalogenation of o-Dihalogen Substituted Arenes and a,a'Dihalogen Substituted o-Xylenes with Lanthanum Metal." III.F.2-2 Hilmersson, G.; Flowers, II, R.A. et al., JOC, 68, 4870. "Rapid Sml2-Mediated Reductions of Alkyl Halides and Electrochemical Properties of Sml2/H20/Amine." III.F.2-3 Kadota, I.; Yamamoto, Y. et al., TL, 44, 8645. R~.~.I Zn-Cu, AcOH ~ R,,.~.~I I MeOH/THF 74-95% cis:trans = 100-1:1-3 III.F.2-4 Wang, L. et al., SL, 1137. Ar~,,,Br Sm Br MeOH,45~

R - " ~ rBr

95-98% Z:E = 1:1.5-3.5 (also further reduction to alkenes and alkanes)

III.F.2-5 Taillefer, M.; Cristau, H.-J. et al., TL, 44, 7191. X~__ N2H4"HCI'Pd/C' NaOH R ~ R Ph-Me, rt 42-99% III.F.2-6 Yus, M. et al., T, 59, 1237. R-F + ~ T M S " ~ "TMS

Li, DTBB

R-H 28-86%

130

ORGANIC SYNTHESISm2004

III.F.3. C-S --->C-H

III.F.3-1 Boivin, J. et al., OL, 5, 1645. o H3PO2, AIBN, TEA SO2Ph

O

(EtO)2PH(O)

~SO2Ph 49-89%

S III.F.3-2 Petrini, M. et al., SL, 1129. RL SOzPh NaBH3OAc ~R1 H

dioxane,reflux

R~N

-',, R 1 H

68-96% III.F.3-3 Yoda, H. et al., SC, 33, 1087. o o

o

Sm'

Ph THF, rt R (O)n

6-68%

(also for iactams)

III.G. Reductive Cleavages

III.G.1. Oxiranes

III.G.I-1 Concellon, J.M.; Bardales, E., OL, 5, 4783; Ikariya, T. et al., OM, 22, 4190. o R ~ R I NR2R3 S m I 2 R ~ _ O MeOH '~ NR2R3 R1 62-80% III.G.1-2 Yu, J.-Q. et al., OL, 5, 4665. "Recyclable Polyurea-Microencapsulated Pd(0) Nanoparticles: An Efficient Catalyst for Hydrogenolysis of Epoxides."

REDUCTIONS

131

III.G.1-3 Concellon, J.M. et al., JOC, 68, 1585. R2 R2 R ~ C O 2 R 3 1. SmI2,THF, reflux R~RD1CO2R3 2. D20 R1 49-85%

III.G.1-4 Tu, Y.-Q. et al., CEJ, 9, 4301. OH ~]~ SmI2 ~ ~ OCOR1 O + RI'cHO - N,~,~O" ' r'H R DCE, rt~ 70~

~ _ O~HcoR1 R

R

0-62% 1.5-99:1 III.G.1-5 Mal, D. et al., TL, 44, 2355. .,j(?~[j~ R2 O R-

"~.

R1

Mo(CO)6 A ~ R2t~ ~'~ R3

Ph-H or Ph-Me,

"

R3

'R1

0-96% III.G.1-6 Howell, A.R. et al., JOC, 68, 1480. h/~O Nuc-TMS,T B A ~ p h ~ p CH2C!2

~Nuc OH 27-90%

III.G.2. N--O Cleavages III.G.2-1 Demitz, F.W.J. et al., TL, 44, 8217. R ~'w"q Ni~ Zn anode R ~ O H e

§

R~OH

R" "CO2Me R" "CN 23-99% 1:100-13:1

132

ORGANIC SYNTHESISm2004

III.G.3. Other Reductive Cleavages

III.G.3-1 Faucher, A.-M.; Grand-Maitre, C.; SC, 33, 3503. l~s,,.O P(CH2CH2CO2H)3 ~_ R'- S

kl

k'

98-99% (similar reductions of sulfonyl chlorides, N-oxides and azides)

III.H. Reduction of Azides

No Entries

III.I. Other Reductions

III.I-1 Gosmini, C. et al., TL, 44, 6417. " N e w Progress in the Cobalt-Catalysed Synthesis of Aromatic Organozinc Compounds by Reduction of Aromatic Halides by Zinc Dust." IIl.l-2 Shuto, S. et al., JOC, 68, 9155. Ph i.~

I,.IL...IL

t~'N"~OTBDPS S O

TMS3SiH, Et3B or AIBN "" ~" eh ~,,~',~"~OTBDPS ' THF or Ph-H 22-80% cis:trans = 2.5-14:1

III.I-3 Caddick, S. et al., T, 44, 5417. NiCI2.6H20, NaBI-I4,Boc20 R-CN MeOH

R ~ N -B~ H

21-96% III.I-4 Zhang, C.-R.; Wang, Y.-L., SC, 33, 4205. O O R.J~N~N,,Ar N2H4.H20~ R.,U.,N.N~ArH EtOH H 69-91% (similar reduction of azo compounds)

IV SYNTHESIS OF HETEROCYCLES IV.A. Oxiranes, Aziridines and Thiiranes

IV.A-1 Aggarwal, V.K.; Lee, H.-Y. et al., AG(E), 42, 3274; Forbes, D.C. et al., OL, 5, 2283; Ciaccio, J.A. et al., SC, 33, 2135; Metzner, P. et al., S, 2249. R~O ' ~ R1

+

,O~R2

~N~BF4"

f,\.,S+~R2 KOH or phosphazene b a s e

R,,

~

R1

Q ~

37-93% dr = 1.7-99:1 ee = 71-99%

IV.A-2 Bacieredo, A.; Branchadell, V.; Ortuno, R.M. et al., JOC, 68, 7707. R1

CHO +

--vR2

THF, rt

~

R1

\/', O PR2 S 65-87%

IV.A-3 Che, C.-M. et al., TL, 44, 5917. n

R

~

H 2

PhIO,Rh2(4S-MEOX)4, Al203 Ph-H, 5"C

R

~ 02 68-95% ee = 55-76%

IV.A-4 Cui, Y.; He, C., JACS, 125, 16202; Suga, H. et al., BCJ, 76, 189. R1 R1 AgNO3, tBu3tpy ~- R~~~N~R2 R-~ R 2 + PhI=NTs MeCN I

Ts 66-91% (similar chemistry using Cu catalyst) 133

134

ORGANIC SYNTHESISm2004

IV.A-5 Tang, Y. et al., CC, 2074; Linclau, B. et al., JOC, 68, 8252.

R-CHO -I- B r f " ' ~ R 1

K2CO3

~

tetrahydrothiophene/tBuOH, reflux

R1 75-96% cis:trans = 1:3-1.22:1

IV.A-6 Lindsay, Smith, J.R.; Reginato, G., OBC, 1, 2543. "Asymmetric Alkene Epoxidation Catalyzed by a Novel Family of Chiral Metalloporphyrins: Effect of Structure on Catalyst Activity, Stability and Enantioselectivity." IV.A-7 Vedernikov, A.N.; Caulton, K.G., OL, 5, 2591; Hutchings, G.J. et al., CC, 2808; Kantam, M.L. et al., TL, 44, 9029. "Angular Ligand Constraint Yields an Improved Olefin Aziridination Catalyst." IV.A-8 Jain, S.L.; Sain, B., TL, 44, 575; Thakur, V.V.; Sudalai, A., TL, 44, 989.

R1 R%

R1 CuCI, 5A MS,~ R ' ~ , , R2 R2 + TsNIK MeCN ~? k 3 Ts 40-80%

IV.A-9 Katritzky, A.R. et al., JOC, 68, 407.

R~O LDA .~. B t ~ R + Bt-CH2C! R1 THF, -78~ Rx 62-75% IV.A.10 Loreta, M.A. et al., TL, 44, 4953. R

~ 2

R

1

?O2~21 EtO2CNHONs,CaO CH2C12

39-60% IV.A-11 Alves, M.J. et al., TL, 44, 6277. "Optically Active Aziridine Esters by Nucleophilic Addition of Nitrogen Heterocycles to a Chiral 2H-Azirine-2-Carboxylic Ester."

SYNTHESIS OF HETEROCYCLES

135

IV.A-12 Aggarwal, V.K.; Vasse, J.-L., OL, 5, 3987. ( P h Rh2(OAc)4~PTC, dioxane, 40~

~I~SE

+ TS,,N. N S Na

%•PsEs

, ~ ~,

52% dr = 8:1 ee = 98 %

Iu Yadav, J.S. et al., TL, 44, 5275 and S, 1387; Bergman, R.G.; Tilley, T.D. et al., JOC, 68, 9705. Ar LiCIO4 A R-CHO + Ar-NH2 + N2CHCO2Et MeCN, rt R CO2Et 75-91% cis:trans = 4.55-100:1 IV.A-14 De Kimpe, N. et al., TL, 44, 1137.

,J NaOMe

OMe

~ , ] I I , , .

R- ~ "

MeOH, A

R51-85%

IV.A-15 Davis, F.A. et al., JOC, 68, 6894, 2410. D I LiI-IDMS r" M e ~ ~" ~ Ph-X + O~P(OEt)2 THF, -78~

X-Ph",~ 'P(OEt)2 S, O (3)" Mes 72-82%

IV.A-16 Katritzky, A.R. et al., JOC, 68, 9105. HO.,N

RI~B t

Ts-CI,aq KOH

~Bt R" 58-66%

IV.A-17 Kazemi, F.; Kiasat, A.R.; Ebrahimi, S., SC, 33, 595. R (NH2)2CS,LiBF4 R MeCN, reflux 80-96%

136

ORGANIC SYNTHESIS--2004

IV.A-18 Stockman, R.A. et al., SL, 1985. D Nail tBu~X,N~R + Me3S+[" DMSO, rt

~"'7"7,

NI R

O'%u 63-84%

de = 77-95%

IV.A-19 Filippone, P.; Stanovnik, B. et al., SL, 995. Hz RO2C,N ~ . ~ O 2 R I + ~ CO2Me .. Me2N-~CO2 Me Ph.Me, reflux~ HN"~"~CO2 R1 Me NHBz RO2C Me 51-70% IV.A-20 Hashimoto, M.; Matsumoto, M.; Terashima, S., T, 59, 3041, 3019, 3063, 3089; Fernandez-Bolanos, J.G.; Bolf, M. et al., OBC, 1, 478; Schirmeister, T. et al., TA, 14, 3301.

Bn~..OBn O~~c~OEE Ms

Bn t

,.OBn

KHMDS.1~ THF, 60~

C ,OCo2Et 2Et 63%

IV.A-21 Suarez, E. et al., OL, 5, 3729; Somfai, P. et al., TL, 44, 5339; Gudmundsdottir, A.D. et al., TL, 44, 6763; Alajar~, M. et al., S, 49.

OR A_ c O ~ ~ OHCO

N3

OR Ph.Me,reflux~ A_ _ ~ OHCO 63-85%

IV.A-22 Palacios, F. et al., TA, 14, 689. TSO'N O R"n(OEt)2.~/r II

K2CO~chiral base Ph-H, rt

~-

o,

~P(OEt)2

R~ 49-97% ee - 2-72%

SYNTHESIS OF HETEROCYCLES

137

IV.A-23 Yadav, J.S. et al., SL, 396; Salehi, P.; Khodaei, M. et al., SC, 33. 3041. R InBr3 R ~ R 1 +KSCN MeCN, A ~ ~-S-S-S~R 1 80-95% IV.B. Oxetanes, Azetidines and Thietanes

IV.B-1 Shi, M. et al., OL, 5, 4737. /COY DABCO,4A MS Ar'~NTs + --- " Ph-H ~

/~___/COY Ar"~Nf Ts 42-99%

IV.B-2 Couty, F. et al., SL, 726. c02Et CN Li.o

Bn

.=--CO2Et S

~

THF, -78~

CN Bn 58-73%

IV.B-3 Jiang, J. et al., OL, 5, 4101. "Synthesis of 4-Trifluoromethylated 2-Alkyl and 2,3-DialkylSubstituted Azetidines." IV.B-4 Sakamoto, M. et al., CC, 2218. "Diastereoselective Photocycloaddition of Axially Chiral Monothiosuccinimides to 1,1-Diphenylethylene."

IV.C. Lactams IV.C- 1 Lautens, M. et al., JACS, 125, 4028. Ar O ~ N H + Ar-CH=X MgI2 THF I

Ar

Ar 38-81%

138

ORGANIC SYNTHESIS--2004

IV.C-2 Perlmutter, P. et al., EJOC, 756; Danheiser, R.L. et al., OS, 80, 160; Lectka, T. et al., SL, 1937; Tavani, C. et al., T, 59, 10195; see also: Williams, R.M. et al., OL, 5, 2095. O ,-"~,, "Ph SnCl4, TEA ~ r 4N~"'~Ph C12C12

Me~"ph

25-79% IV.C-3 Shintani, R.; Fu, G.C., AG(E), 42, 4082. / CuBr,Ph(TMSO)C=CH~ KOAc + Me

-0- l~Ar

O~

Me. ICeMe Me~

70% ee = 90%

Me Me

IV.C-4 Tang, Y. et al., CC, 2554; Cordero, F.M.; Salaun, J.; Brandi, A. et al., JOC, 68, 3271; Jimenez, J.L. et al., JOC, 68, 6338; Alcaide, B.; Almendros, P. et al., JOC, 68, 1426; Alcaide, B. et al., JOC, 68, 3106.

R

R1

Cu(CIO4)2"6H2O, cy2NH,ipr-trisoxazoline

IIll + "O"~'R 2

'

/N~ iipr

39-63%

ee = 55-82% ~Pr

IV.C-5 Ryu, I.; Komatsu, M. et al., JACS, 125, 5632. Bu3SnH, AIBN, CO

n

Ph-H

Bu3Sn~)

(~~R 61-88%

IV.C-6 Gottlich, R. et al., S, 1886.

O~~~ 1 R

R1

O~'-k R2

<~No~~ Pd

R

~_(

CuCi .~ o ~ / C l MeOH, 60~ R 12-96%

SYNTHESIS OF HETEROCYCLES

139

IV.C-7 Zhang, T.Y. et al., TL, 44, 5991; Magriotis, P.A. et al., SL, 2398; Benaglia, M. et al., JOC, 68, 2952; Almquist, F. et al., OBC, 1, 1308; Avenoza, A.; Peregrina, J.M. et al., JOC, 68, 2889; Hart, B.P. et al., JOC, 68, 187; Bongini, A. et al., TA, 14, 993; Marchand-Brynaert, J. et al., S, 2483; Gonzalez-Muniz, R. et al., TA, 14, 2161.

OH Phth~,~ P(OEt):~DIAD P h t h ~ O~'-NH~ eh-Me,90~ LCO2PNB

CO2PNB 97%

IV.C-8 Naskar, D. et al., TL, 44, 6297.

Ri 1

R1

R

9

CO2H

H20/MeOH 23-79%

IV.C-9 Zhang, J. et al., OL, 5, 553; Chang, M.-Y.; Chang, N.-C. et al., H, 60, 1865.

CI_ CI O ~ NaBH(OAc)3 OH + R-NH2 AcOH/CH2CI2

o~CI R

40-75% IV.C-10 Jung, K.W. et al., OL, 5, 2259; Hu, W. et al., SL, 1965.

PhSO2T~Ph O-f "N" R

PhSO3,, ~Ph Rh2(OAc)40~ CH2C12,reflux R 50-91%

IV.C-11 Mizutani, T.; Ukaji, Y., Inomata, K., BCJ, 76, 1251.

MeO2~ 1 ~ R R1 CO/O2'PdCI2(MeCN)2' R2OH/THF CuCI2~ O~N~R ~ Ts

Ts 52-88%

140

ORGANIC SYNTHESISm2004

IV.C-12 Clark, A.J. et al., OL, 5, 2063; Kikugawa, Y. et al., JOC, 68, 5429, 6739. RO2~~ RO2~~_.~ CAN ~ OH O /Pr MeCN,rt ~ ipr PMB PMB 65-67% (other examples are given) IV.C-13 De Kimpe, N. et al., OPP, 35, 215.

N

i

1. Br2, CH2C12,0~ 2. K2CO3, MeOH

I~

O ~

R

Br

R

65-77%

IV.C- 14 Stalinski, K. et al., JOC, 68, 1552; Miranda, L.D. et al., T, 59, 4953. ~ R 1 TMS

Br

O~,,.~CO2Me

tBuOH' 80oc

LCO2Me 32-90%

IV.C-15 Overman, L.E. et al., JACS, 125, 6261. ~OT~o

~1OMe Pd(OAc)2,BINAP .~ ~

O

OMe

PMP, THF, 80~ Bn

24-95% ee = 71-98% IV.C-16 Milkiewicz, K.L. et al., TL, 44, 7341. R2

100~

"y_ O

R

23-97%

SYNTHESIS OF HETEROCYCLES

141

IV.C-17 Pinho, P.; Minnaard, A.J." Feringa, B.L., OL, 5, 259. O(~NH ( n,

+

r

R2 R R1

Br R2 Pd(OAc)2'P(T~ Na2CO3'Bu4NCI~ ~ ~l/. . ~ - 'R 1 MeCN, D

Ts

Ls T 49-82%

IV.C.18 O'Connor, S.J.; Liu, Z., SL, 2135. 2

R~CO2Et 1. Ph-CHO,K2CO3,4.~ M S NH2oHC1 2. tBuONa,DMF,-20~ 3. Fe, aq HCI,EtOH, reflux

H

1-24%

IV.C-19 Smith, K. et al., S, 2047. R,~Br

1. MeLi,0oc R N"CONMe2 2. tBuLi,0~ ~ H 3. CO, O~

IV.C-20 Rangappa, K.S. et al., JHC, 40, 607. MeO2C

~ O H

71-79%

HO

aaNi,. o2

Ph

H20/MeOH, reflux

Ph

65-73%

IV.C-21 Imhof, W. et al., T, 59, 8499. Ph

Ph

4- R~ N ~1

CO' Ru3(CO)12 ~ R ~ R1 80-92%

IV.C-22 Hennessy, E.J.; Buchwald, S.L., JACS, 125, 12084; Procter, D.J. et et al., al., CC, CC, 2380. 2380. D.J. R__a~~NI~OI Pd(OAc)2,TEA,Ph-Me,80o.c .-~-R , ~ PBu2 O "Ph R1 76-99%

142

ORGANIC SYNTHESISm2004

IV.C-23 Morimoto, T.; Kakiuchi, K. et al., CL, 32, 155. NI-ITs C6F5CHO'[RhCI(cOd)]2'dppp'K2CO3 ~ I ~ N ~ Ph-Me2, 130~

H

~Br

O 66-92%

IV.C-24 Grigg, R. et al., TL, 44, 7441. , n - " EWG

le-'~)l

r~EWG

co, Pd(OAc)2, Cs2C03 +

R-NH2

Ph-Me, 900C O 52-99%

IV.C-25 Clayden, J. et al., SL, 1701; Clayden, J.; Menet, C.J., TL, 44, 3059. ~ Ph,,~Me tBuLi,DMPU %t~N~Ph,, Me R - ~

~Kipr TI-IF,.78~ ~ O

~ N " O

ipr

46-80%

ee = 99% IV.C-26 Murphy, J.A. et al., OL, 5, 2971. DEPO, V-501 ~_ ~ H20

O Me 97%

I

IV.C-27 Liu, L., S, 1705; Kanda, Y. et al., JMC, 46, 2467; Silva, D.J. et al., TL, 44, 4567. NRR1 BuLi,

Ph-Me

ME

Me

19-53% ee = 5-77%

SYNTHESIS OF HETEROCYCLES

143

IV.C-28 Deshmukh, A.R.A.S. et al., S, 1903; Dechoux, L. et al., TL, 44, 5311. NHR1 NHR1 MeO2 HCO2NH, Pd/C R t. MeOH, rt "NO2 H 62-80%

IV.C-29 Chang, M.-Y.; Chen, S.-T. et al., T, 59, 7547; Chang, N.-C. et al., SC, 33, 1375; Hu, Y. et al., S, 487; Takasu, K.; Ihara, M. et al., TL, 44, 7429. ~..+OBn (n ~ J "OBn Ts

CO2Et

HN,~O

Nail

~.~Ts

THF,reflux '~" O-,.-..N,-~-,-O

I

I

R

R 50-61%

IV.C-30 Hodgetts, K.J.; Kershaw, M.T. OL, 5, 2911. Ar

Br

1. ArB(OH)2,Pd(PPh3)4,K2CO3

I~C C

DME, 80~ 2. 2-NH2C6H4B(OH)2 H 69%

O2Et

IV.C-31 Duchene, A. et al., TL, 44, 5791; Knight, J.G. et al., TL, 44, 757. ..SnBu3

R1

R1

~~ll~O Pd(OAc)2'PPh3' K2CO3,Bu4NBr R ~ MeCN, 80~ O I R 79-87% IV.C-32 Kibayashi, C. et al., OL, 5, 3249. OM OM OH

Pr4NIO4 CHCI3,0~ OHoMoM 80%

144

ORGANIC, SYNTH ES ISin2004

IV.C-33 Beccalli, E.M. et al., JOC, 68, 7625; Beccalli, E.M.; Broggini, G., TL, 44, 1919. Me ~ , ~ ~ NR

PdCI2(MeCN)2,BQ ~ DMF/THF,80~ "-

N R

O

O 60-98%

IV.C-34 Kamal, A. et al., TA, 14, 2587. "Chemoenzymatic Enantioselective Synthesis of 3-Hydroxy-2pyrrolidinones and 3-Hydroxy-2-piperidinones." IV.C-35 Iqbal, J. et al., JOC, 68, 4079. "Cobalt-Catalyzed One-Pot Three-Component Coupling Route to 13Acetamido Carbonyl Compounds: A General Synthetic Protocol for y-Lactams." IV.C-36 Maryanoff, B.E. et al., OL, 5, 4537; Chou, S.-S.P. et al., TL, 44, 4653. + R.N=C=O

CpCo(CO)2 DME, 850C

N~t O 20-70%

IV.C-37 Werdrop, D.J. et al., TL, 44, 2587. Me

Me

Me

PIFA OMe MeOH/CH2CI2 OMe

OMe 94%

dr= 49:1 IV.C-38 Bach, T. et al., JOC, 68, 1107. hv, Ph-Me, -55~ NH

H

"

66% ee = 57%

O

SYNTHESIS OF HETEROCYCLES

145

IV.C-39 Hoornaert, G.J. et al., EJOC, 1868.

~~~h CI

1.Ph-Br,reflux 2. H20/EtOAc,rt

O

O

86% IV.C-40 Batanero, B.; Barba, F., JOC, 68, 3706.

O RI~~k~R~O

R1 electrolysisI~ ~ ~ 1

C13

R 70-82%

IV.C-41 Levacher, V. et al., JOC, 68, 9517; Li, C. et al., OL, 5, 361.

"Novel Extension of Meyers' Methodology: Stereoselective Construction of Axially Chiral 7,5-Fused Bicyclic Lactams." IV.C-42 van Maarseveen, J.H. et al., AG(E), 42, 4373.

RN~O ph/,,,,R r O DABCO o~S,~pphN3 H20/THF'70~ Ph/~ H BH3

35-60%

IV.C-43 Brimble, M.A. et al., OL, 5, 1847; Colombo, L. et al., T, 59, 4501; Gmeiner, P. et al., JOC, 68, 62; Banff, L. et al., TL, 44, 7655.

~'N-N~ co2tBu ~N"CO2B n

PhCH=Ru(PCy3)2CI2 CH2CI2,reflux

co2tBu I CO2Bn 46%

146

ORGANIC SYNTHESISm2004

IV.D. Lactones

IV.D-1 Ma, S. et al., OL, 5, 4429. CI~R R ~

R1

PdCI2,CuCI2, CO

(OH 'R2

THF, 30~

I

JX ,,R1 O=~O~R2 50-91%

IV.D-2 Saravanan, P.; Corey, E.J.; JOC, 68, 2760. "A Short, Stereocontrolled and Practical Synthesis of Methylomuralide, A Potent Inhibitor of Proteasome Function." IV.D-3 Sweeney, J.B. et al., OL, 5, 757. ~ S

O

R2~," R3 Bu3SnH,hv

. o OoV

Ph-Me, 80~

R2

.o

R3 13-61%

IV.D-4 Borhan, B. et al., OL, 5, 3089; Lopp, M. et al., TA, 14, 1565; Suzuki, T.; Hiroi, K. et al., TL, 44, 2003.

~

Oxone, OsO4

"~oin

H

O ~

)n

DMF

42-73%

rCO

IV.D-5 Pohmakotr, M. et al., TL, 44, 6717; Taylor, D.K. et al., S, 668. A

O2Et 1. LDA, THF, -78~

A r

EtO2C

2. ArLCHO, ZnCI2, -78~ -~ rt

2Et

~O~...Arl 47-74%

IV.D-6 Tiecco, M. et al., SL, 655. PhSe Ts(k~~)n

(PhSe)2,DDQ R

O

R

40-76%

SYNTHESISOFHETEROCYCLES

147

IV.D-7 Wirth, T. et al., OL, 5, 2157. Phi(OAt)2 c ii HO2k'~'~Ph CH2C12,rt

O ~

Ac

87%

Ph

IV.D-8 Doyle, M.P.; Catino, A.J., TA, 14, 925; Muller, P. et al., TA, 14, 1503. ~ ~ O

Rh2(MPPIM)4~ CH2CI2,40"C

O:~o~' O " 73% ee=91%

IV.D-9 Fukuzawa, S. et al., JOC, 68, 2042; Naito, T. et al., JOC, 68, 5618. II _,R SmI2 ~ .NMe2 _ II M..~O~

oR

4" oac----~

NBn2 tBuOH,0~

Ph O

IV.D-10 Meyer, C. et al., SL, 663. NHR EtO2@O,,,] 1. BuLi, THF, .78"C 2. TMS-CI 3. Bu4NF,THF

NBn2 13-83% dr = 1-1.87:11.5-1

59-79%

IV.D-11 Willis, M.C.; Flowers, S.E., SL, 1491. ME

0

M~ +

"OJMS

TiCI4 CH2C12'"78~

O

rt "~

O 81%

IV.D-12 Ma, S.; Yu, Z.; JOC, 68, 6149; Takahashi, S. et al., JOC, 68, 8571. R

R1

HO2g

XR2

1{3 X

PdCI3

o ~~R RR

DMA,50oc 69-95%

3

148

ORGANIC SYNTHESIS--2004

IV.D-13 Chatanai, N. et al., AG(E), 42, 1397; Raubo, P. et al., SL, 2021. R

/" ~ ~ ~ " ' R ,

t

[PdCI(h3"C3H5)]2'Cy2NMe~

u

-....- ~o_P(OEt) 2

O

THF, 80~

50.94% IV.D-14 Wada, E. et al., TL, 44, 7953. RI~

H

Ni(CIO4)2 or Yb(OTf)3 R1 R2 H O ~ R ~

+ Et~NO2

38-68% IV.D-15 Quayle, P. et al., SL, 1797. Cl c13c R1 O ~

1 @ ~ R PhCH=Ru(PCy3)3CI2 C CH2C12 '~ ~ X).....R1 25-70%

IV.D.16 Liu, R.-S. et al., JOC, 68, 1872 and JACS, 125, 9610.

It'

,I R 28-92%

IV.D-17 Posner, G.H. et al., TL, 44, 5407. R

R

~

PhI(OAc)2,12_ )n

CH2C12,0*C

OH

)n O

79-91% IV.D-18 De, A. et al., SL, 1474. R-g'~C'SMeNE 1. SBuLi,TMEDA, -780C~ rt O~2' t2 2. AcOH, reflux 71-78%

SYNTHESIS OF HETEROCYCLES

149

IV.D-19 Juhl, K.; Jorgensen, K.A., AG(E), 42, 1498. R1

1. ~ (Ph3'~5"Me2)2 1~~OOR1

CHO +

CO2R2

SiO2, CH2C12,-15~ -' rt 2. PCC, CH2C12

CO2R2 62-93% ee = 80-94%

IV.D-20 Zhang, Z.; Zhang, X. et al., JACS, 125, 6370; Sasai, H. et al., TL, 44, 5201. R

[[

RhCI(PPh3)3 o~

l

DCE, reflux 72-92%

(lactams similarly prepared) IV.D-21 Yadav, L.D.S.; Singh, A.; S, 2395. Ar I Ar 1 ~)t::: I~W AcHN'"" ' ~ ' ~ SAc20 + NH2CH2CO2H + S -------~ O&'~~r~==:S" -O ~ kr

73-86% kr

IV.D-22 Cheng, C.-H. et al., OL, 5, 4903. O R

R

~

R

~

R802Cv R7 NiBr2(dppe), Z n

R

R5 +

AN 6

MeCN,80~

R3 R4

R

I

~

R

"-- R ~ ~ ' ~ " ~ R R3 R4 55-81%

IV.D-23 Shimizu, M. et al., TL, 44, 2061. O ~ R3 R I ~ CO2R2 + I~, Nail R" "-O

R4

O O

dioxane, reflux

R3

"O 58-79%

R"

R7 6 5

150

ORGANIC SYNTHESIS--2004

IV.D-24 Piermatti, O.; Pizzo, F. et al., S, 2331; de Meijere, A. et al., EJOC, 2138. 1. OH', rt t~~~ ,'CO2H OH -I- CH2(CN)2

.o§

R:

3. OH',90~

o

o

50-90%

IV.D-25 Tuanli, Y.; Larock, R.C.; JOC, 68, 5936; Bihel, F.; Kraus, L., OBC, 1,793; Kaye, P.T. et al., S, 531. O E+ ~'.-.', " "~~CO2R L,~ ~ r.~-- " O %.

CH2C12, rt

~-" -

J.-

R1

E

R1

51-99% IV.D-26 Kayser, M.M. et al., JOC, 68, 6222; Mihovilovic, M.D. et al.,

SL, 1973.

R n

cycl~176176176176

n 0~r

0

+ R~O 60-87%1:99

IV.D-27 Trost, B.M. et al., JACS, 125, 4518; Kitamura, T. et al., BCJ, 76, 1889; Kadnikov, D.V.; Larock, R.C.; JOC, 68, 9423. MeO MeO R s

Me

OH

Pd(OAc)2 or Pd2(dba)3 Me

CO2Et

41-69%

IV.D-28 Rigby, J.H.; Aasuml, M., TL, 44, 5029. MeO OMe

,I, ~ N + M~e ~

Me

HO ~

CO2Et

CO2Et

,,CO2Et

1eh. reoux 2. BBr 3, CH2C12v

e 28-39%

SYNTHESIS OF HETEROCYCLES

151

IV.D-29 Itoh, K.; Kanemasa, S., TL, 44, 1799.

O Me. N~Me ~ ~ "O' ~ \ 1 ~ ~ ),---Br + O Me

e p~ ] ~ Ni(CIO4)2.6H2 O,TMMO THF,rt 77%

IV.D-30 Piva, O. et al., TL, 44, 8081.

10~~

+ //'"R PhCH=Rh(PCy3)2CI2,-._O . CH2C12,50~

~ R 15-75%

IV.E. Fur ans and Thiophenes

IV.E-1 Taylor, D.K. et al., JOC, 68, 4239; see also: Rao, H.S.P.; Jothilingham, S., JOC, 68, 5392; R1

O

OH

LiOH THF,rt

H 39-64%

IV.E-2 Guzzo, P.R.; Xu, Y.-C. et al., JOC, 68, 770; Naito, T. et al., OBC, 1, 254.

NRR1 X/~

NRR1

aqHCI X AcOH,90-110"Cy

rn

~

rn

20-95%

IV.E-3 Donohoe, T.J.; Butterworth, S., AG(E), 42, 948; Burke, S.D. et al., JOC, 68, 1150.

BnO

OsO4,Me3NO,CSA CH2C12

HO

84%

OH

152

ORGANIC SYNTHESIS--2004

IV.E-4 Kang, S.H. et al., JACS, 125, 4684; Nishizawa, M. et al., OL, 5, 1609; see also: White, J.D. et al., OL, 5, 4109; Stefani, H.A. et al., JHC, 40, 163; Dembinski, R. et al., JOC, 68, 6788; Hoppe, D. et al., SL, 1969; see also: Detterbeck, R.; Hesse, M., HCA, 86, 343; Sivakumar, M.; Borhan, B., TL, 44, 5547; de la Pradilla, R.F. et al., JOC, 68, 7755. O H ~ ~ R 1. Hg(O2CCF3)2,K2CO3,MeOH/CH2CI2,-78~ /-"~ .R x

68-91% ee = 86-95 % ~.mphth 2-naphth

2. aq KBr

3. LiBH4, Et3BoTHF,-78~ IV.E-5 Wipf, P.; Graham, T.H., JOC, 68, 8798. hn

--9 R1 DH

W(CO)6DABCO

~ i B u

R~ R2 S,ff__~lg3

THF,50-60~ '~ ~ , O r

R~

R'~-~ R2 3

~,S

+

"O" "iBu

15-61% 1-0:0-1 IV.E-6 Padwa, A. et al., JOC, 68, 5139; Rashatasakhon, P.; Padwa, A., OL, 5, 189.

.O o TfeOpyre.Z SOeC R

R

60-8:3% IV.E-7 Coe, J.W. et al., JOC, 68, 9964. O

!

base DMF, 90~

CF302S

R.~R1

19-92%

IV.E-8 Clayden, J. et al., OL, 5, 831. PhO~ ~

~SnBu3

O MeO

+ E+ MeLi, TMEDA THF, -780C MeO 67-71%

SYNTHESIS OF HETEROCYCLES

153

IV.E-9 Raghavan, S. et al., TL, 44, 8253. O

R

OH

1~ ~ f - ~

TBDPS-CI, imidazole

Ar~~R1-

Br

"~ ArS~o/J,JtR1

DMF Br

86-93%

IV.E-10 Serra, S.; Fuganti, C., SL, 2005. ~ C O 2 E t R1 R AcO Ac20, AcONa,HQ ~ ~ R 3 "CO2H ~- R R reflux R~

R~

CO2Et

87-97%

IV.E-11 Liu, G.; Lu, X., TL, 44, 467. E1

CI

:yEIH~RI+?

E x, /f--~-R~O~Ra

I. BuLi

2. Pd(OAc)2, LiCI

21-75% IV.E-12 Bez, G.; Zhao, C.-G., OL, 5, 4991; Chatani, N. et al., JACS, 125, 7812; Nair, V. et al., T, 59, 10279. R2 NHAr

R1

R~~2

+ Ar-NC

GaCI3 ~

CH2C12

NAr

R1

31-90% IV.E-13 Nair, V. et al., S, 1446; see also" Hodgson, D.M. et al., JOC, 68, 6153. CO2Me MeO2~CO2Me R

+ II

+

-~t~OMe

CO2Me ~ ' - " OMe

.... .~Ar'~,~OMe

Ph-Me,11o t;

R u 0Me 43-90%

IV.E-14 Xu, X., Zhang, Y., SC, 33, 2643. A~

R2

Al*

CN

SmI2 ~

+

R

THF, rt

Arl Ar \

R

R2 /

N-2 0-83 %

154

ORGANIC SYNTHESIS--2004

IV.E-15 Flowers, II, R.A. et al., OL, 5, 2363; Kobayashi, K. et al., H, 60, 939. o R R'J~O

+

[~ TMS

CTAN ~ CH2C12,rt

TMS

R 62-80%

IV.E-16 Kita, Y. et al., T, 59, 77. R1

R1

R2 VA-061,E P H P Ar,'~O"~R3 H20, 80~ Ar "O"k~R3 64-99% cis:trans = 1.22-39:

IV.E-17 Marshall, J.A.; Chobanian, H.R., OL, 5, 1931. M e ~ I - J O M~

x--OH

EtoHZn ~ , , O H , , Me . . . . . . k,,.OH 95%

(other examplesgiven) IV.E-18 Clive, D.L.J. et al., CC, 526; Toyota, M.; Ihara, M. et al., CC, 422; Renaud, P. et al., CEJ, 9, 1566; Engman, L. et al., JOC, 68, 8386; Sartillo-Piscil, F.; Quintero, L. et al., TL, 44, 3919; Booker-Milburn, KT et al., OL, 5, 1107; Zhou, L.; Hirao, T., JOC, 68, 1633.

OMe

Ph-Me, 85~

OMe 77-87%

IV.E-19 Dhavale, D.D. et al., JOC, 68, 4531; Yakura, T. et al., CPB, 51, 471; Wardrop, D.J. et al., TA, 14, 929; Fukuyama, T. et al., SL, 1028. EtO2C~~~r ~ O ( ~ EtO2C~

Rh2(OAc)2 .~ EtO2e . ~ O Ph'H' 80~ EtO2C---'e" U 74%

x 0-~

SYNTHESIS OF HETEROCYCLES

155

IV.E-20 Carreno, M.C.; Colobert, F., Solladie, G. et al., JOC, 68, 7779. f"~'n ~STol Et3SiH,TMS-OTf R ~ 'O R"~O O~-J CH2CI2,0~ Y STol 71-97% cis:trans = 6.1-100:1 IV.E-21 Rozhkov, R.V.; Larock, R.C., OL, 5, 797 and JOC, 68, 6314; Lautens, M.; Fang, Y.-Q., OL, 5, 3679; Pache, S.; Lautens, M., OL, 5, 4827; Mathes, B.M.; Filla, S.A., TL, 44, 725; see also: Balme, G. et al., OL, 5, 2441; Pal, M.; Subramanian, V.; Yeleswarapu, K.R., TL, 44, 8221; Wu, M.-J. et al., SL, 2057. Me R4 Me ~ A

O

+ R~R 2 Pd(dba)2,Na2CO3, Bu4NCI O ~ ~ . R'"R1 DMF, 100~

~ O

R~R4 R1 R z 48-80%

I

IV.E-22 Narasaka, K. et al., H, 59, 333. Cr(CO)5 /Br CO, Pd(dba)2,P(Ph-4-CF3)3 ~ 84% IV.E-23 Ma, S.; Zhang, J., AG(E), 42, 184. R~O

R21 PdCI2(MeCN)2,NaI R - ~ ? 1 Me2CO,reflux ~ K'O')~R2 65-82% (withoutNaI, 4H-pyranswereisolated)

IV.E-24 zhang, x. et al., JACS, 125, 11472. Me

Me__~_. O

.I,

ocod,Cl,2,A,Sb6,

~MMe

'

Me

'l' ~

Me+ q,O~,,MMe 49% ee = 99 %

48% ee = 99 %

156

ORGANIC SYNTHESISm2004

IV.E-25 Gansauer, A.; Grimme, S. et al., AG(E), 42, 3687; Hartley, R.C. et al., JOC, 68, 387.

EtO2C~~ EtO2C H~" ~

Zn, CpTiCI2 EtO2C~ OH EtOAc ~- EtO2C/

H

63% IV.E-26 Gevorgyan, V. et al., AG(E), 42, 98; Ma, S. et al., CEJ, 9, 2447.

R~~:__

CuI ~ ]R~--~

R

DMA, D

R2 67-95%

IV.E-27 Ahrendt, K.A.; Bergman, R.G.; Ellman, J.A., OL, 5, 1301; Yu, W.-Y. et al., OL, 5, 2535. CHO 1. Ph-Me, 150~ OMe

PCY3

2. aqHCI,3h

OMe 65%

IV.E-28 Ohe, K.; Uemura, S. et al., OL, 5, 2619. R1

~

+

~ , , ~ SR2

R1

[Rh(OAc)2]2 CH2C12,reflux

R 60-98%

IV.E-29 Peters, D.G. et al., JOC, 68, 1024. e" EtO2C

EtO2~~l Ni(tmc)Br2,Et3NBF~ ~

MeO

76%

/7

+

EtO2C I

24%

/ I

SYNTHESIS OF HETEROCYCLES

157

IV.E-30 Kinoshita, H.; Shinokubo, H.; Oshima, K., JACS, 125, 7784. :~}n

R

H20/Et20 84-93%

IV.E-31 Hidai, M.; Uemura, S. et al., AG(E), 42, 2681. R

R~ OH

+ Me'~ O [Cp*RuCI(Ia'SMe)2RuCp*CI] Me PtCl2, NH4BF4,reflux

~ Me

Me 0-78%

IV.E-32 Liu, R.-S. et al., JOC, 68, 7889; Trost, B.M. et al., CEJ, 9, 4442. Me Me ~L: . j . ~ , "., . R

.

CH2CI2,rt ..,"~

_

PhCH=RuCl2(Pcy3)cy(~)3 R r~les 77-86%

IV.E-33 Lamaty, F. et al., TL, 44, 8659. ~ O

~ I+I C Br,~-O 2 M 3 H + ArB(OH)2 Pd(OAc)2, ~ C OK22CM O33 B u 4 N C I 28-57%

IV.E-34 Xi, Z. et al., TL, 44, 6895. "One-Pot Four-Component Synthesis of Tetrahydrofuran Derivatives Involving an Alkyne, an Ethylene and Two Aldehydes via CuCI-Mediated Reactions of Oxazirconacyclopentenes with Aldehydes." IV.E-35 Lattanzi, A. et al., JOC, 68, 3691. ~ ~ O H R 1. VO(aeac):~TBHP, CH2C12,40~ 2. BFa.Et20or TFA

R 50-82%

158

ORGANIC SYNTHESISm2004

IV.E-36 Karade, N.N. et al., TL, 44, 6729. O ~

+ ph~a O

O

PhI(OAc)2 MeCN, 0~

Ph 52-77%

IV.E-37 Baraldi, P.G. et al., JMC, 46, 794; Scammells, P.J. et al., JMC, 46, 1870; see also: Moghaddam, F.M.; Zali-Boinee, H., TL, 44, 6253. CN S~ morpholine EtOH, 70~ -* rt 77% OMe IV.E-38 E1-Abadelah, M.M. et al., OBC, 1, 822. [~ CO2H N-NHAr ......CDI.. S~Ac THF, rt N-NHAr 74-82% IV.E-39 Owton, W.N., TL, 42, 7147; Sosnovskikh, V.Y. et al., T, 59, 2625; Patel, M.V. et al., TL, 44, 6665. C~FF3 .~ R ' ~ CF3 R O 1. HSCH2CO2Me,TEA, MeCN 2. LiOH, H20/THF 3. lxW,DBU, DMA, 200~ 33-59% IV.E-40 De, A. et al., SL, 1479 and T, 59, 4767. O '

NEt2 " SMe + Ar-CHO

LDA 0~

rt

Ar 69-84%

SYNTHESIS OF HETEROCYCLES

159

IV.E-41 Hessian, K.O.; Flynn, B.L., OL, 5, 4377. Me 12 12 ~ EtOH ~ " ~ S M e -Pr CH2C!2 93% Pr

Et 95%

I

IV.F Pyrroles, Indoles, etc. IV.F-1 Knight, D.W.; Sharland, C.M., SL, 2258; Saksena, A.K. et al., TL, 44, 7997; Dechoux, L. et al., S, 859. OH TsSOn Ph-Me, reflux~ CO2Et

Ts

72-86% IV.F-2 Ranu, B.C.; Dey, S.S., TL, 44, 2865; Yang, D.-Y. et al., TL, 44, 1599; Erian, A.W. et al., SC, 33, 1563; Meyer, N.; Opatz, T., SL, 1427; Takeda, T. et al., TL, 44, 5571; Garbay, C. et al., TL, 44, 7011; Ekkat, A.R.; Bates, D.K., S, 1959. R2 R ~ R2 R~ Bu4NBr . ~ R ) 3~ +O~ + R4"NH2 ~ R3 R NO2 R R4 68-92% IV.F-3 Krow, G.R. et al., OL, 5, 2739; Couty, F. et al., TL, 44, 5209. Z Ri~ AgXorHgX2~ R ~ X \ MeNO2,60"C Y Y 20-74% IV.F-4 Barluenga, J. et al., EJOC, 771; Kudzma, L.V., S, 1661; Park, H.; Jew, S. et al., BMCL, 13, 197; Gopalan, A.S. et al., TL, 44, 4035; Coldham, I. et al., OBC, 1, 2111. E E R.~. Br Br ~ RI 1. tBuLi,Et20, -780C R - ~ R1 ~ N / 2. TMEDA.-78-' 20~ 3. E+ i Tol 4. DDQ, CH2C12 Tol 71-89%

160

ORGANIC SYNTHESIS--2004

IV.F-5 Wang, W.; Hruby, V.J. et al., TL, 44, 1413. Na.

TsO

co2tBu

THF,rt ~

co2tBu

I

I

Boc

Boc 85-93%

IV.F-6 Warren, S. et al., CC, 1648, 1650. ~ R 1 ~,~ ~Iq SiOz, A R2 --'----'-~

R

~

~,j

tR1

R2

1-95% IV.F-7 Komatsu, M. et al., H, 60, 289. ~~

NHTs

AgNO3 ~ R ~ \ N T + TsNCINa Ph~"H,600C- R" ~ / 38-42%

s

8-12%

IV.F-8 Le Merrer, Y. et al., SL, 333; Bunce, R.A. et al., JHC, 40, 113; see also: Hussaini, S.R.; Moloney, M.G., OBC, 1, 1838. ,,,,,,. jO NaBH3CN OHC + R-NH2 ~ O~ ' ' ' , ~ " OTBS MeOH

1~"1VH OTBS 50-75%

IV.F-9 Krishna, P.R. et al., SL, 1619. R R,,'~j EWG

EWG

TosMIC, tBuOK THF, -78~

H 44-69%

IV.F-10 Gabriele, B. et al., JOC, 68, 7853; Ates, A.; Quinet, C., EJOC, 1623; Hultzsch, K.C. et al., CEJ, 9, 4796; Collin, J.; Trifanov, A. et al., CC, 3048; see also" Carreno, M.C.; Ribagorda, M., OL, 5, 2425.

SYNTHESIS OF HETEROCYCLES

R2

161

R3

R2

R I ~ R4

CuCI2 ~,. ~ DMA, 100~ R1

R3

R4 R

63-91% IV.F-11 Zhang, Y.; Herndon, J.W., OL, 5, 2043.

R1 R2

R1 R2 OMe

THF, 65~

Me 9-74%

IV.F-12 Narasaka, K. et al., BCJ, 76, 2003.

R

OAc R

on ~

R

T OH -

R

0-72%

5-75%

IV.F-13 Eilbracht, P. et al., OL, 5, 3213; see also: Lobo, A.M.; Prabhakar, S. et al., EJOC, 190.

Me~'%NPhth R--~

+ NH I N~CPh2

M~

CO/I-I2,[Rh(cod)Cl]2~ R TsOH, 100~ NPhth

~ H 42-78%

IV.F-14 Doyle, M.P. et al., JACS, 125, 4692; Davis, F.A. et al., JOC, 68, 5147; see also: Che, C.-M. et al., OL, 5, 2153; Wang, Y.; Zhu, S., OL, 5, 745; see also: Scheidt, H.A. et al., OL, 5, 3487; Sweeney, J.B. et al., OL, 5, 4775.

RO2~ Cu(OTf)2 Z ~ C O 2 R Ph~N/'"Z ~ Ar 40-74%

N2

Z~. Ph ~N Rh2(OAc)4 i ~ Ph CO2R Ar Ar 12-66%

IV.F-15 Ohe, K.; Uemura, S. et al., OL, 5, 2515.

162

ORGANIC SYNTHESISm2004

R

R

fj~N'R

1+

~R

2

%

~~/N--

[Rh(OAc)2]2~ CH2CI2, rt

R1 ~x . g2

v

18-99% IV.F-16 Nyerges, M. et al., SL, 947. Ph.

~de

:F'~

~ O 2 E t Pb,,

,Me

o

I_iO Me~.-.__"

.... /O .AgOAc, .. (HN~../CO2Et HO~ ' - ~.._L~-~ . . . TEA . ~" R ~ Me ~ Ph-Me, rt l~l "R2 57-81%

~ ~II - N_1 I+ R~~"-R 2 R1

IV.F-17 Sarkar, T.K. et al., JOC, 68, 4206. CO2Me Rh2(OAc)4 N ~ , N ~ CI

~n

H ~. CO2Me

Ph-H, rt

~n

O

Me~ 52-62%

IV.F-18 Imhof, S.: Blechert, S., SL, 609; Mori, M. et al., JACS, 125, 5606; see also: Grubbs, R.H. et al., OS, 80, 85. 9

0

§

II P'hCH-RuCI2(Pcy3)(IMes)

CH2CI2, 80~

Nos"

O 20-55%

IV.F-19 Tanaka, T. et al., AG(E), 42, 2647; Poli, G.; Malacria, M. et al., EJOC, 2702; see also: Narasaka, K. et al., BCJ, 76, 1055; Rutjes, F.P.J.T. et al., OL, 5, 1717 and SL, 2354; see also: Kuduk, S.D. et al., TL, 44, 1437; Yamamoto, Y. et al., H, 61, 247; see also: Sasai, H. et al., TL, 44, 711. R Mts-

R + Ar-I

diox~e, reflux

Ar

.~ Mts36-60%

SYNTHESIS OF HETEROCYCLES

163

IV.F-20 Ghorai, B.K.; Herndon, J.W., OM, 22, 3951; Soderberg, B.C.G. et al., T, 59, 8775.

Cr(CO)5 Ph-Me,ll0~ Bn

Bn

45% IV.F-21 Livinghouse, T. et al., OS, 80, 93. (co)3 Me Co HO) 1. Et3SiH,CyxNH2 Co(CO)3 ~ Ts O Me 2. DME,67~ Ts~ 86-93%

IV.F-22 Sugiura, M. et al., TL, 44, 6241. 1. CICO2Ph R - - ~ 2"P(OPh)3 R - - ~ 3. 03 4. NaHCO3

CHO CO2Ph 8-18%

IV.F-23 Kadouri-Puchot, C. et al., SL, 1058; Ishibashi, H. et al., JOC, 68, 7983; Tsuritani, T.; Shinokubo, H.; Oshima, K., JOC, 68, 3246; Taguchi, T. et al., JOC, 68, 3184. h~~O P

TTMSS,AIBN~_ O p h i~Or

SPh R~I~,~,TMS

Ph-H TMS 40-60%

IV.F-24 Bergman, R.G.; Ellman, J.A.; Souers, A.J. et al., OL, 5, 2131. R

R1-

ah,eeh,,3 , .....

Ph-Cl2, 250~

+

42-97%

ggl

164

ORGANIC SYNTHESISm2004

IV.F.25 Bailey, W.F. et al., TL, 44, 5303; Katritzky, A.R. et al., JOC, 68, 5728; Langer, P. et al., CEJ, 9, 3951.

~ ~ " ~ / 1"tTBM uLi EDE A ' t20'7' 8~ ~ ~ E H

~E1

3. E+then E1+

59-71% IV.F-26 Stevens, R.W. et al., TL, 44, 7269; Caron, S. et al., JOC, 68, 4104.

f..-CO2Me

R - -:'~'~A~"CO2Meo+ ~,~ 'R~~I Br 1. K2CO~Me2CO,rt.~ Rm~ff,--~ ~R N 2. DBU or Cs2CO3 1 SO2Ph 44-93% IV.F-27 Kuzmich, D.; Mulrooney, C., S, 1671. ......

bn

' OH

88-97 %

IV.F-28 O'Shea, D.F. et al., JACS, 125, 4054. R1 R'~N

H 1. R1-Li,Et20,-78~ 2. DMF or R2-CN Boc 3. HCI, EtOAc, rt

R

~

H (or R2) Boc 40-84%

IV.F-29 Witulski, B. et al., SL, 708. N~~ --

R1

RhCI(PPh3)3'AgSbF6 Ph-Me, 20~

R

R

70-89% IV.F-30 Schneider, R.; Fort, Y. et al., OL, 5, 2311. ~ N H R Ni(0),Nail, tBuONa,bpy ~ ""7 "CI

PhCH=CH2, THF, 65~

~

In R

70-95%

SYNTHESIS OF HETEROCYCLES

165

IV.F-31 Zhu, S.; Wang, S. et al., T, 44, 9669; see also: Ragaini, F. et al.,

JOC, 68, 460. R

R1

~O

R1

R

P(OEt):~TEA MeOH, 50-60~

.lbAr

A

45-91%

IV.F-32 Yu, M.; Pagenkopf, B.L., JACS, 125, 8122 and OL, 5, 5099. R__~

y~

+ R1-CN

TMS-OTf ~ CH2C12or MeNO2,rt

~~

R1

60-96%

IV.F-33 Carotti, A. et al., TL, 44, 2121; see also: Taylor, E.C.; Liu, B.,

JOC, 68, 9938. R

R

Ol~~~O2

R1 _ S n C I 2~0 ~ OMF,a

[IN ~ ~

R'y

O

R1

O 95-99%

IV.F-34 Saito, T. et al., H, 60, 1045.

R1 1

Mo(CO)6

I ~ N R DMSO/Ph-Me, reflux 45-70% IV.F-35 Knochel, P. et al., T, 59, 1571; see also: Knochel, P. et al., CEJ, 9, 5323. KH or tBuOK

FG--

NMP, rt

~ FG

R H

51-95% IV.F-36 Wong, A. et al., JOC, 68, 9865; see also: Rossi, R.A. et al.,

JOC, 68, 2807.

166

ORGANIC SYNTHESIS--2004

~ O tR2 1 Pb 2 TEAF,50~

R2 R - ~ R H 66-77%

IV.F-37 Witulski, B. et al., AG(E), 42, 4257; see also: Sakamoto, T. et al., CPB, 51, 1170; Gathergood, N.; Scammells, P.J., OL, 5, 921. R3

X R3 Pd(PPh3)2C12,K2CO3 R - - ~ N/~'',7/ + HNR1R2 '~" NR1R2 THF, 80~ Ts Ts 66-99%

R_~

IV.F-38 Soderberg, B.C.G. et al., OS, 80, 75; Soderberg, B.G.; Dentale, S.W., T, 59, 5507; Scott, T.L.; Soderberg, B.C.G., T, 59, 6323. CO2Me CO2Me ~NO Pd(OAc)2,PPh3, CO MeCN 2 H 91% IV.F-39 Cacchi, S. et al., S, 728 and OL, 5, 3843; Doye, S. et al., AG(E), 42, 3042. R

Ar

pd(PPh3)4,Cs2CO3 4- Ar-X ~ MeCN, 100~ CF3

R 35-99%

IV.F-40 Ciufolini, M.A. et al., OL, 5, 4943; Johnston, J.N. et al., JACS, 125, 163; Vidal, A. et al., TL, 44, 3027. CO2Et R ~ ~ C O 2 Et tBu 9 ~ R 2 R20,,N~P(OEt)2 "N" ]~1

+

tBu

tBuOH, reflux

~[1

31-63%

SYNTHESIS OF HETEROCYCLES

167

IV.F-41 Harris, J.M.; Padwa, A. et al., OL, 5, 4195.

dioxane, 100"12 H 65%

IV.F-42 Nozaki, K. et al., AG(E), 42, 2051. R1-NH2 +

Ph-Me, 80~ X X

kl 28-92%

I V . G . P y r i d i n e s , Q u i n o l i n e s , etc.

IV.G-1 Kwon, O. et al., JACS, 125, 4716; Palenzuela, J.A. et al., JOC, 68, 7845; Hall, D.G. et al., CEJ, 9, 466; Batey, R.A. et al., TL, 44, 7569; Li, C.-J. et al., SL, 732; Palacios, F. et al., H, 61,493; Yadav, J.S. et al., S, 1610; Danheiser, R.L. et al., OS, 80, 133; Arcadi, A. et al., JOC, 68, 6959; see also: Kozhevnikov, V.N.; Konig, B. et al., JOC, 68, 2882; Snyder, J.K. et al., JOC, 68, 4345. tO2C~ PBu3 EtO2C~+ N~'R 1 | R"

Ts

CH2C12, rt

RC'~N-'~ R1 80-99% cis:trans = 5-49:1

IV.G-2 Snapper, M.L.; Hoveyda, A.H. et al., JACS, 125, 4018; Grigg, R. et al., TL, 44, 6979; Alcaide, B.; Almendros, P. et al., CEJ, 9, 3415; Joseph, B. et al., T, 59, 9627; see also: Back, T.G. et al., JOC, 44, 2223. O AcOAg,iprOH OMe M e O ~

~-OMe

~

~"Ar

Me~ 79-98% ee = 88-95 %

168

ORGANIC SYNTHESISm2004

IV.G-3 Ibrahim, Y.A. et al., T, 59, 8489; Wang, K.K. et al., JOC, 68, 5512; Zhang, H.; Larock, R.C., JOC, 68, 5132. R1 --~ N ~R ~ qI "~~ Ar ~ Ar R N~(Y "~R Ph-NO2,reflux 42-58% IV.G-4 Bonnet-Delpon, D. et al., S, 2231.

OR +

~NH

2

[[~OR HFIP,rt

X m ~ H

Me

68-97% IV.G-5 Heller, B. et al., JOC, 68, 9221; see also: McClure, C.K.; Link, J.S., JOC, 68, 8256; Hendrickson, J.B.; Wang, J., OPP, 35, 623; Herndon, J.W. et al., OL, 5, 4261.

R R

R1 hv, CpCo(cod) R ~ , ~ R

IR + N[

Ph-Me

R1 64-89%

IV.G-6 Cho, C.S.; Shim, S.C. et al., T, 59, 7997. ~NH ,H -I- M S Ru(PPh3)2CI2'KOH' 1"C12H24 2 H R dioxane, 80~

42-90% IV.G-7 Bagley, M.C. et al., SL, 1443.

R2 R1 R~O +

[l]

R2 MnO2 + NH4OAc AcOH/Ph.Me,reflux

H~R 3

R~~ R3

60-96%

IV.G-8 Narasaka, K. et al., S, 2415. R ~ TFAA,chloranil Me CH2C12,rt ~" R ~ M e 72-82% OH

SYNTHESIS OF HETEROCYCLES

169

IV.G-9 Ranu, B.C. et al., T, 59, 813; McWilliams, J.C. et al., JOC, 68, 467; Hamada, Y. et al., TL, 44, 8925; Kobayashi, K. et al., CBS, 76, 1257; Ila, H.; Junjappa, H. et al., JOC, 68, 3966; see also: McNaughton, B.R.; Miller, B.L., OL, 5, 4257. R1

R--;~

R1

+ O NH2

pW, InCl3, SiO2

Rz R2

R3

R3

55-87% IV.G-10 Balalaie, S. et al., M, 134, 453; Risch, N. et al., S, 2667; Constantieux, T.; Rodriguez, J. et al., SL, 2301; Springfield, S.A. et al., JOC, 68, 4598; Prajapati, D. et al., TL, 44, 8725; Volochnyuk, D.M. et al., S, 1531; Li, Z.-M. et al., SC, 33, 4229; Fischer, M.; Troschutz, R., S, 1603; Proenca, M.F. et al., JOC, 68, 276; Guillaumet, G. et al., SL, 987; Lindsley, C.W. et al., TL, 44, 4495; Langer, P.; Appel, B., TL, 44, 5133; Sanchez-Salvatori, M.R.; Marazano, C., JOC, 68, 8883; see also: Ila, H.; Junjappa, H. et al., JOC, 68, 3498. O Me

N__ % + Me -I- R2-NH2 CO2R CO2R1

H

O ~2

77-94% IV.G-11 Magomedov, N.A., OL, 5, 2509; Jacob, R.G. et al., TL, 44, 6809; Bandini, M." Umani-Ronchi, A. et al., JOC, 44, 7126; Yamazaki, S. et al., TL, 44, 1429.

Me

O ~

TsOH '~~H-Ph-H, rt Me

NH2"!"OH

M

Me

e 76%

IV.G-12 Saitoh, T. et al., CPB, 51, 667. O~s, Ph T AA T SA P.

~' " ~ - .

i~h

e rt

N,-CHO 2. NiCI2.6H2O, NaBH4

CliO

.

~e

Yde 79%

. CHO ~e 5%

170

ORGANIC SYNTHESISm2004

IV.G-13 Wills, M. et al., OL, 5, 4227; see also: Silva, A.M.S. et al., TL, 44, 5893. 1. I-ICO2H N-B~

4. (RuCICy)2,HCO2H, TEA PI~NHTs

H

H

Pit'~NHTs

20-99%

IV.G-14 Azuma, Y. et al., H, 60, 2241; Goel, A.; Ram, V.J. et al., JOC, 68, 2983. O

OH O

~I N H

PPA Me

OH

O Me

R

/

19-62%

Me

1-27% IV.G-15 Felpin, F.-X.; Lebreton, J., TL, 44, 527; Cases, M. et al., TL, 44, 2995; Billard, T. et al. JOC, 68, 8932; Takahata, H. et al., OL, 5, 2527; s e e also: Katritzky, A.R. et al., JOC, 68, 5724. Ph

PhCH-Ru(PCy3)(IMes)CI2cH2CI2, reflux ~ R~~

88-99%

IV.G-16 Ohwada, T. et al., OL, 5, 2087; Horiguchi, Y. et al., H, 59, 691; Silveira, C.C.; Kaufman, T.S. et al., TL, 44, 6137; Kawabata, T. et al., S, 505; see also: Lavilla, R. eta., OL, 5, 717; Das, B. et al., CL, 222; Crousse, B.; Bonnet-Delpon, D. et al., TL, 44, 217.

x l ~

R

R1

I~x l ~

R

R1

TFAorTFSA X

X3

Xo 67-99% trans:cis = 7.33-19:1

SYNTHESIS OF HETEROCYCLES

171

IV.G-17 Beccalli, E.M. et al., T, 59, 9887. R, "CHO1 - / H2, Pd/C ~

R1

I(.~~ ~~~_R~§ ~tOH"

R~ 6-84%

O IV.G-18 Murphy, J.A. et al., OL, 5, 3655; Magnus, P. et al., OL, 5, 2181.

N3 BF3oEt20 CH2C12

95% IV.G-19 Dobbs, A.P. et al., SL, 1740 and JOC, 68, 7880. e ~~ InCl3 ..~ M MS + RI"CHO MeCN,reflux Md" I I R R

R1

22-85% IV.G-20 Padwa, A. et al., T, 59, 4939. .~e

MCPBA

NHTs

HO'

I

Ts

85% IV.G-21 Harrity, J.P.A. et al., OL, 5, 3427 and JOC, 68, 4286. TBSO ~ =

NTs + ~ AcO

Pd(OAc)2, T B S ( ~ . . . . dppp . TMS THF,65~ _

gle

41%

IV.G-22 Hong, B.-C. et al., OL, 5, 1689.

C

R1 + ~CO2R2N

~ R ~

CO2R2

"

20-92%

172

ORGANIC SYNTHESISI2004

IV.G-23 Taylor, E.C.; Bhatia, B., H, 61, 113. XH

XH N&NH

+0 ~ : ]

H2N ~ , ~ ~ O

H20,800C HO' 34-73%

IV.G-24 Grigg, R. et al., TL, 44, 7445, 9017. CO2Me +

+

R-NH2

~N.. CO2Me R

pd oAc,2,pp

Ph-Me, 80~ 47-90%

IV.G-25 O'Dell, D.K.; Nicholas, K.M., JOC, 68, 6427; Kim, J.N. et al., T, 59, 385. OAc t~~EWG CO, [Cp*Fe(CO)2]2 ~ E W G Z--~-NO][ 2

dioxane, 150oc ~" Z - ' = ' ~ N ~ 47-65%

IV.G-26 Brandi, A. et al., SL, 2305. O I'~OH

Pd(OAc)2,LiOAc, Cu(OAe)2

ph~L'NH I Me

DMF, 100~

Ph

I

Me 70%

IV.G-27 Huang, Q.; Larock, R.C., JOC, 68, 980; Dai, G.; Larock, R.C.; JOC, 68, 920; see also: Ito, T.; Katsuki, T. et al., SL, 1809; Ma, S. et al., JOC, 68, 5943; Hatano, M.; Mikami, K., JACS, 125, 4704. R1

R + ~"R 1 u

DMSO, 70oc 25-97%

SYNTHESIS OF HETEROCYCLES

173

IV.G-28 Gunter, M.; Gais, H.-J., JOC, 68, 8037. BuS"N"~O~ ~ " P h ~,~.NMe 1.2.NMOCO2(COTHF,-78~ )8, ~ B u I~ H_ R

O

R

30-60% dr = 2-49:1 ee = 49:1 IV.G-29 Majumdar, K.C.; Mukhopadhyay, P.P., S, 920. R1

R1

O~N~Br%R2 R" "~ "N" O Me

~TI

Bu3SnCl,AIBN,NaBH4~ O ~ ~ ~ e ' Ph-H, reflux 80-85%

IV.G-30 Coe, J.W. et al., JACS, 125, 3268.

HOCH2CH2OH, 200~ H

64-85%

IV.G-31 Kristensen, J.L. et al., JOC, 68, 4091. ~ F tBuLi THF,-78~ rt Br

74-91%

IV.G-32 Trost, B.M.; Tang, W., JACS, 125, 8744. Me

BuLi,ipr2NH ~ THF, rt Me...~" Me Me ---~NHMe 99%

e

R2

174

ORGANIC SYNTHESIS--2004

IV.G-33 Jacob, J.; Jones, W.D., JOC, 68, 3563. R--~~~L~N~Ar + ~ ~

CO' C~ 95~

"~ R - - ~ ~ e r

I

Ph

15-73%

IV.H Pyrans, Pyrones and Sulfur Analogues IV.H-1 Willis, C.L. et al., OL, 5, 2429; Marra, C. et al., EJOC, 3407. DMe H~OMe + R-CHO 1. TFA, CH2CI2,rt Me

~

2. K2CO~MeOH,rt

Me 39-97% 13.3:1

IV.H-2 Floreancig, P.E. et al., OL, 5, 4521; Rychnovsky, S.D. et al., OL, 5, 3163; Cho, Y.S. et al., CC, 2346; Martin, V.S. et al., OL, 5, 1979. Me ~ ~ Ce(NO3)3.:6H20'C12H25SO3Na Me H20, rt v" '"'//'Me ~TMS H(~Me 8O%

IV.H-3 Barluenga, J. et al., JACS, 125, 9028. ~CHO 1. IPyBF4,HBF4,CH2C12,0*C~rt 2. TMS-Nuc

Nuc (,'-'-i~ O k~~R

R

I

35-87% IV.H-4 Hart, D.J. et al., SL, 1334. .DHIOBn _DHfOBn 9 - Me PhSeCI P h S e , . . ~ M e CH2C12 OBn

87%

"OBn

SYNTHESIS OF HETEROCYCLES

175

IV.H-5 Yadav, J.S. et al., TL, 44, 2221.

Me +

CH2C12,rt

R

~ " ~ N"~Me R

75-87% IV.H-6 Jin, T.-S. et al., SL, 2001. R

R-CHO +(CH2(CN)2 + R1

TBAB ~ R1 OH H20, reflux

NH2 75-9%%

IV.H-7 Evans, P.A.; Hinkle, R.J. et al., JACS, 125, 11456. BiBr 3

TMS MeCN,rt SiEt3

77-81% e19:l

IV.H-8 Hara, S. et al., TL, 44, 4117. I ToI-IF2,TEA.5HF 'C5Hlt,-' ~ C5HII~"' CH2C12

~~

F

70% IV.H-9 Diez, D. et al., OL, 5, 4361.

MgBr2 TsO~--~

THF SO2Ph

IV.H-10 Yang, D. et al., JACS, 125, 158. Y e ~ M

R

Br "O" "SO2Ph 70%

Y

Oxone,NaHCO3 e ~ H20/MeCN M

OH R

0-85% 100-0:1-10

176

ORGANIC SYNTHESISm2004

IV.H-11 Merour, J.-Y. et al., HCA, 86, 2687; Carreaux, F. et al., CC, 276; Paterson, I.; Luckhurst, C.A., TL, 44, 3749; de Meijere, A. et al., EJOC, 472; Gao, X.; Hall, D.G., JACS, 125, 9308; Bolm, C. et al., CC, 2826; Chavez, D.E.; Jacobsen, E.N., OL, 5, 2563; Rameshkumar, C.; Hsung, R.P., SL, 1241; Ding, K.; Meng, J. et al., CEJ, 9, 5989; Harman, W.D. et al., OM, 22, 4170. R

R

~ O ~

R2

Ac ~ l

~~--~X /~

- ~[~1R2 =H

Ph-Me, 140 ~ 1-4d

O 36-62%

Iu Hodgson, D.M. et al., SL, 59 and JOC, 68, 581 and TA, 14, 921; Clark, J.S. et al., CC, 2578.

hex, 0~

O

"-~" - ~ O ~

C~H~,~~~

co2tBu

~ , 1 ~ - o •-']--Rh

tBuO2C

c=az~

O

ee = 87%

IV.I-I-13 Trost, B.M.; Rhee, Y.H., JACS, 125, 7482; see also: Trost, B.M. et al., JACS, 125, 9276. OBn OBn NHBoc RhCl[P(Ph.4.F)3]3,p(ph.3.F)3" ~ N H B o c

~

HO" "Me

,..._

DMF, 85%

"O" "Me 67%

IV.H-14 Wallace, D.J., TL, 44, 2145; Doris, E. et al., TL, 44, 435; Izzo, I.; De Ricarrdis, F. et al., H, 60, 2057; Schmidt, B., EJOC, 816.

=k--o o--/= = ~ - ~ - - / =

PhCH-Ru(PC,3)2CIecH2CI2, rt 87% 5.4:1:0.1

SYNTHESIS OF HETEROCYCLES

177

IV.H-15 Yavari, I. et al., T, 59, 9409; see also: Malinakova, H.C. et al., OM, 22, 2961. CO2Me CO2Me .~ ~ C 0 2 M e R~R2 + I + R-NfC CH2C12,-10~ --' rt R 1 . / " , . , ~ ( ~ N H R 3 OH CO2Me ~ 2 80-95%

V.H-16 Sames, D. et al., OL, 5, 1055; see also: Mascarenas, J.L. et al., OL, 5, 1975. Me

R j,

PtCl2 Ph-Me, 80oc 30-87%

IV.H-17 Hidai, M.; Uemura, S. et al., JACS, 125, 6060.

o. ~e/L

~ ~,

Ill

T]5-CsMesRuCI(~t2-S/Pr)2Ru(n-CsMe5)CI ( ~ ~ 74-82% syn:anti = 16-25:1

IV.H-18 Majumdar, K.C.; Mukhopadhyay, P.P., S, 97; Majumdar, K.C. et al., S, 2385. R1

Bu3SnCI, AIBN,NaBH3CN ~ Ph-H R

R1

' ~ ~ -R ~ - ~ o 70-80%

IV.H.19 Sabitha, G. et al., TL, 44, 7455. O

I

OH

~'eO~C~Rl§

O

I

O

OH

9~s c,, ~ ~ e O ~ C . ~ ~ eO~.~ ~e~N, rt ~ R~'O~R'§ ~J'O'ZR1 80-90% 7.33-100:1

178

ORGANIC SYNTHESIS--2004

IV.H-20 Padwa, A.; Straub, C.S., JOC, 68, 227.

0~0

1. Rh2(pfb)4,Ph-H, rt N'ph 2. Ph-Me2,145~ u

'l~ph 68%

IV.H-21 Ahmed, N.; Ansari, W.H., JCR(S), 572. R1 O R

~

R1 0

SiCI4,BiCI3 R ~ ~ r R2 EtOAc, 70-80~ 1~ R41",,~I~R3

~

R41~,,~R 3 92-94%

IV.H-22 Gurjar, M.K. et al., H, 60, 2293. :~.MPM ~MPM 1. Nal, Me2CO,reflux - 2. Na2S'9H20,DMSO/MeCN,reflux MsOI ~OMs 79% [similar preparation of O and N analogs]

IV.I-l-23 Dunach, E. et al., TL, 44, 853. R1 R3 f f ~ R1 R~~qL..s~ + ph..~R 2 TiCI4 CH2C12,-450C R3~'~N~phR2 13-76% IV.H-24 Detty, M.R. et al., JOC, 68, 3344. NEt2

LDA ...... z

X ~

R2

S e C ~ g TI-IF,0-~ 15*C X 23-90%

SYNTHESIS OF HETEROCYCLES

179

IV.I. Other Heterocycles with One Heteroatom

IV.I-1 Crimmins, M.T.; Cleary, P.A., H, 61, 87; van Otterlo, W.A.L.; de Koning, C.B., SL, 1859; Mazur, A.W. et al., TL, 44, 5511.

~ \ Oo~'=I PhCH=Ru(PCY3)(IMes)CI2 BnO" OBn CH2C12, 40"C BnO~''

O~I OBn

IV.I-2 Rousseau, G. et al., EJOC, 463.

+ X+(colI)2BF6 " 11-95% IV.I-3 Suzuki, T. et al., TL, 44, 2709. D

MPMO " ~ O -"

Euffod)3 MP ah-Me,ll0~ M O ~ 1 Bn HO ,---uBn 76-97%

IV.I-4 Nyerges, M. et al., TL, 44, 793; see also: Kamimura, A. et al., JOC, 68, 4996.

Me EtOH,rt Me TEA

MeO" ~ ~~_~

53-83% IV.I-5 Sakamoto, M. et al., JOC, 68, 1447.

alx~ -I-

O~O R

R

R1

hn 1~ ........ Ph-H

RO

OR2 .

CN OR

60-83%

180

ORGANIC SYNTHESISm2004

IV.I-6 Hirama, M. et al., SL, 891.

Me A .,CO2H Me .... f,,,~CO2H ~ " ~ H eeh3 Me", ~ Me,., THF,550C N3 v 1r O~XO O~O 43%

IV.I-7 Seleque, J.P. et al., JOC, 68, 7455. Me X O + Me~X ~~~. "~

0 Me,ee ~ o M ~ - - ~

TEA rt DMSO, 93%

IV.J. Heterocycles with a Bridgehead Heteroatom

IV.J-1 Lete, E. et al., OL, 5, 1115; see also: Oka, M. et al., JHC, 40, 177; Couty, F. et al., EJOC, 2062; Chai, W. et al., SL, 2086; Ghosh, C.K. et al., H, 60, 825. R3 R3 0

R2~ I _ tBuLi R2 RI/.~ ~~~OMe ~"RI~ R Me

62-87%

IV.J-2 Tye, H. et al., TL, 44, 4369.

~

MeaN

,,,NH2 M' "A~e' ~ 'H~N.../R "/b~ + EN-R+ Ar-CHO lxW,SC(MeoHOTt")3 50-93%

IV.J-3 Wang, Q. et al., S, 1231.

R"~N.~-~S + R1-CN

SbCls

CH2C12,-60~ 85-89%

SYNTHESIS OF HETEROCYCLES

181

IV.J-4 Aube, J. et al., JOC, 68, 8065. (~ hn, Ph-H or ~n Tf20, KOH, Et20 I "O

30-95% IV.J-5 Padwa, A. et al., JOC, 68, 929; Kulinkovich, O.G. et al., T, 59, 5265; see also: Gross, S.; Reissig, H.-U., OL, 5, 4305; see also: Grande, M. et al., JOC, 68, 2024; Moler, G.A.; Pack, S.K., JOC, 68, 9214. Ph

Me

~

e

2. Nail, THF, reflux

Me

N~)

MeO2t.~--

MeO2C ~ - B r

Et

87% IV.J-6 Danheiser, R.L. et al., JACS, 125, 4970.

X~,,~'~ ['"%

R1

BHT

~ ~

[~'R Ph-Me,120*C"CN

H

~

1

CN 61-87%

IV.J-7 Doye, S. et al., EJOC, 2888; Nolan, S.P. et al., SL, 1871. }n Pd2(dba)3'tBuOK'di~ Me ~ R--~~ R--~ Me

Me

0-97 %

(indolines, indolizidinesand pyrrolizidinessimilarlyprepared) IV.J-8 Yum, E.K. et al., H, 60, 2727; Kozawa, Y." Mori, M., JOC, 68, 3064. Ph I

+

[

R

Pd(OAc)2,DMF,BU4NCI,110~ TEA ~- N

R 51-67%

182

ORGANIC SYNTHESIS--2004

IV.J-9 Lazzaroni,R. et al., SC, 33, 2953. ~-~Me 1. Rh4(CO)12 , CO/H2, Ph-Me,100oc ,~ Me

O

Me

2. EtONa,EtOH

CHO Me 56%

IV.J-10 Ishibashi,H. et al., JOC, 68, 312; Malacria, M. et al., OL, 5, 5095; Tokuda, M. et al., T, 59, 827. Mes~ 0 [ ~ N - - ~ Mn(OAc)3,Cu(OAc)2 t~MeO~oMeCF3CH2OH'reflux

MC~eo~OMe 52%

IV.J-11 Hanessian, S. et al., JOC, 68, 7219; Randl, S.; Blechert, S., JOC, 68, 8879. H

PhCH=Ru(PCY3)2CI2 O ~ C ~'~'"~ " ~ CO2Me CH2C12, ~ 0 rt 02Me 93% IV.J-12 Merour, J.-Y. et al., TL, 44, 6553. HO2C----~

O

~ M e ~ PPA,ll0*C 89%

IV.J-13 Pohmakotr,M. et al., OBC, 1, 3495; see also: Rossi, E. et al., TL, 44, 5331. R O R O~s"Ph ~~S"Ph LiHMDS .... O THF,-78~ rt )n II

85-89%

SYNTHESIS OF HETEROCYCLES

183

IV.K. Heterocycles with Two or More Heteroatoms IV.K.I.a 5-Membered Heterocycles with 2 N's IV.K.I.a-1 Hajos, G. et al., JOC, 68, 5652; Grigg, R. et al., T, 59, 4451; Shintani, R.; Fu, G.C.; JACS, 125, 10778; Del Buttero, P. et al., TL, 44, 1425. O o

ArN-I

CHCI3 SR 76-91%

IV.K.I.a-2 Ila, H.; Junjappa, H. et al., T, 59, 2631; Holzer, W.; Krca, I., H, 60, 2323; Cvetovich, R.J. et al., TL, 44,5867; Braibante, M.E.F. et al., S, 1160. MeO ~ O Me ~t~SMe

~M

N2H4.H20 EtOH,D

SMe

OMe

e %

SMe H

80%

IV.K.I.a-3 Seebacher, W.; Weiss, R. et al., T, 59, 2811" see also: Kim, J.N. et al., TL, 44, 6737. R ArI

~o

R

+ (NH3NH3)+22SCN"

DMF, reflux

~ Ar~ ~NH2

25-57% IV.K.I.a-4 Danieli, B. et al., HCA, 86, 2082. tBuONO,AcOH M e O ~ ~ ~ . _ _ _ N M e ~ N H 2 Me MeO ~ O SMe 52%

184

ORGANIC SYNTHESISm2004

IV.K.I.a-5 Lee, W.S. et al., H, 60, 2499. O ~ N 1. RI-cfCCH2MgBr -R .~ 2. H20 O 3. Re-NHNH2,EtOH

NHR

R1 N--N ~R2 18-95%

IV.K.l.a.6 Kobayashi, S. et al., TL, 44, 3351; see also: Xia, M., JCR(S), 418. R1 RR~ 1~ ,'~--~,'R 2 BzHN,N BF3oEt20 ~R 3 + ~ BzN,N ~ R 3 R2 CH2C12'0~ H 37-77% IV.K.I.a-7 Ponticelli, F. et al., S, 2518. Me NHNH2 Mo(CO)6 MeOH, reflux

N'-NH

90%

IV.K.I.a-8 Dominguez, E. et al., OL, 5, 1095; Abadi, A.H. et al., CPB, 57, 838. O

~x

Me 1. DMFDMA ~_ ~ X ~ 2. Ar-NHNH2

N

87-95%

IV.K.I.a-9 Katritzky, A.R. et al., JOC, 68, 4935. 112

R2

R1ZAy.R3

R1ZAyoR3

R

~NH2

Bt

~

~n

.l~ DCE, reflux R,,~N~ N

35-92%

SYNTHESIS OF HETEROCYCLES

185

IV.K.I.a-10 Maligres, P.E. et al., JHC, 40, 229. R~'J

1. KSCN, AcOH, MeCN/H20, 55"C 2. aq H202, H20/AcOH, 35-45"C

+ OH

69-94% IV.K.l.a-ll Li, G. et al., EJOC, 3850 and JOC, 68, 5742; Belai, I., TL, 44, 7475. O Me R~,,~Me

NCS + Ts-NH2 + R1-CN

~

~----~-Me Ts-I~N R1 61-74%

IV.K.I.a-12 Beaulieu, P.L. et al., S, 1683; Ohsawa, A. et al., H, 61, 93; Soufiaoui, M.; Benhida, R. et al., TL, 44, 5807; Wu, Y.-Q. et al., JHC, 40, 191; see also: Zhang, H. et al., S, 2661.

R__~ NH2 Oxone R ~ ~ ~ - - NH + R2"CHO H20/DMF'~

R2

59-95% Ig.K.l.a-13 Pellacani, L. et al., OL, 5, 1019.

EtO2.C OtBu

R • R" "O

CO2Et 4- NsOHN-CO2tBu

CaO CH2C!2, rt

CO2 58-78%

IV.K.l.a-14 Volonterio, A.; Zanda, M., TL, 44, 8549; Ding, M.-W. et al., OPP, 35, 391; Langer, P.; Bodtke, A., SL, 1743 and TL, 44, 5965. a2

R2 R-~N-R

1 + HO2C~co2Et

O~_~-- CO2Et CH2C12' rt ~ R--N~I~R 1 O

0-88%

186

ORGANIC SYNTHESIS--2004

IV.K.I.a-15 Viso, A.; de la Pradilla, R.F. et al., CEJ, 9, 2867. CO2Me R _~CO2Me T~ N. O

r Ar .6 ~AN

~ T~

Ar 40-93% dr ---1.5-49:1

IV.K.1.a-16 Toru, T. et al., S, 1236 and SL, 1117. Ar-CHO

HMDS A~_.. Ar ~ ~NH 120~ Ar 0-89%

IV.K.I.a-17 Kamitori, Y., H, 60, 1185. R-CHO

+ Me2N,,C F 3 _N ~ O

/ _ ~ CF3 NH4OAc AcOH ~- N~NH R 51-74%

IV.K.I.a.18 Peddibhotla, S.; Tepe, J.J., S, 1433. Rq~1 69 R2-CHO .6 R3-NH2

]~2 jCO2H

TMS-CI CH2C12,reflux ~

~ - ~ '''R1 R3~'~ N R

30-79% IV.K.I.a-19 Aggarwal, V.K. et al., JOC, 68, 5381. A

R-CHO

1. Ts-NHNH2,MeCN, rt

~ R-N2+

R1.C-_-CH

2. NaOH

50~

H

(one pot method)

19-67 %

IV.K.I.a-20 McLaughlin, M. et al., JOC, 68, 50. R R~CN~.

NH2

1. R1-NH2,PPTS, CHCI:~670C.I~

9~'~.i,OR2 2. HC(OMe)3,PPTS, 80~

R1

I

R1

0-93%

SYNTHESIS OF HETEROCYCLES

187

IV.K.l.a-21 Gutschow, M. et al., JOC, 68, 4684.

R1 .O o

RI--~H2

R2

RO'~N~ O H

EtoH,EtONaAO ~ N ~ O H 15-85%

IV.K.l.a-22 Almansa, C. et al., JMC, 46, 3463. R

~ I]

F +

R ~

Bet-MIC or Ts-MIC DMSO, 75"C'~ N % t ~

F

58-70% IV.K.I.a-23 Evindar, G.; Batey, R.A., OL, 5, 133; Brain, C.T.; Steer, J.T., JOC, 68, 6814. R1 CuI, 1,10-phenanth ~ , . B r NHR1 or ed(ePh3)4 R r NR2R3

R

I' -'~ "~~NR2R3

Cs2CO3,DME,80*C~" 58-98% (Cu) 0-93% (Pd)

IV.K.1.a-24 Booker-Milburn, K.I. et al., OL, 5, 3313.

O Ph~

+

N-CI

E t O ~ 02 1. MeCN, -42"C

it=.

S.

2. EtOK, EtOH, -42"C~ rt

02

60%

IV.K.l.a-25 Mignani, S. et al., JHC, 40, 159.

q O H 2 1 ~ OH 1" TEA' CHCI3 P(OEt)2 + ~CO2Et 2. Ph-Me2, reflux

/_~__(P(OEt)2 I~NH CO2Et 27%

Ph

188

ORGANIC SYNTHESISm2004

IV.K.I.b 6 Membered Heterocvcles with 2 N's IV.K.I.b-1 Gonzalez-Gomez, J.C. et al., SL, 2225; Balci, M. et al., JOC, 68, 7009. Cl CI O

~

~

+ ~~N

OMe

ipr2NEt CH2C12,140~

O ~

~

CI

'.---N

OMe

98% IV.K.I.b-2 Qabar, M. et al., TL, 44, 583.

~

piiSO2

0

O2Bn IBD

INH NH

CH2C12

_~Ac

~,

CO2Bn

_f--N~ I~

PhSO2

OAc

DAc ~OAc

v 84%

.oOAC

O~.,OAc "OAc

IV.K.I.b-3 Buonora, P.T. et al., TL, 44, 7799; Maas, G. et al., S, 2679. Ph R1

.,R3

O

NH2NH2~

._ Ph~ "

R2 H20/dioxane,85"C

~3R2

%.% H 34-99%

IV.K.I.b-4 Sabitha, G. et al., SL, 858; Adapa, S.R. et al., SL, 67; Tu, S. et al., TL, 44, 6153 and JCR(S), 544; Mitra, A.K.; Banerjee, K., SL, 1509; Abdel-Fattah, A.A.A., S, 2358; Reddy, V.V.N. et al., TL, 44, 8173; Maiti, G. et al., TL, 44, 2757; Salehi, P. et al., TL, 44, 2889; Xia, M.; Wang, Y., S, 262; Bose, D.S. et al., JOC, 68, 587; Shanmucam, P.; Perumal, P.T., JCR(S), 601. O O R RI~ NH2 TMS-CI, NaI R ~ ~ J ' ~ I NH R3~N~X R~" "-O+ HzN~X + R-CHO MeCN, rt ~

H

83-98%

SYNTHESIS OF HETEROCYCLES

189

IV.K.l.b-5 Orru, R.V.A. et al., CC, 2594. R1

R-CN + R1-CHO + R2-NCO + MeP(O)(OEt)2

Re N~

BuLi -78~ ~ rt

O H 10-80%

IV.K.I.b-6 Marcaccini, S. et al., S, 691, 1553. Ph,., ~0 Ph

NoNH2

x 1. c-C6Hll-NC Ph_ ~ ~.0 2. R-CHO 3. XCH2CO2H Ph

NH R cI-C6Hn 41-74%

IV.K.I.b-7 Woo, J.C.S.; MacKay, D.B., TL, 44, 2881. tBuO2C R ~ I NHR2 IBr ~,~~N~ CH2C!2, -78~ SR1 I R2 67-95% dr = 20:1 IV.K.I.b-8 Ferraccidi, R.; Carenzi, D., S, 1383; see also: Rad-Moghadam, K.; Mohseni, M., JCR(S), 487. ~'~N ~Bn Pd0PPh3)4, K2CO3 t ~ ~ N "Bn + R-NCO .~" I [ I [ ~ N ~ O -,BrH Ph-Me, 70~ R

62-85% IV.K.I.b-9 Jahng, Y. et al., TL, 44, 1883. o

88-95%

IV.K.l.b-10 Hiemstra, H. et al., JOC, 68, 4486. "Synthesis of 2,6-Bridged Piperazine-3-ones by N-Acyl-iminium Ion Chemistry"

190

ORGANIC SYNTHESIS--2004

I V . K . I . b - l l Karpov, A.S.; Muller, T.J.J., OL, 5, 3451. NH2 1. Pd(PPh3)2CI2, CuI, TEA, THF I ~ , Ar-COCI + 1l ~. . / H2X" 2. Na2CO3ol0H2O, THF or MeCN, reflux A

R

30-81% IV.K.I.b-12 Mercer, G.J.; Sigman, M.S., OL, 5, 1591; Moreau, J.J.E. et al., SC, 33, 183. Ar

H

~N N

Mn, pyr.HC! _~ MeCN/Ph-Me

,u.A r

~~.,IA r r

76-99%

IV.K.I.b-13 Deniaud, D. et al., JOC, 68, 4912, 8583. Me2N

..,,. / F -

+ R-CH=C=O

CH2C12, rt

~

R1 O 63-86%

IV.K.l.b-14 Zaleska, B. et al., JOC, 68, 2334. H

(C~I2)n J.., + Et k'J'lNH2 PhHN

II S

NHAr EtOH, reflux~ (C ~ _ / , , ~ , , , , ( NHAr H ~aes 45-78%

IV.K.I.b-15 Gallagher, T. et al., OL, 5, 811. Bn*N'-~O2 +MeO2C~Me II,.. t,,~O Ph

NHTs

O 1. Nail or Cs2CO3, DMF .~ B n . ~ M e

DhN/IH

3.2" CI, rt reflux

IV'"~ " N, T s Ph 71%

....-...e,

IV.K.I.b-16 Katritzky, A.R. et al., JOC, 68, 4938. Me

Me

.c.o

NH2 H20/MeOH, rt 96%

Bt

SYNTHESIS OF HETEROCYCLES

191

IV.K.I.c 7-Membered Heterocycles with 2 N's

IV.K.I.c-1 Katritzky, A.R. et al., JOC, 68, 5713. ~~N

+ Ar-NCO T~uL~8.C ~

~ ~ O~N~~A r Art 65%

IV.K.I.c-2 Zhao, H.-B.; Alper, H., JOC, 68, 3439. g1

+ Ar-NCO

Pd2(dba)3.CHCl3, dppp THF, 40-60~

R

11-80% IV.K.I.c-3 McElwee-White, L. et al., JOC, 68, 1615. SEMQ DSEM SEMO CO, W(CO)5,12, K2CO3 .... \ ph H20/CH2CI2 - ph / .... Ph/ H2

DSEM NH

O 75% IV.K.I.c-4 Zhu, J. et al., AG(E), 42, 4774. Pd(dppf)Cl2, KOAc DMSO, 120~ R

. ~O N ~ I Me R O Me 51-98%

192

ORGANIC SYNTHESIS--2004

IV.K.2. Heterocvcles with 2 O's or 2 S's IV.K.2-1 Pansare, S.V.; Bhattacharyya, A., T, 59, 3275. Me

Me

M e ' N " ~ P h (CH20)n, H2SO4, M e ' N " ~ P h O,,~,lOO O~l O AcOH,85~ D' S~S 1

R~LO,J 75-93%

IV.K.2-2 Shaabani, A. et al., JCR(S), 578. O ~ 0

Oo 0 + R-N~C CHCI3,reflux R

67-81% IV.K.2-30ku, A. et al., JOC, 68, 10040. M~

O

+ R-CHO

Rh2(OAc)4, Ti(Oipr)4 - Me I_ CH2C12, rt

|

R

~) OH

35-66% dr = 3.6-5.6:1 IV.K.2-4 Murphy, P.J. et al., JOC, 68, 7115.

Ph-H, rt76% IV.K.2-5 Zard, S.Z. et al., CC, 1408. ~O ~ s ~ S E t O

TiCI4

~ ~ O 0 10-84%

SYNTHESIS OF HETEROCYCLES

193

IV.K.2-6 Shi, M. et al., JOC, 68, 1559; Huang, J.-W.; Shi, M., JOC, 68, 6705.

&R

CO2,TEA, CH2CI 2X ~

~ ~ . _~Y

89-99%

X

IV.K.3. Heterocycles with 1 N and 1 0

IV.K.3-1 Florio, S. et al., JOC, 68, 10187. M ~ O

e

"l"

Cl

---9"~,tBu~,N~~ R

~'Me"~"~ s " t n u

LDA THF, -98~

~ '.R 48-85% dr -- 1.5-49:1

IV.K.3-2 Karlsson, S.; Hogberg, H.-E., EJOC, 2782; Caddick, S.; Bush, H.D., OL, 5, 2489; Kezuka, S. et al., BCJ, 76, 2197; Chiacchio, U.; Merino, P.; Romeo, G. et al., T, 59, 4733; Cardona, F. et al., OL, 5, 1475; Aggarwal, V.K. et al., OBC, 1, 684; Heany, F. et al., OBC, 1, 1122; Alonso, R. et al., JOC, 68, 4772. RR RR o

CHO

+ R~..N~IR

cat. =

2 1. eat., wet DMF ~_~._/OH .~,.2. NaBH, MeOH uk,,~,,~R2 iN

~ Q

38-76% endo:exo - 12.8-99:1 ee (exo) = 37-92%

H 2HCI IV.K.3-3 Clark, A.J. et al., TL, 44, 7763.

O O R O 2 C ~ ~ N ,Me e

RO2~O Ph-Me, reflux ~ Me'~o'N (Me2N)3P=-1~ tBu~P(NMe2)2 50-57%

194

ORGANIC SYNTHESISm2004

IV.K.3-4 Holzer, W.; Hahn, K., JHC, 40, 303; see also: Dechoux, L. et al., TL, 44, 7667. R

Ph

R

H

Ph

DMF ~

fil

1~1 53-88%

IV.K.3-5 Reissig, H.-U. et al., EJOC, 1153. ,.OtBu

..OtBu

..OtBu

'

~--~OMe

,~.

,OMe

CDCI3, rt

+ .

OMe

OH

99% 3:2

IV.K.3-6 Katritzky, A.R. et al., JOC, 68, 9093. Me RCH2"X +

HO'~

Me

K2CO3

0 "t "Me DMF,55-65~

~

R"~%

Me

24-61% IV.K.3-7 Sauers, R.R.; Van Arnum, S.D., JHC, 40, 655. O M

-ff~O e

EtONO,HCI

M e ~ ~ t~t Me

Me

67%

IV.K.3-8 Ukaji, Y.; Inomata, K. et al., CL, 32, 582; Gallos, J.K. et al., TL, 44, 3905.

~

OH

O PrZnBr, ipr2Zn, solvent, 00C ph sN

Ph

HOTCO2R1 HO~ICO2R1

17-86% ee = 11-91%

IV.K.3-90hwada, T. et al., JACS, 125, 5282. R~~NO CO2Me TFSA ~ [~~,,,CO2Me 2

CH2C12,0~ 50"C R"~,,~"O "N 16-98%

SYNTHESIS OF HETEROCYCLES

195

IV.K.3-10 Beam, C.F. et al., SC, 33, 4163.

Me Me 1. LDA,THF ~ . ~_ n R1 R,,J~N..OH ~- K---~N,-2. R1-COMe 3. H3 O+, reflux 24-83% IV.K.3-11 Dilman, A.D.; Ioffe, S.L. et al., OL, 5, 4907.

RL

R1

+

R2 R,,~~N ~ O"

Br.,~R2 TBDMS-CI,TEA, rt ~ NO2

17-91% IV.K.3-12 Ahmed, F.; Donaldson, W.A., SC, 33, 2685; Lee, J.C. et al., SC, 33, 1611.

NH2

Q~CO2Et 1. NaHCO3,THF

~/~N'-~ 'CO2Et

+

Br

2. TFAA,THF 77%

IV.K.3-13 Gajda, T. et al., TL, 44, 4747. R

SNCAtP(OEt)2 + R-CHO NaN or tBuOK S~~~'w O THF P(OEt)2 H

O

70-95% IV.K.3-14 Arndtsen, B.A. et al., JACS, 125, 1474. 1~1

N"R1 Pd cat., ipr2NEt R.COCI + CO +

!1

.....

R2"

Re

t~N+~-~

-~ R - ~ o ~ O "

32-93%

IV.K.3-15 Sibi, M.P. et al., JACS, 125, 11796.

r,~ ~.~.~ ~ J . ~R. H Mg(NTf2)2,CH2C12,-40~ .R%~' iP -[[ ~ vRl-I - Bn-NHOH ~- (~'XO, lV"Bn O

O

(~

~ '/NI uN - ' ~ oZ~Xo ~

28-95% 93-98% ee = 60-96%

de =

196

ORGANIC SYNTHESISm2004

IV.K.3-16 Endo, T. et al., TL, 44, 7889; Lee, W.K.; Ha, H.-J. et al., JOC, 58, 43, 104. H LiBr or Bu4NBr X ~ N ~ R ~'~R + Cx2 1~ H 70-94% IV.K.3-17 Mann, E.; Kessler, H., OL, 5, 4567; Seebach, D. et al., OS, 80, 57; see also: Reddy, G.O. et al., TL, 44, 6323; Luppi, G.; Tomasini, C., SL, 797; see also: Bandgar, B.P." Pandit, S.S., TL, 44, 2331.

/CO2Me R--NH HN--( HN-Fmoc I2, PPh3,TEA sl~o ~R 2 THF, 0~

H

.N-~CO2~e

R"RIN~ O~R~2il"'Fmoc 63-85%

IV.K.3-18 Suzuki, K. et al., SL, 1746 and OL, 5, 391; see also: Chai, C.L.L. et al., T, 59, 8731; Risitano, F. et al., H, 60, 857; Coutouli-Argyropoulou, E.; Pilanidou, P., TL, 44, 3755; Gree, R.; Houk, K.N. et al., CEJ, 9, 5664; see also: Rossi, E. et al., EJOC, 1423. R +N.O" NR" ~~ _ ~ / ~ ~ R 1 0 +q ~

R2

O

4~M S ~ iprOH, 50"C

[ ~ ~ R10 ~b~ ' )

R2

72-84%

IV.K.3-19 Parker, K.A.; Chang, W., OL, 5, 3891. Me Me O~,,O,, ~'~O PhI(OAc)2,Rh2(OAc)4, MgO ./O~,.~"~ O H2NMe~ CH2C12,40"C ~ O==t~N~.,~ H Me 86% IV.K.3-20 Gabriele, B. et al., JOC, 68, 601; see also: Crich, D. et al., JOC, 68, 2034.

R H~R CO, O2,PdI2~ O~~~.~ H2 R1 DME,100C r R1 H 81-96%

SYNTHESIS OF HETEROCYCLES

197

IV.K.3-21 Hayashi, M. et al., OL, 5, 3713; see also: Kercher, T. et al., 5, 2727. H 2 ~ 02, Darco| KB R-~~-CHO + R] H(r,,--,,,oa~ Ph.Me2,120oc ~ R - ~ - - ~ N ~

OL, R1

67-88% IV.K.3.22 Ciufolini, M.A. et al., AG(E),42, 1411. CI

,,,

AIMe2 IV.K.3-23 Ganem, B. et al., 6829. R~O R1

/CO2R1

51-91%

TL, 44, 6825; Wang, Q.; Ganem, B., TL, 44,

+ O~NR2R 3 + R42NH

,~ R42 MeOH or CH2C12

NR2R3 20-92%

IV.K.3-24 Suarez, E. et al., JOC,68, 1012. (0H) m

I""(]O~ R

(0H)m

1

hn, PhIO or DIB, I2, solvent ~ ~ ~ R 1

R..NH

~'~ 44-96%

IV.K.3-25 Hancock, M.T.; Pinhas, A.R.,

TL,44, 5457. Bn

Bn--< R

R

1"Lil' THF' reflux~ o~oNoNo~ R' R 1 2. CO2, rt

85-90% IV.K.3-26 Banik, B.K. et al., .

TL,44, 1699.

-

In, NH4CI H20/EtOH

198

ORGANIC SYNTHESISm2004

IV.K.3-27 Nair, V. et al., TL, 44, 729; Suga, S.; Yoshida, J. et al., OL, 5, 945. CO2Me

CO2Me

CO2Me ~CO2Me

O

O 76% IV.K.3-28 West, F.G. et al., TA, 14, 917.

O O

~.--o~-~__ ~...1~ N2 ~e

IJ

~u0

Ph-Me,reflux~--

O~h ~ =

Ph 67%4.5:1 IV.K.3-29 Mitchell, M.O.; Hurley, A.R., AG(E), 42, 553. H

~NH2 iprzNEI % ~ + CICH2CN ~ "CO2H DMF

NH

66%

IV.K.3-30 Merour, J.-Y. et al., H, 60, 1793.

QOH

~ .jPh Ar.,N~~ O

Ph O~-~

Pd(OAc)2,LiCI,K2CO3 DMF,100~

O Ar 32-62%

IV.K.3-31 Tanaka, T. et al., AG(E), 42, 1749.

#r

F~OR1 R y e * H R1ONa,Pd(PPh3)4.~ Ts. ~ ~ u c Ts'I~NucH R1OH,rt 48-84%

SYNTHESIS OF HETEROCYCLES

199

IV.K.3-32 Chan, M.K. et al., OL, 5, 4795; see also: Rogers, B.N. et al., JOC, 68, 644; Shin, D.-S.; Yoon, Y.-J. et al., JOC, 68, 7918; see also: Caubere, P.; Guillaumet, G. et al., S, 2033. R

Me

R

O2N

Me

7-96%

IV.K.3-33 Yadav, J.S. et al., AG(E), 42, 5198. O

NH2

+ t~,O~,.,OA c CH2el2,rt

~

" ~ . OAc H 75-89%

IV.K.3-34 Giacomini, D.; Galletti, P. et al., TL, 44, 6269. TBSO H~[H

A

TB~

Me~CO2Et I | O/fi--NH

5 CO2Et

K2CO3 M( "~/"N + R-COX Me2CO~ O ~ . . ~ 11 R 47-77%

IV.K.4. Heterocycles with 1 N and 1 S

IV.K.4-1 Pak, C.S. et al., SL, 166.

O +

K2CO3 ~ DMF

R

H

N [ ~ , / ~ N ~ S' R

H 0-99%

IV.K.4-2 Stachel, H.-D.; Weigand, W. et al., HCA, 86, 2471. Me Me MeO2~NH MeO2C~ . ~ O~ N ~ ' B r 1. Na2S.5H20, MeOH, rt ~ O ~ ~ 2. H202, H20 Ph H

Ph

H 48%

200

ORGANIC SYNTHESISm2004

IV.K.4-3 Lee, W.S.; Nam, K.S. et al., SL, 1967.

~

O CO2Me 1. AcNH~ Ph-Me, reflux

~ N H

S.)2.

2. H202, 50"C 3. HCI, rt

90%

IV.K.4-4 Domling, A. et al., TL, 44, 8947. MeO2C,

MeO2C~NC NMe2 R-CHO + R1-COSH

N

1

6 9-35%

IV.K.4-5 Kelly, J.W. et al., AG(E), 42, 83. CbzH~ H R~.~.,ICO2Me II

CbzH~ + (Ph3P+)202rfo"

R%S~

.,CO2Me

/

O

k,.STr

84-98% dr = 10-32.3:1 ee = 99 %

IV.K.4-6 Chen, J.; Forsyth, C.J., OL, 5, 1281. R ~ o ."S ~ c o 2 M e rs3

PPh3 THF, 50"C

R...~,~~

CO2Me

67-88% IV.K.4-7 Jordan, A.D. et al., JOC, 68, 8693; see also: Castillon, S. et al., TL, 44, 6073; see also: Burger, K. et al., JHC, 40, 435. H

~",~,e, 1 ~ NR1R2 BnNMe3Br3 R - - ~ ~ ~ - R-~ ~ ~ AcOH, rt 7O-88%

NR1R2

IV.K.4-8 Langer, P.; Albrecht, U., SL, 1503. NH

~

CN + f R NCS

CN

Nail, reflux or

.]D,.-

BuLi,THF,-78~ 30-75%

SYNTHESIS OF HETEROCYCLES

201

IV.K.4-90chiai, M. et al., JOC, 68, 7887; see also: Deniaud, D. et al., EJOC, 421. s

A~ p h / I--BF4 + H2~~...R1

TEA Me0H, rt

R1 43-95%

IV.K.4-10 Besson, T. et al., TL, 44, 4455. Br O ~ N ~ j ~ ~[,,N.Bn %~]~cI~N

~

NC /)7" O ~ N .Bn pW, CuI pyr, 115~ 83%

IV.K.4-11 Misu, Y.; Togo, H., OBC, 1, 1342. R~~H~S 02

Ar(OH)OTS • R MeCN,0~ -* rt

~

I

s

02 OMe 44-86% I

OMe

IV.K.4-12 Harmata, M.; Hong, X., JACS, 125, 5754. CO2Me :./CO2Me

h

LDA or LiHMDS TI-IF,.78~

Ph 77-93%

IV.K.4-13 Fernandes, M.A.; Reid, D.H., SL, 2231. Ph

I ~ H-~ CR , ~ ] Ph .,CHS

I

DBU THF, rt

69-82% IV.K.4-14 Lee, J. et al., OL, 5, 4175. Nf~~n 1. MsCI,TEA,THF,5-10~ /~)n HX.H2 ..... ~ H X 2. BuLi, HN(/Pr)2,THF, -30-* 0~ 02 55-90%

202

ORGANIC SYNTHESIS--2004

IV.K.4-15 Yadav, L.D.S.; Singh, A. et al., TL, 44, 5637. ArlNH HOzCvN~R Acz~),NaOAc Arl R S~S'NH4 ++ O + Ar-CHO :-~ S ~ S ~ A r O 76-92% VoK.5. Heterocycles with 1 0 and 1 S IV.K.5-1 Enders, D. et al., S, 1856. 1. H20/EtOH, reflux-,

CbzHN

Oc.C6H11 2.12, THF, -78~ 2

,A

rt

CbzHN

'

02 76-77%

IV.K.5-2 Okuma, K. et al., EJOC, 3727. R s

R

CO2H

Ph-Me, reflux

65-99% IV.K.5-3 Franck, R.W. et al., T, 59, 4249. O A c O ~ " O~ + O ~ ~-AcO~" O~"~O~;aMe AcO' " ~ ",lMe CHCI3 AcO"'~-ob~~ O AcO AcO O 53% IV.K.5-4 Cossy, J. et al., SL, 667. R (k4ns.,.O 02

PhCH=Ru(PCy3)(IMes)CI2~ Ph-H, 7O~

R (k4.~.O 02 51-99%

SYNTHESIS OF HETEROCYCLES

203

IV.K.5-5 Nair, V. et ai., S, 662. R--~

pyr OH + RLN--C Ph-Me, 100~ v SNPhth

~-'[~~S

R1

85-99%

IV.K.5-6 Nakayama, J. et al., BCJ, 76, 613. Cl

R Me ( OH + SC12

R --

Me

Nail

~M[e

Et20

e 46-78%

IV.K.6. Heterocycles with 3 or more N's IV.K.6-1 Dabak, K. et al., EJMC, 38, 215. O ~L'R1

0 OHC

Aco.

R 1 + R1-NH2 N2

~ 1~.

EtOH, rt

i R

50-90% IV.K.6-2 Yamamoto, Y. et al., JACS, 125, 7786; Wang, Z.-X.; Qin, H.-L., CC, 2450; Benedetti, F. et al., TL, 44, 9095; Santoyo-Gonzalez, F. et al., OL, 5, 1951; Peng, W.; Zhu, S., T, 59, 4395; Kokotos, G. et al., H, 60, 2637; Link, A.J.; Tirrell, D.A., JACS, 125, 11164; Chang, C.-W.; Lee, G.-H., OM, 22, 3107; Ju, J. et al., JOC, 68, 609. R

R~

R

Pd2(dba)a'CHCl3, PPh3 ~-~ 4- ~,,,~OCO2Me 4- TMS-N3 P(OPh)3,CuCI, EtOAc, 100*C N'N'N 50-83%

IV.K.6-3 Vivona, N. et al., JOC, 68, 605. R1 t ~ N R1 NH2NH2,I~ f ~ / ~ Rflt<'O" MeOH,rt R

H 44-88%

204

ORGANIC SYNTHESISm2004

IV.K.6-4 Matsumoto, N.; Takahashi, M., H, 60, 2677; Luo, Y.; Hu, Y., SC, 33, 3513. M e . . ~ N ~ ..

Me,, ~9

o ,N eSPh2

R

D o

~Ie

~4e 86-98%

IV.K.6.5 Prakash, O. et al., EJMC, 38, 533. No

CH2C!2

H

50-82% IV.K.6-6 Liu, C.; Iwanowicz, E.J., TL, 44, 1409. R-'I~H R1 R"~ R-NCS ~ NvN-.R1 + N,~N 2. RLNHNH2,EDC NH2 NH2 42-90% 3-100:1 1. NaNHCN

IV.K.6-7 Cristau, H.-J.; Pirat, J.-L. et al., TL, 44, 3179; Salama, T.A. et al., M, 134, 1241. MemO + TMS-N3 Me~"CO2Et

M e ~ N , N, ,N

~

Me~CO2Et 40-90% IV.K.6-8 Quan, M.L. et al., BMCL, 13, 369. O H~T~CO2Eti, 1. PPh3, CCi4, reflux 2. NaN3,MeCN NO2 CI

N-N ,9. -

~

CI 82%

NO2

SYNTHESIS OF HETEROCYCLES

205

IV.K.6-9 Katritzky, A.R. et al., JOC, 68, 4941; Noodleman, L.; Sharpless, K.B. et al., JACS, 125, 9983. 1LN AcOH N-N BtI~NR1R 2 + NaN3 CHCI3, rt I~ ~N~NR1R2 i R

27-89% IV.K.6-10 Limanto, J. et al., OL, 5, 2271. X~X 1. morpholine, THF, 45.67"C

~,-R ~ ~ N H 2

2. NH2NHC(=NH)NH2,AcOH]MeOH, 67~ 45-76% IV.K.6-11 Hu, W. et al., SC, 33, 2769. H

R-CHO + NH2NH2~

I~N'-NH EtOH

HN~N~R H

73-92% IV.K.6-12 Salem, M. et al., SC, 33, 3861. R

R~I'NH2

AcOH /~---N + RI-C(OEt)3 ~ ~N~R 1 N"NH I Ts Ts 70-90%

IV.K.6-13 Langer, P. et al., EJOC, 182. R

H2NoNH

CH2C12or EtOH, reflux H

72-99%

S

206

ORGANIC SYNTHESIS--2004

IV.K.7. Heterocycles with 2 N's and 1 0 IV.K.7-1 Kidwai, M.; Mohan, R., OPP, 35, 426. N-N

R-CONHNH2 + R1-CO2H

A1203

or M K10, }xW

85-88%

IV.K.7-2 Hernandez, J.-F. et al., TL, 44, 6079 and JOC, 68, 7316; Moustafa, A.H., S, 837.

H

H

Fmoc-. . K ~ ~ O tBuO2C~

i~

1. NaOAc,H20/EtOH, 86~

O,,N'/,~NH2 2. TFA, CH2C12

Fmo~CO2H '~ R ' < ~ IO

40-48% IV.K.7-3 Tumkevicius, S. et al., TL, 44, 6635.

~~OH , NH2

SOCI2 f f ~ ~ C l reflux

v"ff~I~h~ S -HCI

61%

IV.K.8. Heterocycles with 2 N's and 1 S or 1 Se IV.K.8-1 Pfeiffer, W.-D." Langer, P. et al., SL, 2392. Me Me I I R~O HK,N.Me R.~, N.N.Me Br +

S ~ N "R1 H

EtOH,reflux ~ L S ~ N "R1 59-83%

IV.K.8-2 Huang, X." Chert, J., SC, 33, 2823. AI"

Ar--~NH2 Se +

I(OAc)2 CH2C12,rt

Ar

Se N

80-95%

SYNTHESIS OF HETEROCYCLES

207

IV.K.8-3 Johnson, P.D. et al., TL, 44, 5483; Montero, J.-L. et al., T, 59, 6051. C I2~ N~H 1. R-NH2,TEA,-70"C--,_rt -~ R..N,,s,.N H{/'~'x 2. K2CO~,DMSO,rt 02 22-82% IV.K.8-4 Filippone, P. et al., JOC, 68, 1947. "Expeditious Synthesis of New 1,2,3-Thiadiazoles and 1,2,3Seladiazoles from 1,2-Diaza-l,3-Butadienes via Hurd-Mori-Type Reactions" !V.L. Other Heterocy..cles IV.L-1 Araki, S. et al., OBC, 1, 978. .CO2Me

~

]

,, N + 1[ neat, rt ~ N'+~~ CO2Me R

] ) r ~ CO2Me N ~ / ~ IC"~CO2Me ~I+-N CO2Me l( 78%

IV.L-2 Harpp, D.N. et al., JOC, 68, 7059. R~OH ~1~ R"~ ' o n +

~'~ s/S"

[

CCIh,reflux ~

S=S 14-80%

IV.L-3 Robinson, R.I.; Woodward, S., TL, 44, 1655. ~.1R2 . R~~, -R2 PhIO, SOyDMF g ~[.,.O~ CH2C12 ~ R,,~(~SO2 35-75% IV.L-4 Yoshida, H.; Kunai, A. et al., JACS, 125, 6638. iSiMe2

~

+ .~SiMe2 T

~Me2 Pd(OAc)2, t-OcNC, 18.Cr.6~k\_ //~--Si~,~.,__ R ---R-THF, 2 0 o c ~Si ~-2~ ~Me2 30-77%

208

ORGANIC SYNTHESISm2004

IV.L-5 Dupuy, C. et al., EJOC, 54. PG I HN---~ O~ + R

~

PG

PG pg 37-99%

IV.L-6 DuBois, J. et al., OL, 5, 4823; Rizzo, C.J. et al., TL, 44, 7513. O2 O2 "---

H2N"S"o PhI(OAc)2,Rh2(Oct)4, MgO.~

H-Lv'S"o

H2 '2

Boc/

Bo/ 85% anti:syn = 12:1

IV.L-7 Beignet, J.; Cox, L.R., OL, 5, 4231. R,~,~CHO TMS-OTf,2,6-DTBMP I~~,,,OTMS O-Si~"~'~TM S Et2

CH2C12,-78~

O- S i ~ , ~ Et2 55-88%

a-H:b-H = 2.7-9.7:1 IV.L-8 Kirsch, G. et al., SL, 855. O

R1

R-~R

1

R~O Na2Se,XCH2-EWG M~-~'~Se"~EWG MeS" "SMe 9-55%

IV.L-9 Mathey, F. et al., JOC, 68, 2803. 1. Ph-Me2, 150~ + R.CHO Ph

2. S~ 60~

Me ~ ph,~l~,,0 40-99%

SYNTHESIS OF HETEROCYCLES

209

IV.M. Reviews IV.M-1 Sato, T., Ikeda, M., 11, 59, 429. Review:

"A General Route to Bridged Azabicyclic Compounds Using Radical Translocation/Cyclization Reactions"

IV.M-2 Elwahy, A.H.M., JHC, 40, 1. Review:

"New Trends in the Chemistry of Condensed Heteromacrocycles. Part A: Condensed Azacrown Ethers and Azathiacrown Ethers"

IV.M-3 Chupakhin, O.N. et al., H, 61,593. Review:

"Modification of Macrocyclic Compounds by Azaheterocydes"

IV.M-4 Singh, G.S., T, 59, 7631. Report:

"Recent Progress in the Synthesis and Chemistry of Azetidones"

IV.M-5 Cardillo, G. et al., A4, 36, 39. Review"

"Aziridines and Oxazolines: Valuable Intermediates in the Synthesis of Unusual Amino Acids"

IV.M-6 Lee, W.K., Ha, H.-J., AA, 36, 57. Review:

"Highlights of the Chemistry of Enantiomerically Pure Aziridine-2-carboxylates"

IV.M-7 Shawali, A.S., Mosselhi, M.A.N., JHC, 40, 725. Review:

"Hydarazonyl Halides: Useful Building Blocks for the Synthesis of Arylazoheterocycles"

IV.M-8 Katritzky, A.R., Rogovoy, B.V., CEJ, 8, 4586. Review:

"Benzotriazole: An Ideal Synthetic Auxiliary"

IV.M-9 Hirata, T., et al., H, 60, 689. Review:

"Terpenoid Coumarins of the Genus Ferula"

210

ORGANIC SYNTHESISm2004

IV.M-10 Sosnovskikh, V.Y., RCR, 72, 489. Review:

IV~

"Synthesis and Reactions of Halogen-Containing Chromones"

Riether, D., Mulzer, J., EJOC, 30.

Microreview: "Total Synthesis of Cobyric Acid: Historical Development and Recent Synthetic Innovations" IV.M-12 Sheremetev, A.B., Yudin, I.L., RCR, 72, 87. Review"

"Advances in the Chemistry of Furazano[3.4-b]pyrazines and Their Analogues"

IV.M-13 Jagodzinski, T.S., CR V, 103, 197. Review:

"Thioamides as Useful Synthons in the Synthesis of Heterocycles"

IV.M-14 Balme, G., Bossharth, E., Monteiro, N., EJOC, 4101. Microreview: "Pd-Assisted Multicomponent Synthesis of Heterocycles" IV.M-15 Zhu, J., EJOC, 1133. Microreview: "Recent Developments in the Isonitrile-Based Multicomponent Synthesis of Heterocycles" IV.M-16 Tyrrell, E., Brookes, P., S, 469. Review:

"The Synthesis and Applications of Heterocyclic Boronic Acids"

IV.M-17 Kawashima, T., BCJ, 76, 471. Account:

"Syntheses, Structures, and Thermolyses of Three- and Four-Membered Heterocyclic Compounds Containing Highly Coordinate Main Group Elements"

IV.M-18 Nair, V. et al., ACR, 36, 899. Review:

"Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes"

SYNTHESIS OF HETEROCYCLES

211

IV.M-19 Fagnoni, M., H, 60, 1921. Review:

"Photoinduced Electron Transfer Reactions in Heterocyclic Chemistry"

IV.M-20 Booth, B.L. et al., T, 59, 2749. Report:

"The Chemistry of Diaminomaleonitriles and its Utility in Heterocyclic Synthesis"

IV.M-21 Gallmeier, H.-G., Konig, B., EJOC, 3473. Microreview: "Heteroaromatic Oligoamides with dDNA Affinity" IV.M-22 Ryzhakov, A.V. et al., H, 60, 419. Review:

"Molecular Complexes of Heteroaromatic N-Oxides and Their Reactions with Nucleophiles"

IV.M-23 Sandford, G., CEJ, 9, 1464. Review:

"Macrocycles from Perhalogenated Heterocycles"

IV.M-24 Gansauer, A. et al., AG(E), 42, 5556. Review:

"Strained Heterocycles in Radical Chemistry"

IV.M-25 Schulze, B. et al., H, 61, 639. Review:

"[7t4+ ~2] Cycloadditions of lsothiazole Derivatives"

IV.M-26 Hamad Elgazwy, A.-S.S., T, 59, 7445. Report:

"The Chemistry of Isothiazoles"

IV.M-27 Lukevics, E. et al., H, 60, 663. Review:

"Methods for the Synthesis of Oligothiophenes"

IV.M-28 Felpin, F.-X., Lebreton, J., EJOC, 3693. Microreview:

"Recent Advances in the Total Synthesis of Piperidine and Pyrrolidine Natural Alkaloids with Ring-Closing Metathesis as a Key Step"

212

ORGANIC SYNTHESIS--2004

IV.M-29 Grosu, I. et al., H, 60, 1477. Review:

"Synthesis, Structural Analysis and Reactivity of 1,3Oxathiane Derivatives"

IV.M-30 Barbachyn, M.R., Ford, C.W., AG(E), 42, 2010. Review:

"Oxazolidinone Structure-Activity Relationships Leading to Linezolid"

IV.M-31 Florio, S., ed. T, 59, 9683-9864. Symposia "Oxiranyl and Aziridinyl Anions as Reactive in-Print: Intermediates in Synthetic Organic Chemistry" IV.M-32 Sabol, J.S. et al., T, 59, 2963. Report:

"Recent Advances in the Synthesis of Piperidones and Piperidines"

IV.M-33 Chandrashekar, T.K., Venkatraman, S., ACR, 36, 676. Review:

"Core-Modified Expanded Porphyrins" New Generation Organic Materials"

IV.M-34 Sessler, J.L., Seidel, D., AG(E), 42, 5134. Review:

"Synthetic Expanded Porphyrin Chemistry"

IV.M-35 Kashima, C., H, 60, 437. Review"

"Synthetic Utilities of N-Acylpyrazoles"

IV.M-36 Kashima, C., H, 60, 959. Review:

"3-Phenyl-l-menthopyrazole[(4R,7S)-7-isopropyl-4-methyl3-phenyl-4,5,6,7-tetrahydroindazole]: A New Type of Chiral Auxiliary"

IV.M-37 Varela, J.A., Saa, C., CRV, 103, 3787. Review:

"Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] Cycloadditions"

IV.M-38 Hoffmann, H., Lindel, T., S, 1753. Review:

"Synthesis of the Pyrrole-Imidazole Alkaloids"

SYNTHESIS OF HETEROCYCLES

213

IV.M-39 Litvinov, V.P., RCR, 72, 69. Review:

"Multicomponent Cascade Heterocyclization as a Promising Route to Targeted Synthesis of Polyfunctional Pyridines"

IV.M-40 Fallahpour, R.-A., S, 155. Review:

"Synthesis of 4'-Substituted-2,2':6',2"-terpyridines"

IV.M-41 Heller, M., Schubert, U.S., EJOC, 947. Microreview: "Syntheses of Functionalized 2,2' :6',2"-Terpyridines" IV.M-42 Marti, C., Carreira, E.M., EJOC, 2209. Microeview: "Construction of Spiro[pyrrolidine-3,3'-oxindoles] u Recent Applications to the Synthesis of Oxindole Alkaloids" IV.M-43 Jeppesen, J.O., Becher, J., EJOC, 3245. Microreview: "Pyrrolo-Tetrathiafulvalenes and Their Applications in Molecular and Supramolecular Chemistry" IV.M-44 Hocek, M., EJOC, 245. Microreview:

"Synthesis of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal- or OrganometalMediated C - - C Bond-Forming Reactions"

IV.M-45 Reddy, P.S. et al., H, 60, 183. Review:

"A Review on 2-Heteryl and Heteroalkyl-4(3H)Quinazolinones"

IV.M-46 Katsuki, T., SL, 281. Review:

"Some Recent Advances in Metallosalen Chemistry"

IV.M-47 Kizhnyaev, V.N., Vereschagin, L.I., RCR, 72, 143. Review:

"Vinyltetrazoles" Synthesis and Properties"

214

ORGANIC SYNTHESIS--2004

IV.M-48 Odinets, I.L. et al., RCR, 72, 787. Review-

"Synthesis, Some Properties and Structural Features of 1,2-Thiaphosphacyclanes"

IV.M-49 Shastin, A.V., Godovikova, T.I., Korsunskii, B.L., RCR, 72, 279. Review:

"Nitro Derivatives of 1,3,5-Triazine: Synthesis and Properties"

IV.M-50 Katritzky, A.R. et al., H, 60, 1225. Review:

"l,2,3-Triazole Formation under Mild Conditions via 1,3Dipolar Cycloaddition of Acetylenes with Azides"

IV.M-51 Zecchi, G. et al., H, 59, 823. Review:

"Transition Metal Complexation in 1,3-Dipolar Cycloaddition"

IV.M-52 Metz, W.A., ed. BMCL, 13, 2955-3111 Symposia "Recent Advances in the Design of Kinase in-Print: Inhibitors as Novel Therapeutic Agents"

V PROTECTING GROUPS V.A. Aldehyde and Ketone Protecting Groups V.A-1 Blanc, A.; Bochet, C.G., JOC, 68, 1138; Dore, T.M. et al., OL, 5, 2119. Photolabile Protecting Groups for Aldehydes and Ketones V.A-2 Fagnoni, M. et al., T, 59, 947. "A Convenient Route to 1,4-Monoprotected Dialdehydes, 1,4Ketoaldehydes, y-Lactols and y-Lactones" V.A-3 Kaneda, K. et al., CL, 32, 648; Rao, K.R. et al., JOC, 68, 2018; Shigemasa, Y. et al., TL, 44, 8623. _., Ti4+-mont ~ROI-~ P~R10 -H20//MezCO' 60~ 94-99% [similarly with 13-cyclodextrinor water under hydrothermal conditions] V.A-4 Roy, S.C. et al., TL, 44, 8597; Kafimi, B.; HazarKhani, H., S, 2547; Karimi, B.; Ma'mani, L., S, 2503; Banik, B.K. et al., TL, 44, 1191. H~ R~R~0+

......M~ ~ I~RXI'~ !a .._ ]1 MeCN,rt

78-98% [similarly with cyanuric chloride: Sc(OTf)3 or Bi(NO3)3catalysts] V.A-5 Khan, A.T. et al., SL, 377. R~ R1 70-97%

-41NaNO2,AcCI/H20. CH2C!2,0~

215

~~1~

~a

216

ORGANIC SYNTHESIS--2004

V.A-6 Dixon, D.J. et al., SL, 2317. ~-~

R-CHO +

OH R,~L~~

BuLl,THF, -78"C

H

86-99% ~.~

DBU, THF, rt or MeONa, THF, rt

,,

8-99%

V.A-7 Firouzabadi, H. et al., SC, 33, 167; Tamami, B.; Borujeny, K.P., SC, 33, 4252; Khan, A.T. et al., TL, 44, 919.

R1

+

neat or DCE 50-98 % %

[similarly with SiO2-AICI3or NiCI2 catalysts] V.A-8 Panek, J.S. et al., OL, 5, 575; Kamal. A. et al., TL, 44, 2857; Chavan, S.P. et al., SC, 33, 879; Rao, K.R. et al., S, 2295.

R~O Dess-Martin R~RIS~ R1 ~H20~IeCN/cH2CI2' 63-99% [similarly with Bi(OTf)yH20; FeCI3-KI; or IBX, ~-cyclodextrin,H20] V.A-9 Kabilan, S. et al., SC, 33, 2979; Mohan, R.S. et al., TL, 44, 9173; Rao, B.V. et al., SC, 33, 3455; Rao, K.R. et al., S, 1968; Narsaiah, A.V.; Nagaiah, K., S, 1881;

R~OR 1 -~NCP'EtOHaq HCIO4 R,~R1N~oH 51-95% [similarly with BiBr3/Bi(OTf)3"H20; H202/sodium tungstate; SbCI5 or IBX/~-cyclodextrin/H20] V.A-10 De, S.K., TL, 44, 9055; Shirini, F. et al., SC, 33, 1839; Mohammadpoor-Baltork, I. et al., M, 134, 539; Hajipour, A.R. et al., JOC, 68, 4553 and M, 134, 45.

R~O SiBr4,wet SiO2 R~RIN~ Z R1 CC!4 79-93% [similarly with SiCI4; KMnO4or BnPh3PHSO~BiCI3/~W]

PROTECTING GROUPS

217

V.A-11 Liu, Q. et al., JOC, 68, 9148.

MeOH,reflux v~O~ISI 79-97%

121

V.B~ Amino Acid Protecting Groups V.B-1 Laursen, R.A. et al., TL, 44, 8585. "Synthesis of Photolabile 2-(2-Nitrophenyl)propyloxycarbonyl Protected Amino Acids" V.B-2 Kawasaki, K. et al., TL, 44, 2849.

Me ~o+ BF4 Ph"~ , , , O L O ~ (Pms-ONp)

,,T,-,

R

l"u2+ H2N~CO2H

Me

ph. ~,~ BF4" O

R "O'~ N~CO2 H H

V.B-3 Kaneda, K. et al., TL, 44, 4981.

~(~?1 .H2'Pd'Cal~ H2 CO2H MeOH,40~ 84-99%

2 Cbz I~R1 N- "CO2H H

V.B.4 Sato, T.; Aimoto, S., TL, 44, 8085. "Use of Thiosulfonate for the Protection of Thiol Groups in Peptide Ligation by the Thioester Method" V.B-50verkleeft, H.S. et al., TL, 44, 9013. "A Novel, Base-Labile Fluorous Amine Protecting Group: Synthesis and Use as a Tag in the Purification of Synthetic Peptides" V.C. Amine Protecting Groups g . c - 1 Alcaide, B.; Almendros, P.; Alonso, J.M., CEJ, 9, 5793 and TL, 44, 8693.

R'NH ~1 49-81%

PhChfRu0PCy3)2CI2 R.N.~~ Ph.Me, 110~ ~1

218

ORGANIC SYNTHESIS--2004

V.C-2 Hodacova, J. et al., CCC, 68, 744. "A Facile Synthesis of Selectively Protected Linear Oligoamines" V.C-3 Kaik, M.; Gawronski, J., TA, 14, 1559; Jung, K.W. et al., 5695. Facile Amino Monoprotection V.C-4 Vatele, J.-M.,

TL, 44,

TL, 44, 9127; Tsukamoto, H. et al., SL, 1105.

O R.NH .,1. I2, MeOH R.N~O~ ~ ~{1 2. Zn ~1 53-88% [allyl and allyloxycarbonyldeprotection also using solid-supported barbituric acid with palladium catalysis] V.C-5 Alonso, J. et al.,

TL, 44, 2301.

R w ~ NH2 _.1. BF3,MeOH 2. TEA

H

._Cr o Me

64-95% V.C-6 Bradley, M. et al., SL, 1791. "Hexadienyloxycarbonyl (Hdoc)--A Mild Acid Labile Protecting Group for Amines" V.C-7 Bennasar, M.-L. et al., OL, 5, 569; Bornhop, D.J. et al., SC, 33, 457; Helgen, C.; Bochet, C.G., JOC, 68, 2483.

,roff~etero /~ ar~etero~ ot/e~l~Cbz ,,:~t/e/~ NH BuaSnH, A I B N Ph-Et, reflux 80-95% [similar Cbz deprotection Using Pd/C, cyclohexene and Cbz protection photochemically] V.C-8 Rouden, J.; Lasne, M.-C. et al., JOC, 68, 7289. O R.N~CI C1211C=Oor triphosgene R.N,,,~Ar ~1 CH2C12,rt ~1 54-99%

PROTECTING GROUPS

219

V.C-9 Chandrasekhar, S. et al., TL, 44, 2057. R"NI-I + (Boc)20 PMHS,Pd(OH)2/C ~1 EtOH, rt

R,.N, BOc 84-92%

V.C-10 Bose, D.S. et al., SC, 33,445; Li, B. et al., TL, 44, 8113; Martin, V.S. et al., JOC, 68, 743. R.NH ~ Sn(OT02 R~N,BOc ]~1 CH2CI2 or neat ~1 87-95% [similarly with HaPO3or LiBr] V.C-11 Chen, F.-E. et al., SC, 33, 2593; Banwell, M.G. et al., JOC, 68, 613. H3POz, I2 R~N,Bn ~1 AcOH ~1 75-85% [similarly with triphosgene] V.C-12 Han, H. et al., TL, 44, 1607. NH2 NHTse C~~ DIEA,DMAP, HOBT C~ ~ RO2 CH2C12,rt '~ RO2 H

H

piperidine DMF, rt, 5min

77-86%

V.C-13 Kaupp, G. et al., CEJ, 9, 4156. "Waste-Free and Facile Solid-State Protection of Diamines, Anthranilic Acids, Diols, and Polyols with Phenyl Boronic Acid" V.C-14 Weinreb, S.V. et al., JOC, 68, 4112. "Preparation of Bis(13-Trimethylsilylethanesulfonyl)imide and Its Use in the Synthesis of Protected Amine Derivatives" V.C-15 Nowak, I.; Robins, M.J., OL, 5, 3345. "Protection of the Amino Group of Adenosine and Guanosine Derivatives by Elaboration into a 2,5-Dimethylpyrrole Moiety"

220

ORGANIC SYNTHESISm2004

V.C-16 Kan, W.M. et al., TL, 44, 1039. .~,, NH2 ~_ TsOH R Ph-Me, reflux 65-99% V.C-17 Alterman, M. et al., TL, 44, 4523. O2 R_../~f" S'~NH2 .~ BCI3 - CH2C12,rt 74-97%

H ~~,OMe R

02 R___~~~y"S" N'tBu H

V.C-18 Vasilevsky, S.F. et al., H, 60, 879. tl I

§

OMe

r

"oEt "i,h-U, 30-40~ lh

H

IJ~OE t 95%

R ~ I

R ~_ HCI H20/CHCI3, rt, lh

H 67-88%

~OEt

V.D. Carboxyl Protecting Groups

V.D-1 Das, B. et al., TL, 44, 1465; Kumar, P. et al., SC, 33, 3017. NaHSO4oSiO4 R - ~ _ j ~ R-CO2H CH2C12,rt, 4-6h

85-96%

[similarly with H-beta zeolite] V.D-2 Ladlow, M. et al., JOC, 68, 4189. "A Novel Anthracenyl Tagged Protecting Group for 'PhaseSwitching' Applications in Parallel Synthesis" V.D-3 Hess, G.P. et al., JOC, 68, 8361; Banerjee, A. et al., OL, 5, 4469. Photolabile Carboxylic Acid Protecting Groups

PROTECTING GROUPS

221

V.D-4 Najera, C. et al., S, 277. "n-Deficient 2-(Arylsulfonyl)ethyl Esters as Protecting Groups for Carboxylic Acids"

V.E. Hydroxyl Protecting Groups

V.E-I Kobayashi, S. et al., JOC, 68, 8723. H20 R-OH a R-O-PG 75-95%

(~~"C18H37 " l " so3n

PG = TBS, MOM, TIPS, Ts, Ac

V.E-2 Mohan, R.S. et al., EJOC, 3827; Bandgar, B.P. et al., M, 134, 425; Yang, L.-M. et al., SC, 33, 3929; Kahn, A.T. et al., EJOC, 4113. DHP, Bi(OTf)3~ R-OH -~ R-OTHP CH2CI2 or neat, rt 63-87% Bi(OTf)3.4H20 .4[

DMP/MeOH, ll0~ 67-89% [similar tetrahydropyranylation using anhydrous CaCI2; NH2SO3H or Me2SBr+Br". Depryanylation using MeSBr+Br"] V.E-3 Karimi, B.; Ma'mani, L., TL, 44, 6051" Das, B. et al., JOC, 44 7101. FDMA, Se(OTf)3 R-OH ~ R-OMOM CHCI3, reflux 77-98% [removal of the MOM group with NaHSO4.SiO2] V.E-4 Chandrasekhar, S. et al., SC, 33, 895. R~OH MeO~_..]SO2Ph + R" "OH MeO Ph-H, Amb 15, reflux 69-87% LiNH2 NH3(L) 72-86 %

RSO2Ph

222

ORGANIC SYNTHESISm2004

V.E-5 Nishizawa, M. et al., OL, 5, 153; Yus, M. et al., S, 2179. 1. TES-OTf, Et3SiH, CH2CI2 R-OH -~ R-OTr 2. AcOH/THF 89-99%

(compatible with esters, MOM, Bn and MPM ethers) [detritylation reported also with Li, C10H8] V.E-6 Schmidt, R.R. et al., EJOC, 4121 and S, 1065. DBU pG,,.flt N H _ . ~ R-OH, TMS-OTf PG-OH + CI3CCN ~ PG-O-R CH2C12 CC13 CH2C12,rt Ph2CH- = DPM 65-92% PG=

~~-

=FI 56-91%

[similarly for phthalimidoylmethyl ether formation]

V.E-7 Basu, A. et al., TL, 44, 2267; Jung, Y.H. et al., TL, 44, 733; Sharma, G.V.M. et al., JAC, 68, 4574. HN~_..o ~ ~ O M e

R-OH +

C13C

La(OTf)3 Ph-Me, rt

~

R-OPMB 61-93%

[deprotection of para-methoxybenzyl ethers reported using CSI or ZrCI4] V.E-8 Hara, H. et al., CPB, 51, 1220; Hilmersson, G. et al., OL, 5, 4085; Rajakumar, P.; Murali, V., SC, 33, 3891; Pal, M.; Parasuraman, K.; Yeleswarapu, K.R., OL, 5, 349. h

Ar-OH ~ Pd/C, KOH MeOH

10-95%

J Ar- O

[similarly with SmI2/H20/amine; TiCI4 or, for a propargyl ether, Pd(PPh3)2CI2/TEA] V.E-9 Rao, J.M. et al., TL, 44, 2525 and CL, 32, 704; see also: Hudlicky, T. et al., TL, 44, 1575. o ,,

70-96% [similarly with TsOH or, for allyl carbonates or carbamates, electrolysis]

PROTECTING GROUPS

223

V.E-10 Bartoli, G. etal.,EJOC, 4611; Das, B. et al., T, 59, 1049; Crouch, R.D. et al., SL, 991. Zn(CIO4)2.6H20 R-OH + Ac20 ~ R-OAc 0-99% [deacetylation reported with NH4OAc or NaOH/TBAHS] V.E-11 Oriyama, T. et al., S, 484; Reddy, C.S. et al., TL, 44, 4693. R-OTr + AcBr .v._ R-OAc DCE, rt 75-99% [similarly by treatment of TBS or THP ethers with ZrCl4/Ac20] V.E-12 Crich, D. et al., JOC, 68, 8453; Beaucage, S.L. et al., JOC, 68, 10003. Carbonate Protecting Groups for Sugar Alcohols V.E-13 Falck, J.R. et al., OL, 5, 4755. s Nail, TItF, rt II R-OH + CI"~NMe2 89-99% "--

II

s

ty'- NMe2 R

NaIO4 92-95% V.E-14 Oyama, K.; Kondo, T., OL, 5, 209; Prabhakar, S., Lobo, A.M. et al., TL, 44, 8819; Sharma, G.V.M. et al., TL, 44, 4689; Vankar, Y.D. et al., SC, 33, 4043; Jiang, Z.-Y.; Wang, Y.-G., TL, 44, 3859 and CL, 32, 568. TMG Ar-OH ~ Ar-OTBDMS 52-93% MeCN,50"C, lh [similarly with SbCIs; ZrCl4; Nation-H, NaI; Me2SBr+Br'; Cs2CO a or KOH] V.E-15 Wagner, A.; Mioskowski, C. et al., TL, 44, 965. H ~ pyr B n S O 2 0 ~ + BnSO2CI -'~ H CHO 99% BnSO2(Y ~ "CHO

M r H

~_ H2,RaNi M c ~ NHAc EtOH,10rain BnSO2 99%

NHAc

224

ORGANIC SYNTHESISm2004

V.E-16 Theodorakis, E.A. et al., BMCL, 13, 1631.

NH2 ipr2Si I CI

H2

79% (R = H) H6

"OR

HF~ 91% (R = Me)

ipr2Si~ (~

">OR

V.E-17 Sajiki, H.; Hirota, K. et al., TL, 44, 7407. "Significant Supplier-Dependent Disparity in Catalyst Activity of Commercial Pd/C Toward the Cleavage of Triethylsilyl Ether" V.E-18 Sarm, J.C.; Tsuboi, S. et al., SC, 33, 4005. ~tw TBDMS-CI or TMS-CI, 12 R1-OH r.-- R1-OSiR3 neat 63-96

V.F. Other Protecting Groups

V.F-1 Corey, E.J. et al., OL, 5, 1999. Me

N.--~O + %NMe H

CH2C12,0*C, lmin 58-99% -4

A, lmin 65-99%

V.F-2 Stuhr-Hansen, N., SC, 33, 641. AcCI, BBr3 Ar-SAc -~ Ar-S.tBu 89-96% CH2CIz/Ph-Me,rt, 2h V.F-3 Kilburn, J.D. et al., JOC, 68, 9416. "Trifluoroacetyl as an Orthogonal Protecting Group for Guanidines"

Vl USEFUL SYNTHETIC PREPARATIONS VI.A. Functional Group Preparations VI.A.1. Acetals and Ketals

u

Vyvyan, J.R. et al., JOC, 68, 9144. R,~

SnCI2 Me2CO,reflux r

S

48-97%

VI.A.1-2 Read, R.W.; Zhang, C., TL, 44, 7045. "Synthesis of Fluorons Acetal Derivatives of Aldehydes and Ketones" VI.A.1-3 Kurihara, M.; Hakamata, W., JOC, 68, 3413. R~O + ~~ R2"OTMS'TMS'OTf ~ ~ROI~ R1 ~ CH2CI2,-20"C 70-99% VI.A.1-4 Feringa, B.L. et al., JACS, 125, 8714. ~O o ~ O Pd(OAc)2,p(OPh)3 ~ 0 R-OH + R1 CH2C12,"30~ RO" 57-98% ee = 82-99% VI.A.1-5 Miller, S.J. et al., SL, 1923. OBn . H~nO.[ ~ j ~ , _O Bn + R'~oHR CH2CI2,4AMS, rt CI3CAOe' "O" "~ OBn

~ a

225

OBn .L ,OBn ~BnO".[~-~]~.'R ~ O ~'' 28-92t~~ OBn

s~ 2 N"~CO~e ~A~~

226

ORGANIC SYNTHESIS--2004

VI.A.1-6 Nishida, Y.; Kobayashi, K. et al., OL, 5, 2377. "One-Pot r Method Using Appel Agents in N,NDimethylformamide" VI.A.1-7 Stachulski, A.V. et al., OL, 5, 4545; and see also: CC, 1266. "Giycosidation with a Disarmed Glycosyl Iodide: Promotion and Scope" VI.A.1-8 Bertozzi, C.R. et al., OL, 5, 3185. "Formation of 1,1-~#-Glycosidic Bonds by Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose" VI.A.1-9 Zhang, J. et al., OL, 5, 5015. X

X

R2 OR +

"-'R 1 H(I

v

X

X

/

CsF ~ CH2CI2, rt

R2 --R 1

70-91% (also amidations)

VI.A.I-10 Takashi, T. et al., AG(E), 42, 1833. SMe

5

+

CH2C12, 4/~ MS

()Bn

~

M OBn

OMe

20-63% ct:[3 = 3.1-6.9:1

VI.A.1-11 van der Marel, G.A. et al., OL, 5, 1947; Crich, D.; Picione, J., OL, 5, 781; see also: Durham, T.B.; Roush, W.R., OL, 5, 1871, 1875. /X"~'~,.....~OH Tf20' Ph2SO~

~o)~

T f20 ~'-(RO) n~"~'O'O~o""5~'--" L.. _ . _ . ~Y

.o-~--o I-iO-~._o 0~o~/-,,~ ss 0~o~7 ~

o / "~, 0~ ), o - ,~~7-'-.X '- o 56-87%

(RO)~

VI.A.l-12 Boebel, T.A.; Gin, D.Y., AG(E), 42, 5874. "Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation"

USEFUL SYNTHETIC PREPARATIONS

227

VI.A.I-13 Moreau, V. et al., TL, 44, 8999 laccess to high mannose typesl; Lowary, T.L. et al., JACS, 125, 415 5 [containing r and 13-arabinofuranosyl linkages]; Whitfield, D.M. et al., JOC, 68, 2426 [lactosamine and sialylated lactosamine]; Wong, C.-H. et al., JAC, 68, 2135 [N-acetyllactosamines]. Glycosylation Routes to Oligosaccharides

VI.A.I-14 Ley, S.V. et al., OL, 5, 1147. 0 HS~ NaOMe R1

r

0

S"~

CH2CI2/MeOH L 84-94%

VI.A.I-15 Hung, S.-C. et al., JOC, 68, 8719; Ibatullin, F.M. et al., TL, 44, 7961; see also: Fuentes, J. et al., TL, 44, 6605; Schmidt, R.R. et al., JOC, 68, 5641. . r.... (AcO)n ~ r , , ,~ _ ',,~ 0 STol (HO)~',---~,~,oOH Ac20, HS-To!, Cu(OTf)2 BF3oEt2O, neat, rt 66-75% r = 0-1:1-0 [similarly with thiourea, BF3oEt20 then R-X; for azasugar thioglycoside, or for S-linked glycopeptide synthesis]

VI.A.I-16 Bettadaiah, B.K.; Srinivas, P., TL, 44, 7257; Das, S.K. et al., SL, 1607. A A

O

+ R-OH

ZnCI2

~ Ac ~ O R 60-91% tx:13= 1-3.5:1 [similarly with InCl3/btW] CH2C12, rt

VI.A.I-17 Dujardin, G. et al., TL, 44, 1491. tBu9 H

80% (other examples given)

228

ORGANIC SYNTHESISm2004

VI.A.l-18 Ley, S.V. et al., OBC,1, 15. "Development of ~-Keto-l,3-dithianes as Versatile Intermediates for Organic Synthesis" VI.A.2. Acids and Anhydrides see also: I.A.2., II.B. 1, V.E VI.A.2-1 Nakata, M. et al., TA, 14, 1251. "Practical Deracemization of NM-3, A Synthetic Angiogenesis Inhibitor" VI.A.2-2 Ikunaka, M. et al., TA, 14, 1385. "A Scalable Chemoenzymatic Preparation of (R)-Tetrahydro-furan-2carboxylic Acid" VI.A.2-3 Lipton, M.A. et al., JOC,68, 7841. "Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6trimethylheptanoic Acid: Proof of Configurational Assignment" VI.A.2-4 Wu, Z.-L.; Li, Z.-Y., Wu, Y., OBC,1,535. X---~

CC, 386 and JOC,68, 2479; Wang, M.-X.;

C~~ RhodococcusSP. 0497 cGMCC Me .~ X CN

,,.,~ ~ ~(~NH2 Me ~"~" " ~ " CO2H 31-96% ee = 97-99%

[similarly for amide to carboxylic acid transformations] VI.A.2-5 Mhaske, S.B.; Argade, N.P., S, 863; see also: Argade, N.P. et al., S, 346. o 2., H+, reflux

RO" "CO2H 90-98%

VI.A.2-6 Yoon, Y.-J. et al., S, 1517. base, THF or CI-I2CI2 R-CO2H ~,~ (R-CO2)O 02 N, N"

C~O ~ C!

48-96%

NO2

USEFUL SYNTHETIC PREPARATIONS

229

VI.A.2-7 Bell, A.T. et al., OL, 5, 3193. "Synthesis of Mixed Acid Anhydrides from Methane and Carbon Dioxide in Acid Solvents" VI.A.2-8 Villemin, D. et al., JCR(S), 433.

I(~ ~ R

' ' • C O 2+ HR-CHO

~tw, Ac20, NH4OAc

",~ -CO2H o 50-90%

VI.A.3. Alcohols and Related Species see also: II.B. 1, III.A, V.E, VI.A. 11 VI.A.3-1 Kishi, Y. et al., TL, 44, 7489. "Application of Chiral Bidentate NMR Solvents for Assignment of the Absolute Configuration of Alcohols: Scope and Limitation" VI.A.3-2 Anson, M.S. et al., SL, 679. "The First Supported N-Pyridinyl Proline-Derived Chiral Catalyst for the Kinetic Resolution of Racemic Alcohols" VI.A.3-3 Clapes, P. et al., JOC, 68, 5351. "Novel Chemoenzymatic Strategy for the Synthesis of Enantiomerically Pure Secondary Alcohols with Sterically Similar Substituents" VI.A.3-4 Anthonsen, T. et al., TL, 44, 8453; see also: Kroutil, W. et al., TA, 14, 275. "Enhanced Selectivity in Novozyn 435 Catalyzed Kinetic Resolution of 2 ~ Alcohols and Butanoates Caused by the (R)-Alcohols" VI.A.3-5 Miyashita, M. et al., CC, 2482. 1. BuB(OH)2, Pd(PPh3)4, Ph-Me, rt ~ C O 2

R1 2. H202, H20/MeOH, rt

OH R J,~/A ~-,,~ ",,,~ --CO2R1 OH 71-94% dr = 19-99:1

230

ORGANIC SYNTHESISm2004

VI.A.3-6 Holland, H.L. et al., TA, 14, 289; Ghanem, A.; Schurig, V., TA, 14, 57; Easwar, S.; Argade, N.P., TA, 14, 333; Yuan, C. et al., TA, 14, 63. Lipase-Catalyzed Resolutions VI.A~ Stewart, I.C.; Bergman, R.G.; Toste, F.D., JACS, 125, 8696. "Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins: Use of a Strong Nucleophile to Generate a Strong Base" VI.A.3-8 Davies, S.G. et al., SL, 1659. O o

H ~ '~Ph OH

R

or LAH, THF, rt

~)n 60-99% de = 98%

VI.A.3-9 Fan, R.-H.; Hou, X.-L., OBC, 1, 1565; Gonzalez, C. et al., JOC, 68, 2248; Rao, K.R. et al,. JOC, 68, 4994. R1

R1

R~O

Bu4NHSO4 ~ _ R ~ o H20, 20-45~

H

()H

61-98% [other epoxide ring openings reported with alkoxide nucleophiles and different catalysts]

VI.A.3-10 Zhong, G., AG(E), 42, 4247. H

Ph-NO +

R^ C H O

1. proline, DMSO, rt

o,N',ph R ~ , , OH

2. NaBH, EtOH

54-86% ee = 94-99%

VI.A.3-11 Mioskowski, C. et al., TL, 44, 4451. ph~SO2Ph R

1. BuLi, Ph-Me, -78~ 2. BRla 3. H202, NaOH

rt

p h ~ ' . . ~ OH R" "g 1 53-82%

USEFUL SYNTHETIC PREPARATIONS

231

VI.A.3-12 Maleczka, Jr., R.E.; Smith, III, M.R. et al., JACS, 125, 7792. Z Z Y-~ ~oqB 1"Ir(Ind,Ir(c~ dmpc' neat Y - - ~ + H ~ OH 2. Oxone, H20/Me2CO, 250C X X 51-89%

VI.A.3-13 Bonin, M.; Micouin, L.; Knochel, P. et al., SL, 2240; Laschat, S. et al., SL, 2175; Fernandez, E. et al., TA, 44, 1611 and Fernandez, E. et al., CEJ, 9, 191. 1. [Ir(cod)Cl]~ CatBI-I,0*C r ~ PPh2 ~.N...CO2Bn I~"~r

Bn

~'~

HO~.N...CO2B n

2. n202, aq NaOH

~

[ " ~ r "CO2Bn

76% ee = 71% [other asymmetrichydroborations reported with different catalysts and substrates]

VI.A.4. Aldehydes and Ketones see also: I.A.1, I.G.2, II.A.1 VI.A.4-1 Suzuki, Y. et al., CC, 1314. O2N--@F

-I- Ar-CNO

Na.

r--a Me'N',~§

~9 02

r

46-77%

VI.A.4-2 Kosrnrli, J.; Weigel, L.O. et al., JACS, 125, 3208. "Unfunctionalized, tx-Epimerizable Nonracemic Ketones and Aldehydes Can Be Accessed by Crystallization-Induced Dynamic Resolution of Imines" VI.A.4-3 Davies, S.G. et al., OBC, 1,2001. "N-Acyl-5,5-Dimethyloxazolidin-2-ones as Latent Aldehyde Equivalents" VI.A.4-4 Shi, Y. et al., JOC, 68, 4963. "An Improved Synthesis of a Ketone Catalyst for Asymmetric Epoxidation of Olefins"

232

ORGANIC SYNTHESISm2004

VI.A.4.5 Hidai, M. et al., JOM, 679, 32. OTMS R~R [RuCI(h2"H2)(dppe)2]OTf -I- D2 1 DCE, 50~

O

40-95%

VI.A.4-6 Rao, K.R. et al., JOC, 68, 9119; Weinreb, S.M. et al., JOC, 68, 3323. O ph..~O IBX .~ p h i . , , x H20, rt 82-92% VI.A.4-7 Uemura, S. et al., JACS, 125, 8862. R _ OH Pd(OAc)2, Cs2CO3, Ph-Me R~N)~R2~V" + R3"X

Jt

R

2

~ 27-99% ee = 22-95 %

VI.A.4-8 Wang, L. et al., TL, 44, 4685. 1. CBr4, PPh 3, CH2C12 R-CHO 2. Zn, H20, 275"C

MemO R 48-88%

VI.A.4-9 Liebeskind, L.S. et al., OL, 5, 3033" Urawa, Y.; Ogura, K., TL, 44, 271. ToI-S~O + Bu3SnR1 Pd2(dba)3, P(furyl)3, CuOP(O)Ph2~ R ~ O R

R

61-97% [similarly with arylboronic acids/acid chlorides and palladium catalysis] VI.A.4-10 Yadav, J.S. et al., SL, 1722 and S, 2390; Fukuyama, T. et al., SL, 1512. (~CI R

+ TMS u

R1

12 ~ CH2C12, rt

~\

-_.

R1

85-90% [similarly with an InBr3 catalyst or with a thioester and a terminal alkyne under Pd catalysis]

USEFUL SYNTHETIC PREPARATIONS

233

VI.A.4-11 LubelI, W.D. et al., OL, 5, 4887. R-CO2Me + "~MgBr

Cu(OAc)2 _ THF, -45~

O R~,,.,~ 26-77%

VI.A.5. Amides and Related Soecir _

VI.A.5-1 Grzyb, J.A.; Batey, R.A., TL, 44, 7485; Beaudoin, S. et al.,

JOC, 68, 115. O

O

IL ~ I ~ i ~ N +.Me + R2.CO2H

T E Art~ R tLN~R2 MeCN, ~1 75-99%

[similarly for sulfonamide synthesis] VI.A.5-2 Shiina, I.; Kawakita, Y., TL, 44, 1951; Giacomelli, G. et al., OL, 5, 2715; Kim, M. et al., SC, 33, 4013; Srinivas, K.V.N.S.; Das, B., JOC, 68, 1165. no base O~NR1R 2 9 R O O 82-99% [similar carboxylic acid activation/displacement with cyanuric chloride/hydroxylamine; trichloromethyl chloroformate/ N,O-dimethylhydroxylamineor with an alkyl carboxylic acid (in competition with an aryl carboxylic acid) and RNH2/Fe3+-K10clay] R-CO2H +

~N~o~

~ O"

VI.A.5-3 Khalafi-Nezhad, A. et al., TL, 44, 7325. R-CO2H + (NH2)2C=O gW, imidazole ~ O~NH2 R

47-88% VI.A.5-4 Williams, L.J. et al., JACS, 125, 7754; Fazio, F.; Wong, C.H., TL, 44, 9083; Damkaci, F.; DeShong, P., JACS, 125, 4408. ~SH n /

R

+ R1.N3

pyr-Me2 MeOH/CHCI3

H R

64-99% [similarly with RuCl3 or with a sugar azide/PPh3 and CuCI2.2H20]

234

ORGANIC SYNTHESIS--2004

VI.A.5-5 Wang, T. et al., OL, 5, 3399. "Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron" VI.A.5-6 Aube, J. et al., JACS, 125, 7914. "Asymmetric Schmidt Reaction of Hydroxyalkyl Azides with Ketones" VI.A.5-7 Ballini, R. et al., T, 59, 1143. O R~ R1 + R2.NH2 NO2

O

~N.R 2 neat, rt

H 6-99%

VI.A.5-8 Kraus, G.A. et al., S, 19. O R

H2#'CO2R1 MeCN, rt ~Pr

O

R

H 30-77%

VI.A.5-9 Ishino, Y.; Komatsu, M. et al., S, 2317. KF/AI203 R.N~CHO R-NH + CHCI3 ~1 MeCN, rt ~1 67-93% VI.A.5-10 Ray, S. et al., TL, 44, 7637; Feroci, M.; Inesi, A. et al., JOC, 68, 1548. O R~OH + HN..R2 CO2,DEAD,PPh3 ~ R ~ O ~ N oR2 ~1 80-120~ ~1 80-98%

[carbamate formation also with CO2 then EtI] VI.A.5-11 Cook, G.R. et al., JACS, 125, 5115. O o o A r ~ . ~ ~ O + H-NPhth [Pd(C3H$)CI]~,BINAP,THFK-NPhth (cat)~ Ph - A r ' ~-H Vh'~r

~ ~lPhth (sulfonamides, amines and malonates add to terminal carbon) 95-99%

USEFUL SYNTHETIC PREPARATIONS

235

VLA.5-12 Reddy, K.L., TL, 44, 1453; Gullickson, G.C.; Lewis, D.E., S, 681" see also: Chen, J.J.; Deshpande, S.V., TL, 44, 8873. O X--~ CN MeCO2tBu~ X ~ ~A- H JL N".~Bu H2SO4,42~ 88-95 %

[similarly with diphenylmethanolor via reaction of acid chlorideswith isocyanides] VI.A.5-13 Lu, S. et al., JCR(S), 442; Chiarotto, I.; Feroci, M., JOC, 68, 7137. R___f-~

k=-r

NH2

;2~/ m

R1 Fe, CO, TEA R _ _ ~ N O H N ~ _ . ~ / ,~ R1 Ph-Me, 130*C

69-91% [symmetricalureas from RNH2,CO, Pd catalysts, electolysis] VI.A.5-14 Shie, J.-J.; Fang, J.-M., JOC, 68, 1158. 1. aq NH3,12 O.~,,,NH2 R-CHO 1 2. H202 R 81-98% VI.A.5-15 Duthaler, R.O., AG(E), 42, 975; Jorgensen, K.A. et al., AG(E), 42, 1367; Brase, S. et al., CC, 2448; see also: Kinart, W.J.; Kinart, C.M., JOM, 665, 233. R~R

N"CO2R2 CH2C12,rt O HN"CO2R2 4. ~.- R ~ C O 2 R 2 1 R202C'N ~COz[. I ll H

67-92% ee = 79-99%

VI.A.5-16 Xia, C.-G. et al., SL, 2337 and CC, 2570; see also: Jung, Y.H. et al., JOC, 68, 3721. O R202C~NH O R ~ R

1

+ R202C NH2

TBAB, BF3oEt20 R .~. rt

[similar SN2'reactions reported]

~

R

29-50%

1

236

ORGANIC SYNTHESISn2004

VI.A.5-17 Kalbalka, G.W." Guchhait, S.K., OL, 5, 4129. H CuCI, 3/k MS R tBuO2C.N,,NH2 + R-B(OH)2 pyr/DCE,rt ,I~ tBuO2C.N,~s,,CO2tBu H 63-87% VI.A.5-18 Wu, Z.-L.; Li, Z.-Y., TA, 14, 2133; Wang, M.-X. et al., JOC, 68, 4570; Sharghi, H." Sarvari, M.H., SC, 33, 207.

ho ococcuss,

CN

CGMCC0497

~

' ~ "ff-NH2 O 20-92% ee = 2-81% [non-enzymatic nitrile to amide conversionreported with MSA/AI203] VI.A.5-19 Buchwald, S.L. et al., JACS, 125, 6653. "Expanding Pal-Catalyzed C--N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination and Complementarity with Cu-Catalyzed Reactions" VI.A.5-20 Ghosh, A. et al., OL, 5, 2207; Wallace, D.J. et al., OL, 5, 4749. R R1 R2 R1 R2 ~,Cl "I" a % ~ o' ( Pd2(dba)3'Cs2CO3'Ph'Me'100~ .~" ~ ~ o ~ O o

x [similar coupling with amides and vinyl triflates]

11-99%

VI.A.5-21 Wannberg, J.; Lathed, M., JOC, 68, 5750. R-~~'~,IX +

H'NR1R2

O tIW, Mo(CO)6,Pd(OAc)2,DBU - Rr ~ ~ N R I R 2 _ ~ " THF, 100 or 1500C,air 35-95%

VI.A.5-22 Cunico, R.F.; Maity, B.C., OL, 5, 4947. %NMe2 X Pd(PPh3)4 O_~_NMe2 TMS

Ph-Me, 110~ 25-92%

USEFUL SYNTHETIC PREPARATIONS

237

VI.A.5-23 Terauchi, J.; Curran, D.P., TA, 14, 587; Taguchi, T. et al., JOC, 68, 9851; see also: Hsung, R.P. et al., JACS, 125, 2368.

u

Ph-Me, -40~

u 2%97%

VI.A.5-24 Overman, L.E. et al., OL, 5, 1809. MeO.,(~ MeO.,f~ R CH2C12,23~ ~ ~'-~_ 2 O p~ (Pr

p~co

R

~ N ~ F3C

O

ee = 82-94%

pl~_~Ph ~Ph

(also with Z-isomers)

VI.A.6. Amines

VI.A.6-1 Wolf, C. et al., JOC, 68, 3287. "A Convenient Method for the Determination of the Absolute Configuration of Chiral Amines" VI.A.6-2 Selva, M. et al., JOC, 68, 7374; Selva, M.; Tundo, P., TL, 44, 8149; Shieh, W.-C. et al., TL, 44, 4563; Kopach, M.E. et al., JOC, 44, 5739; Murty, M.S.R. et al., SC, 33, 2483. Na exchanged Y Faujasite Ph-NH2 + (MeO)2C=O ~ Ph-NHMe 90.150~ 77-92% [alkylations of 2~amines reported with (BnO)2CO, DABCO; benzylic chlorides or Zn/RBr] VI.A.6-3 Flynn, D.L.; Hanson, P.R. et al., TL, 44, 7187. O

1. R-OH, PPh3, DIAD, CH2CL2, reflux 2. PhCH=Ru(IMesH2)(PCy3)CI2, CH2C12 3. EtOCH=CH2 4. MeOH, filter 5. NH2NH2, THF, reflx

R-NH 2 41-90%

238

ORGANIC SYNTHESIS--2004

VI.A.6-4 Shibasaki, M. et al., JACS, 125, 16178; Li, K.; Hii, K.K., CC, 1132; Fustero, S.; Volonterio, A. et al., AG(E), 42, 2060; Adapa, S.R. et al., SL, 720; Srivastava, N.; Banik, B.K., JOC, 68, 2109; Xia, C.-G. et al., SL, 2425; Wabnitz, T.C.; Spencer, J.B., OL, 5, 2141; Naidu, B.N. et al., JOC, 68, 10098. o

(S)-YLB, drierite

R ~ ' , . . . ~ R 1 + NH2OMe

THF, -200C

O H31"OMe ~

R~,~R1

57-07% ee = 81-96%

[Michael aminations reported also with a dicationic BINAP Pd(II) complex; chiral amino acid derivatives/I)ABCO; Bi(OTf)3; Bi(NO3)3; copper salt or Tf2NH] VI.A.6-5 Buchwald, S.L. et al., JOC, 68, 9563. R~,~ + H.NR1R2 Pd(OAc)2or Pd2(dba)3,tBuONa ~" R--~~L~NRIR 2 ONf Ph-Me, ll0~ 59-97% VI.A.6-6 Zim, D.; Buchwald, S.L., OL, 5, 2413; Verkade, J.G. et al., JOC, 68, 452, 8416; Singer, R.A. et al., S, 1727; Maes, B.U.W. et al., SL, 1822; Cho, C.-G. et al., OL, 5, 979; Hartwig, J.F. et al., JOC, 68, 2861; Prashad, M. et al., JOC, 68, 1163; Liu, Y.; Prashad, M. et al., JHC, 40, 713; Gueiffier, A. et al., JOC, 68, 4367; Takamura-Enya, T. et al., TL, 44, 5969; Liu, Z.; Larock, R.C.; OL, 5, 4673; Ji, J. et al., OL, 5, 4611; Queiroz, M.-J.R.P. et al., T, 59, 975. R--~~,~ + H-NR1R2 tBuONa'Ph-Me'A ~ R - - ~ ~ , ~ CI ~ NR1R2 V~2 75-98% PdOAc

[various leaving groups, substrates and catalysts used for related reactions] VI.A.6-7 Kadyrov, R.; Riermeier, T.H., AG(E), 42, 5472; Bhattacharyya, S. et al., S, 2206; E1Kaim, L. et al., JOC, 68, 8733; Basu, B. et al., SL, 555. NH4HCO~ RuCI2(ToI-BINAP)~ R,,~NH 2 T. ~R10 NH3/MeOH, 85~ R1 44-93% ee = 24-95 % [reductive aminations reported also with substituted amines and other catalysts and reducing agents]

USEFUL SYNTHETIC PREPARATIONS

239

VI.A.6-8 Ma, D. et al., OL, 5, 2453; Twieg, R.J. et al., TL, 44, 6289; Kwong, F.Y.; Buchwald, S.L., OL, 5, 793; Fukuyama, T. et al., OL, 5, 4987; see also: Chaudhari, R.V. et al., CC, 2460. y__~ + H-NRR1 CuI, K2COa,proline ~, y _ _ ~ X

DMSO, 40-70~

NRR1 46-91%

[other Cu catalyzed aryl coupling reactions reported with different substrates] VI.A.6-9 Quach, T.D.; Batey, R.A., OL, 5, 4397; Lam, P.Y.S. et al., TL, 44, 1691; Yudin, A.K. et al., JOC, 68, 2045. R--~

+ H-NR1R2 Cu(OAc)2~ BXn

CH2CI2'4~ MS' rt ~ R - ~

02, rt-40*C

NR1R2 40-93% [aziridation of arylboronic acids reported under similar conditions] VI.A.6-10 Guo, Z.-R. et al., SL, 564; Tu, Y.-Q. et al., OL, 5, 3515; Toma, S. et al., M, 134, 37; Singaram, B. et al., OL, 5, 3867.

(:~ r ~ 0 2 X

,w,~,~2c03

+ R-NH2

ff~N~ ~ N

"R

H 60-93% [similarly with tBuOK; K2COa/ultrasound or 2-fluoropyridine/LiH3BHR2]

VI.A.6-11 Fujita, K.; Yamaguchi, R. et al., TL, 44, 2687, R1

NH2

Ph-Me, 110"C

R2 H

63-95% VI.A.6-12 Laval, G.; Golding, B.T., SL, 542. CO2H 1. NBS,DMF, phosphate buffer (pH 5) NH2 H 2. NaBH4,NiCI2.6H20, rt

R~NH2 59-81%

VI.A.6-13 Yasuda, M.; Yamashita, T. et al., JOC, 68, 7618. NH3, Et4NBF4Ar-H/Ph-CI2,Ar-H, Ph-CI2~NH2 Ar,~Ar ,, Ar~~.J,~A r MeCN/H20 71-90%

240

ORGANIC SYNTHESISm2004

VI.A.6-14 Yoshida, Y. et al., SL, 2139. H

OEt

+

X

J.-

2. BH3oTHF

X 65-89%

VI.A.6-15 Hartwig, J.F. et al., JACS, 125, 5608; Belier, M. et al., JACS, 125, 10311. R~,~/ [Rh(cod)(DPEphos)]BF4R ~ + H-NR1R2 Ph-Me, 700C NRIR2 41-79% VI.A.6-16 Belier, M. et al., OL, 5, 4767; Schafer, L.L. et al., CC, 2462. 1. Ph-Me, 100*C,Me-f(

R~

~--O--Ti(NMe2)2 tBu HN-R1 + R1-NH2 ~ R---( 2. NaCNBH3,ZnCl2, MeOH, rt Me 69-99%

VI.A.6-17 Smulik, J.A.; Vedejs, E., OL, 5, 4187. MeO~~ ~ W G

EWG

tBuOK

-O-NH2 +

NH2

THF, -78~

64-67%

OMe VI.A.6-18 Hancock, M.T.; Pinhas, A.R., TL, 44, 7125. _N-Bn

Me4<,,l

+

--N+RR1

LiI

Bn'NH

Me~NRR1 65-85%

VI.A.6-19 Knochel, P. et al., SL, 885; Yang, T." Cho, B.P., TL, 44, 7549. 1. THF,-20~ H Ar-NO + Arl-MgX ~ Ar.N,,Arl 2. FeCl~ NaBH4, rt 42-74% [similarly with ArLi + ArlNO2]

USEFUL SYNTHETIC PREPARATIONS

241

VI.A.6-19 Srivastava, R.S., TL, 44, 3271. Vh-NO + ~ , , , , , R

CuCI2"2H2O, Cu

H

ph.N,,,,,,,'~1 R

dioxane, 100~

14-70%

VI.A.6-20 Shevelev, S.A. et al., JOC, 68, 2498. X

02

X

X

+ Me3N+-NH2I" NO2 DMSO, rt O2N- " ~

"NO2 0 2

NO2

NrI2 15-92% 1.22-9:1

VI.A.6.21 Chakraborti, A.K.; Kondaskar, A., TL, 44, 8315; Sabitha, G. et al., S, 2298; Reedijk, J. et al., TL, 44, 6025; Thibeault, D.; Poirier, D., SL, 1192; Lupatelli, P.; Bonini, C. et al., JOC, 68, 3360; Fringuelli, F.; Vaccaro, L. et al., JOC, 68, 7041; Fan, R.-H.; Hou, X.-L., JOC, 68, 726; Watson, I.D.G.; Yudin, A.K., JOC, 68, 5160; Concellon, J.M. et al., JOC, 68, 9242; Concellon, J.M.; Riego, E., JOC, 68, 6407. R~RI+

H.NR2R3

ZrCl 4

OH ~-- R ~ j . R1

5m2R3 81-99% [various other catalysts used for similar epoxide or aziridine ring opening]

VI.A.7. Amino Acid Derivatives

VI.A.7-1 Jorgensen, K.A. et al., CC, 2602 and CEJ, 9, 6145. O R,~CO2R1

+ LN~__R 2

Lewisacid

NH2 R~CO2R

MeOH, rt

VI.A.7-2 Wanner, K.T. et al., EJOC, 1244. " ~ M. ~t ~B u R1 1. TFA, 60~ MeX O : R

2. NaOH, solvent

1

28-66%

H2~ R1 HO2

R

25-69% ee = 99 %

242

ORGANIC SYNTHESISm2004

VI.A.7-3 Kretsinger, J.K.; Schneider, J.P., JACS, 125, 7907. "Design and Applications of Basic Amino Acids Displaying Enhanced Hydrophobicity" VI.A.7-4 Jew, S.; Park, H. et al., JOC, 68, 4514; Hang, J.; Deng, L., SL, 1927; Takemoto, Y. et al., JOC, 68, 6197. RbOH, Ph-Me, -350C HzNy. co2tBu ~ c_o 2 t B u 4" R-X ~ M~'~R Et Me

~ Br" ~/~j~,,o~r

87-93% ee = 84-96%

~,~ ~l~~'~ [similarly with a chiral phosphate and [Ir(cod)Cl]~ VI.A.7-5 Belokon, Y.N.; Kocovsky, P. et al., JACS, 125, 12860.

1. cat., NaOH, MeOH, rt 4- R-X 2. aq HCI

~NH

cat. = ~ . ~ O H

R HO2C~NH2 1-90% ee = 3-97%

2

VI.A.7-6 Lectka, T. et al., JOC, 68, 5819. O O I~NH ~ 1. benzoyl quinine, napth-l,8-NMe2 R Ph-Me,-78~ -* rt-, -78~ RI~NH O C~ + CI RO2 CI 2. Nuc RO2~" . [ @ N u c k2 48-64% ee = 94-96 % VI.A.7-7 Griesbeck, A.G. et al., JOC, 68, 9899. H R e N~ M

R1

~/~'R H q ~ ' oR hn, R-CHO 1 aq HC! 1 ~- AcH OMe Ph-H, 10oc Me~'~O~"~OMe CH2C12 CO2Me 85-90% 65-78% dr = 49:1 dr = 19-49:1

USEFUL SYNTHETIC PREPARATIONS

243

VI.A.7-8 Hughes, A.B. et al., JOC, 68, 2652. R

R (CH20)n'CSA Cbz" x N ~ O N~ .~ Cbz,. CO2H Ph-H, reflux ~ O H

81-86%

TFA' Et3SiH ~,~ Cbz.. CHCI3

CO2H

Me 80-90%

VI.A.7-9 Xu, P.-F.; Lu, T.-J., JOC, 68, 658 [of either enantiomer by switching tricyclic iminolactone regiochemistry]; Durham, T.B.; Miller, M.J., JOC, 68, 27, 35 [from N-tosyloxy-13-1actams];O'Donnell, M.J. et al., JACS, 125, 2370 [via boron alkylation for IS-substituted]; Hattori, K.; Grossman, R.B., JOC, 68, 1419 [bicyclic via double annulation/dequaternization]; Turner, N.J. et al., CC, 2636 [chemoenzymatic stereoinversion of [3- and y-]. Stereoselective Synthesis of ~-Amino Acids VI.A.7-10 Aggarwal, V.K.; Cox, R.J. et al., JOC, 68, 9433 [using in situ generated diazo compoundsl; Scialdone, M.A.; Nguyen, S.T. et al., JOC, 68, 7884 [using (salen)Ru(II) asymmetric cyclopropanation]; Armstrong, A.; Scutt, J.N., OL, 5, 2331 [3-(trans-2-aminocyclopropyl)-alanine];Kirihara, M. et al., TA, 14, 1753 [2,2-difluorol. Cyclopropyl Amino Acids VI.A.7-11 Wendisch, V. et al., TA, 14, 189 [via diorgano zinc reagents and nitroacrylates]; Roumestant, M.L. et al., S, 2165 [esters via conjugate additions]; Gellman, S.H. et al., JOC, 68, 1575 [via chiral isoxazolidin-onesl; Florio, S. et al., JOC, 68, 9861 [IS-aminoacidsl; Mapp, A.K. et al., JACS, 125, 6846 [via Grignards and isoxazolines]. [~2-Amino Acids VI.A.7-12 Sewald, N., AG(E), 42, 5794 [enantiomericallypure]; Sharma, A.K.; Hergenrother, P.J., OL, 5, 2107 [enantiopure y-keto]; Lurain, A.E.; Walsh, P.J., JACS, 125, 10677 [asymmetric route to y-unsaturated]; Hanselmann, R. et al., JOC, 68, 8739 [via chelation-controlled 1,3-dipolar cycloaddition]; Florio, S. et al., OL, 5, 2723 [r Brussee, J. et al., TA, 14, 1645 [Fmoc (2S,3S)-2-hydroxyl; Raghavan, S.; Rasheed, M.A., TA, 14, 1371 [2-hydroxy-4-phenylbutanoate]; Wee, A.G.H.; McLeod, D.D., JOC, 68, 6268 [(2S,3R)-2-hydroxydecanoicacidl; Masesane, I.B.; Steel, P.G., SL, 735 [polyhydroxylatedcyclohexyl]; Tomioka, K. et al., JACS, 125, 2886 [via N anion Michael addition]; Klempier, N. et al., TL, 44, 5057 [via biotransformation of N-protected 13-aminonitriles];Langenhan, J.M.; Gellman, S.H., JOC, 68, 6440 [r with polar side chains]. [3-Amino Acids

244

ORGANIC SYNTHESISm2004

VI.A.7-13 Bunch, L. et al., JOC, 68, 1489 [glutamic acid analog]; Cataviela, C. et al., TA, 14, 1479 [prolines]; Hideg, K. et al., TL, 44, 9213 [paramagnetic]; Hanessian, S. et al., JOC, 68, 7204 [polycyclicprolines]; Yao, Z.-J. et al. JOC, 68, 6679 [L-tyrosine analog]; Soloshonok, V.A. et al., JOC, 68, 6208 [symmetrical t~,t~-disubstituted]. Conformationally Constrained Amino Acids VI.A.7-14 Kotra, L.P. et al., JOC, 68, 1043 lfluoro]; Robina, I. et al., JOC, 68, 4138 [hetarylenecarbopeptides]; Moeller, K.D. et al., T, 59, 8515 [bicyclic pyrazolines]; Hruby, V.J. et al., CC, 1598 [Leu-enkephalin analogs]. Peptidomimetics VI.A.7-15 Diaz-de-Villegas, M.D.; Galvez, J.A. et al., TA, 14, 2201 [(S)-~methylphenyl; large scale]; and TA, 14, 2209 [(S)-t~-benzyi-t~-methyl-13-];Lygo, B.; Andrews, B.I., TL, 44, 4499 [aroyl derivatives]; Sweeney, J.B. et al., SL, 1898 [aryl via asymmetric aza-Darzens]. Alanine Derivatives VI.A.7-16 Fustero, S. et al., OL, 5, 2523 [seven-membered]; Thust, S.; Koksch, B., JOC, 68, 2290 [r for protease-catalyzed incorporation into peptides]; Curran, D.P. et al., JOC, 68, 4643 [fluorous carbobenzyloxy]. Fluorinated Amino Acids VI.A.7-17 Rolland, V. et al., TA, 14, 1123 [(2s,as- and (2S,3R)-3-methyl]; Oba, M.; Nishiyama, K. et al., CC, 776 [3,4-didehydropyro-glutamate]; Qiu, X.-L.; Qing, F.-L., JOC, 68, 3614 [4-di- and trifluoromethyi-L-pyroglutamic acids]. Giutamic Acids VI.A.7-18 Gelmi, M.L. et al., JOC, 68, 5286 [cyclopentylderivativesl; Soloshonok, V.A. et al., JOC, 68, 7104, 4973 [chiral equivalents of nucleophilic glycine]. Glycines VI.A.7-19 Smythe, M.L. et al., OL, 5, 2711 [strained tetrapeptides]; Cha, J.K. et al., JOC, 68, 2205 [western ring of Sarain Al; Fairlie, D.P. et al., JOC, 68, 4464 [convergent, solution-phasesynthesis of antiinflammatory]. Macrocyclic Peptides VI.A.7-22 Hallinan, E.A. et al., TL, 44, 7345. 6-Trifluoroethyl-L-lysine

USEFUL SYNTHETIC PREPARATIONS

245

VI.A.7-23 Carrasco, M.R.; Brown, R.T., JOC, 68, 8853; Carrasco, M.R. et al., JOC, 68, 195. Neoglycopeptides VI.A.7-24 Gonzalez-Muniz, R. et al., TL, 44, 6145 [aspartic and asparagine derivatives]; Kedrowski, B.L., JOC, 68, 5403 I(R) and (S)-2-methylcysteine]; Tabor, A.B. et al., JOC, 68, 8185 [lanthionines]; Zhu, J. et al., SL, 1455 [(2S,4R)- and (2S,4S)-4-hydroxyornithine]. Orthogonally Protected Amino Acids VI.A.7-25 Iding, H. et al., TA, 14, 1541, 1547; Calmes, M. et al., TA, 14, 1685. Piperidine Derived a-Amino Acids VI.A.7-26 Schmitt, M. et al., TL, 44, 6779 [cis 3-substituted]; Kawabata, T. et al., JACS, 125, 13012 [via alkylative cyclization]; Sugai, T. et al., TA, 14, 1323; Karoyan, P. et al., JOC, 68, 2256 [enzymatic resolution ofN-Boc prolines]; Del Valle, J.R.; Goodman, M., JOC, 68, 3923 [asymmetric hydrogenation to Boc 4alkyl]; Raghavan, S.; Reddy, S.R., TL, 44, 7459 [2R,3R,4R-3-hydroxy-4-methyl]; Yao, Z.-J. et al., JOC, 68, 7479 12S,3R-3-hydroxy-a-methyll;Tomasni, C. et al., JOC, 68, 1982 [pseudoproline turn mimic]; Dietrich, E.; Lubell, W.D.; JOC, 68, 6988 [enantiopure pyrrolizidinone amino acid[. Prolines VI.A.7-27 Lane, J.W.; Halcomb, R.L., OL, 5, 4017 [stereoselectivet~substituted]; Dettwiler, J.E.; Lubell, W.D., JOC, 68, 177 [as chiral educt for Nprotected [~-hydroxyvaline]. Serines VI.A.7-28 Qing, F.-L. et al., JOC, 68, 7544. anti-4,4,4-Trifluorothreonine VI.A.7-29 Dondoni, A. et al., JOC, 68, 6172 [3-component Biginelli and Hantzsch]; Kazmaier, U.; Hebach, C., SL, 1591 [4-component Ugi with ammonia]; Maia, H.L.S. et al., OBC, 1, 1475 [3-component Ugi-easserini]. Multicomponent Amino Acid Syntheses

246

ORGANIC SYNTHESISn2004

VI.A.8. Azides

VI.A.8-1 Gudmundsdottir, A.D. et al., TL, 44, 9169. O O R ~ , ~ x rrlN,DMsoNaN3 _ R~N3 85.95% VI.A.8-2 Liu, Q.; Tor, Y., OL, 5, 2571. aq CuSO4, TEA Ar-NH2 + Tf-N3 MeOH/CH2CI2, rt

Ar-N3 7-96%

VI.A.8-3 Bols, M. et al., JOC, 68, 9453. R-CHO + I-N3

MeCN, 25~

II O ~" R~A"N3 82-99%

VI.A.8-4 E1-Faham, A.; Abdul-Ghani, M., OPP, 35, 369; Sridhar, R.; Perumal, P.T., SC, 33, 607. O TFFH, TEA R,,~,, R-CO2H -I- NaN3 ~ N3 60-80% (also used for anilide and hydrazide formation) [similarly with NaN3/POCI3] VI.A.8-5 Kazemi, F. et al., SC, 33, 999; Coates, R.M. et al., JOC, 68, 75. LiBF4 OH R~ + NaN3 ~" R ~ N 3 wet tBuOH, reflux 89-96% [opposite regioselectivitywith Et2AIN3]

VI.A.9. Carbohydrates

VI.A.9-1 Ibatullin, F.M.; Selivanov, S.I., TL, 44, 9677.

A

_4..OA c AcO

OAc 88%

USEFUL SYNTHETIC PREPARATIONS

247

VI.A.9-2 Akamanchi, K.G. et al., AJC, 56, 909.

A

AcOOAc

Cu(OAc)2~ H20/MeOH

AA

. OH

AcO 64% a:13 = 2.3:1

VI.A.9-3 Yu, H.; Ensley, H.E., TL, 44, 9363.

Ph-"~,

Ph-"-~ NBS,TMS-OTf ~~HO(x ~ SEt wet CH2C!2 ~ R % R1 R1 o

o

84-92% VI.A.9-4 Minakawa, N.; Matsuda, A. et al., T, 59, 1699. "An Improved Large Scale Synthesis of 1,4-Anhydro-4-thio-Dribitor' VI.A.9-5 Krishna, P.R. et al., TA, 14, 419. "Stereoselective Synthesis of C-Phenyl-D- and L-glycero Heptopyranosides" VI.A.9-6 Fraser-Reid, B.; Mathew, J., TL, 44, 9051. "Microwave-Assisted Saccharide Coupling with n-Pentenyl Giycosyl Donors" VI.A.9-7 Gomez, A.M., Lopez, J.C., TL, 44, 8433. "A Novel Entry to C-Glycals via Diethylzinc-Mediated Umpolung of nAllyl Palladium Derived from 1-exo-Methylene-2,3anhydrofuranoses" VI.A.9-8 Liu, H.-M. et al., OBC, 1, 1641. "Stereoselective Synthesis of 2-Amino-3-deoxysugars: N-Alkyl-Dallosamines" VI.A.9-9 Donohoe, T.J. et al., OL, 5, 4995. "Trichloro-Oxazolines as Activated Donors for Aminosugar Coupling"

248

ORGANIC SYNTHESISm2004

VI.A.10. Esters (see also: I.G.2, IV.D, V.D, VI.A.3) VI.A.10-1 in, T.-S. et al., JCR(S), 412; Karimi, B.; Maleki, J., JOC, 68, 4951; Procopio, A. et al., TL, 44, 5621; Chakraborti, A.K. et al., SL, 1805; Chakraborti, A.K.; Gulhane, R., TL, 44, 6749; Trost, B.M.; Mino, T., JACS, 125, 2410. Si.PTA R-OH + Ac20 ) R-OAc CH2C12,rt or reflux 84-98% [similar acylations with LiOTf; Ce(OTf)3; BiOCIO4.xH20; InCl3 or a dinuclear zinc asymmetric catalyst] VI.A.10-2 Cambpell, I.B. et al., JOC, 68, 3844; Spivey, A.C. et al., JAC, 68, 7379. R ~ O H + (R2CO)20 Ph-Me,rt R ~ O H + R.~.,,O~R 2 R1 R1 R1 o~~3e

34-74%conversion ee (alcohol)= 2-99%

VI.A.10-3 Williams, J.M.J. et al., TL, 44, 5523. ( ~ PPh3 O + R-OH Ph-Me, reflux

~'CO2R 51-87%

VI.A.10-4 Vedejs, E. et al., JOC, 68, 5020. A Comparison of Monocyclic and Bicyclic Phopholanes as AcylTrensfer Catalysts" VI.A.10.5 McNulty, J. et al., JOC, 68, 1597. "Dimethyl Malonyltrialkyl Phosphoranes: New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols" VI.A.10-6 Nolan, S.P. et al., JOC, 68, 2812; Chavan, S.P. et al., S, 2695; Bandgar, B.P. et al., OPP, 35, 219. 4A MS, THF, rt R-CO2Me + R1-OH )" R-CO2R1

0- 9

.99,

[trans esterifications reported also with I2 or ZnSO4 catalysts]

USEFUL SYNTHETIC PREPARATIONS

249

VI.A.10-7 Ghanem, A.; Schurig, V., M, 134, 1151. "Lipase-Catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate" VI.A.10-8 Onaran, M.B.; Seto, C.T., JOC, 68, 8136. "Using a Lipase as a High-Throughput Screening Method for Measuring the Enantiomeric Excess of Allyl Acetates" VI.A.10-9 Pamies, O.; Backvall, J.-E., JOC, 68, 4815. OH O Ac O II 1 CI-Ph-OAc,lipase, Ph-Me, 60~ II 1 ~R ~ P( OR )2 R-~ - ~ P ( OR )2 Ph Ph p l ~

O"I r ' ~

ph

e~a9 X-Ph ~ Hph~7 ~Ph Ph "-C 9 ~tJ ' CO o CO CO

69-87% ee = 99%

VLA.10-10 Boruah, R.C. et al., TL, 44, 9099; Ghanem, A.; OBC, 1, 1282; see also: Hanefeld, U., OBC, 1, 2405. "Resolution of Racemic 1-Arylethyl Acetates by Pseudomonas fluorescens in the Presence of a Surfactant" [cyclodextrins used also to enhance lipase-catalyzed transesterifications] VI.A.10-11 Parmar, V.S. et al., T, 59, 1333; Brenelli, E.C.S.; Fernandes, J.L.N., TA, 14, 1255; see also: Remaud-Simeon, M. et al., TA, 14, 317; Gotor, V. et al., JOC, 68, 3333. HO AcO CAL .~. ~~--~O ~~-~O + ~ " O A c Ph-Me, 25-28~ HO HO

N30~

98% de = 100% [other lipase-catalyzed transesterifications reported with other substrates and enzymes] VI.A.10-12 Tanyeli, C. et al., T, 59, 1055. O O R ~ Mn(OAc)3 H P-h -~ R ~ O "A c R1

R1 63-81%

250

ORGANIC SYNTHESIS--2004

VI.A.10-13 Mukaiyama, T. et al., BCJ, 76, 1645 and JACS, 125, 10538 and CL 32, 22; Jang, D.O. et al., SC, 33, 2885; Wu, Y.-C. et al., TL, 44, 331; Kaneda, K. et al., TL, 44, 9205; Sharghi, H.; Sarvari, M.H., T, 59, 3627 and JOC, 68, 4096. DMBQ R-CO2H + Ph2POR1 ~- R-CO2R1 CH2CI2, rt 73-98% (similarly for ether formation) [similar esterifications with PPh3/CI3CCN; CAN; Montmorillonite-enwrapped Ti or AI203/MeSO3H] VI.A.10-14 Sheng, S.-R.; Huang, X., JCR(S)), 491. O--'SeOzH, H202 R-CH=NOH + RLOH ~ R.CO2R1 H20, reflux 68-87%

VI.A.10.15 Singh, A.K. et al., SC, 33, 3461. BF3oEt20 .~- R-CO2R1 R-CN + R1-OH 40.91%

VI.A.10-16 Ishii, Y. et al., TL, 44, 103. R1 [Ir(cod)Cl]~ P(OMe) 3, Na2CO3 R-CO2H +

Ill

Ph-Me, 100~

O R1 O ~- R ~ . O ~ + R~L.~ 22-79%

R1

11-33%

VI.A.11. Ethers

VI.A.11-1 Zolfigol, M.A. et al., TL, 44, 8165; Hung, S.-C. et al., TL, 44, 7837.

W OTIS Na~ R1

hex, rt

70-90% [reduetive etherification reported with ROTMS, R3R4CO, Cu(OTf)2, Et3SiH] VI.A.11-2 Simas, A.B.C. et al., JOC, 68, 5426. "A More Convenient and Central Procedure for O-Mono-benzylation of Diols via Stannylenes: A Critical Reevaluation of the BueSnO Method"

USEFUL SYNTHETIC PREPARATIONS

251

VI.A.11-3 Quach, T.D.; Batey, R.A., OL, 5, 1381; Sagar, A.D. et al., TL, 44, 7061; Takeya, K. et al., TL, 44, 5901. 1. Cu(OAc)2, 4A MS, DMAP, H20/CH2CI2,rt R-BF2" K+ l,- R.O.R 1 2. R1-OH, 02, rt 0-93% [similar Cu-catalyzed etherification with arylboronic acids] VLA.11-4 Ma, D.; Cai, Q., OL, 5, 3799; Xia, C.-G. et al., SL, 2071; Wan, Z. et al., TL, 44, 8257; Willis, M.C. et al., CC, 2222; Sirkecioglu, O. et al., TL, 44, 8483. / ~ X + H ~ y

CuI' CS2CO2b N'N'Me2glycinedioxane, 90"C Z

l~ / ~ O ~ z Y

64-96%

[similar couplings reported with vinyl halides or triflates or benzyl chloride, the latter two with Pd catalysis or Cu(acac)2, respectively] VI.A.11-5 Wipf, P.; Lynch, S.M., OL, 5, 1155; see also: Wang, Q. et al., OL, 5, 2169.

EWG~FHO-~ (Me2N,2C=Nt EWG---~~O-~~ nn ~.._9" ,~

MeCS

~UR

~_._9~-R 41-98%

VI.A.11-6 Hartwig, J.F. et al., AG(E), 42, 5865. 0 Pd(PPh3)4 ~ I''OR + R-OH ~Ph-Me, rt 44-73% VI.A.11-7 Micouin, L. et al., OL, 5, 4771. O COR R Pd2(dba)3, PHOX t + Ph-OH ~ PhO~,.~ . , ~ N , COR O

68-88% ee = 36-58 %

VI.A.11-8 Martin, V.S. et al., JOC, 6 8 , 3216; Kim, D. et al., JACS, 125, 10238; Zhu, J. et al., OBC, 1, 30. Synthesis of Cyclic Ethers

252

ORGANIC SYNTHESISm2004

VI.A.11-9 Bosch, M.; Schlaf, M., JOC, 68, 5225. ~,,~OH + ~OBu

~,vo,,~ 90%

F3C(O)O O(O)CF3 VI.A.11-10 Haught, A.R. et al., JOC, 68, 8092; Hartwig, J.F. et al., JACS, 125, 3426. OCO2tBu R-OH +

~orR 1

Pd(OAc)2,PR3

~ R'(y'".~J"R1

OCO2tBu THF,35-65~ ~ R 1

35-99%

VI.A.11-11 Shi, Y.-L. et al., TL, 44, 3609; Lepore, S.D.; He, Y., JOC, 68, 8261; Toste, F.D. et al., JACS, 125, 6076. R R

BnO2~O~ r ~ !1 _1 Et "~,.~'~R1 51-56% [(dppm)ReOCl3 used with prppargyl alcohols]

BnO2~OH H O ~ r 'Me + Et

DIAD,PPh3

R1 Ph-Me,100~

~

VI.A.11-12 Yi, C.S. et al., OM, 22, 3031. CN Ra'OH + R ~ I R2 CH2CI2'rt ,~ H 3 Cy3P.co R . - IKU~ ~" m'~

I

PCy 3

Me'~oi i~O,~pr

CN R2 R1 60-96%

VI.A.11-13 Yadav, J.S. et al., TL, 44, 5691; Perez, P.J. et al., OM, 22, 2914. O O v ,,..N 2 + R1-OH LiBF4 R~OR 1 R_.J~ MeCN, rt 85-95%

USEFUL SYNTHETIC PREPARATIONS

253

VI.A.12. Halides (see also: II.B.2) VI.A.12-1 Miyashita, M. et al., TL, 44, 8975; Hara, S. et al., S, 1157 and SL, 1530. o

on

x

+

x

OH 87-97% 1.63-11.5-1

[epoxide opening reported also with TEA.ItF or TBABF.NIIF2] VI.A.12-2 Bedekar, A.V. et al., TL, 44, 4085; Waldvogel, S.R. et al., S, 2410; Yu, G. et al., S, 403.

~

Br

Br

OH

HCl, H20 MeOH, reflux, 24h

~

O

H

CI

70% (other examples given) [chlorination of arenes reported also with MoCI5or SO2C12] VI.A.12-3 Kulkarni, S.J. et al., JCR(S), 597; Vibhute, Y.B.; Bhusare, S.R. et al., TL, 44, 4893; Easton, C.J. et al., AJC, 56, 1107; Joseph-Nathan, P. et al., JOC, 68, 305. R--~ NH4Br'Ox~ Br MeCN, rt 53-99% conversion ortho:para = 0.92-99:1 [arene bromination also with pyridinium bromochromate (with hydroxyaromatics),cydodextrin additives or in competion with oxidation of indolylmalonates] VI.A.12-4 Branytska, O.V.; Neumann, R., JOC, 68, 9510; Samant, S.D. et al., SL, 1895; Ramachandraiah, G. et al., TL, 44, 5099; Tingoli, M. et al., TL, 44, 8753. R - ~

HsPV2MoloO4~I2, 02 ),MeCN, 80~

R ~ ~

I 72-100% conversion [arene iodination reported also with SiO2-Bi(NO3)3.5H20/I2; KFKIO3/H+or I2/phenyliodine(III)bis(trifluoroacetate]

254

ORGANIC SYNTHESIS--2004

VI.A.12-5 Zhai, H. et al., TL, 44, 9371. RHN - ~

.l'BuLi2. . ,.......,.~ . . BCC~,~-~RH

R1

3. Br2

Br R1 61-94%

VI.A.12-6 Arvela, R.K.; Leadbeater, N.E., SL, 1145; Wolf, C. et al.,

SL, 1801.

R~.__X

NiY2 ~ R DMF, ~tWor 170~

~

Y

40-99% [conversion of a chloropyridineto an iodo-with HCI then NaI] VI.A.12-7 Firouzabadi, H.; Iranpoor, N.; Shiri, M., TL, 44, 8781; Rodriquez Medina, I.C.; Hanson, J.R., JCR(S), 428. RIR~

Fe(N03)3"I.5N204,X2or NaX R1R~~. Y X charcoal, CH2C12,rt 31-96% [oxidative bromination and iodination of dimethylacetanilides reported also] VI.A.12-8 Linclau, B. et al., TL, 44, 8143 and CC, 260; Sinou, D. et al., TL, 44, 7589; Khan, K.M. et al., SC, 33, 2531. DIC, Cu(OTf)2,NCS R-OH , -,. .~ R-CI l.tWor A 36-93% [alcohols to bromides reported with a fluorous phosphine or to iodides with CsI, BFyEt20] I

VI.A.12-9 Zhang, P.; Chen, Z., JCR(S), 570; Rocaboy, C.; Gtadysz, J.A., CEJ, 9, 88. "Hypervalent Iodine in Synthesis 74: Synthesis and Reactivity of New Functionalized Alkenyliodonium Salts." [fluorous hypervalent iodine compounds reported also] VI.A.12-10 Bellina, F. et al., JOC, 68, 10175. "Reaction of Alkynes with Iodine Monochloride Revised." VI.A.12-11 Lemal, D.M. et al., JOC, 68, 3891. "New Synthesis and Chemistry of Hexafluorotropone"

USEFUL SYNTHETIC PREPARATIONS

255

VI.A.12-12 Gupta, O.D.; Shreeve, J.M., TL, 44, 2799; Sheng, S.-R.; Huang, X., OPP, 35, 383; Lee, J.C.; Bae, Y.H., SL, 507; Stavber, S. et al., T, 59, 5935. R1 1 R2 NF30,TBAH ~ R 2

~

O

O

"'MeUN' rt, 12h ""

O

O

80-85% [ct-bromination and chlorination reported with ~--Se-(4-morpholinyl) then Br2 or SO2C12;ct-iodination with NIS, PTSA, l.tWor Selectfluor, I2] VI.A.12-13 Rozen, S. et al., JOC, 68, 8287; Nordvik, T.; Brinker, U.H., JOC, 68, 9394. S R~CO2Et

BrF3 ~ CFCI3,0~

F ..RF~CO2Et 55-75%

VI.A.12-14 Fustero, S. et al., OL, 5, 2707. "Novel Approach for Asymmetric Synthesis of Fluorinated 13Amino Sulfones and Allylic Amines" VI.A.12-15 Gouverneur, V. et al., AG(E), 42, 3291; Thibaudeau, S.; Gouverneur, V., OL, 5, 4891; see also: Shibata, N. et al., JOC, 68, 2494. cinchona alkaloid, Selectfluor

,,F

MeCN, -20~

R 63-99% ee = 30-96%

VI.A.12-16 Yoshimura, T. et al., TL, 44, 6203. X--~~~

+

F--N~N

Na2CO3 +--CH2CI MecN,0~ 2BF4"

h

80-96% [1,1-dibromo species prepared from 1,1-dimethoxycompounds with BBr3]

256

ORGANIC SYNTHESIS--2004

VI.A.13. Nitriles and Imines

VI.A.13-1 Belier, M. et al., AG(E), 42, 1661.

~ X R--

+

MeC~M~OH Pd(OAc)2, dppe, Na2CO3 ~ TMEDA

_~CN R

21-99% VI.A.13-2 Maddaford, S.P. et al., SL, 2237; Buchwald, S.L. et al., JACS, 125, 2890.

R _ ~ ~ I x Zn(CN)2, Zn, Pd2DMF(dba' ,p ( t~B' r t u)3 _

R_~

cN

58-93% [similarly wuth CuI, KI, NaCN] VI.A.13-3 Ballini, R. et al., SL, 1841; Sarghi, H.; Sarvari, M.H., S, 243. NaI R-CHO + NH2OHoHCI MeCN,reflux ~ R-CN 75-98% [similarly with graphite/MsCl] VI.A.13-4 Tanaka, T. et al., H, 59, 161. EWG

+ L wG

Nail ~ THF ' ~

NCN

EWG NC~EWG 28-75%

VI.A.13-50dom, A.L. et al., JACS, 125, 2880.

R-NH2 + R1

- R2 + R3-NC

Ti(dpma)(NMe2)2

R2 i H

57-83% VI.A.13-6 Jin, T.-S. et al., JCR(S), 591; Kim, J.N. et al., TL, 44, 1231; see also: Wolfe, J.P.; Ney, J.E., OL, 5, 4607. TiO2/SO42" R-CHO + H2NSO2R1 ~ R-CH=NSO2R1 Ph-Me, reflux 56-97% [similarly with TFAA or by opening of N-tosylaziridines with Pd(PCy3)2catalysis]

USEFUL SYNTHETIC PREPARATIONS

257

VI.A.13-7 Zhang, Z." Schafer, L.L., OL, 5, 4733. "Anti-Markovnikov lntermolecular Hydroamination: A Bis(amidate) Titanium Precatalyst for the Preparation of Reactive Aldimines"

VI.A.14. Other N-Containing Functional Groups

VI.A.14-1 Golan, E.; Rozen, S., JOC, 68, 9170; Rozen, S.; Carmeli, M.,

JACS, 125, 8118. 8118. JACS, 125, rI2

F2, 02

R~~O2

2 H20/MeCN 55-95% [similarly from azides] VI.A.14-2 Zolfigol, M.A. et al., SL, 191; Tanemura, K. et al., JCR(S), 497; Suzuki, H. et al., OBC, 1, 2326; Shackelford, S.A. et al., JOC, 68, 267. OH

O

OH

CI"N~N"CI NaNO2'wet SiO2"~ ~ §

X

NO2

C--2 12,rt

CI

X 0-99%

[arene nitration also with CAN/Ac20; NO2/zeolite(for moderately deactivated arenes) or tetramethylammoniumnitrate/(CF3SO2)20] VI.A.14-3 Yoon, Y.-J. et al., JOC, 68, 9113. Cl ~.~ R~N.-NO2

R",Nn + R1

2

CH2C12,rt

k, 28-92%

VI.A.14-4 Legault, C.; Charette, A.B., JAC, 68, 7119; Sain, B. et al., TL, 44, 4385. + H2N,.~

2. Bz-Ci, aq NaOH ~

~,,N;N-IBz 42-99%

[pyridine N-tosylaminoylides with PhI=NTs/Cu(OTf)2]

258

ORGANIC SYNTHESISu2004

VLA.14-5 Knapp, S.; Goldman, A.S. et al., CC, 2060; s e e a l s o : Beller, M. et al.,AG(E), 42, 5615, RI~NR2R3+ ~tnu 1~- R I I ~ , "NR2R3 ~l~I_I

0-98%

H

VI.A.14-6 Aube, J. et al., OL, 5, 3899. O R

+ R1-N3

CH2C12

~

R1

20-93% Z:E = 1-1.5:1 VI.A.14-7 Hayashi, Y. et al., TL, 44, 8293. Ph-NO + ~,,CHO proline ~ PhNHOo.(CHO MeCN R R 62-99% ee = 95-98 %

VI.A.14-8 Mohammed, A.H.A.; Nagendrappa, G., TL, 68, 2753; Ran, C. et al., TL, 44, 8061. , ~ D iAmONO,TMS-CI R R ~ D CH2C12'"20~

see also:

NOH 76-96%

VI.A.14-9 Rajski, S.R. et al., OL, 5, 4357.

x, pph "CO2R

O II

+ Ar-N3

X.v,PPho,

.~ H2OfrH F

.,,,~ y O R NAr 38-67%

VI.A.14-10 Stephens, C.E. et al., S, 2467. N-OR Pd/C v Ar --ffNH Ar----~ + HCO2NH4 "NH2 AcOH, reflux NH2 66-85%

USEFUL SYNTHETIC PREPARATIONS

259

VI.A.14-11 Zhu, S. et al., CJC, 81, 265. R2 RfSO2-N3 + "NH + R-CHO R1

N--SO2Rf ~ R--~ Et20 NR1R2 47-84%

VI.A.14-12 Batey, R.A. et al., JOC, 68, 2300; see also: Fan, E. et al., JOC, 68, 1611; Richeson, D.S. et al., JACS, 125, 8100; Overman, L.E. et al., OL, 5, 4485. NRIR2 NR1R2 KOH, Bu4NI N,~ PG~N,~N,,PG + R-X .~ P G , , N,,PG H H20/CH2CI2, 25~ R

60-99% [guanidines prepared by various other methods]

VI.B. Additions to Alkenes and Aikvnes

VI.B-1 Song, C.E. et al., CC, 1312. "Osmylated Macroporous Resins: Safe, Highly Efficient and Recyclable Catalysts for Asymmetric Aminohydroxylation of olefins." VI.B-2 Shvo, Y.; Green, R., JOM, 675, 77. Rt~

4- R1-CCI3

CI R~CCI2R1

M(CO)6

MeCN

12-85% VI.B-3 de Mattos, M.C.S. et al., S, 45; Bartels, A.; Liebscher, J. et al., S, 67. Cl

§

R .O.,rt O [similarly with NBS]

54-96%

VI.B-4 Tsuchii, K.; Ogawa, A., TL, 44, 8777. Ar~

+ C10F2rI + 0PhSe)2

hn

Ar ,.-r PhSe~ C 1 0 F 2 1 63-85%

260

ORGANIC SYNTHESIS--2004

VI.B-5 Hiegel, G.A. et al., SC, 33, 1997. Cl r N .N .

__.,

O

+

R

CI~,~NCI 0

R1 52-80%

VI.B-6 Sudalai, A. et al., OL, 5, 861. Br R~ R 1 R ~ - = _ R1 ~ Mn(I[I)-salenTSNH~ NBS NHTs CH2CI2,25~ 65-97% anti:syn = >99:1

NHTs TsNH~ NBS, CuI ~ R ~ IR1 MnSO4 or V205 CH2C12, 25~ Br 60-98% anti:syn = >99:1

VI.B-7 Ma, S. et al., CC, 1082; see also: Sliwinska, A.; Zwierzak, A., TL, 44, 9323. RSe I2 RSe _(I _~ ~ m R1 H20/MeCN/hex, rt HN_~o 51-62% Z:E = 18-65:1 VI.B-8 Tiecco, M. et al.,AG(E), 42, 3131. NaN Ar~

+ TfO

MeCN, -30~ MeS~., Me

Ph

MeS~,tMe 90% dr = 32.3:1

VI.C. Boron Compounds

VI.C-1 Matondo, H. et al., SC, 33, 795; Rault, S. et al., T, 59, 10043; Asher, S.A. et al., TL, 44, 7719.

R X ~ I I r-- ~ . r ~ ~r

J

R

1. iprMgCI, 20~ 2h ..-~- X . ' ~ B(OH) 2 2.
USEFUL SYNTHETIC PREPARATIONS

261

VI.C-2 Hartwig, J.F. et al., OM, 22, 365. "A Short Synthesis of Tetraalkoxydiborane (4) Reagents." VI.C-3 Andrus, M.B. et al., OL, 5, 4635; Dehaen, W. et al., SL, 1204. Ar.N2+BF'4 +

~ ~

B~~ --

Pd(OAc'2'THF' rt B~O~ .~ Ar-'/'r ~r

[similarly with Ar-Br, Pd(dppt0Cl2, n~] VI.C-4 Miyaura, N. et al., CC, 2924. Ar-H + I - I ~ ~

"'[Ir(OMe)(eod)]2,hex, rt~ A r - - B ~ 9t~

,~

22-99%

VI.C-5 Josyula, K.V.B. et al., TL, 44, 7789 R~Cl2HB:di~ R1 R1 CH2C12,reflux ~- RB(OH)2~~" 15-75% VI.C-6 Christophersen, C. et al., JOC, 68, 9513. "Synthesis of 2,3-Substituted Thienylboronic Acids and Esters." VI.C-7 Alcaraz, G. et al., CC, 2280. Pd(PPh3)2CI2,TEA H2B-Nipr2 + Ar-X dioxane, 700C

9

H ~B--Ar I

~Pr2N 20-99%

V!.D, Nucleosides, Nucleotides, etc. VI.D-1 Shuto, S. et al., JOC, 44, 3465. "The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2'Deoxy- 2 '- C-ethynylnucleosides"

262

ORGANIC SYNTHESISm2004

VI.D-2 Kang, C.; Kim, Y.H. et al., TL, 44, 7941. "New Synthesis of 3'-Deoxypurine Nucleosides Using Samarium(III) Iodide Complex" VI.D-3 Altona, C. et al., JOC, 68, 5897.

"2'-Chloro-2',3'-dideoxy-3'-fluoro-D-ribon u cleosides: Synthesis, Stereospecificity, Some Chemical Transformations, and Conformational Analysis" VI.D-4 Paquette, L.A. et al., JOC, 68, 8614, 8625. "Conformational Restriction of Nucleosides by Spirocyclic Annulation at C4' Including Synthesis of the Complemantary Dideoxy and Didehydrodideoxy Analogues" VI.D-5 Sekine, M. et al., JOC, 68, 5478 [proton-block strategy for]; Minakawa, N.; Ono, Y.; Matsuda, A., JACS, 125, 11545 [on-columnusing Cu-catalyzed oxidative acetylenic coupling]. "Oligodeoxynucleotides" VI.D-6 Koch, T. et al., OBC, 1,655. "Synthesis of 2'-Amino-LNA: A New Strategy." VI.D-7 Robins, M.J. et al., JOC, 68, 989 [2-chloro-2'deoxy]; Strazewski, P. et al., JOC, 68, 2038 [3'-amino-3'-deoxy]. "Adenosine Derivatives" VI.D-8 Castillon, S. et al., JOC, 68, 1172 [unsaturated, related to D4T]; Ramsay Shaw, B. et al., OL, 5, 2401 [thymidinetriphosphate and s-Pboranotriphosphate]. "Acyclic Nucleosides" VI.D-9 Townsend, L.B. et al., JOC, 68, 4170 [polyhalogenatedquinoline]; Hanessian, S.; Machaalani, R.; TL, 44, 8321 [~- and l~-pseudouridines]; Yadav, L.D.S.; Kapoor, R.; TL, 44, 8951 [3-componentthiazolo-s-triazine synthesis]; Raboisson, P. et al., JOC, 68, 8063 [pyrazolo[1,5-a]-l,3,5-triazinesand 3',5'bisphosphates]. C-Nucleosides VI.D-10 Csuk, R.; Thiede, G., ZN(B), 58b, 97, 345 [monofluorinated]; Csuk, R.; Kern, A., ZN(B), 58b, 843 [flexibleside chain]; Csuk, R.; Thiele, G., ZN(B), 58b, 853 [spaced difluoro]; Csuk, R.; Eversmann, L., ZN(B), 58b, 997. "Cyclopropanoid Nucleosides"

USEFUL SYNTHETIC PREPARATIONS

263

VI.D-11 Herdewijn, P. et al., JOC, 68, 4499 [ARA-type cyclohexenyl]; Chu, C.K. et al., JOC, 68, 9012 [antiviral]; Roy, A.; Schneller, S.W., JOC, 68, 9269 [4'- and l'-methyl-5'-nor]; Ishikura, M. et al., OBC, 1,452 [2',y-epimino]; Rodriguez, J.B.; Marquez, V.E. et al., T, 59, 295 [conformationally locked oxabicyclo[3.1.0lhexane-based]; Leumann, C.J. et al., JOC, 68, 7693 [amide DNA (Cpa-DNA)]. "Carbocyclic Nucleosides" VI.D-12 Nielsen, P. et al., OBC, 1, 811 [dihydroxylation and 2'-deoxygenation]; Etheve-Quelquejeu, M. et al., TL, 44, 9131 [2'-0,3'-0 adenosines]; San-Felix, A. et al., JOC, 68, 6695 [pyrimidine with conformationally-locked sugar puckers]. "Bicyclic Nucleosides" VI.D-13 Chen, X.; Wiemer, D.F., JOC, 68, 6108 [5'-amino-5'-phosphonate pyrimidines]; Bubenik, M. et al., TL, 44, 8261 [bioactive phosphonates]; Ernst, C.; Klaffke, W., JOC, 68, 5780 [uridine diphospho-D-xylose and -L-arabinose]; Hayakawa, H. et al., TL, 44, 8605 [enantio-uracil dinucleotide]; Davisson, V.J. et al., JOC, 68, 3 860 [azole carboxamide triphosphates]. "Nucleotides" VI.D-14 Seela, F.; He, Y., JOC, 68, 367 [6-aza-2'-deoxyisocytidine]; Hada, T. et al., JACS, 125, 8307 [oxazaphospholidine approach to]; Sekine, M. et aI., JOC, 68, 9971 [2'-O-alkyl-2-thiouridine incorporating]; Greenberg, M.M. et al., AG(E), 42, 5882 [containing the C4'-oxidized abasic site]. "Oligonucleotides" VI.D-15 Pouli, N.; Townsend, L.B. et al., JOC, 68, 6466. "The Synthesis of 4-Deazaformycin A" VI.D-16 Qing, F.-L. et al., JOC, 68, 9026 [3-deoxy-3,3-difluoro-D-furanose]; Haraguchi, K. et al., JOC, 68, 2006 [1'-C-branched]; Seela, F. et al., JOC, 68, 5519 [3-bromopyrazolo[3,4-d]pyrimidine-2'-deoxy-2'-fluoro-[~-D-]. "Arabino-Based Nucleosides"

VI.E. Phosphorus, Selenium and Tellurium Compounds

VI.E-1 Willis, M.C. et al., TA, 14, 705 [diphophine monosulfides]; Komarov, I.V.; Borner A. et al., CC, 2240 [stereoselective, P-chiral]. "Chiral Monophosphines"

264

ORGANIC SYNTHESISm2004

VI.E-2 Yoakim, C. et al., SL, 473. "Removable Phosphine Reagents for the Mitsunobu Reaction." VI.E-3 Salvatore, R.N. et al., TL, 44, 8373. CsOHoH20 1~ 9 R2P""" R1 R2PH + X ~ R 1 4AMS 47-99% VI.E-4 Chan, K.S. et al., T, 59, 10295; LeGall, E. et al., T, 59, 7497; van Allen, D.; Venkataraman, D., JOC, 68, 4590; Buchwald, S.L. et al., OL, 5, 2315. OTf

F

DMF or neat, 110-115*C

~

PPh 2 F

20-51% [arene phosphines obtained similarly fron Ar-Br, Ph2PCI, Zn, NiBr2(bpy) or Ar-I, Ph2PH, CuI, tBuONa VI.E-5 Lebel, H. et al., OL, 5, 2347. Ph Bu4N+Br', ar NaOH R~P--BH 3 + RI.x ~ H Ph-Me, rt

Ph R~P--BH3 R1 74-95%

VI.E-6 Azizi, N." Saidi, M.R., TL, 44, 7933; Saidi, M.R. et al., TL, 44, 7933. R,,~0

P(OR1), TMS'CI, LPDE~

RwOTMS O~,,P(OR1)2 70-92%

VI.E-7 Salvatore, R.N. et al., TL, 44, 7579. R~

Ph2PI-I,CsOH

OH R~,,,~

DMF, 4A MS

PPh 2

42-88%

VI.E-8 Marder, S.R. et al., TL, 44, 7989. Ar~OH

+ P(OEt)3

12 0~

~ rt

O II Ar~P(OEt)2 40-85%

USEFUL SYNTHETIC PREPARATIONS

265

VI.E-9 Takaki, K. et al., JOC, 68, 6554; Mimeau, D.; Gaumont, A.-C., JOC, 68, 7016. THF, rt R R1 R ~ R 1 + Ph2PH ~ ~-~ Ph

X

Me%N"Ph gb (hmpu)3

PPh2 41-99%

E:Z = 1:100-19:1

VI.E-10 Peng, A.; Ding, Y., S, 205. R

+

O ...P,, H O ~lOEt

Hg(OAc)2,BF3"Et20 Ph-Me, 80~

[I O ~- R.,~o,.P.~oEt 48-92%

VI.E-11 Centrone, C.A.; Lowary, T.L., JOC, 68, 8115 [glycosyl]; Kafarski, P. et al., TA, 14, 1535 [enantiodifferentiation of amino with a- and 13cyclodextrins]; Cristau, H.-J.; Virieux, D. et al., S, 2216 [arylhydroxymethyi]. "Phosphinic Acids" VI.E-12 Renard, P.-Y.; Mioskowski, C. et al., AG(E), 42, 2389. R2 R2 TMS-OTf I ~P-OR 2 ~. R1.-.2p=0 1~ CHCI3, 20"60~ 1~ 68-98%

VI.E-13 Taillades, J. et al., TL, 44, 6169. R1

~=: R2

O II Et3B + H..PPh2 ...... ~ MeOH, 20"C

R

R~P=-O a 2 65-96%

VI.E-14 Matreeva, E.D.; Zefirov, N.S. et al., SL, 2321; Akiyama, T. et al., SL, 1463; Yang, R. et al., S, 887; Kaboudin, B. et al., S, 2705; see also; Dondoni, A.; Pollini, G.P. et al., EJOC, 1904; see also: Davis, F.A.; Prasad, K.R., JOC, 68, 7249. R1 O Pht O R)e=O + R2.NH2 + i_r.P(OEt) 2 CH2C12~. R2HN~tIP(OEt) 2 R ~" I R 16-98%

266

ORGANIC SYNTHESIS--2004

VI.E-15 Azizi, N.; Saidi, M.R., T, 59, 5329 and EJOC, 4630; Chandrasekhar, S. et al., SL, 505. O II LiClO4rt R~IP(OR2)2 R1-CHO + R2-NH2 + P(OR2)3 Et20, NR2 84-98%

VI.E-16 Villemin, D. et al., JCR(S), 436. ~W NiCl2 or PdCl2 Ar-X + P(OEt)3 neat

O II A r.,,"P(OEt)2 60-98%

VI.E-17 Kabalka, G.W.; Guchhait, S.K., OL, 5, 729; see also: Jiao, X.-Y,; Bentrude, W.G., JOC, 68, 3303. R1 R1 P(OEt)~ Pd(OAc)2, 02 R

B-~n

neat, 95~

R~~?(OEt)2 60-81% E or Z stereospecifically

VI.E-18 Salvatore, R.N. et al., TL, 44, 8617. "Mild and Efficient Cs2CO3-Promoted Synthesis of Phosphonates." VI.E-19 Piettre, S.R. et al., TL, 44, 8837. "First Synthesis of S,S-Dialkyl Difluorophosphonodithioates and Difluorophosphonotrithioates." VI.E-20 Chandrasekaran, S. et al., TL, 44, 2257. R-Br + WSe4"+NEt4

(R-Se)2 82-95%

VI.E-21 Taniguchi, N.; Onami, T., SL, 829; Beletskaya, I.P. et al., TL, 44, 7039; Nishiyama, Y.; Sonoda, N. et al., JOC, 68, 3599. Cu20, Mg, bpy Ar-I + (PhSe)2 ~ Ar-SePh DMF, ll0*C 53-95% [similarly with a tributylstannylselenide, PPh3/CuI]

USEFUL SYNTHETIC PREPARATIONS

267

VI.E-22 Yamaguchi, M. et al., JOC, 68, 8964. RhH(PPh3)4, dppf or dppb R - + (R1-S)2 + ~2Se)2 Me2CO, reflux

R

R ~~-~SeR 2 11-79%

VI.E-23 Kuniyasu, H.; Kambe, N. et al., OL, 5, 3871.; Ananikov, V.P.; Beletskaya, I.P. et al., JOM, 679, 162. R1Se~O Pt0PPh3)4 R~R2 R ~ + R2 Ph-Me,reflux R1S 24-89% VI.E-24 Karaghiosoff, K.; Wessjohann, L.A. et al., TL, 44, 6911; Geisler, K., Langer, P. et al., SL, 1983. 1R2

Se4'

Ph

Ph-H,rt

1R2

21-85% [selenoamides formed also from R-CN, P2Ses] VI.E-25 Movassagh, B.; Mirshojeraei, F., M, 134, 831. O Zn, AICI3 R--~~ q- (R1Se)2 .~ CI DMF, 65*C eR1 74.89% VI.F Silicon Compounds VI.F-1 Denmark, S.E.; Kallemeyn, J.M., OL, 5, 3483. 1. PdCI2,BPTBP R - ~ Me Me ipr2NEt'NMP' 600C R - ~ ' OH Br + Me-Si-Si-Me ~ SiMe2 Me(~ ~OMe 2. Me2NCH2CH2SH AcOH/MeCN 69-81% VI.F-2 Lulinski, S.; Serwatowski, J., JOC, 68, 9384. ~~_ TMS-CI,LDA T M S ( ~ Br ... ~ Br X THF, -70~ X ---~TMS (Br as ortho-directing group)

23-80%

268

ORGANIC SYNTHESIS--2004

VI.F-3 Leighton, J.L. et al., JACS, 125, 1190 [via silane alcoholysis]; Oestreich, M. et al., S, 2725 [enantiomericallyenriched cyclic]. "Chiral Silanes" VI.F-4 Elsevier, C.J. et al., JOM, 679, 149 [of styrene: Pt (1,3-dimesityl dihydroimidazol-2-ylidene) catalyst]; Trost, B.M.; Ball, Z.T., JACS, 125, 30 [intramolecular endo-dig, catalyzed by Ru]; Muller, T. et al., CJC, 81, 1223 [metalfree intramolecular]; Zargarian, D. et al., CJC, 81, 1299 [catalyzed by Ni(II) indenyl complexes]; Cervantes, J. et al., CJC, 81, 1370 [1.alkynes; Pt/SiO2 sol-gel catalysts]; Wu, W.; Li, C.-J., CC, 1668 [1-alkynes; transition metal catalyzed] Katayama, H.; Ozawa, F. et al., JOM, 676, 49 [p.diethynylbenzene; Ru catalyzed]; Trost, B.M. et al., OL, 5, 1895 [1-alkynes; HSiMe2Bn, Ru catalyzed] and AG(E), 42, 2003 [regioselective,of propargylic alcohols]; Field, L.D.; Ward, A.J., JOM, 681, 91 [alkynes; phosphine Co(l), Rh(I), Ir(I) complexes]; Wang, F.; Neckers, D.C., JOM, 665, 1 [alkynes; photoactivated]; Takahashi T. et al., OL, 5, 3479 [alkynes; titanocene catalyzed]. "Hydrosliylation" VI.F-5 Jung, I.N. et al., OM, 22, 529. R1 R1 Bu4PCI R1 R1 R~-~_ + HSiCI3 ,~ ~ - ~ CI neat, 1300C R L---SICI3 20-96% VI.F-6 Prakash, G.K.S. et al., JOC, 68, 4457; Aubert, C.; Malacria, M. et al., OL, 5, 2037. R2

F

R1--Si-Cl 1~

+ PhS(O)n---(-r

X

Mg

DMF

R2 ~

F

Rl--dSi--~xF

51-95% [alcohols and alkynyl magnesium species used for nucleophilic displacements on silylhalides] VI.F-7 Sieburth, S.McN. et al., OL, 5, 1859. SiPh2R

oc.L, u.,,sparte,ne oc. iPheR I

H

82-88% ee = 90-95 %

USEFUL SYNTHETIC PREPARATIONS

269

VI.F-8 Steel, P.G. et al., JOC, 68, 3337. 1. tBuOK, THF TMS4Si 2. ArMgBr, Ar-Br, THF -780C 3. Ar-MgBr, THF, reflux

TMS3SiAr 31-69%

VI.F-9 Fleming, I. et al., CC, 200. O PhMe2Si-Li Me2

R

O

THF, -78--*-20~

PhMe2Si ~ J ~ R 40-76%

VI.F-10 Fry, A.J. et al., JOM, 671, 126. IL,,,,,,COzR1 + Me2SiHCI

LDA

R ~ C O 2 R1 SiMe2H 89-95%

VI.G. Sulfur Compounds

VI.G-1 Becht, J.-M.; Wagner, A.; Mioskowski, C., JOC, 68, 5758. "Facile Introduction of SH Group on Aromatic Substrates via Electrophilic Substitution Reactions." VI.G-2 Wu, Y.-J.; He, H., SL, 1789; Naus, P. et al., SL, 2117. btW, CuI, Cs2CO3 R-SH + Ar-X .~ RS-Ar 64-89% [similarly with sugar thiolsl VI.G-3 Tsutsumi, K.; Kakiuchi, K. et al., OM, 22, 2996. "Effects of a Bidentate Phosphine Ligand on Palladium-Catalyzed Nucleophilic Substitution Reactions of Propargyl and Allyl Halides with Thiol" VI.G-4 Garcia Ruana, J.L. et al., OL, 5, 75. Ph~r--O 1. RMgX eC, L ~S'O" M N 2. HBF4 Cbz 3. RIMgX (one pot)

R1 +~ R" S'~O" 50-78~ ee = 93%

270

ORGANIC SYNTHESISm2004

VI.G-5 Su, W.K. et al., OPP, 35, 613. R-SH + (C13CO)2C=O

Ph3PO

~

R-S-S-R 76-90%

VI.G-6 Zysman-Colman, E.; Harpp, D.N., JOC, 68, 2487. "Optimization of the Synthesis of Symmetric Aromatic Tri- and Tetrasulfides." VI.G-7 Schwan, A.L. et al., CJC, 81,423. R1 D" R-~S-~',OChloesteryl + R2MgX

R1 ~-

._O"

R~+R 2 39-87%

VI.G-8 Bandgar, B.P. et al., SL, 2029; Yadav, J.S. et al., TL, 44, 6055. Ar I Ar-H + SOO2 H20,rt Ar'S~o 46-97% [similarly for sulfonation of 2-halo indoles with ArSOClz/InBr3] VI.G-9 Gais, H.-J. et al., CEJ, 9, 4202 see also: Cacchi, S. et al., SL, 361. ~OCO2Me ~ S O 2 tBu ~n + LiSO2tBu [Pd2(dba)3]'CHCl3,THAB, H20/CH2CI2 '~" ~n /-'X 46-60% o ~ o ~ p Nit" ~ ee = 84-99% Ph 2

VI.G-10 Xu, F. et al., TL, 44, 1283. F ~ B r Br

+ NaSO2Me HzO/DMAc, 110"C~ F ~ , , f S O 2 M e 96%

VI.G-11 Curphey, T.J., JOC, 68, 6461. "Thionation with the Reagent Combination of Phosphorus Pentasulfide and Hexamethyl Disiloxane"

USEFUL SYNTHETIC PREPARATIONS

271

VI.G-12 Barrett, A.G.M. et al., JOC, 68, 8274; Gareau, Y. et al., TL, 44, 7821. 1. Mg, THF, reflux Br R

~

3. SO2, -40~

SO2NR2 R

4. SO2C12, -40~ 5. HNR2, rt

30-85 %

(one pot)

[arenesulfonamides also from haloarenes and ipr3SiSK, Pd(PPh3)4 then KNOatSO2CI2, HNRR1]

VI.G-13 Blotny, G., TL, 44, 1499. Cl N~N R-SOaH +C IllI,,,~N ''~'"

TEA

~

R-SO2CI 47-96%

CI M e 2 C O

VI.G-14 Jia, X.; Zhang, Y., JCR(S), 540; Su, W. et al., JCR(S), 442. Ph-S-S-Ph

1. Sm, Cp2TiCI2, THF _,..-- O ~ S P h 2. R-COCI R 62-91%

VI.G-15 Armstrong, A. et al., TL, 44, 5335. O PhSM + ~ - e ~-~ph~,,Me

Ph CF3CH2OH,-30~

-'

Ph-+~Me n

NR2

CII

85% dr = 1.85:1

VI.G-16 Wade, P.A. et al., JOC, 68, 2859. "Preparation, Properties, and Chemical Reactivity of txNitrosulfoximines, Chiral Analogues of ~-Nitrosulfones" VI.G-17 Mizuno, T. et al., T, 59, 1327; Wynne, J.H. et al., JOC, 68, 3733. CO + S + H-NR1R2

1. DBU_,~ R S ~ 2. R-X

"NRIR2

78-95%

272

ORGANIC SYNTHESISm2004

VI.G-18 Doszczak, L.; Rachon, J., JCS(P1), 1271. S O.~NRIR 2 R-..-~S.._~p,,O,, + H-NR1R2 )'R 85-99%

VI.G-19 Chakrabarty, M." Sarkar, S., TL, 44, 8131. SCN X ~ ~ N

R1 + NH4SCN

M K10 clay, 80~

X

~

~

R1 I

R

R 80-92%

VI.H. Tin Compounds

VI.H-1 Mitchell, T.N.; Podesta, J.C. et al., JOC, 68, 10087; Dodero, V.I." Mitchell, T.N.; Podesta, J.C., OM, 22, 856; Miura, K.; Hosomi, A. et al., JOC, 68, 8730. R --

\~o R1

+ Nph3SnH

Pd(PPh3)2CI2'AIBN)t, N p h ~ THF, rt

R1

R

O

+

~ R R

1

O

80-96% 1-1.63:100-1 VI.H-2 Braune, S.; Kazmaier, U., AG(E), 42, 306; Mancuso, J.; Lautens, M., OL, 5, 1653; Cox, L.R. et al., OL, 5, 3971. SnBu3 Rk : + HSnBu3 W(CO)s(CN-Ph-NO2)~ R ~ ~ S n B u 3 Ph-Me, 60~ 32-87% [similar bisstannylations with (RaSn)2,pd(tBuNC)2CI2 or Me3SnCu; Me2.LiBr] VI.H-3 Kells, K.W.; Chong, J.M., OL, 5, 4215. o, g+,

o

g+,

H~t" tBu

N" tBu

,Jl R"

+ LiSnBu3

THF, -78~

.~

= R~SnBu3 80-96% dr = 75.9-200:1

USEFUL SYNTHETIC PREPARATIONS

273

VI.I-I-4 Gaultier, G.; Geib, S.J.; Curran, D.P., JOC, 68, 5013. "A New Class of Chiral Organogermanes Derived from C2-Symmetric Dithiols: Synthesis, Characterization and Stereoselective Free Radical Reactions"

VII REVIEWS (See also: IV.M, VIII.A.5; VIII.C.7)

VII.A Techniques VII.A-1 Burkart, M.D., OBC, 1, 1 Review:

"Metabolic Engineering--A Genetic Toolbox for Small Molecule Organic Synthesis."

VII.A-2 Tietze, L.F.; Feuerstein, T., AJC, 56, 841. Review:

"Highly Selective Compounds for the Antibody-Directed Enzyme Prodrug Therapy of Cancer."

VII.A-3 Guo, X.; Szoka, Jr., F.C., ACR, 36, 335. Review:

"Chemical Approaches to triggerable Lipid Vesicles for

Drug and Gene Delivery." VII.A-4 Sullivan, T.P.; Huck, W.T.S., EJOC, 17. Microreview: "Reactions on Monolayers: Organic Synthesis in Two Dimensions." VII.A-5 Robinson, D.E.J.E.; Bull, S.D., TA, 14, 1407. Review:

"Kinetic Resolution Strategies Using Non-Enzymatic

Catalysts." VII.A-6 Chen, P., AG(E), 42, 2832. Review:

"Electrospray Ionization Tandem Mass Spectrometry in

High-Throughput Screening of Homogenous Catalysts." VII.A-7 Wuthrich, K., AG(E), 42, 3340. Review" "NMR Studies of Structure and Function of Biological Macromolecules (Nobel Lecture)." 274

REVIEWS

275

VII.A-8 Davis, A.M. et al., AG(E), 42, 2718. Review:

"Application and Limitations of X-Ray Crystallographic Data in Structure-Based Ligand and Drug Design."

VII.A-9 Figadere, B. et al., TA, 14, 963. Technique: "NMR Determination of Absolute Configuration of aAcyloxy Ketones." VII.A-10 Lejczak, B. et al., TA, 14, 1019. Technique: "Quinine as Chiral Discriminator for Determination of Enantiomeric Excess of Diethyl 1,2Dihydroxyalkanephosphonates."

VII.A-11 Adam, W.; Trofimov, A.V.,ACR, 36, 571. Review:

"Viscosity as an Experimental Tool in Studying the Mechanism of Stereoselective and Product-Selective Chemical Transformations Through Frictional Impositions."

VII.A-12 Griesbeck, A.G., SL, 451. Account:

"Spin-Selectivity in Photochemistry: A Tool for Organic Synthesis."

VII.A-13 Mayr, H. et al., ACR, 36, 66. Review:

"II-Nucleophilicity in Carbon-Carbon Bond-Forming Reactions."

VII.A-14 Bernhardt, P.V.; Moore, E.G., EJC, 56, 239. Review:

"Functionalized Macrocyclic Compounds: Potential Sensors of Small Molecules and Ions."

VII.A-15 Suksai, C.; Tuntulani, T., CSR, 32, 192. Review:

"Chromogenic Anion Sensors."

VII.A-16 Shashidhar, M.S. et al., CRV, 103, 4477. Review:

"Regioselective Protection and Deprotection of lnositol Hydroxy Groups."

276

ORGANIC SYNTHESIS--2004

VII.B Asymmetric Synthesis and Molecular Recognition VII.B-1 Mislow, K., CCC, 849. Commentary: "Absolute Asymmetric Synthesis." VII.B-2 Kolodiazhnyi, O.I., T, 59, 5953. Report:

"Multiple Strereoselectivity and Its Application in Organic Synthesis."

VII.B-3 Armstrong, III, J.D.; Martinelli, M.J.; Senanayake, C., eds., TA, 14, 3425-3638. Special Issue:

"Asymmetric Synthesis on a Process Scale."

VII.B-4 Lipkowitz, K.B.; Kozlowski, M.C.; SL, 1547. New Tools "Understanding Stereoinduction in Catalysis in Synthesis: via Computer: New Tools for Asymmetric Synthesis." VII.B-5 Bolm, C., guest ed., CRV, 103, 2761-3400. Reviews:

"Enatioselective Catalysis."

VII.B-6 Zanoni, G.; Franzini, M. et al., CSR, 32, 115. Review:

"Toggling Enantioselective CatalysismA Promising Paradigm in the Development of More Efficient and Versatile Enantioselective Synthetic Methodologies."

VII.B-7 Schreiner, P.R., CSR, 32, 289. Review:

"Metal-Free Organocatalysis Through Explicit Hydrogen Bonding Interactions"

VII.B-8 Gaumont, A.-C.; Plaquevent, J.-C. et al., TA, 14, 3081. Review:

"Ionic Liquids and Chirality: Opportunities and Challenges."

VII.B-9 Pellissier, H., T, 59, 8291. Report"

"Dynamic Kinetic Resolution."

REVIEWS

277

VII.B-10 Ramamurthy, V. et al., ACR, 36, 509. Review:

"Asymmetric Photoreactions Within Zeolites: Role of Confinement and Alkali Metal Ions."

VII.B-11 Renaud, P.; Sibi, M.P. et al., CEJ, 9, 28. Review:

"Chiral Relay: A Novel Strategy for the Control and Amplification of Enantioselectivity in Chiral Lewis Acid Promoted Reactions."

VII.B-12 Tretyakov, Y.D., RCR, 72, 651. Review:

"Self-Organisation Processes in the Chemistry of Materials."

VII.B-13 Sherman, J., CC, 1617 Feature Article:

"Molecules that Can't Resist Temptation."

VII.B-14 Klarner, F.-G.; Kahlert, B., ACR, 36, 919. Review"

"Molecular Tweezers and Clips as Synthetic Receptors. Molecular Recognition and Dynamics in ReceptorSubstrate Complexes."

VII.B-15 Tung, C.-H. et al., ACR, 36, 39. Review:

"Supramolecular Systems as Microreactors: Control of Product Selectivity in Organic Photo-transformation."

VII.B-16 Li, A.D.Q. et al., CEJ, 9, 4594. Review:

"Folding versus Self-Assembling."

VII.B-17 Ma, J.-A.; AG(E), 42, 4290. Minireview: "Recent Developments in the Catalytic Asymmetric Synthesis of ~- and 13-Amino Acids." VII.B-18 Meyer, E.A.; Castellano, R.K.; Diederich, F., AG(E), 42, 1210. Review:

"Interactions with Aromatic Rings in Chemical and Biological Recogntion."

278

ORGANIC SYNTHESISm2004

VII.B-19 Brenna, E. et al., TA, 14, 1. Report:

"Enantioselective Perception of Chiral Odorants."

VII.B-20 Ohfune, Y.; Shinada, T., BCJ, 76, 1115. Account:

"Asymmetric Strecker Route Toward the Synthesis of Biologically Active a,ct-Disubstituted a-Amino Acids."

VII.B-21 Lectka, T. et al., ACR, 36, 10. Review:

"a-Imino Esters: Versatile Substrates for the Catalytic, Asymmetric Synthesis of a- and 13-Amino Acids and 13Lactams."

VII.B-22 Perry, M.C.; Burgess, K., TA, 14, 951. Review"

"Chiral N-Heterocyclic Carbene-Transition Metal Complexes in Asymmetric Catalysis."

VII.B-23 Dai, L.-X.; Hou, X.-L. et al., ACR, 36, 659. Review:

"Asymmetric Catalysis with Chiral Ferrocene Ligands."

VII.B-24 Sutcliffe, O.B.; Bryce, M.R., TA 14, 2297. Review:

"Planar Chiral 2-Ferrocenyloxazolines and 1,1'Bis(oxazolinyl)ferrocenesmSyntheses and Applications in Asymmetric Catalysis."

VII.B-25 Westermann, B., AG(E), 42, 151. Highlight: "Asymmetric Catalytic Aza-Henry Reactions Leading to 1,2-Diamines and 1,2-Diaminocarboxylic Acids." VII.B-26 Roesky, P.W.; Muller, T.E., AG(E), 42, 2708. Highlight: "Enantioselective Catalytic Hydroamination of Alkenes." VII.B-27 Gibson, S.E.; Knight, J.D., OBC, 1, 1256. Review:

"[2.2]Paracyclophane Derivatives in Asymmetric Catalysis."

REVIEWS

279

VII.B-28 Crudden, C.M.; Edwards, D., EJOC, 4695. Microreview: "Catalytic Asymmetric Hydroboration" Recent Advances and Applications in Carbon-Carbon BondForming Reactions." VII.B-29 Genet, J.-P., ACR, 36, 908. Review:

"Asymmetric Catalytic Hydrogenation. Design of New Ru Catalysts and Chiral Ligands: From Laboratory to Industrial Applications."

VII.B-30 Schoffers, E., EJOC, 1145. Microreview: "Reinventing Phenanthroline Ligands--Chiral Derivatives for Asymmetric Catalysis." VII.B-31 Chelucci, G. et al., T, 59, 9471. Report:

"Chiral P,N-Ligands with Pyridine-Nitrogen and Phosporus Donor Atoms. Syntheses and Applications in Asymmetric Catalysis."

VII.B-32 Aggarwal, V.K.; Richardson, J., CC, 2644. Review:

"The Complexity of Catalysis: Origins of Enantio- and Diastereocontrol in Sulfur Ylid Mediated Epoxidation Reactions."

VII.B-33 Christoffers, J., Baro, A., AG(E), 42, 1688. Highlight: "Construction of Quaternary Stereocenters: New Perpectives Through Enantioselective Michael Reactions." VII.B-34 Christoffers, J., CEJ, 9, 4862. Review:

"Formation of Quaternary Sterereoisomers by CopperCatalyzed Michael Reactions with L-Valine Amides as Auxiliaries."

VII.B-35 Walsh, P.J., ACR, 36, 739. Review:

"Titanium-Catalyzed Enantioselective Additions of Alkyl Groups to Aldehydes: Mechanistic Studies and New Concepts in Asymmetric Catalysts."

280

ORGANIC SYNTHESISm2004

VII.B-36 Denissova, I.; Barriault, L., T, 59, 10105. Report:

"Stereoselective Formation of Quaternary Carbon Centers and Related Functions."

VII.B-37 Nakamura, K., TA, 14, 2659. Review:

"Recent Developments in Asymmetric Reduction of Ketones with Biocatalysts."

VII.B-38 Pu, L., T, 59, 9873. Report:

"Asymmetric Alkynylzinc Additions to Aldehydes and Ketones."

VII.B-39 Ramesh, N.G.; Balasubramanian, K.K., EJOC, 4477. Microreview: "2-C-Formyl Glycals: Emerging Chiral Synthons in Organic Synthesis." VII.B-40 Hoffmann, R.W., AG(E), 42, 1096. Review:

"mesoCompounds- Stepchildren or Favored Children of Stereoselective Synthesis."

VII.B-41 Ukaji, Y.; Inomata, K., SL, 1075. Review:

"Development of New Asymmetric Reactions Utilizing Tartaric Acid Esters as Chiral Auxiliaries. The Design of an Efficient Chiral Multinucleating System."

VII.B-42 Demchenko, A.V., SL, 1225. Account:

"Stereoselective Chemical 1,2-cis-O-Glycosylation: From 'Sugar Ray' to Modern Techniques of the 21 st Century."

VII.B-43 Cossy, J. et al., ACR, 36, 766. Review"

"Stereoselective Synthesis of Polypropionate Units and Heterocyclic Compounds by Cyclopropyl-Carbinol RingOpening with Mercury(II) Salts."

VII.B-44 Orr, R.K.; Calter, M.A., T, 59, 3545. Report:

"Asymmetric Synthesis Using Ketenes."

REVIEWS

281

VII.B-45 Tolstikov, A.G. et al., RCR, 72, 803. Review:

"Natural Compounds in the Synthesis of Chiral Organophosphorus Ligands."

VII.B-46 Fernandez, I.; Khiar, N., CRV, 103, 3651. Review:

"Recent Developments in the Synthesis and Utilization of Chiral Sulfoxides."

VII.B-47 Miura, K.; Hosomi, A., SL, 143. Account:

"Stereoselective Synthesis of Substituted Cyclic Ethers and Amines by Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hydroxy or Amino Group."

VII.B-48 Biali, S.E. et al., EJOC, 1825. Microreview: "Stereochemistry of Polyethylated Aromatic Systems." VII.B-49 Collado, I.G. et al., TA, 14, 1229. Review:

"Biotransformations by colletotrichum Species."

VII.C Reactions

VII.C-1 Alcaide, B.; Almendros, P., AG(E), 42, 858. Highlight: "The Direct Catalytic Asymmetric Cross-Aldol Reaction of Aldehydes." VII.C-2 Basavaiah, D. et al., CRIs, 103, 811. Review"

"Recent Advances in the Baylis-Hillman Reaction and Applications."

VII.C-3 Basak, A. et al., CRV, 103, 4077. Review"

"Chelation-Controlled Bergman Cyclization: Synthesis and Reactivity of Enediynyl Ligands."

VII.C-4 Dilman, A.D.; Ioffe, S.L., CRV, 103, 733. Review:

"CarbonmCarbon Bond Forming Reactions Mediated by Silicon Lewis Acids."

282

ORGANIC SYNTHESISm2004

VII.C-5 Majumdar, K.C. et al., T, 59, 7251. Report:

"The Thio-Claisen Rearrangement 1980-2001."

VII.C-6 Fleming, F.; Wang, Q., CRV, 103, 2035. Review:

"Unsaturated Nitriles: Conjugate Additions of Carbon Nucleophiles to a Recalcitrant Class of Acceptors."

VII.C-7 Murakami, M.,AG(E), 42, 718. Highlight: "New Catalyzed Three-Component Cycloadditions for the Synthesis of Eight-Mernbered Carbocycles." VII.C-8 Lenoir, D., AG(E), 42, 854. Highlight: "The Electrophilic Substitution of Arenes: Is the 17 Complex a Key Intermediate and What Is Its Nature." VII.C-9 Adam, W.; Krebs, O., CRV, 103, 4131. Review:

"The Nittroso Ene Reaction: A Regioselective and Stereoselective Allylic Nitrogen Functionalization of Mechanistic Delight and Synthetic Potential."

VII.C-10 Lane, B.S.; Burgess, K., CRV, 103, 2457. Review:

"Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide."

VII.C-11 Poulsen, C.S.; Madsen, R., S, 1. Review:

"Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes."

VII.C-12 Breit, B., ACR, 36, 264. Review:

"Synthetic Aspects of Stereoselective Hydroformylation."

VII.C-13 Beller, M. et al., CEJ, 9, 4286. Review:

"Multicomponent Coupling Reactions for Organic Synthesis: Chemoselective Reactions with AmideAldehyde Mixtures."

REVIEWS

283

VII.C-14 Pohlki, F.; Doye, S., CSR, 32, 104. Review:

"The Catalytic Hydroamination of Alkynes."

VII.C-15 Vernall, A.J.; Abell, A.D., AA, 36, 93. Review:

"Cross Metathesis of Nitrogen-Containing Systems"

VII.C-16 Plumet, J. et al., EJOC, 611. Microreview: "Sequential Metathesis in Oxa- and Azanorbornene Derivatives." VII.C-17 Vlasov, V.M., RCR, 72, 6881. Review:

"Nucleophilic Substitution of the Nitro Group, Fluorine and Chlorine in Aromatic Compounds."

VII.C-18 Dunach, E. et al., S, 2753. Review:

"Epoxide Oxidations: A Valuable Tool in Organic Synthesis."

VII.C-19 Muzart, J., T, 42, 5789. Report:

"Palladium-Catalyzed Oxidation of Primary and Secondary Alcohols."

VII.C-20 Mander, L.N.; Williams, C.M., T, 59, 1105. Report:

"Oxidative Degradation of Benzene Rings."

VII.C-21 Gibson, S.E.; Stevenazzi, A., AG(E), 42, 1800. Review:

"Catalytic Pauson-Khand Reaction."

VII.C-22 Bohm, L.L., AG(E), 42, 5010. Review:

"The Ethylene Polymerization with Ziegler Catalysts: Fifty Years after the Discovery."

VII.C-23 Hajipour, A.R. et al., OPP, 35, 527.

Review:

"Regeneration of Carbonyl Compounds from Oximes, Hydrazones, Semicarbazones, Acetals, 1,1-Diacetates, 1,3Dithiolanes, 1,3-Dithianes and 1,3-Oxathiolanes."

284

ORGANIC SYNTHESISm2004

VII.C-24 Overman, L.E.; Pennington, L.D., JOC, 69, 7143. Review:

"Strategic Use of Pinacol-Terninated Prins Cyclizations in Target-Oriented Total Synthesis."

VII.C-25 Nubbemeyer, U., S, 961. Review:

"Recent Advances in Asymmetric [3,3]-Sigmatropic Rearrangements."

VII.C-26 Wozniak, L.A.; Okruszek, A., CSR, 32, 158. Review:

"The Stereospecific Synthesis of P-Chiral Biophosphatees and Their Analogues by the Stec Reaction."

VII.C-27 Li, C.-J., AG(E), 42, 4856. Highlight: "Suzuki Reaction Takes a 'Naked Hot Bath" Coupling in High-Temperature Water Without Transition Metals." VII.C-28 Kunz, K. et al., SL, 2428. New Tools "Renaissance of Ullmann and Goldberg in Synthesis: ReactionsmProgress in Copper Catalyzed C--N, C--Oand C--S-Coupling." VII.C-29 Hiersemann, M. et al., SL, 1088. Review"

"The Ester Dienolate [2,3]-Wittig Rearrangementm Development, Opportunities, and Limitations."

VII.D Reactive Intermediates

VII.D-1 Lacour, J.; Hebbe-Viton, V., CSR, 32, 373. Review:

"Recent Developments in Chiral Anion Mediated Asymmetric Chemistry."

VII.D-2 Pearson, W.H.; Stoy, P., SL, 903. Account:

"Cycloadditions of Nonstabilized 2-Azoallyllithiums (2Azaallyl Anions) and Azomeethine Ylids with Alkenes: [3+2] Approaches to Pyrrolidines and Application to Alkaloid Total Synthesis."

REVIEWS

285

VII.D-3 Postel, D.; Van Nhien, A.N.; Marco, J.L., EJOC, 3713. Microreview: "Chemistry of Sulfonate- and Sulfonamide-Stabilized CarbanionsmThe CSIC Reactions." VII.D-4 Spino, C., OPP, 35, 1. Review"

"Chiral Enolate Equivalents."

VII.D-5 Listvan, V.N.; Listvan, V.V., RCR, 72, 705. Review:

"Reactions of Phosphorus Ylides with Acyl Chlorides: Pathways and Preparative Potential."

VII.D-6 Taylor, R.E. et al., T, 59, 5623. Report:

"Biosynthetic Inspirations: Cationic Approaches to Cyclopropane Formation."

VII.D-7 Ramamurthy, V. et al., CC, 1987. Feature Article:

"Controlling Chemistry with Cations: Photochemistry within Zeolites."

VII.D-8 Tius, M.A., ACR, 36, 284. Review:

"Cationic Cyclopenteannelation of Allene Ethers."

VII.D-9 Nenajdenko, V.G. et al., CRV, 103, 229. Review:

"l,2-Dications in Organic Main Group Systems."

VII.D-10 Harmata, M.; Rashatasakhon, P., T, 59, 2371. Report:

"Cycioaddition Reactions of Vinyl Oxocarbenium Ions."

VII.D-11 Rossi, R.A. et al., CRV, 103, 71. Review:

"Nucleophilic Substitution Reactions by Electron Transfer."

VII.D-12 Galli, C.; Rappoport, Z., ACR, 36, 580. Review"

"Unequivocal SRN1 Route of Vinyl Halides with a Multitude of Competing Pathways: Reactivity and Structure of the Vinyl Radical Intermediate."

286

ORGANIC SYNTHESISm2004

VII.D-13 Bar, G.; Parsons, A.F., CSR, 32, 251. Review:

"Stereoselective Radical Reactions."

VII.D-14 Sibi, M.P., ed., TA, 14, 2487-3077. Special Issue:

"Stereoselective Radical Reactions."

VII.D-15 Rheault, T.R.; Sibi, M.P., S, 803. Review:

"Radical-Mediated Annulation Reactions."

VII.D-16 Limberg, C.,AG(E), 42, 5932. Review:

"The Role of Radicals in Metal-Assisted Oxygenation Reactions."

VII.D-17 Benerjee, R., guest ed., CRV, 103, 2081-2456. Reviews:

"Radical Enzymology."

VII.D-18 Garcia-Garibay, M.A.; ACR, 36, 491. Review:

"Engineering Carbene Rearrangements in Crystals: From Molecular Information to Solid-State Reactivity."

VII.D-19 Enders, D. et al., S, 1292. Practical Synthetic "Preparation and Application of 1,3,4Procedures: Triphenyl-4,5-dihydro-lH-1,2,4-triazol-5-ylidene, a Stable Carbene." VII.D-20 Dorwald, F.Z., AG(E), 42, 1332. Highlight: "Solvent-Controlled Selectivity in the Synthesis of FiveMembered Carbocycles from Carbene Complexes." VII.D-21 Merlic, C.A.; Zechman, A.L., S, 1137. Review:

"Selectivity in Rhodium(II) Catalyzed Reactions of Diazo Compounds: Effects of Catalyst Electrophilicity, Diazo Substitution, and Substrate Substitution. From Chemoselectivity to Enantioselectivity."

REVIEWS

287

VII.D-22 Kirmse, W., AG(E), 42, 1088. Minireview: "Copper Carbene Complexes: Advanced Catalysts, New Insights." VII.D-23 Alcaide, B.; Almendros, P., CEJ, 9, 1258. Review"

"Non-Metathetic Behavior Patterns of Grubb's Carbene."

VII.D-24 Pellissier, H.; Santelli, M., T, 59, 701. Report:

"The Use of Arynes in Organic Synthesis."

VII.D-25 Sander, W. et al., A G(E), 42, 502. Review:

"One Century of Aryne Chemistry."

VII.E. Organometallics and Metalloids VII.E-1 Long, N.J.; Williams, C.K., AG(E), 42, 2586. Review:

"Metal Alkynyl c-Complexes: Synthesis and Materials."

VII.E-2 Clauvin, R. et al., JOM, 670, 151. Review:

"l,4-Diynes from Alkynyl-Propargyl Coupling Reactions."

VII.E-3 Adams, R.D.; Bunz, U.H.F., eds., JOM, 683, 267-434. Special Issue:

"Carbon-Rich Organometallic Compounds."

VII.E-4 de Vries, J.G.; de Vries, A.H.M., EJOC, 799. Microreview: "The Power of High-Throughput Experimentation in Homogeneous Catalysis Research for Fine ChemicalsD VII.E-5 Coperet, C.; Basset, J.-M. et al.,AG(E), 42, 156. Review:

"Homogeneous and Heterogeneous Catalysis: Bridging the Gap Through Surface Organometallic Chemistry."

288

ORGANIC SYNTHESISm2004

VII.E-6 Bytschkov, I.; Doye, S., EJOC, 935. Minireview: "Group-IV Metal Complexes as Hydroamination Catalysts." VII.E-7 Cardenas, D.J., AG(E), 42, 384. Highlight: "Advances in Functional-Group-Tolerant Metal-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions." VII.E-8 Yamamoto, T., SL, 425. Account:

"Synthesis of H-Conjugated Polymers Bearing Electronic and Optical Functionalities by Organometallic Polycondensations. Chemical Properties and Applications of the H-Conjugated Polymers."

VII.E-9 Mann, B.E.; Motterlini, R. et al., AG(E), 42, 3722. Minireview: "Metal Carbonyls: A New Class of Pharmaceuticals?" VII.E-10 Wilke, G.,AG(E), 42, 5000. Essays:

"Fifty Years of Ziegler Catalysts: Consequences and Development of an Invention."

VII.E-11 Thomas, J.M.; Johnson, B.F.G.; Raja, R. et al., ACR, 36, 20. Review:

"High Performance Nanocatalysts for Single-Step Hydrogenations."

VII.E-12 Marder, T.B.; Mingos, D.M.P., eds., JOM, 680, 1-334. Special Issue:

"Frontiers in Boron Chemistry."

VII.E-13 Garcia, G.V.; Nudelman, N.S., OPP, 35, 445. Review:

"Tandem Reactions Involving Organolithium Reagents."

VII.E-14 Hoffmann, R.W., CSR, 32, 225. Review:

"The Quest for Chiral Grignard Reagents."

REVIEWS

289

VII.E-15 Darses, S.; Genet, J.-P., EJOC, 4313. Microreview: "Potassium Trifluoro(organo)borates: New Perspectives in Organic Chemistry." VII.E-16 Kennedy, J.W.J.; Hall, D.G., AG(E), 42, 4732. Minireview: "Recent Advances in the Activation of Boron and Silicon Reagents for Stereocontrolled Alkylation Reactions." VII.E-17 Dembitsky, V.M.; Srebnik, M., T, 59, 579. Report:

"Synthesis and Biological Activity of ~-Aminoboronic Acids, Amine-Carboxyboranes and Their Derivatives."

VII.E-18 Yus, M. et al., T, 59, 9255. Report:

"Recent Synthetic Uses of Functionalized Aromatic and Heteroaromatic Organolithium Reagents Prepared by Non-Deprotonating Methods."

VII.E-19 Knochel, P. et al., AG(E), 42, 4302. Review:

"Highly Functionalized Organomagnesium Reagents Prepared Through Halogen-Metal Exchange."

VII.E-20 Ricci, A.; Fochi, M., AG(E), 42, 1444. Highlight: "Reactions Between Organomagnesium Reagents and Nitroarenes: Past, Present, and Future." VII.E-21 Bertrand, G.; Corriu, R., JOM, 686, 1-382. Special Issue:

"What's New in Silicon Chemistry."

VII.E-22 Beletskaya, I.P.; Cheprakov, A.V., CCC, 68, 1904. Personal Account:

"Transition Metal Complex Catalysis in Fine Organic Synthesis."

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VII.E-23 Moreno-Manas, M.; Pleixats, R., ACR, 36, 638. Review:

"Formation of Carbon--Carbon Bonds Under Catalysis by Transition-Metal Nanoparticles."

290

ORGANIC SYNTHESIS--2004

VII.E-24 Denmark, S.E.; Ober, M.H., AA, 36, 75. Review:

"Organosilicon Reagents: Synthesis and Applications to Palladium-Catalyzed Cross-Coupling Reactions."

VII.E-25 Ma, S., ACR, 36, 701. Review"

"Transition Metal-Catalyzed/Mediated Reaction of Allenes with a Nucleophilic Functionality Connected to the ~-Carbon Atom."

VII.E-26 Gevorgyan, V. et al., SL, 2265. Account:

"New Advances in Selected Transition Metal-Catalyzed Annulations."

VII.E-27 Lloyd-Jones, G.C., OBC, 1,215. Review:

"Mechanistic Aspects of Transition Metal Catalysed 1,6Diene and 1,6-Enyne Cycloisomerisation Reactions."

VII.E-28 Skoda-Foldes, R.; Kollar, L., CRV, 103, 4095. Review:

"Transition-Metal-Catalyzed Reactions in Steroid Synthesis."

VII.E-29 Gree, R. et al., CR V, 103, 27. Review:

"Transposition of Allylic Alcohols into Carbonyl Compounds Mediated by Transition Metal Complexes."

VII.E-30 Lautens, M. et al., ACR, 36, 48. Review"

"Transition-Metal-Catalyzed Enatioselective RingOpening Reactions of Oxabicyclic Alkenes."

VII.E-31 Mlochowski, J. et al., EJOC, 4329. Microreview: "Selenium-Promoted Oxidation of Organic Compounds: Reactions and Mechanisms." VII.E-32 Dunach, E. et al., EJOC, 1605. Microreview" "Carbon--Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes'

REVIEWS

291

VII.E-33 Ikeda, S. et al., AG(E), 42, 5120. Highlight: "Nickel-Catalyzed Coupling of Carbonyl Compounds and Alkynes or 1,3-Dienes: An Efficient Method for the Preparation of Allylic Homoallylic, and Bishomoallylic Alcohols." VII.E-34 Thiel, W.R., AG(E), 42, 5390. Highlight: "On the Way to a New Class of CatalystsmHigh-Valent Transition-Metal Complexes that Catalyze Reductions." VII.E-35 Hossain, M.M. et al., AA, 36, 3. Review:

"Iron Lewis Acid [(TIs-CsHs)Fe(CO)2(THF)]+ Catalyzed Organic Reactions."

VII.E-36 Ley, S.V.; Thomas, A.W., AG(E), 42, 5400. Review:

"Modern Synthetic Methods for Copper-Mediated C(aryl)mO, C(aryl)mN, and C(aryl)nS Bond Formation."

VII.E-37 Bertrand, G., ed., JOM, 687, 209-573. Special Issue:

"Palladium Chemistry in 2003: Recent Developments."

VII.E-38 Tykwinski, R.R., AG(E), 42, 1566. Highlight: "Evolution in the Palladium-Catalyzed Cross-Coupling of sp- and sp2-Hybridized Carbon Atoms VII.E-39 Culkin, D.A.; Hartwig, J.F., ACR, 36, 234. Review:

"Palladium-Catalyzed ~-Arylation of Carbonyl Compounds and Nitriles."

VII.E-40 Negishi, E.; Anastasia, L., CRV, 103, 1979. Review:

"Palladium-Catalyzed Allylcynylation."

VII.E-41 Zapf, A., AG(E), 42, 5394. Minireview: "Novel Substrates for Palladium-Catalyzed Coupling Reactions of Arenes."

292

ORGANIC SYNTHESISm2004

VII.E-42 Balme, G. et al., S, 2115. Review:

"Cyclisations Involving Attack of Carbo- and Heteronucleophiles on Carbon--Carbon H-Bonds Activated by Organopalladium Compplexes."

VII.E-43 Echavarren, A.M. et al., SL, 585. Account:

"Palladium-Catalyzed Intramolecular Arylation Reaction: Mechanism and Application for the Synthesis of eolyarenes."

VII.E-44 Zeni, G. et al., ACR, 36, 731. Review:

"Palladium-Catalyzed Coupling of spe-Hybridized Tellurides."

VII.E-45 Catallani, M., SL, 299. Account:

"Catalytic Multistep Reactions via Palladacycles."

VII.E-46 Schrock, R.R.; Hoveyda, A.H., AG(E), 42, 4592. Review:

"Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts."

VII.E-47 Schmidt, B.,AG(E), 42, 4996. Highlight: "Ruthenium-Catalyzed Cyclizations: More than Just Oiefin Metathesis." VII.E-48 Fagnou, K.; Lautens, M., CRV, 103, 169. Review:

"Rhodium Catalyzed CarbonmCarbon Bond Forming Reactions of Organometallic Compounds."

VII.E-49 Sedlacek, J.; Vohlidal, J., CCC, 68, 1745. Review:

"Controlled and Living Polymerizations Induced with Rhodium Catalysts."

VII.E-50 Nair, V. et al., SL, 156. Account:

"Carbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate: An Overview."

REVIEWS

293

VII.E-51 Kobayashi, S., ed., T, 59, 10339-10597. Symposia "Recent Advances in Rare Earth Chemistry." in-Print" VII.E-52 Bartoli, G. et al., SL, 2101. Account:

"The CeCI3.nH20/NaI System in Organic Synthesis" An Efficient Water Tolerant Lewis Acid Promoter."

VII.E-53 Williams, D.B.G. et al., OPP, 35, 307. Review:

"Fragmentation and Cleavage Reactions Mediated by Samarium Iodide. Part 2. a- and 13-Elimination Reactions of C--X Substrates."

VII.E-54 Podlech, J.; Maier, T.C., S, 633. Review:

"Indium in Organic Synthesis."

VII.F. Halogen Compounds and Halogenation (see also: VI.A. 10.) VII.F-1 Sandford, G., T, 59, 437. Report:

Perfluoroalkanes.

VII.F-2 Langlois, B.R.; Billard, T., S, 185. Review-

"Some Recent Results in Nucleophilic Trifluoromethylation and Introduction of Fluorinated Moieties."

VII.F-3 Sizov, A.Y. et al., RCR, 72, 357. Review:

"Fluorine-Containing Alkyl (Aryi) Vinyl Sukfides.

VII.F-4 Stang, P.J., JOC, 68, 2997. Review:

"Polyvalent Iodine in Organic Chemistry."

294

ORGANIC SYNTHESISm2004

VII.G Natural Products

VII.G-1 Tietze, L.F. et al., OBC, 1, 3996. Review:

"Natural Product Hybrids as New Leads for Drug Discovery."

VII.G-2 Prunet, J., AG(E), 42, 2826. Minireview: "Recent Methods for the Synthesis of (E)-Alkene Units in Macrocyclic Natural Products." VII.G-3 Ferey, G.,AG(E), 42, 2576. Highlight: "Pd-Catalyzed Enantioselective Allylic Substitution: New Strategic Options for the Total Synthesis of Natural Products." VII.G-4 Linhardt, R.J., JMC, 46, 2551. Review:

"2003 Claude S. Hudson Award Address in Carbohydrate Chemistry. Heparin: Structure and Activity."

VII.G-5 Bond, R.; McAuliffe, J.C., AJC, 56, 7. Current "Silicon Biotechnology: New Opportunities for Chemistry: Carbohydrate Science." VII.G-6 Rutjes, F.P.J.T. et al., EJOC, 2519. Microreview: "Glyoxylates as Versatile Building Blocks for the Synthesis of ~-Amino Acid and c~-Alkoxy Acid Derivatives via Cationic Intermediates." VII.G-7 Fairbanks, A.J., SL, 1945. Account:

"Intramolecular Aglycon Delivery (IAD): The Solution to 1,2-cis Stereocontrol for Oligosaccharide Synthesis?"

VII.G-8 Spitz, I.M.; Petraglia, F., eds., ST, 68, 759-112. Symposia: "The 2nd International Symposium on Progestins, Progesterone Receptor Modulators and Progesterone Antagonists."

REVIEWS

295

VII.G-9 Engeldinger, E.; Armspach, D.; Dominique, M., CRV, 103, 4147. Review:

"Capped Cyclodextrins."

VII.G-10 Chuiko, V.A.; Vyglazov, O.G., RCR, 72, 49. Review:

"Skeletal Rearrangements of Monoterpenoids of the Carane Series."

VII.G-11 Biellmann, J.-F., CRV, 103, 2019. Review:

"Enantiomeric Steroids: Synthesis, Physical, and Biological Properties."

VII.G-12 Posner, G.H.; Kahraman, M., EJOC, 3889. Microreview: "Organic Chemistry of Vitamin D Analogues (Deltanoids)." VII.G-13 Pozsgay, V. et al., SL, 743. Account:

"Towards an Oligsaccharide-Based Glycoconjugate Vaccine Against ShigeUa dysenteriage Type 1."

VII.G-14 Kotha, S., ACR, 36, 342. Review:

"The Building Block Approach to Unusual or-Amino Acid Derivatives and Peptides."

VII.G-15 Gelmi, M.L.; Pocar, D., OPP, 35, 141. Review:

"Heterosubstituted Carbocyclic ~-Amino Acids."

VII.G-16 Albrecht, M. et al., S, 1307. Review:

"Peptide/Metal-Ligand Hybrids for the Metal-Assisted Stabilization of Peptide-Microstructures."

VII.G-17 Friedinger, R.M., JMC, 46, 5553. Award Address:

"Design and Synthesis of Novel Bioactive Peptides and Peptidomimetics."

VII.G-18 Wilson, D.N.; Nierhaus, K.H., AG(E), 42, 3464 Review:

"The Ribosome Through the Looking Glass."

296

ORGANIC SYNTHESISm2004

VII.G-19 Kunz, H. et al., AJC, 56, 519. Review:

"Synthetic Glycopeptides for the Development of Antitumor Vaccines."

VII.G-20 Krasnov, V.P. et al., RCR, 72, 343. Review:

"Synthesis and Properties of 1-Aminocyclopropane-l,2dicarboxylic Acid and Compounds Incorporating It."

VII.G-21 Ramsden, C.A. et al., ACR, 36, 300. Review:

"Tyrosinase Autoactivation and the Chemisrtry of orthoQuinine Amines."

VII.G-22 Suh, J., ACR, 36, 562. Review:

"Synthetic Artificial Peptidases and Nucleases Using Macromolecular Catalytic Systems."

VII.G-23 Williams, D.H. et al., CC, 1973. Focus Article:

"How Can Enzymes be so Efficient?"

VII.G-24 Bugg, T.D.H., T, 59, 7075. Review:

"Dioxygenase Enzymes: Catalytic Mechanisms and Chemical Models."

VII.G-25 Turner, N.J. et al., OBC, 1, 4133. Emerging "Directed Evolution of Enzymes: New Biocatalysts Area: for Asymmetric Synthesis." VII.G-26 Agrofoglio, L.A. et al., CRV, 103, 1875. Review:

Palladium-Assisted Routes to Nucleosides."

VII.G-27 Scharer, O.D., AG(E), 42, 2946. Review:

"Chemistry and Biology of DNA Repair."

VII.G-28 Lawrence, D.S., guest ed., ACR, 36, 353-469. Reviews:

"Special Issue on Chemical Biology of Signal Transduction."

REVIEWS

297

VII.G-29 De Bank, P.A. et al., CSR, 32, 327. Review:

"Chemical Modification of Mammalian Cell Surfaces."

VII.G-30 Lao, A.; Fujimoto, Y. et al., H, 59, 811. Review:

"Studies of the Constituents of the Seeds of Vaccaria

Segetalis." VII.G-31 Waldvogel, S.R., AG(E), 42, 604. Highlight: "Caffeine---A Drug with a Surprise." VII.G-32 Jeanmart, S., AJC, 56, 559. Current "Trends in Chrysanthemic Acid Chemistry: A Survey Chemistry: of Recent Pyrethrum Syntheses." VII.G-33 Clive, D.L.J. et al., CJC, 81, 811. Award Lecture:

"Synthetic Studies Related to CP-225,927."

VII.G-34 Stocking, E.M.; Williams, R.M., AG(E), 42, 3078. Review:

"Chemistry and Biology of Biosynthetic Diels-Alder Reactions."

VII.G-35 Paterson, I.; Florence, G.J., EJOC, 2193. Microreview: "The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent." VII.G-36 Foubelo, F. et al., T, 59, 6147. Review:

"The Role of 1,3-Dithianes in Natural Product Synthesis."

VII.G-37 Hugel, H.M.; Nurlawis, F., H, 60, 2349. Review:

"Short Synthesis of Melatonin."

VII.G-38 Sefkow, M. et al., S, 2595. Review:

"The Stereoselective Synthesis of Neolignans."

298

ORGANIC SYNTHESISu2004

VII.G-39 Lin, H.; Danishefsky, S.J., AG(E), 42, 36. Review:

"Gelsemaine: A Thought-Provoking Target for Total Synthesis."

VII.G-40 Mulzer, J.; Ohler, E., CRV, 103, 3753. Review:

"Microtubule-Stabilizing Maine Metabolite Laulimalide and Its Derivatives: Synthetic Approaches and Antitumor Activity."

VII.G-41 Kibayashi, C. et al., CBJ, 76, 2059. Account:

"Total Synthesis of Bioactive Tricyclic Marine Alkaloids, Lepadiformine and Related Compounds."

VII.G-42 Weinreb, S.M., ACR, 36, 59. Review:

"Lepadiformine: A Case Study of the Value of Total Synthesis in Natural Product Structure Elucidation."

VII.G-43 Williams, R.M.; Cox, R.J., ACR, 36, 127. Review:

"Paraherquamides, Brevianamides, and Asper-paralines: Laboratory Synthesis and Biosynthesis and Biosynthesis. An Interim Report."

VII.G-44 Hoffmann, H.M.R. et al.,AG(E), 42, 2711. Highlight: "The Total Syntheses of Phorboxazoles--New Classics in Natural Product Synthesis." VII.G-45 de Lera, A.R. et al., OPP, 35, 239. Review:

"Recent Advances in the Synthesis of Retinoids."

VII.G-46 Furstner, A., AG(E), 42, 3582. Review:

"Chemistry and Biology of Rosephilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years."

VII.G-47 Brunel, J.M.; Letourneux, Y., EJOC, 3897. Microreview: "Recent Advances in the Synthesis of Spermine and Spermidine Analogs of the Shark Aminosterol Squalamine."

REVIEWS

299

VII.G-48 Yet, L., CRV, 103, 4283. Review:

"Chemistry and Biology of Salicylihalamide A and Related Compounds."

VII.G-49 Birladeanu, L. AG(E), 42, 1202. Essay:

"The Stories of Santonin and Santonic Acid."

VII.G-50 Chen, X. et al., CRV, 103, 1955. Review"

"Properties and Production of Valienamine and Its Related Analogues."

VII.G-51 Hubbard, B,K.; Walsh, C.T., AG(E), 42, 730. Review:

"Vancomycion Assembly: Nature's Way."

VII.H. Others (see also: IV.M.~ VIII.A.5, VIII.C.6, VIII.F.7) VII.H-1 Bourne, J.R., OPRD, 7, 471. Review:

"Mixing and the Selectivity of Chemical Reactions."

VII.H-2 Stoltz, B.M. ,ed., T, 59, 8843-9029. Symposia "New Synthetic Methods--VII." in-Print: VII.H-3 Martin, S.F.; Wasserman, H.H., eds., T, 59, 6667-7070. Symposia "Art, Science and Technology in Total Synthesis in-Print: (Tetrahedron Prize for Creativity in Organic Chemistry 2002mK.C. Nicolaou)." VII.H-4 Wood, J.L. et al., CRV, 103, 2691. Review:

"The Art of Innovation in Organic Chemistry: Synthetic Efforts Toward the Phomoidrides."

VII.H-5 Pascal, R., EJOC, 1813. Microreview: "Catalysis Through Induced Intramoleculararity: What Can Be Learned by Mimicking Enzymes with Carbonyl Compounds that Covalently Bind Substrates."

300

ORGANIC SYNTHESIS--2004

VII.H-6 Kieboom, T. et al., OPRD, 7, 622. Review:

"Concepts of Nature in Organic Synthesis: Cascade Catalysis and Multistep Conversions in Concert."

VII.H-7 Dugave, C.; Demange, L., CRV, 103, 2475. Review:

"cis-translsomerization of Organic Molecules and Biomolecules: Implications and Applications."

VII.H-8 Kolter, T. et al., EJOC, 2021. Microreview: "Bioorganic Chemistry of Ceramide." VII.H-9 Giannis, A. et al., A G(E), 42, 2122. Review:

"Small Molecules as Inhibitors of Cyclin-Dependent Kinases."

VII.H-10 Dembitsky, V.M., T, 59, 4701. Report:

"Oxidation, Epoxidation and Sulfoxidation Reactions Catalyzed by Haloperoxidases."

VII.H-I 1 Kirby, A.J. et al., AG(E), 42, 1448. Minireview: "Gemini Surfactants" New Synthetic Vectors for Gene Transfection." VII.H-12 Wiesner, J., Schlitzer, M. et al., AG(E), 42, 5274. Review:

"New Antimalarial Drugs."

VII.H-13 Sutcliffe, J.A.; guest ed., BMCL, 13, 4165-4249. Symposia "Antibacterial Agents: Solutions for the Evolving in-Print: Problems of Resistance." VII.H-14 Sliwa, W.; Girek, T., H, 60, 2147. Review"

"Metallocyclodextrins and Related Species."

VII.H-15 Kimura, K. et al., BCJ, 76, 225. Account:

"Molecular Design and Applications of Photochromic Crown Compounds--How Can We Manipulate Ions Photochemically?"

REVIEWS

301

VII.H-16 Lesnikowski, Z.J., EJOC, 4489. Microreview: "Boron ClustersmA New Entity for DNAOligonucleotide Modification." VII.H-17 Shoda, S. et al., BCJ, 76, 1. Account:

"Green Process in Glycotechnology."

VII.H-18 Corma, A.; Garcia, H., CRV, 103, 4307. Review:

"Lewis Acids: From Convential Homogeneous to Green Homogeneous and Heterogeneous Catalysis."

VII.H-19 Omae, I., CRV, 103, 3431. Review:

"General Aspects of Tin-Free Antifouling Paints."

VII.H-20 Shenhar, R.; Rotello, V.M., ACR, 36, 549. Review:

"Nanoparticles: Scaffolds and Building Blocks."

VII.H-21 Gibb, B.C., CEJ, 9, 5180. Review:

"Resorcinarenes as Templates."

VII.H-22 Nishimura, J. et al., BCJ, 76, 865. Account:

"Biscycloaddition to [60]Fulleren: Regioselectivity and Its Control with Templates."

VII.H-23 Dai, L. et al., AJC, 56, 635. Review:

"Chemistry of Carbon Nanotubes."

VII.H-24 Haley, M.M. et al., EJOC, 2355. Microreview: "Synthetic Strategies for Dehydrobenzo-[n]annulenes." VII.H-25 de Meijere, A., guest ed., CRV, 103, 931-1648. Reviews:

"Cyclopropanes and Related Rings."

VII.H-26 Kulinkovich, O.G., CRV, 103, 2597. Review:

"The Chemistry of Cyclopropanols."

302

ORGANIC SYNTHESISm2004

VII.H-27 Fujita, T. et al., BCJ, 76, 1493. Account:

"Recent Advances in Phenoxy-Based Catalysts for Olefin Polymerization."

VII.H-28 de Koning, C.B.; Rousseau, A.L.; van Otterlo, W.A.L., T, 59, 7. Report:

"Modern Methods for the Synthesis of Substituted Naphthalenes."

VII.H-29 Pozharskii, A.F., RCR, 72, 447. Review:

"Naphthaldehydes."

VII.H-30 Kantlehner, W., EJOC, 2530. Microreview: "New Methods for the Preparation of Aromatic Aldehydes." VII.H-31 Amri, H. et al., T, 59, 1369. Report:

"Synthetic Methods for c~-Substituted Cyclic ct,f~-Enones."

VII.H-32 Hsung, R.P. et al., ACR, 36, 773 Review:

"The Emergence of Allenamides in Organic Synthesis."

VII.H-33 Elassar, A.-Z.A. et al., T, 59, 8463. Report:

"Recent Developments in the Chemistry of Enaminones."

VII.H-34 Hsung, R.P. et al., SZ, 1379. Account:

"In Search of an Atom-Economical Synthesis of Chiral Ynamides."

VII.H-35 Kotali, A.; Harris, P.A., OPP, 35, 583. Review:

"o-Diacylbenzenes in Organic Synthesis."

VII.H-36 Zyk, N.V. et al., RCR, 72, 769. Review:

"Methods for the Synthesis of Vinyl Sulfides."

REVIEWS

303

VII.H-37 Stepanov, A.V.; Veselovsky, V.V., RCR, 72, 327. Review:

"Reactions of Alkenes with Nitrogen Oxides and Other Nitrosating and Nitrating Agents."

VII.H-38 Jun, J.-G., SL, 1759. Account:

"Introduction of Bicyclic Ketal Chemistry: Synthesis and Transformation Reaction of 6,8-Dioxabicyclo-[3.2.1]octane Skeletal System."

VII.H-39 Calderazzo, F. et al., CRV, 103, 3867. Review:

"Converting Carbon Dioxide into Carbamato Derivatives."

VII.H-40 Murugan, R.; Scriven, E.F.V., AA, 36, 21. Review:

"Applications of Dialkylaminopyridine (DMAP) Catalysts in Organic Synthesis."

VII.H-41 Dauben, P.; Dodd, R.H., SL, 1571. Account:

"Iminoiodanes and CmN Bond Formation in Organic Synthesis."

VII.H-42 Valentine, Jr., D.H.; Hillhouse, J.H., S, 317. Review:

"Alkyl Phosphines as Reagents and Catalysts in Organic Synthesis."

VII.H-43 Valentine, Jr., D.H.; Hillhouse, J.H., S, 2437. Review:

"Electro-Rich Phosphines in Organic Synthesis II. Catalytic Applications."

VII.H-44 Mathey, F., AG(E), 42, 1578. Review"

"Phospha-Organic Chemistry: Panorama and Perspectives."

VII.H-45 Huddleston, R.R.; Krische, M.J., SL, 12. Account:

"Enones as Latent Enolates in Catalytic Processes: Catalytic Cycloreduction, Cycloaddition and Cycloisomerization."

304

ORGANIC SYNTHESIS--2004

VII.H-46 Jesberger, M. et al., S, 1929. Review:

"Applications of Lawesson's Reagent in Organic and Organometallic Syntheses."

VII.H-47 Sakamoto, M., Nishio, T., H, 59, 399. Review:

"Photochemistry of Nitrogen-Containing Thiocarbonyl Compounds."

VII.H-48 Poletti, L.; Lay, L., EJOC, 2999. Microreview: "Chemical Contribution to Understanding Heparin Activity: Synthesis of Related Sulfated Oligosaccharides." VII.H-49 Shchepinov, M.S.; Korshun, V.A., CSR, 32, 170. Review:

"Recent Applications of Bifunctional Trityl Groups."

VII.H-50 Melendez, R.E.; Lubell, W.D., T, 59, 2581. Report:

"Synthesis and Reactivity of Cyclic Sulfonamidites and Sulfamidates."

VII.H-51 Tsuchida, E.; Oyaizu, K., BCJ, 76, 15. Account:

"Alkylsulfonioarylene and Thioarylene Polymers Derived from Sulfonium Electrophiles."

VII.H-52 Verma, R.P., EJOC, 415. Microreview: "Synthesis and Reactions of 3-Oxobutyl Isothiocyanato (OB ITC)." VII.H-53 Paquette, L.A., S, 765. Special Topic:

"Fundamental Mechanistic Characteristics and Synthetic Applications Promoted by Indium Metal in Aqueous Media."

VII.H-54 Davis, Jr., J.H.; Fox, P.A., CC, 1209. Focus Article:

"From Curiosities to Commodities: Ionic Liquids Begin The Transition."

REVIEWS

305

VII.H-55 Handy, S.T., CEJ, 9, 2938. Review:

"Green Solvents: Room Temperature Ionic Solvents from Biorenewable Sources."

VII.H-56 Rogers, R.; Seddon, D., eds., CI(L), 17, 25. Book Review:

"Ionic Liquids: Industrial Applications to Green Chemistry."

VII.H-57 Tomao, K.; West, R., guest eds., JOM, 685, 1-279. Special "A Half Century of Polysilane Chemistry." Issue:

VIII SELECTED TOPICAL AREAS

VIII.A. Fullerene Chemistry

VIII.A.1 Diels-Alder-Type Cycloadditions VIII.A.I-1 Miller, G.P.; Briggs, J., OL, 5, 4203. "Fullerene-Acene Chemistry: Diastereoselective Synthesis of a cic-cicTris[6]Fullerene Adduct of 6,8,15,17-Tetraphenyl-heptacene." VIII.A.1-2 Nishimura, J. et al., BCJ, 76, 865. "Biscycloaddition to [60]Fullerene: Regioselectivity and Its Control with Templates." VIII.A.1-3 Rubin, Y. et al., JACS, 125, 2066. "Synthesis of Stable Derivatives of C62: The First Nonclassical Fullerene Incorporating a Four-Membered Ring." VIII.A.2 Other Cycloadditions VIII.A.2-1 Martin, N.; Guldi, D.M. et al., OL, 5, 557. "Addition Reaction of Axido-ex TTFs to C60" Synthesis of Fuilerenetriazoline and Azafulleroid Electroactive Diads~ VIII.A.2-2 Yinghuai, Z. et al., TL, 44, 5473. "An Effective System to Synthesize Methanofullerenes: SubstrateIonic Liquid-Ultrasound Irradiation." VIII.A.2-3 Taylor, R. et al., CC, 1374. "[60] and [70]Fullerenes are Trifluoromethylated Across 5:6-Bonds." 306

SELECTED TOPICAL AREAS

307

VIII.A.2-4 Floris, B. et al., JOM, 679, 202. "Synthesis of New Ferrocenyl Derivatives and Their Use in the First Cyclopropanation of Fullerene C60 with Ferrocenes." VIII.A.2-5 Prato, M. et al., EJOC, 4741. "Synthesis and Water Solubility of Novel Fullerene Bisaddnct Derivatives." VIII.A.2-6 Balzarini, J.; Prato, M. et al., BMCL, 13, 4437. "Synthesis and Anti-HIV Properties of New Water-Soluble BisFunctionalized [60] fullerene Derivatives." VIII.A.2-7 Bassani, D.M. et al., JACS, 125, 13004. "Facile Synthesis of a Fullerene-Barbituric Acid Derivative and Supramolecular Catalysis of Its Photoinduced Dimerization." VIII.A.2-8 Ulmer, L.; Mattay, J., EJOC, 2933. "Preparation and Characterization of Sulfonyl-Azafulleroid and Sulfonylaziridino-Fullerene Derivatives." VIII.A.2-9 Guldi, D.M.; Leigh, D.A.; Prato, M. et al., OL, 5, 689. "Hydrogen Bond-Assembled Fullerene Molecular Shuttle." VIII.A.2-10 an Dorsselaer, A.; Nierengarten, J.-F. et al., TL, 44, 3043. "A Supramolecular Oligophenylenevinylene-C60 Conjugate."

VIII.A.3. Photochemical Reactions

VIII.A.3-1 Mattay, J. et al., EJOC, 3811.

"Functionalization of [60]Fullerene and of [60]Fullerene Monoadducts by Photochemical Cycloaddition of 4-Methyl-l,2,4triazoline-3,5-dione."

308

ORGANIC SYNTHESISm2004

VIII.A.3-2 Rubin, Y. et al., JACS, 125, 2066. "Synthesis of Stable Derivatives of C62: The First Nonclassical Fullerene Incorporating a Four-Membered Ring." VIII.A.3-3 Butts, C.P.; Jazdzyk, M., CC, 1530. "The Preparation and Structures of Non-Hydrocarbon Functionalised Fullerene-Diamine Adducts."

VIII.A.4. Other Fullerene Chemistry

VIII.A.4-1 Ballot, S.; Noiret, N., TL, 44, 8811. "Synthesis of New C60 Based Phosphines." VIII.A.4-2 Komatsu, K. et al., TL, 44, 8199. "Mechanochemical Synthesis of a Novel C60 Dimer Connected by a Germanium Bridge and a Single Bond." VIII.A.4-3 Cravino, A. et al., M, 134, 519. "A Soluble Donor-Acceptor Double-Cable polymer: Polythiophene with Pendant Fullerenes." VIII.A.4-4 Nakamura, E. et al., JACS, 125, 2834. "Synthesis, Structure, and Aromaticity of a Hoop-Shaped Cyclic Benzenoid [10]Cyclophenacene." VIII.A.4-5 Wang, G.-W. et al., T, 59, 55. "Solvent-Free Reactions of Fullerenes and N-Alkylglycines With and Without Aldehydes Under High-Speed Vibration Milling." VIII.A.4-6 Dyke, C.A.; Tour, J.M., JACS, 125, 1156. "Solvent-Free Functionalization of Carbon Nanotubes." VIII.A.4-7 Vougioukalakis, G.C.; Orfanopoulos, M., TL, 44, 8649. "Functionalization of Azafullerene C59N. Radical Reactions with 9Substituted Fluorenes."

SELECTED TOPICAL AREAS

309

VIII.A.4-8 Goodby, J.W.; Deschenaux, R. et al., CC, 1520. "Functional PolypedesmChiral Nematic Fullerenes." VIII.A.4-9 Iwamatsu, S. et al., CC, 1268. "A Novel Migrative Addition Reaction of Hydrazines to the Diketone Derivative of C60." VIII.A.4-10 Wilson, S.R. et al., JOC, 68, 7612. "Selective Syntheses of Novel Polyether Fullerene Multiple Adducts." VIII.A.4-11 Cross, R.J.; Khons, A.; Saunders, M., JOC, 68, 8281. "Using Cyanide to Put Noble Gases Inside C60." VIII.A.4-12 Akasaka, T. et al., JOC, 68, 6791. "Synthesis and Characterization of Tetrakis-Silylated C60 Isomers." VIII.A.4-13 Taylor, R. et al., OBC, 1, 1764. "Electrophilic Substitution of C60Fla into Phenols: HF Elimination Between OH and a 1,3-Shifted Fluorine Giving Benzofurano[2',3':10,26}hexadecafluoro[60]fullerene and Derivatives." VIII.A.4-14 Echegoyen, L. et al., JOC, 68, 5009. "Retrocyclopropanation Reactions of Fullerenes: Complete Product Analyses." VIII.A.4-15 Cheng, C.-H. et al., JOC, 68, 3811. "Novel Acid-Catalyzed Rearrangement of Methanofullerenes Bearing an a-Ylidic Ester to Cyclopentofullerenes: A Vinyl CyclopropaneType Ring Expansion." VIII.A.4-16 Saigo, K. et al., OL, 5, 2643. "[60]Fullerenoacetyl Chloride as a Versatile Precursor for Fullerene Derivatives: Efficient Ester Formation with Various Alcohols."

310

ORGANIC SYNTHESIS--2004

VIII.A.4-17 Burley, G.A. et al., OBC, 1, 2015. "Synthesis of 18rI Annulenic Fluorofullerenes from Tertiary Carbanions: Size Matters!" VIII.A.4-18 Nishimura, J. et al., JOC, 68, 3251. "Systematic Enantiomeric Separation of [60]Fullerene Bisadducts Possessing an Inherent Chiral Addition Pattern." VIII.A-19 Wang, Z.; Meier, M.S., JOC, 68, 3043. "Monoalkylation of C60 and C70 with Zn and Active Alkyl Bromides." VIII.A.4-20 Gonzalez, S.; Martin, N.; Guldi, D.M., JOC, 68, 779. "Synthesis and Properties of Bingel-Type Methanofullerene-rIExtended-TTF Diads and Triads." VIII.A.4-21 Wang, G.-W. et al., TL, 44, 4407. "Novel Solvent-Free Reaction of C60 with Active Methylene Compounds in the Presence of Na2CO3 under High-Speed Vibration Milling." VIII.A.4-22 Komatsu, K. et al., CEJ, 9, 1600. "Synthesis, Structure, and Properties of Novel Open-Cage Fullerenes Having Heteroatom(s) on the Rim of the Orifice." VIII.A.4-23 Martin, N. et al., T, 59, 6569. "Synthesis of Water Soluble Fulleropyrrolidines Bearing Biologically Active Arylpiperazines." VIII.A.4-24 Nakamura, E. et al., AG(E), 42, 3530. "Rhenium-Templated Regioselective Polyhydrogenation Reaction of [60]Fullerene." VIII.A.4-25 Orfanopoulos, M. et al., OL, 5, 4603. "Addition of Electron-Rich Aromatics to Azafullerenium Carbocation. A Stepwise Electrophilic Substitution Mechanism."

SELECTED TOPICAL AREAS

311

VIII.A.4-26 Jensen, A.W.; Daniels, C., JOC, 68, 207. "Fullerene-Coated Beads as Reusable Catalysts." VIII.A.4-27 Guo, Z.-X. et al., SC, 33, 2469. "Effective Mechanochemical Synthesis of [60]Fullerols." VIII.A.4-28 Cardinali, F.; Nierengarten, J.-F., TL, 44, 2673. "Synthesis of a New C60-Subtitiuted Tris(2,2'-bipyridine)ruthenium(If) Complex." VIII.A.4-29 Garlaschelli, L.; Paolucci, F. et al., EJOC, 375. "Methanofullerenes from Macrocyclic Malonates." VIII.A.4-30 Natalini, B. et al., SC, 33, 903. "Thermal and Catalytic Reactions of Diazoacetylmetallocenes with [60]Fullerene." VIII.A.4-31 Bianco, A. et al., OBC, 1, 4141. "Solid-Phase Synthesis and Characterization of a Novel FullerenePeptide Derived from Histone H3." VIII.A.4-32 Wang, G.-W. et al., OBC, 1, 4403. "Reaction of [60]Fullerene with Free Radicals Generated from Active Methylene Compounds by Manganese(III) Acetate Dihydrate." VIII.A.5. Reviews

VIII.A.5-1 Tagmatarchiy, N.; Prato, M., SL, 768. Account:

"The Addition of Azomethine Ylides to [60]Fullerene Leading to Fulleropyrrolidines."

VIII.A.5-2 Nakamura, E.; Isobe, H., A CR, 36, 807. Review:

"Functionalized Fullerenes in Water. The First 10 Years of Their Chemistry, Biology, and Nanoscience."

312

ORGANIC SYNTHESIS--2004

VIII.A.5-3 Park, J.T. et al., ACR, 36, 78. Review:

"[60]Fullerene-Metal Cluster Complexes: Novel Bonding Modes and Electronic Communication."

VIII.A.5-4 Mihailovic, D., M, 134, 137. Review"

"Ferromagnetism in Metallocene-Doped Fullerenes."

VIII.B. Taxol and Related Taxane Chemistry

VIII.B-1 Appendino, G. et al. EJOC, 4422. "The Reductive Fragmentation of 7-Hydroxy-9,10-dioxotaxoids." VIII.B-2 Paquette, L.A.; Hofferberth, J.E., JOC, 68, 2266, 2276, 2282. "Effect of 9,10-Cyclic Acetal Stereochemistry on Feasible Operation of the ~-Ketol Rearrangement in Highly Functionalized Paclitaxel (Taxol) Precursors." VIII.B-3 Greenwald, R.B. et al., JOC, 68, 4894. "Synthesis, Isolation, and Characterization of 2'-Paclitaxel Glycinate: An Application of the Bsmoc Protecting Group." VIII.B-4 Williams, R.M. et al., T, 59, 267. "Studies on Taxol Biosynthesis. Preparation of 5et-Acetoxytaxa4(20),11-dien-2~,10~-diol Derivatives by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew." VIII.B-5 Shea, K.J. et al., TL, 44, 9379. "Stereoselective Synthesis of an Advanced Taxusin Intermediate: An Application of the Type 2 Intermolecular Diels-Alder Reaction." VIII.B-6 Singh, A.K. et al., OPRD, 7, 25. "Trifluoroacetic Acid-Mediated Cleavage of a Triethylsilyl Protecting Group. Application in the Final Step of the Semisynthetic Route to Paclitaxel (Taxol)."

SELECTED TOPICAL AREAS

313

VIII.B-7 Battaglia, A.; Gelmi, M.L. et al., JOC, 68, 9773. "Diastereoselective 1413-Hydroxylation of Baccatin III Derivatives." VIII.B-8 Mulchandani, A. et al., CC, 1188. "A Novel Bioassay for Screening and Quantification of Taxanes." VIII.B-9 Zamir, L.O. et al., CJC, 81,406. "Canadensenes: Natural and Semi-Synthetic Analogues." VIII.B-10 Kiyota, H. et al., T, 59, 1529. "Synthesis and Antitumor Activity of 2-(mSubstitutedbenzoyl)baccatin III Analogs from Taxinine." VIII.B-11 Soga, T. et al., BMCL, 13, 185. "New Highly Active Taxoids from 913-Dihydrobaccatin-9,10-acetals. Part 3." VIII.B-12 Katz, F. et al., BMCL, 13, 355. "Synthesis and in vitro, Efficacy of Acid-Sensitive Poly(ethylenegylcol) Paclitaxel Conjugates." VIII.B-13 Battaglia, A. et al., JMC, 46, 4822. "Synthesis and Biological Evaluation of 2'-Methyl Taxoids Derived from Baccatin III and 1413-OH-Baccatin III 1,14-Carbonate." VIII.B-14 Dubois, J. et al., JMC, 46, 3623. "Synthesis of Novel Macrocyclic Docetaxel Analogues. Influence of Their Macrocyclic Ring Size on Tubulin Activity." VIII.B-15 Kiso, Y. et al., JMC, 46, 3782. "A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct: Design and Synthesis of Isotaxel."

314

ORGANIC SYNTHESIS--2004

VIII.B-16 Kiyota, H. et al., BMCL, 13, 1075. "Synthesis and Biological Evaluation of 4-Deacetoxy-l,7-dideoxy Azetidine Paclitaxel Analogues." VIII.B-17 Zhou, Z.; Mei, X., SC, 33, 723. "A Practical and Stereoselective Synthesis of Taxol Side Chain." VIII.B-18 Voronkov, M.V. et al., TL, 44, 407. "Improved Large-Scale Synthesis of Phenylisoserine and the Taxol C13 Side Chain." VIII.B-19 Ando, M. et al., TL, 44, 1091. "Specific Oxidation of C-14 Oxygenated 4(20),11-Taxadienes by Microbial Transformation." VIII.B-20 Kakiuchi, K. et al., TL, 44, 1401. "A New Route for the Construction of the AB-Ring Core of Taxol." VIII.B-21 Scheeren, H.W. et al., EJOC, 689. "Semisynthesis of 7-Deoxypaclitaxol Derivatives Devoid of an Oxetane D-Ring, Starting from Taxine B." VIII.B-22 Dubois, J. et al., EJOC, 542. "Synthesis of 2-O,Y-N-Linked Macrocyclic Taxoids with Variable Ring Size." VIII.B-23 Kingston, D.G.I. et al., TL, 44, 2049. "Synthesis and Bioactivities of Paclitaxel Analogs with a Cyclopropanated Side-Chain." VIII.B-24 Pattenden, G. et al., T, 59, 5115. "A Concise Enantioselective Synthesis of a Fully Oxygen Substituted Ring A Taxol Precursor."

SELECTED TOPICAL AREAS

315

VIII.B-25 Hayashi, Y. et al., BMCL, 13, 4441. "OmN Intramolecular Acyl Migration Strategy in Water-Soluble Prodrugs of Taxoids."

VIII.C Dendrimers, Calixeranes and Other Unnatural Products

VIII.C.I.a Dendrimers

VIII.C.I.a Dendrimer Synthesis VIII.C.I.a-1 Hong, Y.-R.; Gorman, C.B., JOC, 68, 9019. "Synthetic Approaches to an Isostructural Series of Redox-Active, Metal Tris(bipyridine) Core Dendrimers." VIII.C.I.a-2 Peng, Z. et al., JOC, 68, 6952. "Synthesis and Optical Properties of Unsymmetrical Conjugated Dendrimers Focally Anchored with Perylenes in Different Geometries." VIII.C.I.a-3 Diez-Barra, E.; Rodriguez-Lopez, J.; Segura, J.L.; Martin, N. et al., JOC, 68, 3178. "Synthesis and Photoluminescent Properties of 1,1'-Binaphthyl-Based Chiral Phenylene Vinylene Dendrimers." VIII.C.I.a-4 Ueda, M. et al.,JACS, 125, 8120. "Rapid Synthesis of Polyamide Dendrimers from Unprotected AB2 Building Blocks." VIII.C.I.a-5 Steffenesen, M.B.; Simanek, E.E., OL, 5, 2359. "Chemoselective Building Blocks for Dendrimers from Relative Reactivity Data." VIII.C.I.a-6 Kitaoka. M. et al., EJOC, 2462. "Synthesis of a Cellobiosylated Dimer and Trimer and of CellobioseCoated Polyamidoamine (PAMAM) Dendrimers to Study Accessibility of an Enzyme, Cellodextrin Phosphorylase."

316

ORGANIC SYNTHESIS--2004

VIII.C.I.a-7 Nierengarten, J.-F. et al., JOC, 68, 9787. "Amphiphilic Diblock Dendrimers with a Fullerene Core." VIII.C.I.a-8 De Schryver, F.C.; Mullen, K. et al., JOC, 68, 9802. "Synthesis and Optical Properties of Polyphenylene Dendrimers Based on Perylenes." VIII.C.I.a-9 Caminade, A.-M. et al., JOC, 68, 6043. "'Lego' Chemistry for the Straightforward Synthesis of Dendrimers." VIII.C.I.a-10 Gibson, H.W. et al., JOC, 68, 2385. "Crowned Dendrimers: pH-Responsive Pseudorotaxane Formation." VIII.C.1.a-11 Neckers, D.C. et al., JOC, 68, 5377. "Synthesis of Highly Fluorescent Y-Enyne Dendrimers with Four and Six Arms." VIII.C.I.a-12 Bronk, K.; Thayumanavan, S., JOC, 68, 5559. "Synthesis of Nonconjugated Dendrons with a Redox Gradient." VIII.C.I.a-13 Nierengarten, J.-F.; Armaroli, N. et al., CEJ, 9, 36. "[60]Fullerene: A Versatile Photoactive Core for Dendrimer Chemistry." VIII.C.I.a-15 Bhattacharjya, A. et al., JOC, 68, 617. "An Expedient Approach to Internally Functionalized Chiral Dendrimers: Synthesis of a Dendritic Molecule Incorporating Furanoside Skeleton." VIII.C.l.a-16 Lindhorst, T.K. et al., EJOC, 4376. "Glycerol and Glycerol Glycol Glycodendrimers." VIII.C.1.a-17 Modarelli, D.A. JOC, 68, 247. "Efficient Synthesis of Porphyrin-Containing BenzoquinoneTerminated, Rigid Polyphenylene Dendrimers."

SELECTED TOPICAL AREAS

317

VIII.C.I.a-18 Pei, J. et al., JACS, 125, 12430. "Extended n-Conjugated Dendrimers Based on Truxene." VIII.C.I.a-19 van Koten, G. et al., JOC, 68, 675. "Shape-Presistent Nanosize Organometallic Complexes: Synthesis and Application in a Nanofiltration Membrane Reactor." VllI.C.l.a-20 Diez-Barra, E.; Garcia-Martinez, J.C.; Rodriguez-Lopez, J.,

JOC, 68, 832. "Synthesis of Novel Cross-Conjugated Dendritic Fluorophores Containing Both Phenylenevinylene and Phenyleneethynylene Moieties." VIII.C.I.a-21 Thayumanavan, S. et al., JOC, 68, 1146. "A Mild Deprotection Strategy for Allyl-Protecting Groups and Its Implications in Sequence Specific Dendrimer Synthesis." VIII.C.l.a-22 Kobayashi, N. et al., CEJ, 9, 5757. "A Phthalocyanine Dendrimer Capable of Forming Spherical Micelles." VIII.C.l.a-23 Grindley, T.B. et al., CJC, 81,505.

"New Potential Dendritic Cores: Selective Chemistry of Dipentaerythritol." VIII.C.l.a-24 Krishna, T.R.; Jayaraman, N., JOC, 68, 9694. "Synthesis of Poly(propyl Ether Imine) Dendrimers and Evaluation of Their Cytotoxic Properties." VIlI.C.l.a-25 Hayes, W. et al., TL, 44, 37. "Synthesis of a Novel Class of Chiral Polyaromatic Amide Dendrimers Bearing an Amino Acid Derived C3-Symmetric Core." VIII.C.l.a-26 Newkome, G.R. et al., EJOC, 3666. "Linear Analogues of Acid- and Ester-Terminated Polyamido Dendrimers: Design, Synthesis, and Physical Properties."

318

ORGANIC SYNTHESISm2004

VIII.C.l.a-27 Mongin, O.; Blanchard-Desce, M. et al., TL, 44, 2813. "Synthesis and Two-Photon Absorption of Triphenylbenzene-Cored Dendritic Chromophores." VlII.C.l.a-28 Yamamoto, K. et al., CL, 32, 674. "Synthesis of Novel Carbazole Dendrimers Having a Metal Coordination Site." VIII.C.l.a-29 Peng, Z. et al., T, 59, 5495. "Synthesis and Optical Properties of Conjugated Dendrimers with Unsymmetrical Branching." VIII.C.l.a-30 Umali, A.P.; Simanek, E.E., OL, 5, 1245. "Thiol-Disulfide Exchange Yields Multivalent Dendrimers of Melamine."

VIII.C.I.a-31 Arai, T. et al., OBC, 1, 1635. "l,3,5-Tristyrylbenzene Dendrimers: A Novel Model System to Explore Oxygen Quenching in a Highly Organized Environment."

VIII.C.I.b Dendrimer Catalysts VIII.Col.b-1 Reymond, J.-L. et al.,AG(E), 42, 1381. "Catalytic Peptide Dendrimers." VIII.C.I.b-2 Lu, S.-M.; Alper, H., JACS, 125, 13126. "Hydroformylation Reactions with Recyclable Rhodium-Complexed Dendrimers on a Resin."

VIII.C.I.c Hetero-Containin~ and Miscellaneous Dendrimers

VIII.C.I.c-1 de Groot, F.M.H. et al., AG(E), 42, 4490. "'Cascade-Release Dendrimers' Liberate All End Groups upon a Single Triggering Event in the Dendritic Core."

SELECTED TOPICAL AREAS

319

VIII.C.I.c-2 Salamonczyk, G.M., TL, 44, 7449. "Acyclovir Terminated Thiophosphate Dendrimers." VIII.C.I.c-3 Shabat, D. et al., AG(E), 42, 4494. "Self-Immolative Dendrimers." VIII.C.I.c-4 Zimmerman, S.C.; Suslick, K.S. et al., JACS, 125, 13504. "Molecular Imprinting Inside Dendrimers." VIII.C.I.c-5 Furuta, P.; Frechet, J.M.J., JACS, 125, 13173. "Controlling Solubility and Modulating Peripheral Function in Dendrimer Encapsulated Dyes." VIII.C.I.c-6 Kim, C. et al., JOM, 667, 96. "Diels-Alder Reaction of Anthracene and N-Ethylmaleimide on the Carbosilane Dendrimer." VIII.C.I.c-7 Takaguchi, Y. et al., TL, 44, 5777. "Facile and Reversible Synthesis of an Acidic Water-Soluble Poly(amidoamine) Fullerodendrirner." VIII.C.I.c-8 Rodriguez-Lopez, J. et al., SL, 1587. "Synthesis of 4-Dendronized [3-Lactams."

VIII.C.2 Calixeranes

VIII.C.2.a Calixarane Receptor s

VIII.C.2.a-1 Bitter, I. et al., TA, 14, 1025. "Synthesis of Chiral 1,3-Calix[4](crown-6) Ethers as Potential Mediators for Asymmetric Recognition Processes." VIII.C.2.a-2 Jabin, I.; Reinaud~ O., JOC, 69, 3416. "First C34-Symmetrical CAlix[6](aza)crown."

320

ORGANIC SYNTHESIS--2004

VIII.C.2.a-3 Kwit, M.; Gawronski, J., TA, 14, 1303. "Chiral Calixsalen-Type Macrocycles from trans-l,2Diaminocyclohexane." VIII.C.2.a-4 Sessler, J.L. et al., AG(E), 42, 2278. "Calix[n]bipyrroles: Synthesis, Characterization, and Anion-Binding Studies." VIII.C.2.a-5 Zheng, Q.-Y.; Huang, Z.-T. et al., JCR(S), 489. "Synthesis and Structure of Copper(II) Calix[4]arene Tetraimidazole Complex." VIII.C.2.a-6 Sharma, P. et al., SC, 33, 373. "Synthesis of 25,26,27-tris(Ethoxycarbonylmethoxy)-28-(substituted Oxy-carbonylmethoxy) Calix-4-arene: First Example of Caliximidazole/Benzimidazole Analog." VIII.C.2.a-7 Sessler, J.L. et al., JACS, 125, 13646. "Calix[2]bipyrrole[2]furan and CAlix[2]bipyrrole[2]thiophene: New Pyrrolic Receptors Exhibiting a Preference for Carboxylate Anions." VIII.C.2.a-8 Ito, K. et al., JHC, 40, 405. "Syntheses and Properties of Dithia-tetrahomodiaza-calix[4]arenes Bridged by Cystine Unit."

VIII.C.2.b Synthesis of Calixarane VIII.C.2.b-1 Kim, J.S.; Toon, J. et al., JOC, 68, 597. "Molecular Taekwondo. 2. A New Calix[4]azacrown Bearing Two Different Binding Sites as a New Fluorescent Ionophore." VIII.C.2.b-2 Kleij, A.W.; de Mendoza, J. et al., JOC, 68, 8711. "Unexpected Single-Step Formation of 1,2-anti-Heterodi-substituted Calix[4]arenes Upon Alkylation of a Tribenzoyl Precursor."

SELECTED TOPICAL AREAS

321

VIII.C.2.b-3 Bitter, I. et al., TL, 44, 4681. "Unprecedented Cyclisations of Calix[4]arenes with Glycols Under the Mitsunobu Protocol. Part 1: A New Perspective for the Synthesis of Calixcrowns." VIII.C.2.b-4 Arnaud-Neu, F.; Bohmer, V. et al., AJC, 56, 1113. "Synthesis and Extraction Behaviour of Calix[4]arenes Partially Substituted at the Wide Rim by Carbamoylmethylphosphine Oxide (CMPO) Functions." VIII.C.2.b-5 Lhotak, P. et al., TL, 44, 8093. "Synthesis of a Deep-Cavity Thiacalix[4]arene." VIII.C.2.b-6 Shi, X. et al., CJC, 81, 1019. "Synthesis and Molecular Recognition of the Uridine-Containing Derivative ofp-tert-Butylcalix[4larene." VIII.C.2.b-7 Sansone, F.; Ungaro, R. et al., OBC, 1, 1802. "Thiourea-Linked Upper Rim Calix[4]arene Neoglyco-conjugates: Synthesis, Conformations and Binding Properties." VIII.C.2.b-8 Kutateladze, A.G. et al., CJC, 81, 807. "Photolabile Calixarene-Based Rosette." VIII.C.2.b-9 Bohmer, V. et al., CC, 1124. "Self-Assembled Dimers with Supramolecular Chirality." VIII.C.2.b-10 Mongrain, P.; Harvey, P.D., CJC, 81, 1246. "Wide-Rim Functionalization of Calix[4]arene: The Di- and Tetraisocyanocalix[4]arene Assembling Ligands and Their Silver(I) Polymers and Oligomers." VIII.C.2.b-ll Antipin, I.S. et al., T, 59, 1469. "The Synthesis of Tetracarbonyl Derivatives of Thiacalix[4]-arene in Different Conformations and Their Complexation Properties Towards Alkali Metal Ions."

322

ORGANIC SYNTHESIS--2004

VIII.C.2.b-12 Neri, P. et al., TL, 44, 9155. "Synthesis of the First Examples ofp-Brornodienone and Transannular Spirodienone Calixarene Derivatives." VIII.C.2.b-13 Amaud, F.; Vicens, J. et al., TL, 44, 9061. "Synthesis of Mono-, Di-, and Trinitro Tricarboxymethyl Calix[6]arenes for the Complexation of Uranium(VI)." VIII.C.2.b-14 Bitter, I.; Csokai, V., TL, 44, 2261. "An Expedient Route to p-tert-Butylthiacalix[4]arene 1,3-Diethers via Mitsunobu Reactions." VIII.C.2.b-15 Yang, X.; Lowe, C.R., TL, 44, 1359. "Synthesis of Novel Rigid Triazine-Based Calix[6]arenes." VIII.C.2.b-16 Seneque, O.; Reinaud, O., T, 59, 5563. "Selective Functionalization at the Small Rim of Calix[6]arene. Synthesis of Novel Non-Symmetrical Na, N4 and N3ArO Biomimetic Ligands." VIII.C.2.b-17 Casnati, A. et al., T, 59, 5539. "The First Synthesis and Characterization of Elusive Cone 1,2Diformyl Tetralkoxycalix[4]arenes and Their Derivatives." VIII.C.2.c Synthesis on Calixarane VIII.C.2.c-1 Lamartine, R.J. et al., JOC, 68, 6632. "Synthesis and Structure of Lower Rim C-Linked N-Tosyl Peptidocalix[4]arenes." VIII.C.2.c-2 Mountford, P.; Radius, U. et al., CEJ, 9, 3634. "Synthesis and Reactivity of Calix[4]arene-Supported Group 4 Imido Complexes." VIII.C.2.c-3 Kuhnert, N.; Le-Gresley, A., CC, 2426. "The Synthesis of Tetra-Acylamido-calix[4larene Capsules."

SELECTED TOPICAL AREAS

323

VIII.C.2.c-4 Simaan, S.; Biali, S.E., JOC, 68, 3634. "Synthesis ofp-tert-Butylcalix[4]arene Derivatives with trans-Alkyl Substituents on Opposite Methylene Bridges." VIII.C.2.c-5 Shimizu, S. et al., JOC, 68, 2187. "Selective Synthesis and Isolation of All Possible Conformational Isomers of Proximally para-Disubstituted Calix[4]arene." VIII.C.2.c-6 Morohashi, N.; Miyano, S. et al., JOC, 68, 2324. "Synthesis of All Stereoisomers of Sulfinylcalix[4]arenes." VIII.C.2.c-7 Reinaud, O. et al., JOC, 68, 7004. "Unprecedented Selective ipso-Nitration of Calixarenes Monitored by the O-Substituents." VIII.C.2.c-8 Huang, Z.-T. et al., T, 59, 2539. "Synthesis of New Calix[4]arenes Containing Nucleoside Bases." VIII.C.2.c-9 Vicens, J.; Kim. J.S. et al., TL, 44, 805. "Modular Chemistry. Double- and Multi-l,3-Alternate-Calixcrowns." VIII.C.2.c-10 Tuntulani, T. et al., TL, 44, 29, 33 "Calix[4]arenes Containing Urea and Crown/Urea Moieties: Effects of the Crown Ether Unit and Na + Towards Anion Binding Ability."

VIII.C.2.d Calixarane Isolation, Conformation, etc. VIII.C.2.d-1 Biali, S.E. et al., JOC, 68, 7140: "A Conformationally Flexible Tetrahydroxycalix[4]arene Adopting the Unusual 1,3-Alternate Conformation."

324

ORGANIC SYNTHESIS--2004

VIII.C.2.d-2 Ueoka, R. et al., JOC, 68, 865. "Catalytic Specificity Exibited byp-Sulfonatocalix[n]arenes in the Methanolysis of N-Acetyl-L-Amino Acids." VIII.C.3 Rotaxanes VIII.C.3-1 Li, Z.-T. et al., JOC, 68, 2704.

"Self Assembly of Novel [3]- and [2]Rotaxanes Based on DonorAcceptor and Hydrogen-Bonding Interactions. Intensified Inter-Ring Repulsion Interaction and Shuttling Behavior." VIII.C.3-2 Smukste, I.; Smithrud, D.B., JOC, 68, 2547, 2559. "Structure-Function Relationship of Amino Acid[2]rotaxanes." VIII.C.3-3 Gibson, H.W. et al., CC, 2122. "Water Assisted Formation of a Pseudorotaxane and Its Dimer Based on a Supramolecular Cryptand." VIII.C.3-4 Anderson, H.L. et al., CEJ, 9, 6167. "Synthesis of Conjugated Polyrotaxanes." VIII.C.3-5 Jeppesen, J.O.; Vignon, S.A.; Stoddart, J.F., CEJ, 9, 4611. "In the Twilight Zone Between [2]Pseudorotaxanes and [2]Rotaxanes." VIII.C.3-6 Takata, T. et al., CEJ, 9, 2895. "Dynamic Covalent Approach to [2]- and [3]Rotaxanes by Utilizing a Reversible Thiol-Disulfide Interchange Reaction." VIII.C.3-7 Easton, C.J. eta|., CEJ, 9. 5978. "Installations of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane." VIII.C.3-8 Grubbs, R.H. et al., AG(E), 42, 3281. "Magic Ring Rotaxanes by Olefin Metathesis."

SELECTED TOPICAL AREAS

325

VIII.C.3-9 Tokunaga, Y. et al., CC, 2250. "A Rotaxane Synthesis Based on Stilbene Photoisomerization. A Photoswitchable Catch and Release Process." VIII.C.3-10 Charnbron, J.-C.; Collin, J.-P.; Heitz, V.; Sauvage, J.-P. eta|., CEJ, 9, 4247. "Templated Synthesis of a Rotaxane with a [Ru(diimine)3] 2+ Core." VIII.C.3-11 Jeong, K.-S. et al., CC, 1450. "A Pseudorotaxane-Based Molecular Machine Controlled by Light and Thermal Stimuli." VIII.C.3-12 Arduini, A. et al., CEJ, 9, 793. "Unidirectional Threading of Triphenylureidocalix[6]arene-Based Wheels: Oriented Pseudorotaxane Synthesis." VIII.C.3-13 Stoddart, J.F. et al., CEJ, 9, 4046. "Kinetic versus Thermodynamic Control During the Formation of [2]Rotaxanes by a Dynamic Template-Directed Clipping Process." VIII.C.3-14 Nishimura, J. et al., AG(E), 42, 3158. "Preparation of Neutral [60]Fullerene-Based [2]Catenanes and [2]Rotaxanes Bearing an Electron-Deficient Aromatic Diimide Moiety." VIII.C.3-15 Rowan, A.E. et al., AG(E), 42, 650. "Synthesis of Porphyrin-Containing [3]Rotaxanes by Olefin Metathesis." VIII.C.3-16 Tamaoki, N. et al., TL, 44, 2307. "Synthesis of a Mechanically Linked Oligo[2]rotaxane." VIII.C.3-17 Stoddart, J.F.; Venturi, M. et al., CCC, 68, 1488. "Redox-Induced Ring Shuttling and Evidence for Folded Structures in Long and Flexible Two-Station Rotaxanes."

326

ORGANIC SYNTHESISm2004

VIII.C.3-18 Gunter, M.J. et al., CC, 1396. "A Self-Assembling Polymer-Bound Rotaxane Under Thermodynamic Control." VIII.C.3-19 Jeppesen, J.O.; Gandolfi, M.T.; Venturi, M.; Stoddart, J.F. et al., CEJ, 9, 2982. "Amphiphilic Bistable Rotaxanes."

VI!I.C.4 Supramolecules

VIII.C.4-1 Dyker, G. et al., EJOC, 4355. "From a Calix[4]arene to a Hexameric Supracycle." VIII.C.4-2 Smith, B.D. et al., JOC, 68, 10073. "Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids." VIII.C.4-3 Kern, J.-M.; Sauvage, J.-P. et al., OL, 5, 1887. "Synthesis of a [2]Catenane Around a Ru(diamine)32+ Scaffold by Ring-Closing Metathesis of Olefins." VIII.C.4-4 Schalley, C.A. et al., CEJ, 9, 1332. "Tetra- and Octalactam Macrocylces and Catenanes with Exocyclic Metal Coordination Sites" Versatile Building Blocks for Supramolecular Chemistry."

VIII.C.4-5 Infantes, L. et al., HCA, 86, 1205. "l,2,4,5-Tetrazines vs Carboxylic Acid Dimers: Molecular Chemistry vs Supramolecular Chemistry." VIII.C.4-6 Chi, K.-W.; Stang, P.J. et al., JOC, 68, 9798. "Bidentate Ligands Capable of Variable Bond Angles in the SelfAssembly of Discrete Supramolecules." VIII.C.4-7 Mirkin, C.A. et al., JACS, 125, 10508. "A Supramolecular Approach to an Allosteric Catalyst."

SELECTED TOPICAL AREAS

327

VIII.C.4-8 Lehn, J.-M. et al., JACS, 125, 10257.

"Self-Assembly, Structure, and Dynamic Interconversion of Metallosupramolecular Architectures Generated by Pd(II) BindingInduced Unfolding of a Helical Ligand." VIII.C.4-9 Petridis. D. et al., CEJ, 9, 3904. "Clays as a Host Matrix in the Synthesis of Organic Macrocycles." VIII.C.4-10 Bouteiller, L. et al., CEJ, 9, 3008. "N,N'-Disubstituted Ureas: Influence of Substituents on the Formation of Supramolecular Polymers." VIII.C.4-11 Turro, N.J. et al., OL, 5, 2025. "A Supramolecular 'Ship in Bottle' Strategy for Enantiomeric Selectivity in Geminate Radical Pair Recombination." VIII.C.4-12 Wuest, J.D. et al., JOC, 68, 240. "Molecular Tectonics. Construction of Porous Hydrogen-Bonded Networks from Bisketals of Pentaerythritol." VIII.C.4-13 Tarase, M.; Inouye, M., JOC, 68, 1134. "Highly Efficient Recognition of Native TpT by Artificial Ditopic Hydrogen-Bonding Receptors Possessing a Conformationally WellDefined Linkage." VIII.C.4-14 Elemans, J.A.A.W. et al., JOC, 68, 9040. "Synthesis and Hierarchical Self-Assembly of Cavity-Containing Facial Amphiphiles." VIII.C.4-15 Liu, Y.; Inoue, Y. et al., JOC, 68, 8345. "Supramolecular Self-Assemblies of B-Cyclodextrins with Aromatic Tethers: Factors Governing the Helical Columnar versus Linear Channel Suprastructures."

328

ORGANIC SYNTHESISm2004

VIII.C.5 Cyclophanes

VIII.C.5-1 Warrener, R.N. et al., AJC, 56, 263,269. "Position-Addressable Nauo-Scaffolds. I and II."

VIII.C.6 Other

VIII.C.6-1 Yuan, D.-Q.; Fujita, K. et al., JOC, 68, 9456. "Functionalization of Cyclodextrins via Reactions of 2,3Anhydrocyclodextrins." VIII.C.6-2 Wong, M.-K. et al., JOC, 68, 6576. "A Cyclodextrin-Modified Ketoester for Stereoselective Epoxidation of Alkenes." VIII.C.6-3 Akashi, M. et al., CC, 3020. "A Facile Synthesis of Novel Cyclodextrin Derivatives Incorporating One [3-(1,4)-Glycosidic Bond and Their Unique Inclusion Ability." VIII.C.6-4 Yannakopoulou, K. et al., JOC, 68, 8550. "Synthesis of 6-Mono-6-deoxy-13-cyclodextrins Substituted with Isomeric Amino Benzoic Acids." VIII.C.6-5 Park, J.W. JOC, 68, 7071. "Homodimerization and Heteroassociation of 6-o-(2-Sulfonated-6naphthyl)-~,-cyclodextrin and 6-deoxy-(pyrene-l-carboxamido)-13cyclodextrin." VIII.C.6-6 Liu, Y. et al., JOC, 68, 527. "Synthesis of Novel Bis(13-cyclodextrin)s and Metallobridged Bis(13cyclodextrin)s with 2.2'-Diselenobis(benzoyl) Tethers and Their Molecular Multiple Recognition with Model Substrates."

SELECTED TOPICAL AREAS

329

VIII.C.7 Reviews VIII.C.7-1 Vilar, R., AG(E), 42, 1460. Review: "Anion-Templated Synthesis." VIII.C.7-2 Smith, D.K., guest ed., T, 59, 3799-4017. Symposia "Recent Developments in Dendrimer Chemistry." in-Print: VIII.C.7-3 Ungaro, R. et al., ACR, 36, 246. Review: "Peptido- and Glycocalixarenes: Playing Around Hydrogen Bonds with Hydrophobic Cavities." VIII.C.7-4 Biali, S.E., SL, 1. Account: "The Spirodienone Route for the Functionalization of Calixarenes."

VIII.C.7-5 Kim, K. et al., ACR, 36, 621. Review: "Cucurbiturii Homologues and Derivatives: New Opportunities in Supramolecular Chemistry." VIII.C.7-6 Calzaferri, G. et al., AG(E), 42, 3732. Review: "Host-Guest Antenna Materials." VIII.D. Total Syntheses of Selected Natural Products

(see also VIII.B) VIII.D.-A Hanson, J.R. JCR(S), 426 Kumar, P., TL, 44, 6149 Uenishi, J., EJOC, 3909 Whitby, R.J., CC, 2786 Kundig, E.P., JACS, 125, 5642 Arno, M., JOC, 68, 1242 Riera, A., OL, 5, 3001 Groth, U., EJOC, 4445 Chida, N., TL, 44, 5047 Wardrop, D.J., SL, 1352

Abscisic Acid (-)-Acaterin (-)-Acetomycin (• (+) & (-)-Acetoxytubipofuran (-)-Acetyldendrillol-1 Acosamine (s)-(-)-Acromelobic Acid (+) & (-)-Actinobolin Adalinine

330

ORGANIC SYNTHESIS--2004

Davis, B.G., AG(E), 42, 3788 Adenophorine Shibasaki, M., JACS, 125, 11206 Aeruginosin 298-A Valls, N., OL, 5, 447 Aeruginosin EI461 Trost, B.M., JACS, 125, 3090 (+)-Aflatoxin B1 & B2a Ducrot, P.-H., EJOC, 1184, 1172 pyrano-Agarofuran Hale, K.J., OL, 5, 2927 (-)-Agelastatin A Ghosh, A.K., EJOC, 821 AI-77-B Lee, Y.-J., JOC, 68, 2968 Ailanthoidol Mukai, C., OL, 5, 2335 (-)-AL-2 Kende, A.S., OL, 5, 3205 (+)-Aiantrypinone Overman, L.E., OL, 5, 1543 Alcyonin Cook, J.M., JOC, 68, 5852 Alkaloid 9 Toyooka, N., AG(E), 42, 3808 Alkaloid 205B Panek, J.S., JACS, 125, 626 Alkaloid (-)-217A Ma, D., JOC, 68, 4400 Alkaloid (-)-223A Ma, D., JOC, 68, 4400 Alkaloid (-)-6-epi-223A Mander, L.N. JACS, 125, 2400 Alkaloid GB13 Cook, J.M., TL, 44, 543; JOC, 68, 7565 Alkaloid (-)-Q3 Moeller, K.D., JACS, 125, 36 Alliacol A Wulff, W.D., JOC, 68, 5826 (-)-7s-Allocolchicine Passarella, D., JOC, 68, 9525 Allosedamine Davis, F.A., OL, 5, 925 (-)-Allosedridine Yadav, J.S., TL, 44, 5831 Altholactone Ghosh, A.K., JACS, 125, 2374 (+)-Amphidinolide T1 Furstner, A., JACS, 125, 15512 Amphidinolide T1, T3, T4 &T5 Yoda, H., TL, 44, 1643 Amphorogynine A Delair, P., OL, 5, 1741 (+)-Amphorogynine A Bringmann, G., OL, 5, 2805 Ancistroealaine A Bringmenn, G., OL, 5, 2805 Ancistrotanzanine B Liebeskind, L.S., JACS, 125, 2878 (-)-Andrachcinidine Knolker, H.-J., SL, 1752 (+)-Anhydrocalopine Deslongchamps, P., JOC, 68, 6847 (+)-Anhydrochatancin Steglich, W., S, 101 Anhydrolycorinonr Jauch, J., EJOC, 3060 Anhydromarasmone Estevez, R.J., T, 59, 8057 Annoretine Takikawa, H., TL, 44, 7023 Annuionone A Kim, S., OL, 5, 2703 (-)-Antofine Zhai, H., JOC, 68, 8268 (-)-Aphanorphine Taylor, R.J.K., OBC, 1, 104 (+)-Apicularen A Nicolaou, K.C., CEJ, 9, 6177 (-)-Apicularen A Mas,T., S, 1878 Apigeninidin Chloride Arno, M., JOC, 68, 1242 (-)-Aplyroseol-14 Nicolaou, K.C., JACS, 125, 15443, 15433 Apoptolidin Forsyth, C.J., JACS, 125, 8 7 3 4 Apratorin A Brands, K.M.J., JACS, 125, 2 1 2 9 Aprepitant Pilli, R.A., TL, 44, 8 7 2 1 (R)-Argentilactone Hsung, R.P., T, 57, 311 (+)-Arisugacin A

SELECTED TOPICAL AREAS

Fukuyama, T., OL, 5, 1891 Fukuyama, T., T, 59, 8571 Shishido, K., OL, 5, 749 Yadav, J.S., TL, 44, 387 Cha, J.K., JACS, 125, 5415 Blechert, S.,JOC, 68, 2913 Theodorakis, E.A., TL, 44, 3281 Enders, D., SL, 2185 Katoh, T., SL, 329 Sharma, G.V.M., T, 59, 95 Ma, D., TL, 44, 3 963 Kibayashi, C., OL, 5, 3839

331

Aspidophytine (-)-Aspidophytine (-)-Aspispermine (+)-Artemisinin (+)-Asteltoxin (+)-Astrophylline Atroviridin Attenol A & B (+)-Aureol Aza-calanolide A (+)-Azimic Acid (+)-Azimine

VIII.D.-B Chen, S.-T., TL, 44, 5271 Sudalai, A., TA, 14, 581 Helmchen, G., SL, 1539 Kanazawa, A., JOC, 68, 3831 Langlois, Y., SL, 1488 Kogen, H., OL, 5, 269 Park, K.H., TL, 44, 5905 Jurczak, J., TL, 44, 8685 Miller, M.J., JOC, 68, 6501 Liao, C.-C., OL, 5, 4741 Seki, M., TL, 44, 8905 Pan, X., TA, 14, 75 Furstner, A., CC, 2112 Hattori, T., JOC, 68, 2099 Yuste, F., TA, 14, 549 Yuste, F., TA, 14, 549 Singh, V.K., JOC, 68, 4039 Morken, J.P., JACS, 125, 1458 Hanessian, S., JACS, 125, 13784 Alexakis, A., TL, 44, 7901 Coop, A., JOC, 68, 1929 Raghavan, S., TL, 44, 8237 Takikawa, H., TL, 44, 5235 Kitahara, T., H, 61, 481 Overman, L.E., JACS, 125, 6650 Rice, K.C., JOC, 68, 2010 Kitahara, T., T, 59, 1773 Maycock, C.D., OL, 5, 4321 Trost, B.M., AG(E), 42, 5987 Han, J.-S., JOC, 68, 4116 Scheinmann, F., TA, 14, 567 Organ, M.G., TL, 44, 6805

Baclofen (R)-(-)-Baclofen (R)-(-)-Baclofen Barbacenic Acid (• (+)-Benzastatin E (-)-Bestatin (-)-Bestatin (• (• A&B (+)-Biotin (7s, 9R)-(+)-Bisacumol Bisdehydro=o-Methylisopiline (-)-Blestriarene C N-Boc-3-epistatine N-Boc-statine (+)-Boronolide Borrelidin (-)-Borrelidin (-)-Botrydiplodin (+)-Bractazonine

(+)-exo-Brevicomin (• B (+) & (-)-Brevioxime Briarellin E & F (8s)-Bromomorphide (+)-Bromoxone (+)-Bromoxone (+)-Broussonetine C Buergerinin F & G Bufuralol Bupleurynol

332

ORGANIC SYNTHESISm2004

VIII.D.-C F orsyth, C.J., OL, 5, 991 Du, Y., TL, 44, 6887 Paterson, I., OL, 5, 4477 Lopez, S., OL, 5, 3725 Kalesse, M., CEJ, 9, 1129 Steglich, W., T, 59, 123 Chai, C.L.L., JOC, 68, 8906 Madsen, R., JOC, 68, 2115 Coates, R.M., JOC, 68, 6935 Williams, R.M., JACS, 125, 8561 Knolker, H.-J., CC, 1170 Knolker, H.-J., EJOC, 741 Kibayashi, C., OL, 5, 3839 Yu, B., JOC, 68, 6309 Matabe, H., OL, 5, 27 Ruveda, E.A., TA, 14, 717 Somfai, P., T, 59, 1293 Park, K.H., S, 2473 Parrain, J.-L., TL, 44, 2311 Evans, P.A., OL, 5, 3883 Li, W.-D.Z., OL, 5, 2931 Mori, K., TL, 44, 9197 Deslongchamps, P., JOC, 68, 9983 Helmchen, G., EJOC, 2122 Couture, A., OBC, 1, 1701 Marcos, I.S., T, 59, 685 Nagasaka, T., H, 59, 527 Kim, G, TL, 44, 8207 Yoda, H., TL, 44, 9057 Li, Y., TA, 14, 2355 Snapper, M.L., JACS, 125, 9032 Chen, S.-T., TL, 44, 5271 Marcos, I.S., TL, 44, 5419 Timari, G., T, 59, 7509 Rizzacasa, M.A., OBC, 1, 3672 Rizzacasa, M.A., OBC, 1, 3672 Kitahara, T., TL, 44, 9219 Paquette, L.A., JACS, 125, 1567 Furstner, A., JOC, 68, 1521 Hirama, M., H, 59, 87 Clive, D.L.J., CC, 2062 Yamada, Y., JOC, 68, 3476 Marcos, I.S., JOC, 68, 7496 Yamada, Y., T, 59, 61 Bracher, F., M, 134, 573 Mukherjee, D., TL, 44, 4985 Mukherjee, D., TL, 44, 4985

(-)-Cacospongionolide F Calabricoside A (-)-Callipeltoside A Callyberyne A & B (-)-Callystatin A (+)-Calopin Calothrixin A & B Calystegine B2,B3 & B4 (• Capreomycin IB Carbazomadurin A Carbazomycin G & H (+)-Carpaine Cassiaside C2 (-)-Cassine (+)-Cassiol (+)-Castanospermine (+)-Castanospermine (=t=)-Caulerpenyne (-)-Centrolobine Cephalotaxine Ceramide B (+)-Chatancin (-)-Chaumoogric Acid (+) & (-)-Cherline (-)-Chettaphanin I & II Chilenine Chilenine Chilenine Chiricanine B Chloropeptin 1 Chlorpheg (-)-Chrysolic Acid Cicerfuran (-)-Cinatrin C1 (+)-Cinatrin C3 Cineromycin B Citlalitrione (s)-(+)-Citreofuran (=~)-CJ-12,372 Cladobotryal Cladocorin A & B 15-epi-ent-Cladocoran A & B Claenone Clathryimine (~=)-Clovan-3-one (~=)-epi-Clovan-3-one

SELECTED TOPICAL AREAS

Tamura, O., SL, 35 Larcheveque, M., SL, 274 Murphy, J.A., OBC, 1, 117 Rychnovsky, S.D., AG(E), 42, 1267 Kraus, G.A., T, 59, 7935 Roush, W.R., OL, 5, 1697 Kumar, P., TL, 44, 1957 Davies, H.M.L., TA, 14, 941 Zheng, S.-L., TL, 44, 1445 Pietruszka, J., SL, 1698 Yabuta, G., TL, 44, 6915 Villamizar, J., JCR(S), 504 Villamizar, J., JCR(S), 504 Chakrabarty, M., S, 2011 Olse, S.H., TL, 44, 61 Huang, P.-Q., OL, 5, 1927 Banwell, M.G., AJC, 56, 577 Banwell, M.G., AJC, 56, 577 Murphy, P.J., TL, 44, 251 Brimble, M.A., OBC, 1, 4227 Rizzacasa, M.A., AJC, 56, 783 Chakraborty, T.K., TL, 44, 4989 Lu, W., TL, 44, 2073 Srikrishna, A., OL, 5, 2295 Grainger, R.S., CC, 1072 Ghosh, S., T, 59, 5175 Mukhetjee, D., TL, 44, 737 Satoh, T., TA, 14, 281 Keay, B.A., SL, 1349 Furstner, A., JACS, 125, 13132 Trost, B.M., OL, 5, 4599 Akita, H., T, 59, 2679 Charette, A.B., OL, 5, 4163

333

(-)-Codonopsinine (-)-Codonopsinine (+)-Coerulescine (-)-Colombiasin A Colutequinone A & B Conduritol B, C, D & F (-)-~-Conhydrine (-)-a-Conhydrine

(+)-epi-Conocarpan Constanolactone A & B Cordiaquinone K (+)-Coronarin

(-)-7-epi-Coronarin A Coscinamide B Coumermycin A1 (+)-CP-99 CP-225,917 CP-263,114 Crambescidin 359 Crisamicin A (+)-Crocacin A (+)-Crocacin A (• (-)-Cucumin H (-)-Cuparene (+)-Cuparene (• 1,4-Cu paren ed iol (+)-~-Cuparenone Curcumene Ether Cycloviracin B1 (+)-Cyindricine C, D & E (+)-Cystothiazole A (+)-Cystothiazole A

VIII.D.-D Hoye, T.R., JACS, 125 9576 Lichtenthaler, F.W., AG(E), 42, 5838 Riera, A., OL, 5, 3001 Jin, Z., OL, 5, 4481 Riera, A., OL, 5, 3001 Covarrubias-Zuniga, A., SC, 33, 3173 Merino, P., EJOC, 2877 Shioiri, T., H, 59, 465 Ganesan, A., OL, 5, 1801 De Nanteuil, G., TL, 44, 9263 Donaldson, W.A., TA, 14, 757 Harayama, T., H, 59, 293

(-)-Dactylolide (-)-Daucic Acid Daunosamine Daurichromenic Acid epi-Dausamine DB-2073 (-)-Deacetylanisomycin Deacylbengazole Debromoflustramine B Debromohymenialdisine (+)-Decarestrictine L Decarine

334

Georg, G.I., JOC, 68, 9687 Sames, D., OL, 5, 4053 Takahashi, S., TL, 44, 1875 Knolker, H.-J., SL, 1752 Tian, W., TL, 44, 9383 Cook, J.M., JOC, 68, 5852 Monti, H., TL, 44, 6463

ORGANIC SYNTHESISm2004

Dechlorodryptophycin-52 (=t=)-Deguelin Dehydroaltenusin (+)-Dehydrocalopin (-)-Dehydroclausenamide (+)-Dehydro-16-epiaffinisine Dehydro-13-monocyclonerolidol (-)-Dehydrotubifoline (-)-Delactonmycin Demethoxyisoacronycine (-)-Deoxocassine (-)-3-epi-Deoxoprosopin in e (-)-Deoxoprosopylline 7-Deoxycasuarine 7-Deoxycasuarine

Mori, M., JACS, 125, 9801 Pilli, R.A.,AG(E), 42, 3017 Nyerges, M., H, 60, 817 Ma, D., TL, 44, 3963 Lebreton, J., EJOC, 4518 Ma, D., TA, 14, 1403 Goti, A., TL, 44, 2315 Carmona, A.T., HCA, 86, 3066 Li, Y., SL, 1977 14-Deoxycrassin Banwell, M.G., OBC, 1, 2035 (-)-l-Deoxymannojirimycin Langlois, N., TL, 44, 5961 Deoxydysibetaine Kobayashi, S., JACS, 125, 3793 (+)-9-Deoxygoniopypyrone Knight, J.G., T, 59, 281 Deoxymannojirimycin Williams, D.R., JACS, 125, 1843 (+)-4,5-Deoxyneodolabelline Somfai, P., T, 59, 1293 (+)-l-Deoxynojirimycin 4'-Deoxysyringolide 2 Ricards, R.W., TL, 44, 6927 Smith, III, A.B., JACS, 125, 350 (+)-13-Deoxytedanolide Deoxyvariolin B 1 Alvarez, M., JOC, 68, 10020 Kelly, J.W., JOC, 68, 9506 Dendroamide A McWhorter, Jr., W.W., JACS, 125, 4240 8-Desbromohinckdentine A Muller, M., S, 1803 Desertorin C 12,13-Desoxyepothilone Danishefsky, S.J., JACS, 125, 2899 Heimgartner, H., HCA, 86, 2805 (+)-Desoxynoreseroline Desoxymorellin Theodorakis, E.A., OBC, 1, 4418 (-)-Detoxime Reissig, H.-U., CEJ, 9, 1405 Diazonamide A Nicolaou, K.C., AG(E), 42, 1753 (-)-Diazonamide A Harran, P.G., AG(E), 42, 4961 (+)-Dibromophakellstatin Romo, D., JACS, 125, 6344 Dichroanal B Banerjee, A.K., OL, 5, 3931 Dichroanone Banerjee, A.K., OL, 5, 3931 (s)-(+)-Dictyoprolene Faber, K., TA, 14, 2427 Didehydropristinamycin II AII B Ronan, B., T, 59, 2929 (+)-Didehydrostemofoline Overman, L.E., JACS, 125, 15284 Lombardo, M., TL, 44, 9147 Dideoxy-l,4-L-iminoribitol 1,6-Dideoxy-L-nojirimycin Martin, O.R., TA, 14, 47 (+)-l,7-Diepiaustraline Pyne, S.G., JOC, 68, 7818 20s &20R-Dihydrocleavamine Amat, M., OL, 5, 3139 6,7-Dihydroeponemycin Rivalle, C., EJOC, 4569 (9s)-Dihydroerythronolide A Woerpel, K.A., JACS, 125, 6018

SELECTED TOPICAL AREAS

Liebeskind, L.S., JACS, 125, 2878 Parrain, J.-L., SL, 1719 Correia, C.R.D., TL, 44, 1553 Donohoe, T.J., OL, 5, 999 Takayama, H., OBC, 1, 1863 Bagley, M.C., OL, 5, 4421 Singh, V.K., JOC, 68, 3356 Paterson, I., OL, 5, 35 Smith, III, A.B., OL, 5, 4405 Myles, D.C., JOC, 68, 6646 Kita, Y., JACS, 125, 11235 Hutton, C.A., TL, 44, 4895 Yamada, Y., T, 59, 61 Kumaraswamy, G., OPP, 35, 603 Fukuyama, T., JACS, 125, 6636 Tietze, L.F., EJOC, 562 Kang, S.H., SL, 993

335

(-)-Dihydropinidine (• DMDP DMDP 2,2-Dimethyl- 1,25-dihyd roxy vitamin Ds Dimethyl Sulfomycinamate Diplodialide A (+)-Discodermolide (+)-Discodermolide (+)-Discodermolide Discorhabdin A Dityrosine Dolabellatrienone (• (+)-Duocarmycin A & SA seco-Duocarmycin SA (-)-Dysiherbaine

VIII.D.-E Hemdon, J.W., T. 59, 5609 Mulzer, J., JACS, 125, 4680 Rawal, V.H., JACS, 125, 13022 Rychnovsky, S.D., AG(E), 42, 1267 Eklund, P., OL, 5, 491 Eklund, P., OL, 5, 491 Fukuyama, T., JACS, 125, 8112 Cook, J.M., JOC, 68, 5852 Pyne, S.G., JOC, 68, 7818 Park, K.H., S, 2473 Kitahara, T., T, 59, 1773 Kitahara, T., T, 59, 1773 Davis, F.A., JOC, 68, 8061 Cook, J.M., JOC, 68, 5852 Pyne, S.G., TA, 14, 3885 Linker, T.,AG(E), 42, 2487 Okamura, H., T, 59, 10159 Garbaccio, R.M., TL, 44, 9185 Villamizar, J., JCR(S), 504 Mehta, G., TL, 44, 3569 Padwa, A., OL, 5, 5067 Hatakeyama, S., TL, 44, 8047 Martin, S.F., AG(E), 42, 3278 Ogasawara, K., CPB, 51, 104 Kobayashi, S., TL, 44, 9303 Huang, P.-Q., SL, 1663 Bach, T., S, 925

Egonol Elisabethin A Elisapterosin B (-)-Elisapterosin B (-)-Enterodiol (-)-Enterolactone (-)-Ephedrine A (-)-(E)-16-Epiaffinsinine (-)-7-Epiaustraline (+)-6-Epicastanospermine (+)-Epiepoformin (+)-Epiepoxydon (-)-Epimyrtine (+)-(E)-Epinormacusine B (-)-Epipentenomycin I (-)-Epipodophyllotoxin (+)-Epipoformin (+) & (-)-Epiuleine (+)-15,16-Epoxylabdatriene Epoxyquinol A & B (+)-Erysotramidine (+)-Erythravine Erythromycin B (+)-Estrone (+)-Ethosuximide (+)-O-Ethyl Febrifugine Eupomatenoid 3,4,5,6 & 15

ORGANIC SYNTHESISm2004

336

Nishiyama, S., TL, 44, 7949

Eurypamide A & B

VIII.D.-F Harayama, T., H, 59, 293 Snider, B.B. OL, 5, 451 Snider, B.B. OL, 5, 451 Cravotto, G., TL, 44, 8383 Blume, T., OL, 5, 1837 Theodorakis, E.A., OBC, 1, 4418 Roush, W.R., OL, 5, 377 Imanishi, T., JACS, 125, 8238 Evans, D.A., JACS, 125, 13531 Paleo, M.R., JOC, 68, 130 Jimenez, L.S., OL, 5, 785 Wentworth, Jr., P., JOC, 68, 8902 Piras, P.P., T, 59, 9433 Yus, M., EJOC, 2745 Couture, A., T, 59, 6615 Snider, B.B., JOC, 68, 545 Trost, B.M., JACS, 125, 13155

Fagaridine (+)-FD211 (• Ferujol FF-MAS Forbesione Formamicin Fostriecin (-)-FR 182 877 (+)-FR 900 482 FR-900 482 FR-901 375 Fraganol (-)-Frontalin Fumaridine (-)-Fumiquiazoline A,B,C,E, H&I Furaquinocin A,B & E

VIII.D.-G Raghavan, S., JOC, 68, 5754 Yamamoto, Y., JACS, 125, 46 Kadota, I., JACS, 125, 11893 Kadota, I., JACS, 125, 11893 Lee, H.-Y., TL, 44, 5803 Andrus, M.B., JOC, 68, 8162 Kamal, A., TL, 44, 8457 Kogen, H., T, 59, 1685 Ley, S.V., OBC, 1, 3263 Sasaki, M.,JACS, 125, 14294 Banwell, M.G., AJC, 56, 585 Couture, A., EJOC, 1231 Pilli, R.A., TL, 44, 8721 Piras, P.P., T, 59, 9433 Figueredo, M., JOC, 68, 2437 Snider, B.B., JOC, 68, 1030

Galantinic Acid Gambierol Gambierol

16-epi-Gambierol Gelastatin A & B (+)-Geldanamycin GL-331 Globomycin (-)-Gloeosporone Glymnocin A (+)-Goniodiol Goniopedalin (R)-Goniothalamin Grandisol (+)-Grandisol (+)-Guanacastepene A

VIII.D.-H Lee, V. T, 59, 1719 Kawasaki, T., TL, 44, 8849 Clive, D.L.J., A G(E), 42, 3406 Clive, D.L.J., TL, 44, 7731

Hachijodine F & G Hamacanthin A & B Hamigeran B (-)-Hamigeran B

SELECTED TOPICAL AREAS

337

6-epi-(-)-Hamigeran B (+)-Hapalindole ent-Haterumalide NA 15-epi-Haterumalide NA Methyl Ester (• B Li, Y., SC, 33, 1417 (-)-Heliannuol A Shishido, K., CC, 350 (-)-Heliannuol C Shishido, K., TL, 44, 8505 (+)-Heliannuol D Shishido, K., H, 61, 125 (• D Macias, F.A., T, 59, 1679 Nishiyama, S., SL, 411 Heliannuol E Nishiyama, S., TL, 44, 4877 Heliannuol E Shishido, K., SL, 2395 (-)-Heliannuol E Cordero, F.M., EJOC, 4373 (+)-Heliotridine Holton, R.A., JACS, 125, 7822 Hemibrevetoxin B Ley, S.V.,SL, 1186; HCA, 86, 3717 Herbarumin II Ghosh, S., T, 59, 5175 (+)-Herbertene Kita, Y., TL, 44, 411; JOC, 68, 5917 (-)-Herbertenediol Mukherjee, D., TL, 44, 737 (• Srikrishna, A., TL, 44, 1027 (• 1,13-Herberten ed iol Kita, Y., JOC, 68, 5917 (-)-Herbertenol Mukherjee, D., TL, 44, 737 (• & [3-Herbertenol Srikrishna, A., TL, 44, 1027 (• & 13-Herbertenol Chavan, S.P., T, 59, 2737 (• Joseph-Nathan, P., T, 59, 959 Heterocurvistone Gil, P., TA, 14, 1617 (R)-4-Hexanolide Lu, X., JOC, 68, 6463 (-)-Hinesol Steglich, W., S, 101 Hippadine Krische, M.J., AG(E), 42, 5855 (• Overman, L.E., AG(E), 42, 2528 Hodgkinsine Overman, L.E.,AG(E), 42, 2528 Hodgkinsine B Murphy, J.A., OBC, 1, 117 (• Goti, A., TL, 44, 2315 Hyacinthacine Izquierde, I., TA, 14, 3933 (+)-Hyacinthacine A2 Seifert, K., HCA, 86, 2009 Hyatellaquinone Gunes, M., T, 59, 8799 Hydrangenol Hesse, M., HCA, 86, 2028 (-)-3-Hydroxycelacinnine Gurjar, M.K., TL, 44, 4853 Hydroxyglimepriride Gung, B.W., JOC, 68, 5956 S-18-Hydroxyminguartynoic Acid Yadav, J.S., TL, 44, 2983 6-Hydroxy-4E-sphingenine Ma, D., OL, 5, 5063 Hyperaspine Ma, D., TL, 44, 8609 (-)-8-epi-Hyperaspine Carda, M., TL, 44, 1737 (+)-Hyptolide Mehta, G., TL, 44, 7049 Kerr, M.A., JACS, 125, 14120 Snider, B.B., OL, 5, 4385 Kigoshi, H., OL, 5, 957

VIII.D.-I, -J

Overman, L.E. AG(E), 42, 2525

Idiospermuline

338

ORGANIC SYNTHESISn2004

Imbiline 1 (+)-Imperanene (+)-Indolizidine 167D & 209D (-)-Indolizidine 209B Ingenol 6-epi-Inolizidine 223A allo, L & D-chiro,epi,myo & scyllo-lnositol (+)-Ipalbidine Honda, T., TL, 44, 3035 Ipalbidinium Bracher, F., M, 134, 573 Isoaltholaetone Yadav, J.S., TL, 44, 5831 Isocembrene Li, Y., TL, 44, 5921 Isocryptolepine Maes, B.U.W., SL, 615 Isodidehydrostemofoline Overman, L.E., JACS, 125, 15284 Isodomoic Acid G Montgomery, J., OL, 5, 3771 Isofagomine Guanti, G., TL, 44, 357 (+)-Isofebrifugine Huang, P.-Q., SL, 1663 (+)-Isofregenedol Marcos, I.S., TL, 44, 5419 Isokotanin A Muller, M., S, 1803 (+)-Isomenthone Gardiner, J.M., OL, 5, 467 Isonaamidine A & C Ohta, S., H, 60, 583 Smith, III, A.B., OL, 5, 587; HCA, 86, 3 9 0 8 (-)-21-1sopentenylpaxilline Molander, G.A., JOC, 68, 9 5 3 3 (+)-Isoschizandrin

Kitahara, Y., T, 59, 2885 Davies, H.M.L., TA, 14, 941 Baskaran, S., OL, 5, 583 Davis, F.A., OL, 5, 5011 Kuwajima, I., JACS, 125, 1498 Padwa, A., JOC, 68, 4371 Altenbach, H.-J., EJOC, 1958

VIII.D.-J Simpkis, N.S. OL, 5, 535 Paquette, L.A., JACS, 125, 1567 Zanoni, G., JOC, 68, 6005

Jamtine Jatrophatrione J2 Isoprosane

VIII.D.-K Anderson, J.C., JOC, 68, 6160 Trost, B.M. OL. 5, 1467 White, J.D., CC, 2012 Booker-Milburn, K.I., OL, 5, 3309 Yokokawa, Y., CL, 32, 844 Knolker, H.-J., H, 60, 1049 Muller, M., S, 1803 Cook, J.M., TL, 44, 8013

(+)-Kainic Acid (+)-a-Kainic Acid (+)-Kalkitoxin (+)-Kessane (+)-KODA Koeniginequinone A & B Kotanin (-)-Koumidine

VIII.D.-L Rao, B.V. TL. 44, 915 Huang, P.-Q., OL, 5, 1927 Scheinmann, F., TA, 14, 567 Chavan, S.P., JOC, 68, 6817

L-733,060 (+)-L-733,060 LAAM L-CCG-I

SELECTED TOPICAL AREAS

Minnikin, D.E., TA, 1211 Danishefsky, S.J., A G(E), 42, 5629 Iwao, M., TL, 44, 4443 Tadano, K., SL, 2252 Kana, S.H., AG(E), 42, 4779 Lee, E., JOC, 69, 8080 Davis, F.A., OL, 5, 3855 Couture, A., TA, 14, 1309 Furstner, A., AG(E), 42, 5358 Mulzer, J., JOC, 68, 3026 Suzuki, T., TL, 44, 3175 Lowary, T.L., TA, 14, 737 Araki, S., S, 751 Stoltz, B.M., JACS, 125, 15000 Nagasaka, T., H, 59, 527 Kim, G, TL, 44, 8207 Ichikawa, Y. SL, 1034 Zhou, W.-S., TL, 44, 497 Sha, C.-K., TL, 44, 499 Sha, C.-K., TL, 44, 499 Hunter, R., SL, 271 Marshall, J.A., JOC, 68, 7428 Nan, F., JOC, 68, 1636 Paterson, I., AG(E), 42, 343 Crimmins, M.T., OL, 5, 4641 Carreira, E.M., JOC, 68, 9274 Fukuyama, T., JACS, 125, 4048 Ohta, S., JOC, 68, 1217 Cuny, G.D., TL, 44, 8149 Estevez, R.J., T, 59, 8057 Le Drian, C., HCA, 86, 661 Stratakis, M., AG(E), 42 5465 Porco, Jr., J.A., JACS, 125, 7889 Mander, L.N., AJC, 56, 805 Kelly, T.R., JOC, 68, 4970 Harayama, T., SL, 847 Mas,T., S, 1878 Tomioka, K., OL, 5, 1122

339

(11R,12s)-Lacrobacillie Acid Lactonamycinone Lamellarin G Trimethyl Ether (-)-Lasiol (+)-Lasonolide A Lasonolide A (-)-Lasubine I (+) & (-)-Latifine Latrunculin B Laulimalide (+)-Laurallene

trans-(+)-La u red iol Lavandulol (-)-Lemonomycin Lennoxamine Lennoxamine Lentiginosine Lentiginosine (• (• l-epi-Len tigin osin e Lepadifprmine Leptofuranin D Leucamide A (+)-Leucascandrolide A (+)-Leucascandrolide A Leucascandrolide A Leustroducsin B (• A (• Litebamine (-)-Lithospermoside Litseaverticillol A,C,D,F & G Lobatamine C Longirabdolactone Lousianin C Luotonin A & B Luteolinidin Chloride (• & ~-Lycorane

VIII.D.-M Cook, J.M., JOC, 68, 6279 Tadano, K. JACS, 125, 14722 Crimmins, M.T., OL, 5, 4641 Gunes, M., T, 59, 8799 Takahashi, T., TL, 44, 8857 Sharma, G.V.M., TL, 44, 8161 Cook, J.M., JOC, 68, 6279

Macalstonidine (+)-Macquarimicin A Macrolactone Macrophyllol Macrosphelide A Macrosphelide C & F (+)-Majvinine

340

Hanessian, S., OL, 5, 4277 Carda, M., T, 59, 857 Koumbis, A.E., TL, 44, 2513 Kocienski, P.J., JOC, 68, 4008 Knight, J.G., T, 59, 281 Ito, Y., CEJ, 9, 1435 Whitehead, R.C., SL, 651 Henegar, K.E., JHC, 40, 601 Greene, A.E., AG(E), 42, 5059 Guillou, C., OL, 5, 1845 Ma, D., JOC, 68, 442 Pons, J.-M., SL, 107 Eklund, P., OL, 5, 491 Marshall, J.A., OL, 5, 1729 Inoue, M., JACS, 125, 10772 Cook, J.M., JOC, 68, 6279 Nakahara, S., H, 60, 2717

ORGANIC SYNTHESISm2004

Malayamycin A (+) & (-)-Malyngolide (-)-Malyngolide (+)-Manaolide D-Mannolactam Mannosyl Tryptophan Manzamenone A Mappicine Mappicine Ketone (• Martinellic Acid (• (-)-Matairesinol (+) & (-)-Membrenone C Merrilactone A (+)-10-Methoxyaffinisine 9-Methoxy-9-Deethoxycribrostatin 6 Watanabe, T., OBC, 1, 3024 12-Methoxydihydrochelerythrine Zard, S.Z., OL, 5, 3717 O-Methylasparvenone Panek, J.S., OL, 5, 1991 Methyl-L-Callipeltose Kraus, G.A., JOC, 68, 4517 O-Methyl Claussequinone Hsung, R.P., OL, 5, 3935 Methyl Daurichromenic Ester Cook, J.M., TL, 44, 543; JOC, 68, 7565 (+)-Na-Methyl-16epipericyclivine Bennasar, M.-L., TA, 14, 469 (-)-Na-Methylervitsine Venkateswaran, V., T, 59, 8375 O-Methyl epi-Heliannual E Nicolaou, K.C., AG(E), 42, 4225 1-O-Methyllateriflorone Mukherjee, D., TL, 44, 4835 Methyl (• carpate Jeong, J.W., SL, 391 Methyl (-)-Nonactate Cheng, M.S., JOC, 68, 3658 Methyl Protodioscin (+)-Na-Methylsarpagine Cook, J.M., JOC, 68, 6279 Cook, J.M., JOC, 68, 7565 (+)-Na-Methylvellosimine Czarnocki, Z., TA, 14, 3335 (R)-(-)-Mianserin Gurjar, M.K., TL, 44, 2873 Microcarpalide Ma, D., AG(E), 42, 5348 Microsclerodermin E (+)-Migrastatin Danishefsky, S.J., JACS, 125, 6042 Pettus, T.R.R., SL, 2234 Mimosifoliol (• Kalaus, G., T, 59, 5661 Mitomycin Jimenez, L.S., OL, 5, 785 Larsen, D.S., TL, 44, 5193 MM 47755 Pattenden, G., T, 59, 2701 Mollamide Tamura, R.A., CC, 2678 (-)-Monatin Kim, G., JOC, 59, 5395 (+)-Monomorine Yamauchi, S., OBC, 1, 1323 Morinol C & D Tanaka, T., CEJ, 9, 389 Mosin B

SELECTED TOPICAL AREAS

Takahashi, S., T, 59, 1627 Knolker, H.-J., T, 59, 5317 Knolker, H.-J., T, 59, 5317 Popsavin, V., TL, 44, 8897 Raghavan, S., TA, 14, 101 Yoshimitsu, T., JOC, 68, 7548 Knolker, H.-J., H, 60, 1049 Ariza, X., TA, 14, 1127 Furstner, A., A G(E), 42, 308 Ferraz, H.M.C., 7', 59, 5817 Shioiri, T., T, 59, 6579 Lazzaroni, R., TA, 14, 1447

341

Muconin Mukonidine Mukonine (+) & (-)-Muricatacin (-)-Muricatacin (-)-Muricatacin Murrayquinone A Musclide A1, A2 & B (R)-(+)-Muscopyridine (• Mycothiazole (S)-(-)-Myrmicarin 217

VIII.D.-N Nishida, A. JACS, 125, 7484 Bonjoch, J., JOC, 68, 7400 Liu, H.-J., T, 59, 1209 Rando, R.R., BMCL, 13, 901 Rault, S., JOC, 68, 10178 Katoh, T., SL, 329 Katoh, T., SL, 329 Kim, D., TL, 44, 6609 Hesse, M., HCA, 86, 465 Maycock, C.D., OL, 5, 4097 Reiser, O., CEJ, 9, 260 Iwao, M., TL, 44, 4443 Gupton, J.T., T, 59, 207 Ley, S.V., H, 60, 2707 Clive, D.L.J., CC, 2464 Cook, J.M., JOC, 68, 7565 Zard, S.Z., OL, 5, 3717 Ley, S.V., AG(E), 42, 5996 Kamal, A., TL, 44, 8457 Cuny, G.D., TL, 44, 8149

Nakadomarin A (-)-Nakamurol A Nanaimoal (+) & (-)-Neamine Nemertelline (+)-Neoavarol (-)-Neoavarone (+)-Neoisoprelaurefucin (-)-(s)-Neoperiphylline (+)-Nephrosteranic Acid (-)-Nephrosteranic Acid Ningalin B Ningalin B Hexamethyl Ether (-)-Norarmepavine (+)-Norcardione A (+)-Normacusine B 10-Norparvulenone Nortrilobolide NPF (•

VIII.D.-O Crimmins, M.T. JACS, 125, 7592 Ganesan, A., OL, 5, 2825 Corey, E.J., JACS, 125, 5628 Kobayashi, Y., JOC, 68, 7825 Steel, P.G., OL, 5, 239 Tian, W., TL, 44, 9375 Katoh, T., OL, 5, 3903 Mehta, G., TL, 44, 6733 Katoh, T., SL, 2401 Zhai, H., T, 59, 9379

(+)-Obtusenyne (+)-Okaramine J Okaramine N OPC-8:0 (-)-Oryzoxymycin OSW-1 Aglycone Ottelione A & B Ottelione A & B 3-epiOttelione A Oxerine

342

Porco, Jr., J.A., JACS, 125, 6040 Kobayashi, Y., JOC, 68, 7825

ORGANIC SYNTHESISn2004

Oximidine II 12 Oxo-PDA

VIII.D.-P Palominol Yamada, Y., T, 59, 61 (-)-Panarine Cook, J.M., TL, 44, 543 Panaxytriol Yun, H., JOC, 68, 4519 Panepophenanthrin Baldwin, J.E., OL, 5, 2987 (+)-Panepophenanthrin Porco, Jr., J.A.,AG(A), 42, 3913 Paraherquamide A Williams, R.M. JACS, 125, 12172 Passifloricin Acid Murga, J., TL, 44, 7909 (+)-Patulolide A Zercher, C.K., JOC, 68, 1878 (• B Zercher, C.K., JOC, 68, 1878 (+)-Patulolide C Shibasaki, M., OL, 5, 3021 Pedunculagin Khanbabaee, K., EJOC, 2128 De Brabander, J.K., AG(E), 42, 1648 Peloruside A Peloruside A Taylor, R.E., OL, 5, 4959 Penaresidin B Yoda, H., TL, 44, 977 rac-Peniolactol Saeed, A., M, 134, 457 (-)-Penitrem D Smith, III, A.B., JACS, 125, 8228 (+) & (-)-Pentenomycin Rao, B.V., TL, 44, 5103 Perfragilin A & B Schmitz, F.J., T, 59, 1349 Permethyl Storniamide A Iwao, M., TL, 44, 4443 (-)-PF 1163B Gesson, J.-P., OL, 5, 4049 Phebalosin Lauret, C., T, 59, 4363 (• A1 Snider, B.B., OL, 5, 765 (+)-Phomactin Halcomb, R.L., JACS, 125, 1712 (• A Pattenden, G., OBC, 1, 3949, 3917 Phomoidride B Fukuyama, T., OL, 5, 2235 Phorboxazole A Pattenden, G., AG(E), 42, 1255 Phorboxazole A Williams, D.R., AG(E), 42, 1258 (+)-Phorboxazole A Pattenden, G., OBC, 1, 4173 Photodeoxytridachione Trauner, D., AG(E), 42, 549 Phyllodulcin Gunes, M., T, 59, 8799 (-)-Phyllostine Okamura, H., T, 59, 10159 (+)-Phyltetralin Brun, P., EJOC, 1410 d,l-Physostigmine Johnson, F., JOC, 68, 6133 Phytoprostane 1 & 2 Spur, B.W., TL, 44, 7411 Phytoprostane F1 Durand, T., TL, 44, 2105 D-ribo-C 18-Phytosph in gosin e Kumar, P., TL, 44, 1035 Phytuberin Suarez, E., JOC, 68, 4422 (-)-~-Pinguisene Sha, C.-K., JOC, 44, 8704 (-)-Pinguisenol Sha, C.-K., JOC, 44, 8704 (• Acid Arimoto, H., H, 59, 441 (~=)-Pinnatal Trauner, D., JACS, 125, 9554 Piperolactam C Couture, A., EJOC, 1231 (-)-Pironetin Dias, L.C., OL, 5, 265

SELECTED TOPICAL AREAS

Mehta, G., TL, 44, 5243 Mehta, G., TL, 44, 5243 Py, S., OL, 5, 4081 Raghavan, S., TL, 44, 6713 Dodd, R.H., JOC, 68, 9521 Ley, S.V., OBC, 1, 3957 Csaky, A.G., SL, 2092 Chakraborty, T.K., TL, 44, 2541 Pihko, P.M., TL, 44, 7607 Enders, D., SL, 2182 Pons, J.-M., SL, 107 Kobayashi, S., JACS, 125, 3793 Dikshit, D.K., SL, 1737 Raghavan, S., T, 59, 10307 Zanoni, G., JOC, 67, 6437 Reiser, O., CEJ, 9, 260 Mukherjee, D., TL, 44, 4985 Kawasaki, T., TL, 44, 1591 Li, Y., SL, 1977 Corey, E.J., JACS, 125, 13486 Hayashi, Y., OL, 5, 2287 Huang, S.-T., T, 59, 1277 Balme, G., OBC, 1, 4209 Balme, G., OBC, 1, 4209 Lee, D.Y.W., TL, 44, 6857 Lauret, C., T, 59, 4363 Takahashi, S., OL, 5, 1353 Kiyota, H., SL, 219 Morimoto, Y., OL, 5, 2611 Argade, N.P., S, 2304

343

Pleurotellic Acid Pleurotellol PM-94128

(+)-Polyoxamic Acid (-)-Polyoxamic Acid Polysphorin (+)-Prelactone B (+)-Prelactone B (+)-Prelactone B (+)-Prelactone B & V (• B (+)-Prelactone C Preussin (+)-ereussin Prostaglandin J2 (-)-Protopraesorediosic Acid (• (-)-Pseudophrynaminol Pseudoplexaurol Pseudopteroxazole Pseurotin A Pterulinic Acid Pterulone

Pterulone B Puerarin Puetuberosanol Pyranicin (• (-)-Pyrinodemin A Pyrrolidine-2,5-dicarboxylic Acid

VIII.D.-Q, -R Andrus, M.B., JOC, 68, 8162 Zhang, X. JOC, 68, 4523 Toyooka, N., TL, 44, 569

(-)-O-Quinoceldanamycin Quinolactone A & B (+)-Quinolizidine 2071

Boger, D.L. JACS, 125, 1877 Boger, D.L. JACS, 125, 1877 Rizzacasa, M.A., OBC, 1, 2044 Bailey, P.D., CC, 2800 Gross, J.L., TL, 44, 8563 Valla, A., TL, 44, 5789 Canwell, M.G., OBC, 1,296 Rivett, D.E.A., T, 59, 165 Leahy, J.W., JOC, 68, 4215 Hsung, R.P., OL, 5, 3935

Ramoplanin A2 Ramoplanose Aglycon (+)-Raspailol A & B (-)-Raumacline Repinotan E-Retinoic Acid (• Rhinocerotinoic Acid Rhizoxin D Rhododaurichromanic Acid A &B

344

Ogasawara, K., H, 59, 485 Kim, G., TL, 44, 3051 Krische, M.J., OL, 5, 1737 Danishefsky, S.J., CEJ, 9, 3242 Riera, A., OL, 5, 3001 Reiser, O., CEJ, 9, 260 Fensterbank, L., AG(E), 42, 5342 Crimmins, M.T., OL, 5, 3009 Rizzacasa, M.A., OBC, 1, 2044 Evans, D.A., JACS, 125, 10899 Zhu, J., AG(E), 42, 4238 Groth, U., SL, 1886

ORGANIC SYNTHESIS--2004

(+)-Rhopaloic Acid L-Ribose (• A Rishirilide B Ristosamine (-)-Roccellanic Acid

(+)-erythro-Roccellic Acid (+)-Rogioloxepane A (+)-Rottnestol (+)-Roxaticin RP-66453 (+)-Rubiginone BE

VIII.D.-S Perez-Prieto, J. TL, 44, 6683 Pinto, B.M., SL, 1259 Rizzacasa, M.A., JOC, 68, 2200 Georg, G.I., JOC, 68, 10030 Majetich, G., OL, 5, 3847 Bai, D., SC, 53, 3355 Silverman, R.B., JOC, 68, 8774 Delfourne, E., TL, 4, 2473 Passarella, D., JOC, 68, 9525 Davis, F.A., OL, 5, 925 Sonnet, P., TL, 44, 3293 De, A., T, 59, 1339 Gill, M., AJC, 56, 49 Kogen, H., T, 59, 1685 Trost, B.M., AG(E), 42, 3943 Muller, M., S, 1803 Jianc, B., JOC, 68, 2376 Chen, Q., SC, 33, 2125 Lygo, B., TL, 44, 2529 Mander, L.N., OL, 5, 1321 Ham, W.-H., TA, 14, 87 Davies, S.G., CC, 2132 Marco, J.A., JOC, 44, 5672 Williams, R.M., OL, 5, 3135 Carreira, E.M., AG(E), 42, 694 Imanishi, T., OL, 5, 2683 Arno, M., JOC, 68, 1242 Seifert, K., HCA, 86, 2009 Smith, III, A.B., OL, 5, 761 Zhou, W.-S., OL, 5, 3257 Kende, A.S., OL, 5, 1785 Kende, A.S., JOC, 68, 7422 Prabhakar, S., TL, 44, 2577

Sabina Ketone Salacinol Salicylihalamide A & B (+)-Salieylihalamide A & B (+)-Salvadione A Sarmentosin Seytalidamide A Sebastianine A Sedamine (+)-Sedridine Segetalin B & G (+)-Semivioxanthin (R)-Semixanthomegnin SF-1902 A2 (-)-Siccanin Siderin Slagenin A,B & C

trans-(+)-Sob rerol (• A&B Sordarcin (+)-Spectaline Sperabillin B & D Spicigerolide Spirotryprostatin A (-)-Spirotryprostatin B (+)-Spiroxin C (-)-S pon gia n- 16-oxo- 17-al Spongiaquinone (+)-Spongistatin 1 Squalamine Stachybotrylactam (-)-Stachybotrylactam Staurosporinone

SELECTED TOPICAL AREAS

Williams, D.R., OL, 5, 361 Trauner, D., JACS, 125, 9554 Harmata, M., OL, 5, 59 Cossy, J., OL, 5, 1995 Couture, A., EJOC, 1231 Mori, M., JACS, 125, 9801 Nakahara, S., H, 60, 2017 Banwell, M.G., AJC, 56, 585 Mori, K., EJOC, 848 Basabe, P., T, 59, 9173 Genet, J.-P., TL, 44, 6383 Lindel, T., ZN(B), 586, 451

345

(-)-Stemonine (• A (• (+)-Strictifolione Stigmalactam (-)-Strychnine Styelsamine C Styryllactone (-)-Subersic Acid (+)-Subersic Acid Sulfobacin A Sventrin

VIII.D.-T (-)-TAN-2483A Snider, B.B. OL, 5, 451 (• Hsung, R.P. OL, 5, 4709 (• Jokela, R., T, 59, 8589 Tanikolide Zhai, H., TL, 44, 2893 (+)-Tanikolide Carda, M., T, 59, 857 (+)-Tanikolide Koumbis, A.E., TL, 44, 2513 Tanshinon IIA Lu, W., TL, 44, 2073 Tarchonanthuslactone Enders, D., EJOC, 4450 Taurospongin A Ley, S.V., OBC, 1, 1664 Boland, W., T, 59, 149 Tetrahydrodicranenone B (-)-Tetrangomycin Larsen, D.S., TL, 44, 5193 McLeod, M.D., AJC, 56, 795; TL, 44, 2869 (-)-Tetrahydrolipstatin Isobe, M., JACS, 125, 8798 Tetrodotoxin Du Bois, J., JACS, 125, 11510 (-)-Tetrodotoxin Liu, H.-J., AG(E), 42, 1851 Teucin Liu, H.-J., AG(E), 42, 1851 12-epi-Teucin Ley, S.V., AG(E), 42, 5996 Thapsivillosin F Tjipanazole B,D,E & I Kuethe, J.T., OL, 5, 3721 Furstner, A., A G(E), 42, 5361 TMC-69-6H Inoue, M., AG(E), 42, 2654 TMC-95A Hibino, S., H, 60, 13 TMC-120B Mukherjee, D., TL, 44, 737 (+)-Tochuinyl Acetate Porco, Jr., J.A., JACS, 125, 5095 (§ Acid Marcos, I.S., TL, 44, 8831 (+)-Totarol Hatakeyama, S., OL, 5, 857 (• Acid Ley, S.V., AG(E), 42, 5996 Trilobolide Gundersen, L.-L., T, 59, 115 (+) & (-)-Trixagol Pattenden, G., T, 59, 2713 Trunkamide A Menendez, J.C., JOC, 68, 6944 Tryprostatin B Schore, N.E., T, 59, 5377 (• Jamison, T.F., JACS, 125, 11514 (-)-Terpestacin Mori, M., JACS, 125, 9801 (-)-Tubifoline

346

ORGANIC SYNTHESISm2004

Sarabia, F., OBC, 1, 3716 Spilling, C.D., JOC, 68, 9502

Tunicaminyl Uracil (s)-(+)-at'-Turmerone

VIII.D.-U, -V, -W, -Y, -Z Takayama, H. OL, 5, 2967 Wandless, T.J., JACS, 125, 6864

Us-7 & 8 Usitiloxin D

Hagiwara, H. TL, 44, 1595 Molina, P., JOC, 68, 489 Alvarez, M., TL, 44, 6191 Alvarez, M., JOC, 68, 10020 Huang, P.-Q., H, 60, 1833 Cook, J.M., JOC, 68, 7565 Kalaus, G., T, 59, 5661 Paquette, L.A., JOC, 68, 6096 Kogen, H., AG(E), 42, 2540 Sabitha, G., S, 2699 Pare, P.W., TL, 44, 831

Valeriananoid D Variolin B Variolin B Variolin B (s)-Vasicol (+)-Vellosimine (• Vinigrol Virantmycin (+)-Virol C Volicitin

Bach, T., AG(E), 42, 4685 Chen, J.H., JOC, 68, 8500 Furstner, A., CEJ, 9, 307, 320 Ruchirawat, S., SL, 1037

(+)-Wailupemycin B Wedelolactone Woodrosin Writghiadione

Ye, T. OL, 5, 2821

Yanucamide A

Hashimoto, S AG(E), 44, 5351 Hoye, T.R., JACS, 125 9576 Meyer, C., OL, 5, 4037

Zaragozic Acid C Zampanolide Zincophorin Methyl Ester

VIII.E. Reactions in Aqueous Media

VIII.E.I-1 Li, C.-J. et al., EJOC, 998. "Ruthenium-Catalyzed Tandem Olefin Migration/Aldol and Mannich-Type Reaction in Water and Protic Solvents." VIII.E.1-2 Darbre, T.; Machuqueiro, M., CC, 1090. "Zn-Proline Catalyzed Direct Aldol Reaction in Aqueous Media." VIII.E.1-3 Sinou, D. et al., TA, 14, 3891. "Catalytic Asymmetric Alkylation in Water in the Presence of Sufactants: Influence of the Nature of the Nucleophile and the Allylic Acetate on the Activity and Enantioselectivity."

SELECTED TOPICAL AREAS

347

VIII.E.1-4 Liu, L.; Guo, Q.-X. et al., OL, 5, 1833. "Novel Carbonyl Allylation Mediated by SnCI2/TiCI3 in Water." VIII.E.1-5 Loh, T.-P. et al., TL, 44, 911. "Indium-Mediated Allylation of Carbonyl Compounds with an Allylic Bromide in Aqueous Media: Anomolous syn-Diastereoselectivity Regardless of Allylic Bromide Geometry." VIII.E.1-6 Welch, J.T. et al., T, 59, 10031. "Indium- and Zinc-Mediated Allylation of Difluoroacetyltrialkylsilanes in Aqueous Media." VIII.E. 1-7 Loh, T.-P. et al., S, 755. "Indium-Mediated Allylation Reaction in Aqueous Media: Synthetic Studies Towards the Total Synthesis of Dysiherbaine." VIII.E.1-8 Kim, Y. et al., S, 775. "Palladium-Catalyzed Allylation of Carbonyl Compounds with Various Allylic Compounds Using In-lnCl3 in Aqueous Media." VIII.E.1-9 Kobayashi, S. et al., CC, 676. "Allylation Reactions of Carbonyl Compounds Using an Organosilicon Reagent in Aqueous Media." VIII.E.I-10 Manabe, K.; Kobayashi, S., SL, 5, 3241. "Palladium-Catalyzed, Carboxylic Acid-Assisted Allylic Substitution of Carbon Nucleophiles with Allylic Alcohols as Allylating Agents in Water." VIII.E.I-ll Naito, T. et al., OL, 5, 3835. "Indium-Mediated Tandem Radical Addition-Cyclization-Trap Reactions in Aqueous Media." VIII.E.I-12 Knight, D.A.; Schull, T.L., SC, 33, 827. "Rhodium Catalyzed Allylic Isomerization in Water."

348

ORGANIC SYNTHESISm2004

VIII.E.I-13 Estevam, I.H.S.; Bieber, L.W., TL, 44, 667. "Barbier-Type Allylation of Iminium Ions Generated In Situ in Aqueous Medium." VIII.E.I-14 Li, C.-J. et al., JACS, 125, 4062. "The Barbier-Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in Water." VIII.E.I-15 Jiang, J.; Lai, Y.-H., TL, 44, 1271. "A Novel Birch Reduction of Aromatic Compounds Using Aqueous Titanium Trichloride: Anions of trans-lOb,lOc-Dimethyl-2,7,1Ob,lOetetrahydropyrene." VIII.E.I-16 Xia, C.-G. et al., SL, 2246. "Efficient Lewis Base-Catalyzed Conjugate Addition of Azide Ion to Cyclic Enones in Water." VIII.E.I-17 Wender, P.A. et al., SL, 1295. "Rhodium-Catalyzed [5+2] Cycloaddition Reactions in Water." VIII.E.I-18 Ikushima, Y. et al., CC, 1548. "Noncatalytic Heck Coupling Reaction Using Supercritical Water." VIII.E.I-19 Cordova, A.; Barbas, III, C.F., TL, 44, 1923. "Direct Organocatalytic Asymmetric Mannich-Type Reactions in Aqueous Media: One-Pot Mannich-Allylation Reaction." VIII.E.1-20 Matsukawa, S.; Hinakubo, Y., OL, 5, 1221. "Samarium(lI)-Mediated Pinacol Coupling in Water: Occurence of Unexpected Disproportionation and Action on Low-Valent Samarium as an Active Species." VIII.E.1-21 Uozumi, Y.; Kobayashi, Y., H, 59, 71. "The Sonogashira Reaction in Water via an Amphiphilic ResinSupported Palladium-Phosphine Complex under Copper-Free Conditions."

SELECTED TOPICAL AREAS

349

VIII.E.1-22 Menendez, J.C. et al., SL, 2159. "Practical and User-Friendly Procedure for Michael Reactions of ctNitroketones in Water." VIII.E.1-23 Krafft, M.E. et al., TL, 44, 3417. "Aqueous-Phase, Thermal Pauson-Khand Reactions in the Presence of Surfactants." VIII.E.1-24 Chung, Y.K. et al., S, 2169. "Rh(I)-Catalyzed Asymmetric Intramolecular Pauson-Khand Reaction in Aqueous Media." VIII.E.1-25 Prajapati, D. et al., TL, 44, 6755.

"Indium-Mediated Propargylation of Imines and Imine Oxides in Aqueous Media: Propargylation of C=N- Centres." VIII.E.1-26 Wang, L.; Li, P., SC, 33, 3679. "Sonogashira Coupling Reaction with Palladium Powder, Potassium Fluoride in Aqueous Media." VIII.E.1-27 Van der Eycken, E. et al., EJOC, 4713. "Transition-Metal-Free Sonogashira-Type Coupling Reactions in Water." VIII.E.1-28 Williams, J.M.J. et al., TL, 44, 5095. "Suzuki Cross-Coupling Reactions Using Reverse-Phase Glass Beads in Aqueous Media." VIII.E.1-29 Ballini, R., JOC, 68, 9173. "Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, 8Nitroalkanois, and Hydroxy Tetrahydrofurans," VIII.E.1-30 Kobayashi, S. et al., OL, 5, 101. "Hydrophobic Polymer-Supported Catalyst for Organic Reactions in Water: Acid-Catalyzed Hydrolysis of Thioesters and Transprotection of Thiols."

350

ORGANIC SYNTHESIS--2004

VIII.E.1-31 Pizzo, F.; Vaccaro, L. et al., SL, 2293. "ZnCI2 as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium." VIII.E.1-32 Pizzo, F. et al., JOC, 68, 8248. "Zn(II)-Catalyzed Thiolysis of Oxiranes in Water under Neutral Conditions." VIII.E.1-33 Henin, F.; Muzart, J. et al., TL, 44, 8099. "Water-Mediated Transition-Metal-Free Tsuji-Trost-Type Reaction." VIII.E.1-34 Leadbeater, N.E.; Marco, M., JOC, 68, 888. "Rapid and Amenable Suzuki Coupling Reaction in Water Using Microwave and Conventional Heating." VIII.E.1-35 Nakamura, E. et al., OL, 5, 4461. "Synthesis of Fullerene Glycoconjugates Through Sulfide Connection in Aqueous Media." VIII.E.1-36 Matsumura, Y. et al., TL, 44, 5519. "Indium-Mediated Nucleophilic Substitution Reaction of [3,vUnsaturated ~-Methoxypiperidine Derivative in Water." VIII.E.1-37 Bandgar, B.P.; Makone, S.S., SL, 262. "Organic Reactions in Water: Highly Rapid CAN Mediated One-Pot Synthesis of Nitriles from Aldehydes under Mild Conditions." VIII.E.1-38 Bhattacharya, P.K. et al., OL, 5, 3967. "Water Exclusion Reaction in Aqueous Media: Nitrone Formation and Cycloaddition in a Single Pot." VIII.E.1-39 Li, C.-J. et al., TL, 44, 153. "InCl3-Catalyzed Reaction of Aromatic Amines with Cyclic Hemiacetals in Water: Facile Synthesis of 1,2,3,4-Tetrahydroquinoline Derivatives."

SELECTED TOPICAL AREAS

351

VIII.E.1-40 Comdom, R.F.P. et al., SC, 33, 1771, 1783. "Synthesis of N-Phenylanthranilic Acid Derivatives Using Water as Solvent in the Presence of Ultrasound Irradiation." VIII.E.1-41 Yadav, J.S. et al., JOC, 68, 2525. "[Bmim]PF6: A Novel and Recyclable Ionic Liquid for Conversion of Oxiranes to Thiiranes in Aqueous Media."

VIII.E.1-42 Prajapati, D.; Sandhu, J.S. et al., CL, 32, 258. "Potassium Triiodide. A New and Efficient Catalyst for C a r b o n - Carbon Bond Formation in Aqueous Media." VIII.E.1-43 Xia, C. et al., AG(E), 42, 1042. "Chiral-Mn(Salen)-Complex-Catalyzed Kinetic Resolution of Secondary Alcohols in Water." VIII.E.1-44 Miyamoto, H. et al., TL, 44, 6963. "Carbon--Carbon Bond Formation Using Bismuth in a Water Medium."

VIII.E.2 Reactions in Ionic Liquids VIII.E.2-1 Yadav, J.S. et al., TL, 44, 2217. "[Bmim]BF6 and BF4 Ionic Liquids as Novel and Recyclable ReactiOn Media for Aromatic Amination." VIII.E.2-2 Hagiwara, H. et al., SL, 873. "Sustainable Self-Aldol Condensation of Unmodified Aldehyde: A Combination of Ionic Liquid and Heterogeneous Secondary-Amine Grafted on Silica." VIII.E.2-3 Bernini, R. et al., TL, 44, 8991. "CH3ReO3/H202 in Room Temperature Ionic Liquids: An Homogeneous Recyclable Catalytic System for the Baeyer-Villiger Reaction."

352

ORGANIC SYNTHESIS--2004

VIII.E.2-4 Chen, Z.-C. et al., SC, 33, 2817. "Organic Reactions in Ionic Liquids: Alkylation of Meldrum's Acid." VIII.E.2-5 Ross, J.; Xiao, J., CEJ, 9, 4900. "The Effect of Hydrogen Bonding on Allylic Alkylation and Isomerization Reactions in Ionic Liquids." VIII.E.2-6 Calo, V. et al., EJOC, 1382. "Arylation of Allylic Alcohols in Ionic Liquids Catalyzed by a PdBenzothiazole Carbene Complex." VIII.E.2-7 Zheng, X.; Zhang, Y., SC, 33, 161. "SmI3 Catalyzed Condensation of Aliphatic Cycloketones and Aldehydes in Ionic Liquid." VIII.E.2-8 Ko, S.Y. et al., HCA, 86, 894. "Acceleration of the Baylis-Hillman Reaction in the Presence of Ionic Liquids." VIII.E.2-9 Lee, S. et al., SC, 33, 2301. "Thermal Behaviors of Ionic Liquids under Microwave Irradiation and Their Application on Microwave-Assisted Catalytic Beckmann Rearrangement of Ketoximes." VIII.E.2-10 Srinivasan, K.V. et al., TL, 44, 1815. "Ionic Liquid Promoted Regioselective Monobromination of Aromatic Substrates with N-Bromosuccinimide." VIII.E.2-11 Han, B. et al., JCR(S), 549. "Oxidative Carbonylation of Methanol to Dimethyl Carbonate in Ionic Liquid 1-Butyl-3-methylimidazolium Hexafluorophosphate." VIII.E.2-12 Gigante, B. et al., TL, 44, 6813. "Vanadyl Salen Complexes Covalently Anchored to an Imidazolium Ion as Catalysts for the Cyanosilylation of Aldehydes in Ionic Solvent."

SELECTED TOPICAL AREAS

353

VIII.E.2-13 Gois, P.M.P.; Afonso, C.A.M., TL, 44, 6571. "Dirhodium(II)-Catalyzed C m H Insertion on ~-Diazo-e~-phosphonoacetamides in an Ionic Liquid." VIII.E.2-14 Kemperman, G.J. et al., EJOC, 1681. "Cleavage of Aromatic Methyl Ethers by Chloroaluminate Ionic Liquid Reagents." VIII.E.2-15 Chandrasekhar, S. et al., TL, 44, 3629. "The First Corey-Chaykovsky Epoxidation and Cyclopropanation in Ionic Liquids." VIII.E.2-16 Wolan, A.; Zaidlewicz, M., OBC, 1, 3274. "Synthesis of Arylboronates by the Palladium Catalyzed CrossCoupling Reaction in Ionic Liquids." VIII.E.2-17 Kabalka, G.W. et al., OL, 5, 893. "Rhodium-Catalyzed Cross-Coupling of Allylic Alcohols with Aryland Vinylboronic Acids in Ionic Liquids." VIII.E.2-18 Barhdadi, R. et al., CC, 1434. "Room Temperature Ionic Liquids as New Solvents for Organic Electrosynthesis. The First Examples of Direct or Nickel-Catalyzed Electroreductive Coupling Involving Organic Halides." VIII.E.2-19 Qiao, K.; Deng, Y., TL, 44, 2191. "A Novel Reaction in Ionic Liquids: Selective Cyclization of 1Dodecane under Moderate Pressure." VIII.E.2-20 Sega, A. et al., TL, 44, 5327. "l,3-Cycloaddition of Nitrile Oxides in Ionic Liquids. An Easier Route to 3-Carboxy Isoxazolines, Potential Constrained Glutamate Acid Analogues." VIII.E.2-21 Zambrano, J.L.; Dorta, R., SL, 1545. "Improving the Dakin Reaction by Using an Ionic Liquid Solvent."

354

ORGANIC SYNTHESISn2004

VIII.E.2-22 Meracz, I.; Oh. T., TL, 44, 6465. "Asymmetric Diels-Alder Reactions in Ionic Liquids." VIII.E.2-23 Yadav, J.S. et al., T, 59, 1599. "Aza-Diels-Alder Reactions in Ionic Liquids: A Facile Synthesis of Pyrano- and Furanoquinolines." VIII.E.2-24 Savelli, G. et al., TL, 44, 6583. "Efficient Esterification of Carboxylic Acids with Alkyl Halides Catalyzed by Fluoride Ions in Ionic Liquids." VIII.E.2-25 Ming, Y.L. et al., TL, 44, 5037. "Ionic Liquid-Regulated Sulfamic Acid: Chemoselective Catalyst for the Transesterification of 13-Ketoesters." VIII.E.2-26 Salunkhe, M.M. et al., CJC, 81, 1057. "An Ionic Liquid Mediated Friedel-Crafts Addition of Arenes to Isothiocyanates." VIII.E.2-27 Vaultier, M. et al., OL, 5, 2219. "Activation of Bismuth(III) Derivatives in Ionic Liquids: Novel and Recycable Catalytic Systems for Friedel-Crafts Acylation of Aromatic Compounds." VIII.E.2-28 Srinivasan, K.V. et al., JOC, 68, 9371. "Ionic liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines." VIII.E.2-29 Yadav, J.S. et al., TL, 44, 6493. "Glaser Oxidative Coupling in Ionic Liquids: An Improved Synthesis of Conjugated 1,3-Diynes." VIII.E.2-30 Calo, V. et al., OM, 22, 4193. "Pd Nanoparticle Catalyzed Heck Arylations of 1,1-Disubstituted Alkenes in Ionic Liquids. Study on the Factors Affecting the Regioselectivity of the Coupling Process."

SELECTED TOPICAL AREAS

355

VIII.E.2-31 Pakulski, Z., S, 2074. "Glycosylation in Ionic Liquids." VIII.E.2-32 Poletti, L. et al., SL, 2297. "Trichloroacetimides as Glycosyl Donors in Recyclable Ionic Liquids." VIII.E.2-33 Park, S.B.; Alper, H., OL, 5, 3209. "Highly Efficient Recyclable Pd(lI) Catalysts with Bisimidazole Ligands for the Heck Reaction in Ionic Liquids." VIII.E.2-34 Handy, S.T.; Okello, M., TL, 44, 8395. "Halide Effects on the Heck Reaction in Room Temperature Ionic Liquids." VIII.E.2-35 Chen, Z.-C. et al., S, 555. "Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate." VIII.E.2-36 Barbas, III, C.F. et al., SL, 1906. "Organocatalysis in Ionic Liquids: Highly Efficient L-ProlineCatalyzed Direct Asymmetric Mannich Reactions Involving Ketone and Aldehyde Nucleophiles." VIII.E.2-37 Chen, S.-L.; Ji, S.-J.; Loh, T.-P., TL, 44, 2405. "Asymmetric Mannich-Type Reactions Catalyzed by Indium(lll) Complexes in lonic Liquids." VIII.E.2-38 Ranu, B.C. et al., T, 59, 2417. "Catalysis by an Ionic Liquid: Efficient Conjugate Addition of Thiols to Electron Deficient Alkenes Catalyzed by Molten Tetrabutylammonium Bromide under Solvent-Free Conditions." VIII.E.2-39 Sodeoka, M. et al., OL, 5, 3225. "Immobilization and Reuse of Pd Complexes in Ionic LiquidEfficient Catalytic Asymmetric Fluorination and Michael Reactions with 13-Ketoesters."

356

ORGANIC SYNTHESIS--2004

VIII.E.2-40 Li, C.-J. et al., OL, 5, 657. "Aldol- and Mannich-Type Reactions via In Situ Olefin Migration in Ionic Liquid." VIII.E.2-41 Salunkhe, M.M. et al., TL, 44, 5351. "Influence of Ionic Liquids on the Phase Transfer-Catalyzed Enantioselective Michael Reaction." VIII.E.2-42 Wasserschied, P. et al., CC, 2038. "New, Functionalised Ionic Liquids from Michael-Type Reactions--A Chance for Combinatorial Ionic Liquid Development." VIII.E.2-43 Yadav, J.S. et al., CL, 32, 988. "Aza-Michael Reactions in Ionic Liquids. A Facile Synthesis of 13Amino Compounds." VIII.E.2-44 Yadav, J.S. et al., JOC, 68, 7098. "Green Protocol for Conjugate Addition of Thiols to c~,l~-Unsaturated Ketones Using a [Bmim]BF6/H20 System. VIII.E.2-45 Lancaster, N.L.; Llopis-Mestre, V., CC, 2812. "Aromatnc Nitrations in Ionic Liquids: The Importancs of Cation Choice." VIII.E.2-46 Rajagopal, R.; Srinivasan, K.V., SC, 33, 961. "Regio-Selective Mono Nitration of Phenols with Ferric Nitrate in Room Temperature Ionic Liquid." VIII.E.2-47 Louenco, N.M.T.; Afonso, C.A.M., T, 59, 789. "Ionic Liquid as an Efficient Promoting Medium for Two-Phase Nucleophilic Displacement Reactions." VIII.E.2-48 Yao, Q.; Zhang, Y., AG(E), 42, 3395. "Olefin Metathesis in the Ionic Liquid 1-Butyl-3-methylimidazolium Hexafluorophosphate Using a Recyclable Ru Catalyst: Remarkable Effect of a Designer Ionic Tag."

SELECTED TOPICAL AREAS

357

VIII.E.2-49 Mauduit, M.; Guillemin, J.-C. et al., JACS, 125, 9248. "An Ionic Liquid-Supported Ruthenium Carbene Complex: A Robust and Recyclable Catalyst for Ring-Closing Olefin Metathesis in ionic Liquids." VIII.E.2-50 Chi, D.Y. et al., JOC, 68, 4281. "Significantly Enhanced Reactivities of the Nucleophilic Substitution Reactions in Ionic Liquid." VIII.E.2-51 Xia, C.-G. et al., TL, 44, 9229. "Oxidation of Alkanes Catalyzed by Manganese(III) Prophyrin in an Ionic liquid at Room Temperature." VIII.E.2-52 Parsons, A.F. et al., SC, 33, 213. "CAN-Mediated Oxidative Free Radical Reactions in an Ionic Liquid." VIII.E.2-53 Chan, T.H. et al., OL, 5, 3423. "Manganese/Bicarbonate-Catalyzed Epoxidation of Lipophilic Alkenes with Hydrogen Peroxide in Ionic Liquids." VIII.E.2-54 Li, Z.; Xia, C.-G., TL, 44, 2069. "Epoxidation of Olefins Catalyzed by Manganese(III) Porphyrin in a Room Temperature Ionic Liquid." VIII.E.2-55 Song, C.E. et al., CC, 1100. "Chiral Co(III)(salen)-Catalyzed Hydrolytic Kinetic Resolution of Racemic Epoxides in Ionic Liquids." VIII.E.2-56 Perumal, P.T. et al., SL, 2249. "An Ionic Liquid Mediated Efficient Oxidation of Alcohols Using oIodoxy Benzoic Acid (IBX)--A Simple and Eco-Friendly Protocol." VIII.E.2-57 Chauhan, S.M.S. et al., CC, 2348. "Oxidation of Thiols with Molecular Oxygen Catalyzed by Cobalt(II) Phthalocyanines in Ionic Liquid."

358

ORGANIC SYNTHESISm2004

VIII.E.2-58 Chen, Z.-C. et al., OL, 5, 3321. "Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX) in Ionic Liquid 1-Beutyl-3-methyl-imidazolium Chloride and Water." VIII.E.2-59 Khan, F.A. et al., TL, 44, 7783. "Chemoselective Reduction of Aromatic Nitro and Azo Compounds in Ionic Liquids Using Zinc and Ammonium Salts." VIII.E.2-60 Li, S. et al., CC, 2627. "Catalytic Asymmetric Hydrogenation in a Room Temperature Ionic Liquid Using Chiral Rh-Complex of Ionic Liquid Grafted 1,4Bisphosphine Ligand." VIII.E.2-61 Yinghuai, Z.; Ke, P.K.; Hawthorne, M.F. et al., A G(E), 42, 3792." "(R)-Binap-Mediated Asymmetric Hydrogenation with a Rhodacarborane Catalyst in Ionic-Liquid Media." VIII.E.2-62 Han, B. et al., CC, 1654. "Hydrogenation of Olefins Using Ligand-Stabilized Palladium Nanoparticles in an Ionic Liquid." VIII.E.2-63 Dupont, J. et al., CEJ, 9, 3263. "The Use of Imidazolium Ionic Liquids for the Formation and Stabilization of Ir ~ and Rh 0 Nanoparticles: Efficient Catalysts for the Hydrogenation of Arenes." VIII.E.2-64 Xu, Z.-Y. et al., SC, 33, 4143. "An Effective Approach for the Silylation of Hydroxyl Compounds in Room Temperature Ionic Liquids." VIII.E.2-65 Toma, S. et al., M, 134, 545. "The Sonogashira Reaction in Ionic Liquids." VIII.E.2-66 Ren, R.X. et al., SL, 1734. Ullman Diaryl Ether Synthesis in Ionic Liquids."

SELECTED TOPICAL AREAS

359

VIII.E.2-67 Therisod, M. et al., TA, 14, 2487. "Ionic Liquids as a New Reaction Medium for Oxidase-Peroxidase Catalyzed Sulfoxidation." VIII.E.2-68 Miao, W.; Chan, T.H., OL, 5, 5003. "Exploration of Ionic Liquids as Soluble Supports for Organic Synthesis. Demonstration with a Suzuki Coupling Reaction." VIII.E.2-69 Welton, T. et al., OM, 22, 5350. "Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Ambient Temperature Ionic Liquids: Evidence for the Importance of Palladium Imidazoylidene Complexes." VIII.E.2-70 Kamal, A.; Chouhan, G., TL, 44, 3337. "Chemoselective Thioacetalization and Transthioacetalization of Carbonyl Compounds Catalyzed by Immobilized Scandium(Ill) Triflate in Ionic Liquids." VIII.E.2-71 Yadav, J.S. et al., CL, 32, 672. "Eco-Friendly and Highly Chemoselective 1,3-Oxathio- and 1,3Dithioacetalization of Aldehydes Using Ionic Liquids." VIII.E.2-72 Leadbeater, N.E. et al., T, 59, 2253. "Ionic Liquids as Reagents and Solvents in Conjunction with Microwave Heating: Rapid Synthesis of Alkyl Halides from Alcohols and Nitriles from Aryl Halides." VIII.E.2-73 Kabalka, G.W. et al., TL, 44, 4673. "Preparation of Substituted Allyl Acetates and Sulfones from BaylisHillman Adducts in Ionic Liquid Media." VIII.E.2-74 Mohan, R.S. et al., OL, 5, 55. "Synthesis of Homoallyl Ethers via Allylation of Acetals in Ionic Liquids Catalyzed by Trimethylsilyl Trifluoromethanesulfonate." VIII.E.2-75 Astolfi, D.L.; Mayville, Jr., F.C., TL, 44, 9223. "Synthesis of Methyl Orange Using Ionic Liquids."

360

ORGANIC SYNTHESIS--2004

VIII.E.2-76 Yadav, J.S. et al., S, 883. "[Bmim]BF4 Ionic Liquid: A Novel and Recyclable Reaction Media for the Synthesis of Homoallylic Amines." VIII.E.2-77 Yadav, J.S. et al., TL, 44, 1047. "[Bmim]BF4 Ionic Liquids: A Novel Reaction Medium for the Synthesis of [3-Amino Alcohols." VIII.E.2-78 Xia, C.-G. et al., TL, 44, 2409. "Synthesis of Aziridines from Imines and Ethyl Diazoacetate in Room Temperature Ionic Liquids." VIII.E.2-79 Srinivasan, K.V. et al., TL, 44, 1835. "Room Temperature Ionic Liquid Promoted Synthesis of 1,5Benzodiazepine Derivatives under Ambient Conditions." VIII.E.2-80 Calo, V. et al., JOC, 68, 2929. "Pd Nanoparticles Catalyzed Stereospecific Synthesis of 13-Aryl Cinnamic Esters in Ionic Liquids." VIII.E.2-81 Chauhan, S.M.S. et al., SC, 33, 3607. "Copper(I) Chloride Catalyzed Synthesis of Diaryl Ethers in Ionic Liquids Under Mild Conditions." VIII.E.2-82 Salunkhe, M.M. et al., TL, 44, 1255. "An Ionic Liquid-Mediated Expeditious Route to the Synthesis of Diaryl Sulfoxides." VIII.E.2-83 Taddei, M. et al., OL, 5, 4029. "Ionic Liquid as a Suitable Phase for Multistep Parallel Synthesis of an Array of Isoxazoles." VIII.E.2-84 Fraga-Dubreuil, J.; Bazureau, J.P., T, 59, 6121. "Efficient Combination of Task-Specific Ionic Liquid and Microwave Dielectric Heating Applied to One-Pot Three Component Synthesis of a Small Library of a Small Library of 4-Thiazolidinones."

SELECTED TOPICAL AREAS

361

VIII.E.2-85 Chen, Z.-C. et al., S, 1891. "Organic Reactions in Ionic Liquids: Ionic Liquid-Accelerated ThreeComponent Reaction: A Rapid One-Pot Synthesis of 3-Alkyl-5-[(Z)arylmethylidene]-l,3-thiazolidine-2,4-diones." VIII.E.2-86 Yadav, J.S. et al., T, 59, 1805. "Room Temperature Ionic Liquids Promoted Three-Component Coupling Reactions: A Facile Synthesis of cis-Isoquinolonic Acids." VIII.E.2-87 Salunkhe, M.M. et al., TL, 44, 1371. "Lipase-Catalyzed Polyester Synthesis in 1-Butyl-3methylimidazoliu m Hexafluorophosphate Ionic Liquid." VIII.E.2-88 Li, Y.-Q. et al., SC, 33, 3777. "A New Simple and Efficient Synthesis of N-Aryl Phthalimides in Ionic Liquid [bmim][PF6]." VIII.E.2-89 Yadav, J.S. eta|., EJOC, 1779. "Lewis Acidic Chloroaluminate Ionic Liquids: Novel Reaction Media for the Synthesis of 4-Chloropyrans." VIII.E.2-90 Xu, D.-Q. et al., S, 2626. "A Novel and Eco-Friendly Method for the Preparation of Ionic Liquids." VIII.E.2-91 Shreeve, J.M. et al., S, 1579. "Mono- and Disubstituted Polyfluoroalkylimidazolium Quarternary Salts and Ionic Liquids."

VIII.E.2-92 Mirzaei, Y.R.; Shreeve, J.M., S, 24. "New Quarternary Perfluoroalkyl-l,2,4-Triazolium Salts Leading to Ionic Liquids." VIII.E.2-93 Handy, S.T.; Okello, M., TL, 44, 8399. "Fructose-Derived Ionic Liquids: Recyclable Homogeneous Supports."

362

ORGANIC SYNTHESIS--2004

VIII.E.2-94 Bradley, M. et al., CC, 2310. "Dyad Beads and the Combinatorial Discovery of Catalysts."

VIII.F. Combinatorial Chemistry.

VIII.F.1 Supports, Linkers and Protecting Groups VIII.F.I-1 Cammidge, A.N. et al., TL, 44, 6633. "Surface-Functionalized Nano-Beads as Novel Supports for Organic Synthesis" VIII.F.1-2 Gardossi, L.; Ulijn, R.V. et al., TL, 44, 6083. "Organically Modified Xerogels as Supports for Solid-Phase Chemistry" VIII.F.1-3 Chen, C.H.-T.; Zhang, W., OL, 5, 1015. "FIuMAR, a Fluorous Version of the Marshall Resin for Solution Library Synthesis" VIII.F.1-4 Wisnoski, D.D. et al., TL, 44, 4321. "Microwave-Initiated Living Free Radical Polymerization" Rapid Formation of Custom Rasta Resins" VIII.F.1-5 Flynn, D.L., Hanson, P.R. et al., OL, 5, 15. "Ring-Opening Metathesis Phase-Trafficking (ROMpT) Synthesis: Multistep Synthesis on Soluble ROM Supports" VIII.F.1-6 Basso, A.; Bradley, M., TL, 44, 2699. "Site-Site Interactions Within High-Loading PAMAM Dendrimer Resin Beads"

VIII.F.1-7 Ladlow, M. et al., CC, 2048. "Wavelength Dependent Photo-Controlled Differential Release of Compounds from Solid Phase Resin" VIII.F.1-8 Bhattacharyya, S. et al., TL, 44, 6099; Glatz, H.; Bannwarth, W. TL, 44, 149; Kay, C. et al., TL, 44, 4153; Forns, P.; Fernandez-Forner, D.; Albericio, F. et al., TL, 44, 6907. "Expedient Synthesis of Secondary Amines Bound to Indole Resin and Cleavage of Resin-Bound Urea Amides and Sulfonalnide under Mild Conditions"

SELECTED TOPICAL AREAS

363

VIII.F.1-9 Giese, B.; Bochet, C.G. et al., OL, 5, 1179. "Sequentially Photocleavable Protecting Groups in Solid-Phase Synthesis" VIII.F.I-10 Taddei, M. et al., EJOC, 907. "A New, Rapid, General Procedure for the Synthesis of Organic Molecules Supported on Methoxy-Polyethylene Glycol (MeOPEG) Under Microwave Irradiation Conditions" VIII.F.I-ll Bradley, M. et al., T, 59, 7163. "Improving Resins for Solid Phase Synthesis: Incorporation of 1-[2(2-Meth oxyeth oxy)eth oxy]-4-vin yl-benzen e" VIII.F.I-12 Ladlow, M. et al., OBC, 1, 1711; Lazny, R. et al., S, 2858; Waldmann, H. et al., CEJ, 9, 3270, 3282; Peters, C.; Waldmann, H., JOC, 59, 6053. "The Development and Preparation of the 2,4-Dimethoxy-benzyl Arylhydrazine (DMBAH) 'Latent' Safety-Catch Linker: Solid Phase Synthesis of Ketopiperazines" VIII.F.I-13 Procter, D.J. et al., CC, 1402. "Application of an Ephedrine Chiral Linker in a Solid-Phase, 'Asymmetric Catch-Release' Approach to r-Butyrolactones" VIII.F.I-14 Lepore, S.D.; Wiley, M.R., OL, 5, 7. "Application of Aryloximes as Solid-Phase Ketone Linkers" VIII.F.I-15 Lazny, R.; Nodzewska, A., TL, 44, 2441. "Synthesis of Polymeric Supports wiyh Spacer-Modified Triazine Linkers: Aldol and Grignard Reactions of Immobilized Nortropinone" VIII.F.I-16 Nakamura, K. et al., TL, 44, 5445; Sheng, S.-R. et al., SC, 33, 2867; Huang, X.; Xu, W.-M., OL, 5, 4649. "New Selenyl Linker for Solid-Phase Synthesis of Dehydropeptides" VIII.F.I-17 Gu, W.; Silverman, R.B., OL, 5, 415. "New, Stable Backbone Linker Resins for Solid-Phase Peptide Synthesis" VIII.F.I-18 Ulijn, R.V. et al., CC, 1296. "Improved Biotransformations on Charged PEGA Supports"

364

ORGANIC SYNTHESISm2004

VIII.F.I-19 Nicolas, E.; Albericio, F. et al., TL, 44, 5319. "Solid-Phase Synthesis: A Linker for Side-Chain Anchoring of Arginine" VIII.F.1-20 Bauer, J.; Rademann, J., TL, 44, 5019. "Trimellitic Anhydride Linker (TAL)mHighly Orthogonal Conversions of Primary Amines Employed in the Parallel Synthesis of Labeled Carbohydrate Derivatives" VIII.F.1-21 Wittman, V. et al., TL, 44, 9243. "Temporary Attachment of Carbohydrates to Cyclopeptide Templates: A New Strategy for Single-Bead Analysis of Multivalent Neoglycopeptides" VIII.F.1-22 Guzaev, A.P.; Manoharan, M., JACS, 125, 2380. "A Conformationally Preorganized Universal Solid Support for Efficient Oligonucleotide Synthesis" VIII.F.1-23 Hulme, A.N. et al., SL, 1096. "Chiral Monomers with Minimal Functional Group Linkages for Suspension Co-Polymerization: A Suzuki Coupling Approach" VIII.F.1-24 Najera, C. et al., SL, 809. "New Polymer-Supported Allyloxycarbonyl (Ailoc) and Propargyloxycarbonyl (Proc) Amino-Protecting Reagents" VIII.F.1-25 Cavelier, F. et al., TL, 44, 4757. "Towards a Selective Boc Deprotection on Acid Cleavable Wang Resin" VIII.F.1-26 Lee-Ruff, E. et al., JOC, 59, 9843. "Synthesis and Investigation of Novel Branched PEG-Based Soluble Polymer Supports" VIII.F.2 Supported Reagents, Catalysts, Ligands and Scavengers VIII.F.2-1 Sasai, H. et al., AG(E), 42, 5711. " Metal-Bridg e d Polymers as Insoluble Multicomponent Asymmetric Catalysts with High Enantiocontroh An Approach for the Immobilization of Catalysts Without Using any Support"

SELECTED TOPICAL AREAS

365

VIII.F.2-2 Wentworth, Jr., P.; Janda, K.D. et al., CC, 480. "Soluble Polymer-Supported Convergent Parallel Library Synthesis" VIII.F.2-3 Flynn, D.L.; Hanson, P.R. et al., OL, 5, 105, 4241. "ROMP-Generated Oiigomeric Sulfonyl Chlorides as Versatile Soluble Scavenging Agents" VIII.F.2-4 Zhang, W. et al., TL, 44, 2065. "Fluorous Electrophilic Scavengers for Solution-Phase Parallel Synthesis" VIII.F.2-5 Schon, U.; Kirschning, A. et al., SL, 983. "A Polymer-Bound 1,3-Diketone: A Highly Efficient Scavenger for Hydrazines and Primary Amines" VIII.F.2-6 Turner, N.J. et al., OL, 5, 849. "Solid-Supported Cyclohexane-l,3-dione (CHD): A 'Capture and Release' Reagent for the Synthesis of Amides and Novel Scavenger Resin" VIII.F.2-7 Nishikido, J. et al., TL, 44, 8791; Zolfigol, M.A. et al., SL, 1877; Palaniappan, S. et al., SL, 1793; Kobayashi, S. et al., OBC, 1, 2416; Hon, Y.S. et al., SC, 33, 2829. "Fluorous Reverse-Phase Silica Gel-Supported Lewis Acids as Recyclable Catalysts in Water" VIII.F.2-8 Sauer, D.R. et al., OL, 5, 4721; Frank, R. et al., TL, 44, 6557; Ishikawa, T. et al., SL, 115; Linclau, B. et al., OL, 5, 853; Mane, R.A. et al., SC, 33, 1923; Savelli, G. et al., TL, 44, 2027. "Microwave-Assisted Synthesis Utilizing Supported Reagents: A Rapid and Efficient Acylation Procedure" VIII.F.2-9 Doyle, M.P. et al., OL, 5, 561; Banaglia, M. et al., TA, 14, 461; Moreau, J.J.E. et al., EJOC, 99; Zech, G.; Kunz, H., AG(E), 42, 787; Calmes, M. et al., TA, 14, 1223. "Catalysts with Mixed Ligands on Immobilized Supports. Electronic and Steric Advantages" VIII.F.2-10 Barrett, A.G.M. et al., TL, 44, 2703; Davies, H.M.L.; Walji, A.M., OL, 5, 479. "ROMPgel-Supported Tris(triphenylphosphine)rhodium(1) Chloride: A Selective Hydrogenation Catalyst for Parallel Synthesis"

366

ORGANIC SYNTHESIS--2004

VIII.F.2-11 Weissberg, A.; Portnoy, M., CC, 1538; Kobayashi, S. et al., CC, 192; see also: Moberg, C. et al., OL, 5, 3663; Venkataraman, D. et al., TL, 44, 6445; Luis, S.V.; Martens, J. et al., T, 59, 1797. "Unprecedented Preparation of Pincer Bis(oxazolinyl)phenyl Ligands on Solid Support and Their Use in the First HeterogeneouslyCatalyzed Enantioselective Allylation of Aldehydes" VIII.F.2-12 Bradley, M. et al., TL, 44, 4779; Luo, F.-T. et al., TL, 44, 7565; Gonthier, E.; Breinbauer, R., SL, 1049; Peris, E.; Fernandez, E. et al., TL, 44, 6595; Song, M.; Wu, Y. et al., TL, 44, 3955; Gros, P.; Fort, Y. et al., TL, 44, 5613; Chang, Y.-T. et al., TL, 44, 6141; see also: Kilbum, J.D. et al., TL, 44, 8601. "Reusable Resin Plug-Bound Palladium Catalysts for Organic Synthesis" VIII.F.2-13 Bhattacharyya, S. et al., TL, 44, 4957. "Polymer-Supported Triacetoxyborohydride: A Novel Reagent of Choice for Reductive Amination" VIII.F.2-14 Hodge, P. et al., OBC, 1, 3238. "Towards More Chemically Robust Polymer-Supported Chiral Catalysts: a,a-Diphenyl-L-Prolinol Based Catalysts for the Reduction of Prochiral Ketones with Borane" VIII.F.2-15 Xiao, J. et al., OL, 5, 4559; Itsuno, S. et al., TL, 44, 3825; see also: Basu, B. et al., TL, 44, 8931; Takahashi, T. et al., TL, 44, 2161. "Asymmetric Hydrogenation of Ketones with Polymer-Supported Chiral 1,2-Diphenylethylenediamine" VIII.F.2-16 Gibson, S.E. et al., OBC, 1, 1959. "The Application of Polymer-Bound Carbonylcobalt(0) Species in Linker Chemistry and Catalysis" VIII.F.2-17 Zheng, Z. et al., TL, 44, 7081. "Highly Enantioselective Resolution of Terminal Epoxides with Cross-Linked Polymeric Salen-Co(IIl) Complexes" VIII.F.2-18 Sakuratani, K.; Togo, H., 5', 21; Tanyeli, C.; Gumus, A., TL, 44, 1639. "Environmentally-Friendly TEMPO-Mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"

SELECTED TOPICAL AREAS

367

VIII.F.2-19 Sutherland, A.J. et al., TL, 44, 1635; Lee, Y.-S. et al., TL, 44, 9251. "A Facile Route to a Polymer-Supported IBX Reagent" VIII.F.2-20 Toy, P:H. et al., T, 59, 7171. "Soluble Polystyrene-Based Sulfoxide Reagents for Swern Oxidation Reactions" VIII.F.2-21 Saladino, R. et al., T, 59, 7403. "Selective Epoxidation of Monoterpenes with H20 and PolymerSupported Methylrheniumtrioxide Systems" VIII.F.2-22 Das, P.J. et al., SC, 33, 3147; Kirschning, A. et al., TL, 44, 637; Matsuo, J. et al., BCJ, 76, 1433; see also" Shirini, F. et al., SC, 33, 1833. "Solid Phase Oxidation of Alcohols and Benzyl Halides to Carbonyls Using Bromate Exchange Resin" VIII.F.2-23 Neitzel, M.L.; Tucker, J. et al., TL, 44, 7537. "Selective Catch and Release of a Synthetically Useful Phosphine Ligand" VIII.F.2-24 Lu, Y.; Taylor, R.T., TL, 44, 9267; see also" Garanti, L.; Molteni, G., TL, 44, 1133. "Preparation and Applications of a Polymer-Supported Phosphoryl Azide" VIII.F.2-25 B lass, B.E. et al., TL, 44, 2153. "Applications of Solid Supported Azide Anions: A One-Pot, TwoStep Preparation of Functionalized 1,2,3-Triazoles" VIII.F.2-26 Mann, A. et al., TL, 44, 3645. "Polymer-Supported Electron-Rich Diene for Hetero Diels-Alder Reactions" VIII.F.2-27 Barlos, K. et al., TL, 44, 179; Bertini, V. et al., SL, 864; Macquarrie, D.J.; Rousseau, H., SL, 244. "Resin-Bound Aminothiols: Synthesis and Applications" VIII.F.2-28 Hon, Y.-S.; Wu, K.-C., T, 59, 493. "Polymer-Supported Tertiary Amine in Organic Synthesis: A Useful Reagent in the Conversion of Alkenes to Carbonyl Compounds via the Corresponding Ozonides"

368

ORGANIC SYNTHESIS--2004

VIII.F.2-29 Tamami, B.; Iranpoor, N.; Rezaei, R., SC, 33, 3153. "Highly Regioselective Conversion of Epoxides to ~-Hydroxy Nitriles with Cyanide Exchange Resin" VIII.F.3 Solid-Phase Heterocyclic Synthesis VIII.F.3-1 Giulianotti, M.; Nefzi, A., TL, 44, 5307. "Efficient Approach for the Diversity-Oriented Synthesis of MacroHeterocycles on Solid-Support" VIII.F.3-2 Burgess, K. et al., CC, 1674. "Syntheses of Second Generation, 14-Membered Ring [3-Turn Mimics" VIII.F.3-3 Ley, S.V. et al., AG(E), 42, 2521. "A Total Synthesis of Epothilones Using Solid-Supported Reagents and Scavengers" VIII.F.3-4 Albericio, F.; Alvarez, M. et al., OL, 5, 2959. "Solid-Phase Total Synthesis of the Pentacyclic System Lamellarins U and L" VIII.F.3-5 Raghavan, S.; Anuradha, K., SL, 711. "Solid-Phase Synthesis of Heterocycles from 1,4-Diketo Synthons" VIII.F.3-6 Westman, J.; Lundin, R., S, 1025. "Solid Phase Synthesis of Aminopropenones and Aminopropenoates: Efficient and Versatile Synthons for Combinatorial Synthesis of Heterocycles" VIII.F.3-7 Vourloumis, D. et al., TL, 44, 2807; Wu, Z. et al., TL, 44, 2293. Benzimidazoles VIII.F.3-8 Hulme, C. et al., TL, 44, 1947. Benzodiazepines VIII.F.3-9 Sun, C.-M. et al., SL, 1688 Benzopiperazinones

SELECTED TOPICAL AREAS

369

VIII.F.3-10 Huang, X.; Tang, J., T, 59, 4851. Benzothiazoles and Thiophenes VIII.F.3-11 Makino, S. et al., TL, 44, 5539.

1,2,3-Benzotriazin-4-ones VIII.F.3-12 Player, M.R. et al., TL, 44, 175 Benzoxazoles VIII.F.3-13 Nefzi, A. et al., TL, 44, 2211. 13-Carbolines VIII.F.3-14 Dujardin, G. et al., EJOC, 4118. Dihydropyrans VIII.F.3-15 Wang, Y.-G. et al., TL, 44, 4113 4,5-Dihydro-l,2,4-oxadiazoles VIII.F.3-16 Sabitha, G. et al., TL, 44, 6497. Dihydropyrimidin-(2H)-ones VIII.F.3-17 Berteina-Raboin, S. et al., TL, 44, 6265. Imidazo[1,2-a]pyridines and Ilnidazo[1,2-a]pyrimidines VIII.F.3-18 Dai, W.-M. et al., OL, 5, 2919; Knepper, K.; Brase, S., OL, 5, 2829; Wu, Z.; Ede, N.J., OL, 5, 2935; Tois, J.; Koskinen, A., TL, 44, 2093. Indoles VIII.F.3-19 Houghten, R.A. et al., TL, 44, 2569. Indolines VIII.F.3-20 Stella, L. et al., T, 59, 3719.

[3-Lactams VIII.F.3-21 Nicewonger, R. et al., TL, 44, 9337.

VIII.F.3-22 Wang, Y.-G. et al., CL, 32, 842 and SL, 1064 and S, 1569.

1,2,4-Oxadiazolines

370

ORGANIC SYNTHESISm2004

VIII.F.3-23 Chassaing, C. et al., OL, 5, 1851. Phthalimides

VIII.F.3-24 Olsson, R.; Almqvist, F. et al., EJOC, 4586; Makino, S. et al.,

SL, 817. Piperidines

VIII.F.3-25 Boyle, R.W. et al., TL, 4, 5083. Porphyrins VIII.F.3-26 Suckling, C.J. et al., TL, 44, 1267 and OBC, 1, 1909. Pteridines

VIII.F.3-27 Smith, D.B. et al., TL, 44, 8361. Purines

VIII.F.3-28 Wang, Y.-G. et al., SL, 1467; Lam, Y. et al., OL, 5, 1067. Pyrazolines VIII.F.3-29 Sotelo, E.; Ravina, E., SL, 1113. 3 (2H)-Pyrid azin on es VIII.F.3-30 Robertson, A.A.B. et al., TL, 44, 1627; see also: Shimazaki, M. et al., TL, 44, 6567; Angiolini, M. et al., TL, 44, 519. Pyridines

VIII.F.3-31 Zanda, M. et al., T, 59, 7147; Darvas, F. et al., T, 59, 655; Meisenbach, M. et al., SC, 33, 553; Spivey, A.C. et al., OBC, 1, 1638. Pyrimidines

VIII.F.3-32 Graybill, T.L. et al., TL, 44, 5041; Zechel, G.; King, A. et al., BMCL, 13, 165; see also: Graveleau, N.; Masquelin, T., S, 1739. Pyrimidinones

VIII.F.3-33 Komatsu, M. et al., T, 59, 197; Brown, R.C.D. et al., OBC, 1, 2699. Pyrrolidines and Pyrroles

SELECTED TOPICAL AREAS

371

VIII.F.3-34 Song, S.J.; Kwon, T.W. et al., TL, 44, 255. Quinolines VIII.F.3-35 Kundu, B. et al., SL, 2147. Quinoxalines VIII.F.3-36 Makino, S. et al., T, 59, 5603; see also: Weber, C. et al., TL, 44, 7533. Quin azolin e-2,4-dion es VIII.F.3-37 Hone, N.D. et al., TL, 44, 8493; see also: Migihashi, C.; Sato, F., JHC, 40, 143. Tetrahydro-l,4-benzodiazepin-2-ones VIII.F.3-38 Sun, C.-M. et al., TL, 44, 4923.

Tetrahydro-13-carbolines VIII.F.3-39 Huang, X. et al., BMCL, 13, 2505. Tetramic Acid VIII.F.3-40 Lin, M.-J.; Sun, C.-M., TL, 44, 8739. Thiohydantoin VIII.F.3-41 Frutos Hoener, A.P. et al., SL, 63. Thiophenes VIII.F.3-42 Chang, Y.-T. et al., OL, 5, 117. Triazines VIII.F.3-43 Henkel, B. et al., SL, 2410; Larsen, S.D. et al., BMCL, 13, 3491; Kilburn, J.P. et al., TL, 44, 7825; Domling, A. et al., TL, 44, 3679. Thiazoles VIII.F.3-44 Houghton, R.A. et al., TL, 44, 3705. 1,3,5-T riazino [1,2-a] benzim id azoles VIII.F.3-45 Fehrentz, J.-A. et al., OL, 44, 4465; Houghten, R.A. et al., TL, 44, 7841. 1,2,4-Triazoles

372

ORGANIC SYNTHESISm2004

VIII.F.3-46 Nettekoven, M. et al., TL, 44, 1675. [1,2,4]Triazolo[1,5-a]pyridines VIII.F.4 Solid-Supported Organic Reaction Processes VIII.F.4-1 Sensfuss, U., TL, 44, 2371. "Solid-Phase Aldol Condensations Mediated by Zinc Acetate and 2,2'-Bipyridine under Weakly Basic Conditions" VIII.F.4-2 Cossy, J. et al., TL, 44, 8581. "Solid Phase Synthesis of Amides by the Beckmann Rearrangement of Ketoxime Carbonates" VIII.F.4-3 Levacher, V. et al., OL, 5, 3061. "A Novel Tracerless Solid-Phase Friedlander Synthesis" VIII.F.4-4 De Clerq, P.J. et al., TL, 44, 6657. "Carbon--Carbon Bond Formation on Solid Support. Application of the Classical Julia-Lythgoe Olefination" VIII.F.4-5 Kobayashi, S. et al., CC, 1644. "Mannich-Type Reactions in Water Using a Hydrophobic PolymerSupported Sulfonic Acid Catalyst" VIII.F.4-6 Spencer, J.B. et al., SL, 1070. "A General Polymer-Supported Acid Catalyzed Hetero-Michael Addition" VIII.F.4-7 Smith, R.A. et al., TL, 44, 2939. "Development of a 9-Borabicyclo[3.3.1]nonane-Mediated Solid-Phase Suzuki Coupling for Preparation of Dihydrostilbene Analogs" VIII.F.4-8 Portlock, D.E.; Naskar, D. et al., TL, 44, 5121. "Solid-Phase Synthesis of Five-Dimensional Libraries via a Tandem Petasis-Ugi Multi-Component Condensation Reaction" VIII.F.4-90'Donnell, M.J.; Alsina, J.; Scott, W.L., TL, 44, 8403; Cahard, D. et al., TA, 14, 1671; Hammer, R.P. et al., JOC, 68, 9854; Yu, H.; Koshima, H., TL, 44, 9209. "Solid-Phase Synthesis and Utilization of Side-Chain Reactive Unnatural Amino Acids"

SELECTED TOPICAL AREAS

373

VIII.F.4-10 Henkel, B. et al., TL, 44, 7015. "New Method for the Preparation of Solid-Phase Bound Isocyanocarboxylic Acids and Ugi Reactions Therewith" VIII.F.4-11 Alvarez-Builla, J. et al., OL, 5, 4057. "Westphal Reaction in Solid-Phase" VIII.F.4-12 Grieco, P. et al., SL, 2216. "Rapid and Efficient Methodology to Perform Macro-cyclization Reactions in Solid-Phase Peptide Chemistry VIII.F.4-13 Harrowven, D.C. et al., TL, 44, 503. "Sulfur-Mediated Radical Cyclization Reactions on Solid Support" VIII.F.4-14 Naito, T. et al., CPB, 51, 540. "Diastereoselective Solid-Phase Radical Addition to Oxime Ether Anchored to Polymer Support" VIII.F.4-15 Bertini, V. et al., SL, 1201. "Reductive Cleavage of 1,3-Dithiane Systems Anchored on Polymers Useful for Supported Organic Syntheses" VIII.F.4-16 Lizarzaburu, M.E.; Shuttleworth, S.J., TL, 44, 4873. "Convenient Preparation of Aryl Ether Derivatives Using a Sequence of Functionalized Polymers" VIII.F.4-17 Coats, S.J. et al., OL, 5, 721. "Alternative Solvents foe Elevated-Temperature Solid-Phase Parallel Synthesis. Application to Thionation of Amides" VIII.F.4-18 Weik, S.; Rademann, J., AG(E), 42, 2491. "A Phosphorane as Supported Acylanion Equivalent: Linker Reagents for Smooth and Versatile C - - C Coupling Reactions" VIII.F.4-19 Fattori, D. et al., TL, 44, 811. "Solid-Phase Synthesis of Unsymmetrical Ureas Through the Use of Kenner Safety-Catch Linker" VIII.F.4-20 Ravn, J.; Lau, J.F. et al., TL, 44, 6931. "A Novel Solid-Phase Synthesis of Di- and Trisubstituted N-Acyl Ureas"

374

ORGANIC SYNTHESISm2004

VIII.F.4-21 Devocelle, M. et al., OBC, 1, 850. "A Convenient Parallel Synthesis of Low Molecular Weight Hydroxamic Acids Using Polymer-Supported 1-Hydroxybenzotriazole" VIII.F.4-22 Kamal, A. et al., TL, 44, 4741. "Facile Reduction of Aromatic Nitro/Azido Functionality on Solid Support Employing AI/NiCI2o6H20 and AI/NH4CI: Synthesis of Pyrrolo [2,1-c] [1,4] benzodiazepines" VIII.F.4-23 Kanemitsu, T.; Seeberger, P.H., OL, 5, 4541. "Use of Olefin Cross-Metathesis to Release Azide-Containing Sugars from Solid Support" VIII.F.4-24 Ito, Y. et al., SL, 979. "Polymer-Resin Hybrid Capture-Release Strategy for Rapid Oligosaceharide Construction" VIII.F.4-25 Cleophax, J. et al., S, 1015. "A Practical Large-Scale Access to 1,6-Anhydro-13-D-hexopyranoses by a Solid-Supported Solvent-Free Microwave-Assisted Procedure" VIII.F.4-26 Guanti, G. et al., TL, 44, 2367; see also: Virta, P.; Lonnberg, H., JOC, 68, 8534; Karskela, T. et al., EJOC, 1687; Barlos, K. et al., TL, 44, 3979; Galande, A.K.; Spatola, A.F., OL, 5, 3431; Snaith, J.S. et al., TL, 44, 9115; Albericio, F.; Jensen, K.J. et al., OL, 5, 2951. "Solid-Phase Synthesis of Modified Oligopeptides via Passerini Multicomponent Reaction" VIII.F.4-27 Fehrentz, J.-A. et al., TL, 44, 4797; see also: Lowden, C.T. et al., TL, 44, 7575; Franzy, K.H. et al., OL, 5, 4183. "Synthesis of gem-Diamino Derivatives on Solid Support" VIII.F.4-28 Caruthers, M.H. et al., JACS, 125, 13427, 940; see also: Haner, R. et al., HCA, 86, 3476; Zhang, L. et al., HCA, 86, 3516; Ravikumar, V.T. et al., BMCL, 13, 281; Reddy, P.M.; Bruice, T.C., BMCL, 13, 1281. "Solid-Phase Oligodeoxynucleotide Synthesis: A Two-Step Cycle Using Peroxy Anion Deprotection" VIII.F.4-29 Chen, Z. et al., SC, 33, 729. "Soluble Polymer-Supported Synthesis of Tertiary Amines"

SELECTED TOPICAL AREAS

375

VIII.F.5 Targeted Library. Synthesis VIII.F.5-1 Verdine, G.L. et al., OL, 5, 621,633. "Extensively Stereodiversified Scaffolds for Use in Diversity-Oriented Library Synthesis" VIII.F.5-2 Kunz, H. et al., EJOC, 1527 "D-Glucose as a Peutavalevt Chiral Scaffold" VIII.F.5-3 Takahashi, T. et al., TL, 44, 3053. "Parallel Synthesis of Multi-Branched Oligosaccharides Related to Elicitor Active Pentasaccharide in Rice Cell Based on Orthogonal Deprotection and Glycosylation Strategy" VIII.F.5-4 Mori, A. et al., TL, 44, 1251. "Synthesis of a New Troponoid Liquid Library on Solid Support" VIII.F.5-5 Maletic, M. et al., BMCL, 13, 1125. "Preparation of Potential Inhibitors of the Mur-Pathway Enzymes on Solid-Support Using an Acetal Linker" VIII.F.5-6 Ladlow, M.; Ley, S.V. et al., OBC, 1, 2419. "Fully Automated Multi-Step Solution Phase Synthesis Using Polymer Supported Reagents: Preparation of Histone Deacetylase Inhibitors" VIII.F.5-7 Grieder, A.; Thomas, A.W., S, 1707. "A Concise Building Block Approach to a Diverse Multi-Arrayed Library of the Cirumdatin Family of Natural Products" VIII.F.5-8 Pirrung, M.C.; Liu, H., OL, 5, 1983. "Modular, Parallel Synthesis of an Illudinoid Combinatorial Library" VIII.F.5-9 Sanders, J.K.M. et al., OBC, 1, 1625. "Metal-Ion Induced Amplification of Three Receptors from Dynamic Combinatorial Libraries of Peptide-Hydrazones" VIII.F.5-10 Wattanasin, S. et al., BMCL, 13, 499. "l,4-Diazepane-2-ones as Novel Inhibitors of LFA-I"

376

ORGANIC SYNTHESIS--2004

VIII.F.5-11 Albericio, F. et al., OL, 5, 2115. "Tentoxin as a Scaffold for Drug Discovery. Total Solid-Phase Sysnthesis of Tentoxin and a Library of Analogues" VIII.F.5-12 Itami, K.; Kamei, T.; Yoshida, J., JACS, 125, 14670. "Diversity-Oriented Synthesis of Tamoxifen-Type Tetrasubstituted Olefins" VIII.F.5-13 Eliseev, A.V. et al., JMC, 46, 356. "Ketones as Building Blocks for Dynamic Combinatorial Libraries: Highly Active Neuraminadase Inhibitors Generated via Selection Pressure of the Biological Target" VIII.F.5-14 Meng, C.Q. et al., BMCL, 13, 745; see also: Wang, G.; Yao, S.Q., OL, 5, 4437; Yao, S.Q. et al., OL, 5, 737. "Lead Discovery of ~,13-Unsaturated Sulfones from a Combinatorial Library as Inhibitors of Inducible VCAM-1 Expression" VIII.F.5-15 Lange, U.E.W.; Braje, W.M. et al., BMCL, 13, 1721. "Solid-Phase Synthesis of Endothelin Receptor Antagonists" VIII.F.5-16 Pirrung, M.C. et al., JACS, 125, 1575. "High-Throughput Catch-and-Release Synthesis of Oxazoline Hydroxamates. Structure-Ativity Relationships in Novel lnhibitors of Escherichia Coli LpxC: In Vitro Enzyme Inhibition and Antibacterial Properties" VIII.F.5-17 Hecht, S.M. et al.,JACN, 125, 8218. "Solid-Phase Synthesis of Bleomycin Group Antibiotics. Construction of a 108-Member Deglycobleomycin Library" VIII.F.5-18 Parlow, J.J. et al., JMC, 46, 4050; South, M.S. et al., BMCL, 13, 2363. "Design, Parallel Synthesis, and Crystal Structures of Pyrazinone Antithrombotics as Selective Inhibitors of the Tissue Factor VIIa Complex" VIII.F.5-19 Jacobs, J.W. et al., BMCL, 13, 3409. "Combinatorial Modification of Natural Products: Synthesis and In Vitro Analysis of Derivatives of Thiazole Peptide Antibiotic GE2270A: A-Ring Modifications"

SELECTED TOPICAL AREAS

377

VIII.F.5-20 Jackson, R.W. et al., BMCL, 13, 205. "Identification of TNF-~ Inhibitors from a Split-Pool Library Based on a Tyrosine-Proline Peptidomimetic Scaffold" VIII.F.5-21 Kiessling, L.L. et al., OL, 5, 1407. "Parallel Synthesis of Glycomimetic Libraries" Targeting a C-Type Leetin" VIII.F.5-22 Slomczynska, U. et al., BMCL, 13, 2553. "Solid-Phase Synthesis of Methyl Carboxylnycobactin T7 and Analogues as Potential Antimycobacterial Agents" VIII.F.5-23 Wang, M.-L.; Nassim, B.E., TL, 44, 1487; Semple, G. et al., BMCL, 13, 1141. "Solid-Phase Synthesis of Novel Hybrid Opiates" VIII.F.5-24 Boatman, P.D. et al., BMCL, 13, 1445. "High-Throughput Synthesis and Optimization of Thrornbin Inhibitors via Urazole ct-Addition and Michael Addition" VIII.F.5-25 Egle, I. et al., BMCL, 13, 3419. "(R)-3-(N-Methylpyrrolidin-2-ylmethyl)-5-(1,2,3,6-tetrahydropyridin4-yl)-lH-indole Derivatives as High Affinity h5-HTIB/1D Ligands" VIII.F.5-26 Bradley, M. et al., TL, 44, 3195. "Solid-Phase Synthesis of a Focused Library of Trypanothione Reductase Inhibitors" VIII.F.5-27 Isabel, E. et al., BMCL, 13, 2137. "Nicotinyl Aspartyl Ketones as Inhibitors of Caspase-3" VIII.F.6 Novel Techniques in Combinatorial Chemistry VIII.F.6-1 Paio, A.; Seneci, P. et al., TL, 44, 1867. "A New Analytical Method for Anchoring Quantification of Amines on Resin Support" VIII.F.6-2 Deeg, O.; Bauerle, P., OBC, 1, 1609. "Combinatorial Organic Materials Research (COMR): Design, Synthesis and Screening of a 225-Membered Materials Library of Liquid Crystalline Fluorinated p-Quaterphenyls"

378

ORGANIC SYNTHESISm2004

VIII.F.6-3 Seeberger, P.H r. et al., HCA, 86, 3975. "Automated Synthesis of Oligosaccharides" VIII.F.6-4 Tietze, L.F. et al., AG(E), 42, 4254. "Catalyst-Controlled Stereoselective Combinatorial Synthesis" VIII.F.6-5 Andrews, S.P.; Ladlow, M., JOC, 68, 5525. "Convenient Preparation and Use of a New Analytical Construct for the Analysis and Development of Solid-Phase Chemistry" VIII.F.6-6 Haswell, S.J. et al., T, 59, 10173. "Solution Phase Synthesis of Esters Within a Micro Reactor" VIII.F.6-7 Turner, N.J. et al., JACS, 125, 13952. "Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a 'Capture and Release' Strategy" VIII.F.6-8 Flitsch, S.L. et al., OBC, 1, 1277. "Understanding Protease Catalyzed Solid Phase Peptide Synthesis" VIII.F.6-9 Brugel, T.A.; Hegedus, L.S., JOC, 68, 8409. "N-Functionalization of Poly(ethylene Glycol)-Linked Mono- and BisDioxocyclams as Potential Lignans for Gd 3+'' VIII.F.6-10 van Koten, G. et al., OL, 5, 2021. "Organoplatinum(II) Complexes as a Color Biomarker in SolidPhase Peptide Chemistry and Screening" VIII.F.6-11 Toone, E.J. et al., JOC, 68, 5805. "Solid-Phase Synthesis for the Identification of High-Affinity Bivalent Lectin Ligands" VIII.F.6-12 Johansson, A.; Abrahamsson, P.; Davidsson, O., TA, 14, 1261. "Solid-Phase Supported Chiral Lithium Amides Used in Deprotonation Reactions" VIII.F.6-13 Olsson, R. et al., OL, 5, 1551. "A Combinatorial Scaffold Approach Based Upon a Multicomponent Reaction"

SELECTED TOPICAL AREAS

379

VIII.F.6-14 Portland, D.E. et al., TL, 44, 603. "A Tandem Petasis-Ugi Multi Component Condensation Reaction" Solution Phase Synthesis of Six Dimensional Libraries" VIII.F.6-15 Rosania, G.R.; Chang, Y.-T. et al., JACS, 125, 1130. "Combinatorial Approach to Organelle-Targeted Fluorescent Library Based on the Styryl Scaffold" VIII.F.6-16 van Boom, J.H.; Overkleeft, H.S. et al., JOC, 68, 9406. "The Use of a Mannitol-Derived Fused Oxacycle as a Combinatorial Scaffold" VIII.F.6-17 Struber, F. et al., CEJ, 9, 2582. "Polymer-Supported Triazines as Small Reagents for the Alkylation of Carboxylic Acids" VIII.F.6-18 Brandi, A. et al., SL, 1889. "Resin Linked Dipolarophiles to Mask Nitrones" VIII.F.6-19 Clarke, M.L., JOM, 665, 65. "One Ponytail Will Do: New Partially Fluorinated Phosphines with Applications in Fluorous Biphasic Solvent Systems" VIII.F.6-20 Fache, F.; Piva, O., TA, 14, 139. "Synthesis and Applications of the First Polyfluorous Proline Derivative" VIII.F.7 Reviews VIII.F.7-1 Far, A.R., AG(E), 42, 2340. Minireview: "Ketenes in Polymer-Assisted Synthesis" VIII.F.7-2 Boger, D.L. et al.,AG(E), 42, 4138. Review: "Solution-Phase Combinatorial Libraries: Modulating Cellular Signaling by Targeting Protein-Protein or Protein-DNA Interactions" VIII.F.7-3 Wang, P.G. et al., CEJ, 9, 372. Review: "Superbeads: Immobilization in 'Sweet' Chemistry"

380

ORGANIC SYNTHESIS--2004

VIII.F.7-4 Benaglia, M. et al., CRV, 103, 3401. Review: "Polymer-Supported Organic Catalysts" VIII.F.7-5 Seeberger, P.H., CC, 1115. Feature "Automated Carbohydrate Synthesis to Drive Article: Chemical Giycomics" VIII.F.7-6 Blackwell, H.E., OBC, 1, 1251. Review: "Out of the Oil Bath Into the Oven--Microwave-Assisted Combinatorial Chemistry Heats Up" VIII.F.7-7 Spring, D.R., OBC, 1, 3867. Emerging "Diversity-Oriented Synthesis; A Challenge for Area: Synthetic Chemists" VIII.F.7-8 Shevchenko, V.P. et al., RCR, 72, 423. Review: "Solid-Phase Method for Tritium Labelling of Biologically Active Compounds" VIII.F.7-90rru, R.V.A.; de Greef, M., S, 1471. Review: "Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds" VIII.F.7-10 Brase, S. et al., T, 59, 885. Report: "Palladium-Catalyzed Reactions in Solid Phase Organic Synthesis" VIII.F.7-11 Zhang, W., T, 59, 4475. Report: "Fluorous Technologies for Solution-Phase HighThroughput Organic Synthesis" VIII.F.7-12 Lonnberg, H. et al., T, 59, 5137. Report: "Solid-Supported Synthesis of Oligomeric Bioconjugates" VIII.F.7-13 Tois, J. et al., T, 59, 5395. Report: "Synthetic Approaches Towards Indoles on Solid Phase Recent Advances and Future Directions"

AUTHOR INDEX

381

382

Abadi, A.H. 184 Abdel-Fattah, A.A.A. 188 Abele, E. 60 Abell, A.D. 283 Ackerman, L. 114 Adamczyk, M. 81 Adams, R.D. 287 Adapa, S.R. 37, 117, 188, 238 Adolfsson, H. 113, 119 Adrian, Jr., J.C. 15 Afarinkia, K. 8, 67 Afonso, C.A.M. 353, 356 Ager, D.J. 127 Aggarwal, V.K. 14, 41, 60, 89, 109, 133, 135, 186, 193, 243, 279 Agofoglio, L.A. 296 Aimoto, S. 217 Ajjou, A.N. 103 Akamanchi, K.G. 109, 124, 247 Akasaka, T. 309 Akashi, M. 328 Akita, H. 333 Aldyama, T. 33, 265 Alajarin, M. 136 Albericio, F. 362, 364, 368, 374, 376 Albrecht, M. 295 Alcaide, B. 138, 167, 217, 281,287 Alcaraz, G. 261 Alexakis, A. 28, 34, 331 Alle~etti, M. 45 Allenmark, S. 67 Almansa, C. 187 Almeida, W.P. 14, 25 Almendros, P. 138, 167, 217, 281, 287 . Almquist, F. 139 Almqvist, F. 370 Alonso, J. 218 Alonso, R. 193 Alper, H. 191,318, 355 Altenbach, H.-J. 338 Altona, C. 262 Alvarez, M. 334, 346, 368 Alvarez-Builla, J. 373 Alves, M.J. 134 Aly, A.A. 67 Amat, M. 30, 334

AUTHOR INDEX

Amii, H. 16 Amri, H. 302 Ananikov, V.P. 114, 267 Anderson, H.L. 324 Anderson, J.C. 338 Andersson, P.G. 119 Ando, M. 314 Andrade, Z. 30 Andres, C. 67, 73 Andrews, D.M. 18 Andrus, M.B. 37, 57, 261,336, 343 Angiolini, M. 370 Ansari, W.H. 17 8 Anson, M.S. 229 Anthonsen, T. 229 Antipin, I.S. 321 Appendino, G. 312 Arai, T. 318 Arai, Y. 36 Araki, S. 207, 339 Aramini, A. 45 Arcadi, A. 167 Ardisson, J. 10 Arduini, A. 325 Argade, N.P. 46, 228, 229, 343 Arimoto, H. 342 Ariza, X. 341 Armaroli, N. 316 Armspach, D. 295 Armstrong, A. 67, 95, 111,243, 271 Armstrong, III, J.D. 276 Amaud, F. 322 Amaud-Neu, F. 321 Arndtsen, B.A. 195 Amo, M. 329, 330, 344 Arrayas, R.G. 9 Asao, N. 67, 68 Asensio, G. 86 Asher, S.A. 260 Ates, A. 160 Aube, J. 74, 181,234, 258 Aubert, C. 69, 268 Auge, J. 23 Austin, D.J. 88 Avenoza, A. 139 Aversa, M.C. 72

AUTHOR INDEX

Azuma, Y. 170 Bach, T. 73, 75, 144, 335, 346 Bacieredo, A. 133 Back, ToG. 167 Backvall, J.-E. 54, 95, 110, 113, 249 Bagherzadeh, M. 102 Bagley, M.C. 335 Bai, D. 344 B alley, P.D. 343 Bailey, W.F. 93, 164 Bakos, J. 125 Balalaie, S. 169 Balci, M. 188 Baldwin, J.E. 70, 342 Balicki, R. 124 Ballini, R. 50, 62, 234, 256, 349 Balme, G. 75, 155, 210, 292, 343 Balzarini, J. 307 Ban, H. 78 Banaglia, M. 365 Bandgar, B.P. 196, 221,248, 270, 350 Bandini, M. 39, 169 Banerjee, A. 220 Banerjee, A.K. 334 Banfi, L. 145 Banik, B.K. 197, 215, 238 Bannwarth, W. 362 Banwell, M.G. 72, 333, 334, 336, 345 Baraldi, P.G. 158 Barba, F. 145 Barbachyn, M.R. 212 Barbas, III, C.F. 14, 68, 72, 348 Barhdadi, R. 353 Barlos, K. 367,374 Barluenga, J. 68, 93, 115, 159, 174 Barrett, A.G.M. 271,365 Barriault, L. 67, 280 Bartoli, G. 223, 293 Bartsch, R.A. 21 Basabe, P. 345 Basak, A. 281 Basavaiah, D. 14, 281 Bashiardes, G. 65 Baskaran, S. 338 Bassani, D.M. 307

383

Basset, J.-M. 47, 287 Basso, A. 362 Basu, A. 222 Basu, B. 238, 366 Bates, D.K. 159 Batey, R.A. 24, 167, 187, 233, 239, 251,259 Batra, S. 14, 25, 120 Battaglia, A. 313 Baudoin, O. 79 Bauerle, P. 377 Bauta, W.E. 2 Bazureau, J.P. 360 Beak, P. 34 Beam, C.F. 195 Beaucage, S.L. 223 Beaudoin, S. 233 Beaulieu, P.L. 185 Beccalli, E.M. 144, 171 Becher, J. 213 Bedekar, A.V. 253 Bedford, R.B. 79, 81 Begue, J.-P. 109 Bei, X. 102 Belai, I. 185 Beletskaya, I.P. 58, 114, 125, 266, 267, 289 Bell, A.T. 229 Beller, M. 82, 111, 113, 126, 240, 256, 258, 282 Bellina, F. 254 Belokon, Y.N. 242 Benaglia, M. 139, 380 Benedetti, F. 203 Benerjee, R. 286 Benhida, R. 118, 185 Bennasar, M.-L. 218, 340 Bentrude, W.G. 266 Bergdahl, M. 36 Bergman, R.G. 135, 156, 163, 230 Berkessel, A. 24, 61 Bernard, A.M. 99 Bernardi, L. 26 Bernhardt, P.V. 275 B ernini, R. 351 Berteina-Raboin, S. 369 Bertini, V. 367, 373 Bertozzi, C.R. 226

384

Bertrand, G. 289, 291 Bertus, P. 62 Besson, T. 201 Betzer, J.-F. 54 Bhat, N.G. 55 Bhattacharjya, A. 316 Bhattacharya, P.K 350 Bhattacharyya, S. 238,362, 366 Bhusare, S.R. 253 Biali, S.E. 281,323, 329 Bianco, A. 311 Bieber, L.W. 348 Biellmann, J.-F. 295 Billard, T. 22, 170 Birladeanu, L. 299 Bitter, I. 319, 321,322 Bittman, R. 27 Blackwell, H.E. 380 Blackwell, L.F. 104 Blanchard-Desce, M. 318 Blass, B.E. 367 Blechert, S. 47, 50, 162, 331 Blotny, G. 271 Blum, J. 82 Blume, T. 336 Boatman, P.D. 377 Bochet, C.G. 215, 218, 363 Bodtke, A. 185 Bogdal, D. 103 Boger, D.L. 67, 343, 379 Bohm, L.L 283 Bohmer, V. 48, 321 Boivin, J. 130 Boland, W. 345 Bolf, M. 136 Bolm, C. 6, 110, 176, 276 Bols, M. 246 Bonaccorsi, P. 72 Bongini, A. 139 Bonin, M. 231 Bonini, C. 241 Bonjoch, J. 341 Bonnet-Delpon, D. 29, 168, 170 Booker-Milbum, K.I. 73, 154, 187, 338 Booth, B.L. 211 Borhan, B. 105, 146, 152 Bomer A. 263

AUTHOR INDEX

Bomer, A. 121,126 Bomhop, D.J. 218 Borschberg, H.-J. 97 Boruah, R.C. 249 Bosch, J. 30 Bose, D.S. 117, 188, 219 Botta, M. 107 Boulton, L.E. 127 Bourne, J.R. 299 Bouteiller, L. 327 Bovicelli, P. 112 Boykin, D.W. 79 Boyle, R.W. 370 Bracher, F. 332, 338 Braddock, D.C. 72 Bradley, M. 110, 218, 362, 363, 366, 377 Braga, A.L. 20, 54, 58 Braibante, M.E.F. 183 Brain, C.T. 187 Braje, W.M. 376 ~ Branchadell, V. 133 Brand, S. 64 Brandi, A. 138, 172, 379 Brands, K.M.J. 330 Brase, S. 235, 369, 380 Breinbauer, R. 366 Breit, B. 90, 282 Brenelli, E.C.S. 249 Brenna, E. 278 Brimble, M.A. 58, 145, 333 Bfingmann, G. 20, 330 Brinker, U.H. 255 Brion, J.-D. 10 Brook, M.A. 22 Brown, R.C.D. 49, 370 Bruice, T.C. 374 Brummond, K.M. 88 Brun, P. 75, 342 Brunner, H. 6 Brussee, J. 243 Bryce, M.R. 78, 278 Bubenik, M. 263 Buchmeiser, M.R. 47 Buchwald, S.L. 55, 57, 78, 98, 125, 126, 141,236, 238, 239, 256 Bugg, T.D.H. 296 Bull, S.D. 45, 274

AUTHOR INDEX

Bunce, R.A. 160 Bunch, L. 244 Bunz, U.H.F. 287 Buonora, P.T. 188 Burger, K. 19, 200 Burgess, K. 125, 278, 282, 368 Burkart, M.D. 274 Burke, S.D. 151 Burley, G.A. 310 Butts, C.P. 79, 308 Byers, J.H~ 84 Cacchi, S. 82, 86, 90, 166, 270 Caddick, S. 132, 193 Cadiemo, V. 119 Cahard, D. 2, 372 Cai, D. 2 Cai, M. 54, 82, 83, 91 Calderazzo, F. 303 Calmes, M. 365 Calo, V. 352 Calter, M.A. 13, 280 Calzaferri, G. 329 Cambpell, I.B. 248 Caminade, A.-M. 316 Cammidge, A.N. 362 Campos, K.R. 2 Camps, P. 124 Canwell, M.G. 343 Cao, S. 35 Carda, M. 337, 340, 345 Cardenas, D.J. 288 Cardillo, G. 50, 209 Cardona, F. 193 Carmona, A.T. 334 Caron, S. 22, 164 Carotti, A. 165 Carrasco, M.R. 245 Carreaux, F. 176 Carreira, E.M. 36, 125,213, 339, 344 Carreno, M.C. 67, 155, 160 Carretero, J.C. 6, 9, 82, 88 Caruthers, M.H. 374 Casamitjana, N. 36 Cases, M. 170 Casey, C.P. 91 Casnati, A. 322 Castanet, Y. 89

385

Castellano, R.K. 277 Castillon, S. 200, 262 Castle, S.L. 3 Catallani, M. 292 Cataviela, C. 244 Catellani, M. 82 Caubere, P. 199 Caulton, K.G. 134 Cavelier, F. 364 Cervantes, J. 268 Cha, J.K. 63, 92, 96, 244, 331 Chadha, A. 118 Chai, C.L.L. 196, 332 Chai, W. 180 Chaikof, E.L. 48 Chakrabarty, M. 272, 333 Chakraborti, A.K. 241,248 Chakraborty, T.K. 333, 343 Chambron, J.-C. 325 Chan, A.S.C. 27, 36, 37, 119, 126 Chan, K.S. 264 Chan, M.K. 199 Chan, T.H. 14, 357, 359 Chandrasekaran, S. ! 11,266 Chandrasekhar, S. 113, 219, 221, 266, 353 Chandrashekar, T.K. 212 Chang, C.-W. 203 Chang, M.-Y. 121, 139, 143 Chang, N.-C. 5,121, 139, 143 Chang, S. 50, 90, 94 Chang, Y.-T. 366, 379 Charette, A.B. 28, 60, 61,257, 333 Chassaing, C. 370 Chatanai, N. 148 Chatani, N. 89, 153 Chaudhari, R.V. 239 Chaudhuri, M.K. 109 Chauhan, S.M.S. 357, 360 Chauvin, R. 126 Chavan, S.P. 216, 248, 337, 338 Che, C.-M. 60, 61,133, 161 Chelucci, G. 279 Chemla, F. 21, 37 Chen, C. 119 Chen, H. 20, 119, 127 Chen, J.H. 346 Chen, J.J. 235

386

Chen, K. 14, 112 Chen, P. 274 Chen, Q. 344 Chen, Q.-Y. 61 Chen, S.-T. 143, 331,332 Chen, X. 299 Chen, Y.-J. 77 Chen, Z. 254, 374 Chen, Z.-C. 352, 355, 358, 361 Cheng, C.-H. 59, 83, 85, 91, 149, 309 Cheng, M.S. 340 Chi, K.-W. 326 Chiacchio, U. 193 Chida, N. 329 Cho, B.P. 240 Cho, C.-G. 69, 87, 238 Cho, C.S. 1, 168 Cho, Y.S. 174 Chong, J.M. 272 Chou, S.-S.P. 144 Choudary, B.M. 110, 113 Christoffers, J. 279 Christophersen, C. 261 Chu, C.K. 263 Chuiko, V.A. 295 Chung, Y.K. 82, 89, 349 Chupakhin, O.N. 209 Ciaccio, J.A. 133 Cintrat, J.-C. 9 Ciufolini, M.A. 166, 197 Clapes, P. 229 Clark, A.J. 140, 193 Clark, J.S. 49, 176 Clarke, M.L. 379 Clauvin, R. 287 Clayden, J. 73, 142, 152 Cleophax, J. 374 Clive, D.L.J. 154, 297, 332, 336, 341 Coates, R.M. 246, 332 Coats, S.J. 373 Coe, J.W. 152, 173 Coelho, F. 25 Coelho, P.J. 69 Coldham, I. 159 Collado, I.G. 281 Collin, J. 160

AUTHOR INDEX

Collin, J.-P. 325 Colobert, F. 21, 79, 155 Colombo, L. 145 Comdom, R.F.P. 351 Compain, P. 50 Concellon, J.M. 25, 46, 63, 130, 131,241 Constantieux, T. 169 Constantino, M.G. 72 Cook, G.R. 234 Cook, J.M. 88, 330, 335, 338, 339, 340, 341,342, 346 Coop, A. 331 Coperet, C. 287 Cordero, F.M. 138, 337 Cordova, A. 14 Corelli, F. 107 Corey, E.J. 66, 70, 105, 113, 146, 224, 341,343 Corma, A. 14, 301 Correia, C.R.D. 85, 335 Corriu, R. 289 Cossy, J. 4, 84, 116, 119, 202, 280, 345,372 Coutouli-Argyropoulou, E. 196 Couture, A. 332, 336, 339, 342, 345 Couty, F. 159, 180 Covarrubias-Zuniga, A. 7,333 Cowden, C.J. 42 Cox, L.R. 208,272 Cox, R.J. 243 Cozzi, P.G. 27, 118, 125 Cravino, A. 308 Cravotto, G. 336 Crich, D. 128, 196, 223, 226 Crimmins, M.T. 12, 179, 339, 341, 344 Cristau, H.-J. 129, 204, 265 Cross, R.J. 309 Crotti, P. 93 Crouch, R.D. 223 Crousse, B. 29, 170 Crudden, C.M. 279 Csaky, A.G. 343 Csuk, R. 262 Cummins, C.C. 59 Cunico, R.F. 32, 236

AUTHOR INDEX

Cuny, G.D. 339, 341 Curci, R. 106, 112 Curini, M. 53 Curphey, T.J. 270 Curran, D.P. 41, 71, 82, 237, 244, 273 Cvetovich, R.J. 183 Czarnocki, Z. 340 d'Angelo, J. 34 Dabak, K. 203 Dai, L. 301 Dai, L.-X. 53, 82, 278 Dai, W.-M. 369 Dake, G.R. 100 Dang, H.-S. 128 Danheiser, R.L. 59, 138, 167, 181 Danieli, B. 183 Danishefsky, S.J. 48, 67, 298, 334, 339, 340, 344 Dankwardt, J.W. 85 Darbre, T. 346 Darvas, F. 370 Das, B. 170, 220, 221,223, 233 Das, P.J. 367 Das, S. 117 Das, S.K. 227 Dauben, P. 303 Davidsson, O. 378 Davies, H.M.L. 42, 93, 333, 338, 365 Davies, S.G. 98, 120, 230, 231, 344 Davis, A.M. 275 Davis, B.G. 330 Davis, F.A. 135, 161,265, 330, 335, 338,339, 344 Davis, Jr., J.H. 304 Davisson, V.J. 263 De Bank, P.A. 297 De Brabander, J.K. 342 De Clerq, P.J. 372 de Fays, L. 48 de Groot, F.M.H. 318 De Kimpe, N. 135, 140 de Koning, C.B. 179, 302 de la Moya Cerero, S. 101 de la Pradilla, R.F. 67, 111,152, 186

387

de Lera, A.R. 298 de Mattos, M.C.S. 259 de Meijer, A. de Meijere, A. 53, 62, 79, 117, 150, 176, 301 de Mendoza, J. 320 De Nanteuil, G. 333 de Oliveira, A.R.M. 36 De Ricarrdis, F. 176 De Schryver, F.C. 316 De, A. 148, 344 De, S.K. 216 Dechoux, L. 143, 159, 194 Del Buttero, P. 183 Delair, P. 330 Delfoume, E. 344 Dembinski, R. 152 Dembitsky, V.M. 289, 300 Demchenko, A.V. 280 Demir, A.S. 32, 79, 106 Demitz, F.W.J. 131 Deng, G.-H. 15 Deng, J. 119 Deng, L. 21,242 Deng, Y. 353 Deniau, E. 128 Deniaud, D. 190, 201 Denmark, S.E. 13, 14, 22, 32, 70, 81, 83, 88, 267,290 Deodhar, K.D. 71 Deschenaux, R. 309 Deshmukh, A.R.A.S. 143 Deshong, P. 81 Desimoni, G. 67 Deslongchamps, P. 69, 71,330, 332 Detty, M.R. 178 Devocelle, M. 374 Dhal, R. 52 Dhavale, D.D. 154 Dias, L.C. 342 Diaz-de-Villegas, M.D. 244 Diederich, F. 277 Dieter, R.K. 28, 93 Diez, D. 62, 175 Diez-Barra, E. 82, 315, 317 Dikshit, D.K. 343 Dilman, A.D. 195, 281

388

Ding, K. 31, 176 Ding, M.-W. 185 Ding, S. 78 Ding, Y. 265 Diver, S.T. 49 Dixneuf, P.H. 53, 63 Dixon, D.J. 216 Dobbs, A.P. 171 Dobler, M.R. 84 Dodd, R.H. 303, 343 Doherty, S. 126 Dolbier, Jr., W.R. 61 Domingo, L.R. 71 Dominguez, E. 84, 184 Dominique, M. 295 Domling, A. 200, 371 Donaldson, W.A. 61,195, 333 Dondoni, A. 30, 245, 265 Donohoe, T.J. 16, 151,247, 335 Dore, T.M. 215 Doris, E. 109, 176 Dorwald, F.Z. 286 Dory, Y.L. 71 dos Santos, E.N. 90 Doucet, H. 53, 57, 79, 87 Douthwaite, R.E. 6 Doye, S. 166, 181,283, 288 Doyle, M.P. 147, 161,365 Dransfield, P.J. 30 Du Bois, J. 345 Du, Y. 332 DuBois, J. 208, 313, 314 Duchene, A. 54, 79, 143 Ducrot, P.-H. 330 Dugave, C. 300 Dujardin, G. 227, 369 Dumas, F. 34 Dunach, E. 67, 178,283, 290 Dupont, J. 79, 358 Dupuy, C. 208 Durand, T. 342 Durandetti, M. 21, 23 Durst, T. 64 Duthaler, R.O. 235 Dutton, C.J. 48 Dvorak, D. 21 Dyker, G. 326 Easton, C.J. 253, 324

AUTHOR INDEX

Eberlin, M.N. 96 Echavarren, A.M. 92, 292 Echegoyen, L. 309 Egle, I. 377 Eilbracht, P. 161 Eisenstein, O. 53 Eklund, P. 335, 340 E1 Kaim, L. 238 E1-Abadelah, M.M. 158 E1-Faham, A. 246 E1-Sayed, M.A. 79 Elassar, A.-Z.A. 302 Elemans, J.A.A.W. 327 Eliseev, A.V. 376 Ellman, J.A. 16, 29, 67, 109, 156, 163 Elsevier, C.J. 268 Elwahy, A.H.M. 209 Enders, D. 13, 84, 202, 286, 331, 343, 345 Endo, T. 196 Engeldinger, E. 295 Engman, L. 154 Ensley, H.E. 247 Epifano, F. 53 Erian, A.W. 159 Estevez, R.J. 18, 330, 339 Etheve-Quelquejeu, M. 263 Etzkorn, F.A. 52 Evans, D.A. 12, 13, 19, 66, 77, 126, 336, 344 Evans, G.B. 84 Evans, P. 113 Evans, P.A. 2, 48, 175, 332 Evans, W.J. 21 Ezquerra, J. 28 Faber, K. 334 Fache, F. 379 Fagnoni, M. 84, 211, 215 Faigl, F. 123 Fairbanks, A.J. 96, 294 Fairlamb, I.J.S. 58, 93 Fairlie, D.P. 244 Falck, J.R. 8, 46, 223 Fallahpour, R.-A. 213 Fallis, A.G. 53 Fan, E. 259 Fang, J.-M. 235

AUTHOR INDEX

Fang, X. 105 Far, A.R. 379 Fattori, D. 373 Faucher, A.-M. 132 Faul, M.M. 94 Fehrentz, J.-A. 371,374 Feng, X. 21 Fensterbank, L. 344 Ferey, G. 294 Feringa, B.L. 36, 37, 126, 141,225 Fernandez, E. 231,366 Fernandez-Bolanos, J.G. 136 Fernandez-Fomer, D. 362 Fernandez-Mateos, SA. 41 Femandez-Zertuche, M. 23 Feroci, M. 234, 235 Ferraccidi, R. 189 Ferraz, H.M.C. 117, 341 Field, L.D. 268 Figadere, B. 275 Figueredo, M. 336 Filippone, P. 136, 207 Filla, S.A. 155 Fillion, E. 75 Finley, K.T. 110 Finn, M.G. 118 Firouzabadi, H. 45, 126, 216, 254 Fischer, H. 48 Fleming, F.F. 36, 37, 282 Fleming, I. 9, 269 Flitsch, S.L. 378 Floreancig, P.E. 174 Florent, J.-C. 48, 96 Florio, S. 62, 193, 212, 243 Floris, B. 307 Florjancic, A.S. 27 Flowers, II, R.A. 129, 154 Flynn, B.L. 12, 159 Flynn, D.L. 237, 362, 365 Fogg, D.E. 47, 49 Font, J. 73 Forbes, D.C. 133 Forns, P. 362 Forsyth, C.J. 58, 104, 200, 330, 332 Fort, Y. 84, 121,164, 366 Foubelo, F. 297 France, M.B. 61

389

Franck, R.W. 202 Frank, R. 365 Franzini, M. 276 Franzy, K.H. 374 Fraser-Reid, B. 247 Frechet, J.M.J. 319 Freistad, G.K. 33 Frejd, T. 85 Frey, L.F. 28 Friedinger, R.M. 295 Friedrich, H.B. 113 Friestad, G.K. 122 Fringuelli, F. 67, 241 Fry, A.J. 269 Fu, G.C. 9, 15, 54, 58, 83, 92, 99, 138, 183 Fuentes, J. 227 Fuji, K. 79 Fujimoto, Y. 297 Fujita, K. 239, 328 Fujita, T. 302 Fukuyama, T. 154, 232, 239, 331, 335, 339, 342 Fukuyama, Y. 6 Fukuzawa, S. 147 Funabiki, K. 16 Funk, R.L. 69 Furman, B. 38 Furstner, A. 298, 330, 331,332, 333, 339, 341,345, 346 Fustero, S. 238, 244, 255 Gabriele, B. 160, 196 Gagne, M.R. 79 Gais, H.-J. 173, 270 Gajda, T. 195 Galande, A.K. 374 GaUagher, T. 78, 190 Gallardo, I. 82 GaUetti, P. 199 Galli, C. 285 Gallos, J.K. 194 Galvez, J.A. 28, 244 Gandolfi, M.T. 326 Ganem, B. 197 Ganesan, A. 333, 341 Gansauer, A. 11, 156, 211 Gao, J. 80 Garbaccio, R.M. 335

390

Garbay, C. 159 Garcia Ruana, J.L. 269 Garcia Ruano, T.L. 29 Garcia, H. 14, 301 Garcia-Garibay, M.A. 286 Garcia-Mera, X. 72 Garcia-Tellado, F. 27 Gardiner, J.M. 338 Gardossi, L. 362 Gareau, Y. 271 Garlaschelli, L. 311 Gau, H.-M. 20 Gaultier, G. 273 Gaumont, A.-C. 265, 276 Gaunt, M.J. 62 Gawronski, J. 218, 320 Geib, S.J. 273 Gellman, S.H. 243 Gelmi, M.L. 244, 295, 313 Genet, J.-P. 119, 279, 289, 345 Gennari, C. 48 Georg, G.I. 334, 344 Gesson, J.-P. 342 Gevorgyan, V. 91, 156, 290 Ghanem, A. 249 Ghorbani-Vaghei, R. 104, 107 Ghosez, L. 48 Ghosh, A. 236 Ghosh, A.K. 113, 330 Ghosh, C.K. 180 Ghosh, S. 73, 333, 337 Giacomelli, G. 104, 233 Giacomini, D. 199 Giannis, A. 300 Gibb, B.C. 301 Gibson, H.W. 316, 324 Gibson, S.E. 82, 278, 283, 366 Giese, B. 363 Gigante, B. 352 Gil, P. 337 Gill, M. 344 Gimeno, J. 119 Gin, D.Y. 226 Gin, M.S. 69 Gift, V.S. 126 Gladysz, J.A. 254 Gleason, J.L. 92 Gleiter, R. 59

AUTHOR INDEX

Gmeiner, P. 145 Gmins, D.L. 57 Godovikova, T.I. 214 Goel, A. 170 Gogoll, A. 57 Golding, B.T. 239 Goldman, A.S. 258 Gomez, A.M. 247 Gona, L.-Z. 14 Gong, L. 79 Gong, L.-Z. 27, 28 Gonzalez, C. 230 Gonzalez-Gomez, J.C. 188 Gonzalez-Muniz, R. 139, 245 Goodby, J.W. 309 Goodman, M. 245 Goosen, L.J. 127 Gopalan, A.S. 159 Gorman, C.B. 315 Gosmini, C. 23, 28, 81, 83, 132 Goti, A. 23, 124, 334, 337 Gotor, V. 249 Gottlich, R. 138 Gouvemeur, V. 49, 255 Gowda, D.C. 124 Grainger, R.S. 2, 333 Grande, M. 181 Graybill, T.L. 370 Grayson, D.H. 25 Gree, R. 13, 196, 290 Green, J.R. 69 Greenberg, M.M. 263 Greene, A.E. 340 Greenwald, R.B. 312 Grela, K. 47, 50 Grieco, P. 373 Griesbeck, A.G. 242, 275 Grigg, R. 24, 49, 54, 142, 167, 172, 183 Grimme, S. 156 Grindley, T.B. 317 Gros, P. 366 Gross, J.L. 343 Grossman, R.B. 34, 243 Grosu, I. 212 Groth, U. 69, 329, 344 Grubbs, R.H. 47, 49, 162, 324 Guanti, G. 54, 338, 374

AUTHOR INDEX

Gudmundsdottir, A.D. 136, 246 Gueiffier, A. 238 Guillaumet, G. 169, 199 Guillemin, J.-C. 357 Guillou, C. 340 Guldi, D.M. 306, 307, 310 Gundersen, L.-L. 345 Gunes, M. 337, 339, 342 Gung, B.W. 337 Gunter, M.J. 326 Guo, Q.-X. 347 Guo, Z.-R. 239 Guo, Z.-X. 311 Gupton, J.T. 341 Guram, A.S. 102 Gurjar, M.K. 48, 178, 337, 340 Gusevskaya, E.V. 90 Gushchin, A.V. 82 Gutschow, M. 187 Guzaev, A.P. 364 Guzzo, P.R. 151 Ha, D.-C. 20 Ha, H.-J. 196, 118, 209 Hada, T. 263 Hadjiarapoglou, L.P. 7, 71 Hagiwara, H. 34, 346, 351 Hagiya, K. 120 Hajipour, A.R. 103, 216, 283 Hajos, G. 183 Hakansson, M. 21 Halcomb, R.L. 245,342 Hale, K.J. 330 Haley, M.M. 301 Hall, D.G. 24, 36, 167, 176, 289 Hallberg, A. 85 Hallinan, E.A. 244 Ham, W.-H. 344 Hamad Elgazwy, A.-S.S. 211 Hamada, Y. 169 Hammer, R.P. 372 Han, B. 358 Han, J.-S. 331 Hana, I. 96 Hanamoto, T. 83 Hanan, G.S. 81 Handy, S.T. 305, 355, 361 Hanefeld, U. 249 Haner, R. 374

391

Hanessian, S. 244, 262, 331,340 Hanselmann, R. 243 Hanson, J.R. 254, 329 Hanson, P.R. 61,237, 362, 365 Hara, H. 222 Hara, S. 175, 253 Harada, T. 34, 95 Haraguchi, K. 263 Harayama, T. 333, 336, 339 Harman, W.D. 176 Harmata, M. 11,201,285, 345 Harpp, D.N. 207, 270 Harran, P.G. 334 Harrity, J.P.A. 171 Harrowven, D.C. 82, 373 Hart, B.P. 139 Hart, D.J. 174 Hartley, R.C. 156 Hartung, J. 113 Hartwig, J.F. 1, 80, 84, 238, 240, 251,252, 261, 291 Harvey, P.D. 321 Hasegawa, E. 116 Hashemi, M.M. 115 Hashimoto, M. 136 Hashimoto, S. 91,346 Hashmi, A.S.K. 70 Haswell, S.J. 378 Hatakeyama, S. 30, 335, 345 Hattori, K. 113 Hattori, T. 331 Haught, A.R. 252 Hawkins, J.M. 67 Hawthorne, M.F. 358 Hayakawa, H. 263 Hayashi, M. 115, 197 Hayashi, T. 22, 52, 86 Hayashi, Y. 14, 258, 315, 343 Hayes, W. 317 He, C. 133 He, Y. 67 Headley, A.D. 15 Heany, F. 193 Hecht, S.M. 376 Heck, J. 93 Hegedus, L.S. 378 Heimgartner, H. 334 Heitz, V. 325

392

Heller, B. 168 Helmchen, G. 331,332 Hendrickson, J.B. 168 Henegar, K.E. 340 Henin, F. 350 Henkel, B. 371,373 Herdewijn, P. 263 Hergenrother, P.J. 114, 243 Hernandez, J.-F. 206 Herndon, J.W. 71, 161, 163, 168, 335 Hess, G.P. 220 Hesse, M. 152, 337, 341 Heuze, K. 57 Heydari, A. 26 Hibino, S. 345 Hidai, M. 2, 77, 157, 177, 232 Hideg, K. 244 Hie g e1, G .A. 104, 2 60 Hiemstra, H. 73, 189 Hiersemann, M. 284 Hierso, J.-C. 79 Hii, K.K. 238 Hillhouse, J.H. 303 Hilmersson, G. 21,129, 222 Hilt, G. 68 Hinkle, R.J. 175 Hirama, M. 180, 332 Hirao, T. 119, 154 Hirashita, T. 29 Hirata, T. 209 Hiroi, K. 104, 146 Hirota, K. 126, 224 Hitchcock, S.R. 12 Hiyama, T. 57 Ho, T.-I. 58 Hocek, M. 213 Hodacova, J. 218 Hodge, P. 366 Hodgetts, K.J. 143 Hodgson, D.M. 8, 10, 153, 176 Hoffmann, H.M.R. 298 Hoffmann, R.W. 21,280, 288 Hofle, G. 48 Hoge, G. 125 Holland, H.L. 229 Hollis, T.K. 78 Holton, R.A. 337

AUTHOR INDEX

Holz, J. 126 Holzer, W. 183, 194 Hon, Y.-S. 51,365, 367 Honda, T. 69, 98, 338 Hone, N.D. 371 Hong, B.-C. 171 Hong, J.H. 97 Hoornaert, G.J. 67, 145 Hoppe, D. 152 Horiguchi, Y. 170 Hoshino, O. 88 Hosomi, A. 34, 272, 281 Hossain, M.M. 291 Hou, X.-L. 6, 26, 53, 82, 230, 241, 278 Hou, Z. 54 Houghten, R.A. 369, 371 Houk, K.N. 196 Hoveyda, A.H. 9, 30, 35, 167, 292 Howell, A.R. 131 Hoye, T.R. 333,346 Hoz, S. 82 Hruby, V.J. 3, 160, 244 Hsung, R.P. 22, 176, 237, 302, 330, 340, 343, 345 Hu, W. 139, 205 Hu, X. 36, 79 Hu, Y. 143, 204 Huang, J. 83 Huang, P.-Q. 20, 333, 335, 338, 346 Huang, S.-T. 343 Huang, X. 37, 91, 127, 206, 250, 255, 363, 369, 371 Huang, Z.-T. 320, 323 Hubbard, B,K. 299 Huck, W.T.S. 274 Hudlicky, T. 222 Hugel, H.M. 297 Hughes, A.B. 243 Hulme, A.N. 364 Hulme, C. 368 Hultin, P.G. 12 Hultzsch, K.C. 160 Hung, S.-C. 227, 250 Hunter, R. 339 Huo, S. 83 Hutchings, G.J. 134

AUTHOR INDEX

Hutton, C.A. 335 Ibatullin, F.M. 227, 246 Ibrahim, Y.A. 48, 168 Ichikawa, J. 46 Ichikawa, Y. 339 Iesce, R. 86 Iguchi, K. 64 Ihara, M. 39, 90, 98, 143, 154 Ikariya, T. 34, 130 Ikeda, M. 209 Ikeda, S. 291 Ikegami, S. 79 Ikunaka, M. 228 Ikushima, Y. 348 Ila, H. 169, 183 Imamoto, T. 125 Imanishi, T. 336, 344 Imhof, W. 141 Inanaga, J. 22 Inesi, A. 234 Infantes, L. 326 Inomata, K. 23, 139, 194, 280 Inoue, M. 340, 345 Inoue, Y. 21, 37, 81,327 Inouye, M. 327 Ioffe, S.L. 195 Iqbal, J. 17, 48, 53, 111, 144 Iranpoor, N. 45, 126, 254 Irimie, F.-D. 120 Isabel, E. 377 Ishar, M.P.S. 73 Ishibashi, H. 163, 182 Ishii, K. 77 Ishii, Y. 53, 94, 106, 250 Ishikawa, T. 27, 65, 365 Ishikura, M. 263 Ishimaru, K. 17 Ishino, Y. 234 Ishizaki, M. 88 Isobe, M. 27,345 Itami, K. 82, 376 Ito, H. 64 Ito, K. 320 Ito, T. 81, 172 Ito, Y. 5, 340, 374 Itoh, A. 106 Itoh, K. 42 Itsuno, S. 366

393

Iuliano, A. 36 Iwamatsu, S. 309 Iwao, M. 339, 341,342 Iwasa, S. 61 Iwasawa, N. 38, 40 Izquierde, I. 337 Izzo, I. 176 Jabin, I. 319 Jackson, R.F.W. 83, 93 Jackson, R.W. 377 Jacob, R.G. 169 Jacobs, J.W. 376 Jacobs, P.A. 53 Jacobsen, E.N. 17, 31, 34, 39, 176 Jaenicke, S. 119 Jagodzinski, T.S. 210 Jahng, Y. 189 Jamison, T.F. 26, 87, 92, 345 Janda, K.D. 365 Jang, D.O. 250 Jao, E. 65 Jarosz, S. 69 Jauch, J. 330 Jayaraman, N. 317 Jeanmart, S. 297 Jensen, A.W. 311 Jensen, K.J. 374 Jeong, I.H. 26 Jeong, J.W. 340 Jeong, K.-S. 325 Jeppesen, J.O. 213, 324, 326 Jesberger, M. 304 Jew, S. 159, 242 Jha, A. 13 Ji, J. 238 Ji, S.-J. 39, 355 Jia, X. 271 Jianc, B. 344 Jiang, B. 30 Jiang, W. 116 Jiang, Y.-G. 27 Jimenez, J.L. 138 Jimenez, L.S. 336, 340 Jin, T.-S. 175, 248, 256 Jin, Z. 333 Johannsen, M. 79 Johansson, A. 378 Johnson, B.F.G. 288

394

Johnson, F. 342 Johnson, P.D. 207 Johnston, J.N. 166 Jokela, R. 345 Jones, S. 118 Jones, W.D. 174 Jordan, A.D. 200 Jorgensen, K.A. 14, 17, 19, 34, 38, 77, 149, 235, 241 Joseph, B. 21, 167 Joseph-Nathan, P. 253, 337 Joshi, N.N. 41 Josyula, K.V.B. 261 Journet, M. 2 Ju, J. 203 Juaristi, E. 4, 13, 20 Jubault, P. 5 Jun, J.-G. 303 Jung, I.N. 268 Jung, K.W. 82, 139, 218 Jung, M.E. 51,100 Jung, Y.H. 222, 235 Junjappa, H. 169, 183 Jurczak, J. 77, 331 K., Langer, P. 267 Kabalka, G.W. 79, 87, 91,266, 353, 359 Kabilan, S. 216 Kaboudin, B. 265 Kadota, I. 129, 336 Kadouri-Puchot, C. 163 Kadyrov, R. 121,238 Kafarski, P. 265 Kahn, A.T. 221 Kakiuchi, F. 78 Kakiuchi, K. 142, 269, 314 Kalaus, G. 340, 346 Kalbalka, G.W. 33, 236 Kalesse, M. 332 Kaliappan, K.P. 48 Kamal, A. 144, 216, 336, 341,359, 374 Kamal. A. Kambe, N. 9, 267 Kamimura, A. 179 Kamino, T. 78 Kamitori, Y. 186 Kana, S.H. 339

AUTHOR INDEX

Kanai, M. 18 Kanazawa, A. 331 Kanda, Y. 142 Kane, V.V. 67 Kaneda, K. 33, 115, 215, 217, 250 Kanemasa, S. 34, 151 Kang, C. 262 Kang, S.H. 152, 335 Kanger, T. 119 Kantam, M.L. 134 Kantlehner, W. 302 Kappe, C.O. 47 Karade, N.N. 158 Karaghiosoff, K. 267 Karam, O. 76 Karikomi, M. 96 Karimi, B. 105, 123, 215, 221,248 Karlsson, S. 193 Karskela, T. 374 Kashima, C. 212 Kataoka, T. 14, 40 Katayama, H. 93, 268 Katoh, T. 331, 341 Katritzky, A.R. 7, 18, 76, 134, 135, 164, 170, 184, 190, 191, 194, 205, 209, 214 Katsuki, T. 60, 103, 109, 172, 213 Katti, S.B. 121 Katz, F. 313 Kaufman, T.S. 170 Kawabata, T. 3, 5, 170, 245 Kawakami, J. 28 Kawanami, Y. 118 Kawasaki, K. 217 Kawasaki, T. 336, 343 Kawashima, T. 210 Kay, C. 362 Kaye, P.T. 150 Kayser, M.M. 150 Kazemi, F. 135, 246 Kazmaier, U. 245, 272 Ke, P.K. 358 Keay, B.A. 67, 333 Kedrowski, B.L. 245 Kelly, J.W. 200, 334 Kelly, T.R. 339 Kemperman, G.J. 353 Kende, A.S. 330, 344

AUTHOR INDEX

Kercher, T. 197 Kern, J.-M. 326 Kerr, M.A. 68,337 Kessler, H. 196 Kezuka, S. 193 Khalafi-Nezhad, A. 233 Khan, A.T. 215, 216 Khan, F.A. 358 Khan, K.M. 254 Khanbabaee, K. 342 Khiar, N. 281 Khodaei, M. 137 Khodaei, M.M. 110 Khrimian, A. 67 Khwana, J.M. 11 Kiasat, A.R. 135 Kibayashi, C. 143, 298, 331,332 Kidwai, M. 206 Kieboom, T. 300 Kiessling, L.L. 377 Kigoshi, H. 337 Kikugawa, Y. 140 Kilburn, J.D. 224, 366 Kilbum, J.P. 371 Kim, B.H. 124 Kim, B.M. 47 Kirn, C. 319 Kim, D. 49, 251, 341 Kim, G. 332, 339, 340, 344 Kim, J.N. 172, 183, 256 Kim, J.S. 320 Kim, K. 329 Kim, M. 233 Kim, S. 41,330 Kim, S.S. 102, 103, 109 Kim, T.-J. 6 Kim, Y. 46, 347 Kim, Y.H. 262 Kim. J.S. 323 Kimura, K. 300 Kinart, W.J. 235 King, A. 370 Kingston, D.G.I. 314 Kira, M. 119 Kirby, A.J. 300 Kirihara, M. 243 Kirmse, W. 287 Kirsch, G. 208

395

Kirschning, A. 365,367 Kishi, Y. 229 Kiso, Y. 313 Kissel, W.S. 125 Kita, Y. 53, 104, 154, 335, 337 Kitahara, T. 331,332, 335 Kitahara, Y. 338 Kitamura, T. 150 Kitaoka. M. 315 Kiyooka, S. 50 Kiyota, H. 313, 314, 343 Kizhnyaev, V.N. 213 Klaffke, W. 263 Klarner, F.-G. 277 Kleij, A.W. 320 Klempier, N. 243 Klimova, E.I. 67 Knapp, S. 258 Knappwost-Gieseke, C. 67 Knight, D.A. 347 Knight, D.W. 13, 159 Knight, J.G. 143, 334, 340 Knochel, P. 6, 30, 54, 80, 84, 93, 94, 114, 125, !65, 231,240, 289 Knolker, H.-J. 330, 332, 334, 338, 341 Ko, S.Y. 352 Kobayashi, K. 74, 154, 169, 226 Kobayashi, N. 317 Kobayashi, S. 13, 17, 29, 78, 184, 221,293,334, 335, 343, 347, 349, 365, 366, 372 Kobayashi, Y. 341,342 Kocevar, M. 108 Koch, T. 262 Kocienski, P.J. 340 Kocovsky, P. 22, 23, 242 Kogen, H. 331,336, 344, 346 Kokotos, G. 203 Koksch, B. 244 Kolis, S.P. 128 Kollar, L. 290 Kolodiazhnyi, O.I. 276 Kolter, T. 300 Komarov, I.V. 263 Komatsu, K. 308, 310 Komatsu, M. 52, 64, 138, 160, 234, 370

396

Konakahara, T. 84 Kondo, T. 223 Kondo, Y. 85 Konig, B. 59, 167, 211 Koo, S. 7, 77 Kopach, M.E. 237 Korsunskii, B.L. 214 Koshima, H. 372 Kosmrli, J. 231 Kotali, A. 302 Kotera, M. 45 Kotha, S. 295 Kotra, L.P. 244 Kotschy, A. 58 Kotsuki, H. 14 Kouklovsky, C. 66 Koumbis, A.E. 340, 345 Koutek, B. 28 Koutentis, P.A. 78 Kozhevnikov, V.N. 167 Kozikowski, A.R. 41 Kozlowski, M.C. 33, 80 Krafft, M.E. 6, 48, 88,349 Krasnov, V.P. 296 Kraus, G.A. 11, 42, 45, 234, 333, 340 Kraus, J.-L. 150 Krebs, O. 282 Kreher, U.P. 50 Krische, M.J. 15, 23, 31, 37, 66, 73, 92, 303, 337,344 Krishna, P.R. 14, 25, 160, 247 Kristensen, J.L. 173 Kroutil, W. 104, 229 K.row, G.R. 159 Kruger, L. 110 Kuduk, S.D. 162 Kudzma, L.V. 159 Kuethe, J.T. 345 Kuhn, F.E. 110 Kuhnert, N. 322 Kulinkovich, O.G. 94, 181,301 Kulkami, S.J. 253 Kumar, P. 103,220, 329, 333, 342 Kumaraswamy, G. 112, 335 Kunai, A. 10, 207 Kundig, E.P. 329 Kundu, B. 371

AUTHOR INDEX

Kuniyasu, H. 267 Kunz, H. 296, 365, 375 Kunz, K. 284 Kurihara, M. 225 Kurita, J. 6, 59 Kuroda, C. 97 Kuroda, T. 13 Kutateladze, A.G. 321 Kuwajima, I. 338 Kuwano, R. 5 Kuzmich, D. 164 Kwon, O. 13, 167 Kwon, T.W. 371 Kwong, H.-L 60 Labadie, G.R. 34 Lacour, J. 284 Ladlow, M. 220, 362, 363, 375, 378 Lahuerta, P. 60 Lai, Y.-H. 348 Lam, P.Y.S. 87, 239 Lam, Y. 370 Lamartine, R.J. 322 Lamaty, F. 47, 157 Lancaster, N.L. 356 Landais, Y. 48 Lang, F. 13 Lange, U.E.W. 376 Langer, P. 34, 85, 164, 169, 185, 200, 205, 206 Langlois, B.R. 22, 293 Langlois, N. 334 Langlois, Y. 66, 331 Lao, A. 297 Larcheveque, M. 333 Larhed, M. 82, ,89, 236 Larock, R.C. 55, 89, 91,150, 155, 168, 172, 238 Larsen, D.S. 340, 345 Larsen, S.D. 371 Laschat, S. 231 Lassaletta, J.M. 38 Lattanzi, A. 111,157 Lau, J.F. 373 Lauret, C. 342, 343 Laursen, R.A. 217 Lautens, M. 83, 87, 128, 137, 155, 272, 290, 292

AUTHOR INDEX

Lavastre, O. 47 Lavilla, R. 170 Lawrence, D.S. 296 Lay, L. 304 Lazarova, T. 49 Lazny, R. 363 Lazzaroni, R. 182, 341 Le Drian, C. 339 Le Floch, P. 119 Le Merrer, Y. 160 Leadbeater, N.E. 57, 79, 82, 254, 350, 359 Leahy, J.W. 343 Lebel, H. 61,264 Lebreton, J. 170, 211,334 Lectka, T. 138, 242, 278 Lee, D. 48 Lee, D.Y.W. 343 Lee, E. 339 Lee, H.-Y. 43, 48, 49, 127, 133, 336 Lee, J. 201 Lee, J.C. 106, 195, 255 Lee, P.H. 36, 38, 82, 94 Lee, S. 352 Lee, V. 336 Lee, W.K. 118, 196, 209 Lee, W.S. 184, 200 Lee, Y.-J. 330 Lee, Y.-S. 115, 367 Lee- Ruff, E. 364 LeGall, E. 264 Lehn, J.-M. 327 Leigh, D.A. 307 Leighton, J.L. 22, 29, 36, 96, 268 Leitch, S.K. 22 Lejczak, B. 275 Lemal, D.M. 67, 254 Lennon, I.C. 127 Lenoir, D. 282 Lepore, S.D. 252 Lequeux, T. 8 LeRoux, C. 76 Lesnikowski, Z.J. 301 Lete, E. 180 Letourneux, Y. 298 Levacher, V. 75, 145,372 Levason, W. 116

397

Lewis, D.E. 235 Ley, S.V. 4, 80, 227, 228, 336, 337, 341,343, 345, 368, 375 Lhotak, P. 321 Li, A.D.Q. 277 Li, B. 219 Li, C. 36, 145 Li, C.-J. 11, 30, 167, 268, 284, 346, 348, 350, 356 Li, G. 185 Li, H. 54 Li, J.-H. 81 Li, L. 84 Li, S. 358 Li, W. 80 Li, W.-D.Z. 332 Li, X. 37, 126 Li, Y. 41,332, 334, 337,338, 343 Li, Y.-Q. 361 Li, Z. 113 Li, Z.-M. 169 Li, Z.-T. 324 Li, Z.-Y. 228, 236 Liang, X. 112 Liao, C.-C. 67, 331 Licandro, E. 122 Lichtenthaler, F.W. 118,333 Licini, G. 108 Liebeskind, L.S. 78, 232, 330, 335 Lievre, C. 48 Limanto, J. 205 Limberg, C. 286 Linclau, B. 134, 254, 365 Lindel, T. 212, 345 Lindhorst, T.K. 316 Lindner, E. 119 Lindsay, Smith, J.R. 134 Lindsley, C.W. 169 Linhardt, R.J. 294 Linker, T. 85, 335 Liotta, D.C. 16 Lipkowitz, K.B. 276 Lipshutz, B.H. 80, 118, 125 Lipton, M.A. 59, 228 List, B. 14 Listvan, V.N. 285 Little, R.D. 14 Litvinov, V.P. 213

398

Liu, B. 165 Liu, C. 204 Liu, H.-J. 91,341,345 Liu, H.-M. 247 Liu, L. 142, 347 Liu, P. 84 Liu, Q. 217 Liu, R.-S. 52, 148, 157 Liu, Y. 327, 328 Livinghouse, T. 67, 163 Lloyd-Jones, G.C. 22, 290 Lobo, A.M. 161,223 Loh, T.-P. 25, 39, 97, 347, 355 Lombardo, M. 24, 334 Long, N.J. 287 Long, Y.-Q. 15 Lonnberg, H. 380 Lopez, S. 332 Lopp, M. 146 Loreta, M.A. 134 Loughlin, W.A. 35 Lovely, C.J. 48, 70 Low, P.J. 58 Lowary, T.L. 265, 339 Lowden, C.T. 374 Lowe, C.R. 322 Lu, S. 235 Lu, T.-J. 243 Lu, W. 333, 345 Lu, X. 42, 153, 337 Lu, Y. 11 Lubell, W.D. 233,245, 304 Luh, T.-Y. 52, 82 Luis, S.V. 366 Lukevics, E. 211 Luo, F.-T. 55, 86, 366 Lupatelli, P. 241 Luzzio, F.A. 10 Lygo, B. 244, 344 Ma, D. 239, 251,330, 331,334, 337, 340 Ma, J.-A. 277 Ma, S. 36, 75, 87, 115, 146, 147, 155, 156, 172, 260, 290 Maas, G. 188 Macias, F.A. 337 MacKay, D.B. 189 MacMillan, D.W.C. 34, 80, 106

AUTHOR INDEX

Macquarrie, D.J. 367 Maddaford, S.P. 256 Madsen, R. 282, 332 Maes, B.U.W. 238, 338 MaGee 28 Magnus, P. 171 Magomedov, N.A. 169 Magriotis, P.A. 139 Mahadevan, A. 84 Mahmoodi, N.O. 120 Maia, H.L.S. 245 Maier, M.E. 45 Maid, G. 188 Majetich, G. 344 Majumdar, K.C. 173, 177, 282 Makino, S. 369, 370, 371 Mal, D. 131 Malacria, M. 6, 69, 162, 182, 268 Maleczka, Jr., R.E. 58, 231 Maletic, M. 375 Malhotra, S.V. 20, 47 Maligres, P.E. 185 Malinakova, H.C. 177 Malkov, A.V. 22, 23 Mander, L.N. 330, 339, 344 Mane, R.A. 365 Mangeney, P. 22 Mann, A. 367 Mann, B.E. 288 Manzoni, L. 48 Mapp, A.K. 243 Marazano, C. 169 Marcaccini, S. 189 Marcantoni, E. 39 Marchand-Brynaert, J. 67, 139 Marco, J.A. 344 Marco, J.L. 285 Marcos, I.S. 332, 338, 345 Marcune, B.F. 113 Marder, S.R. 264 Marder, T.B. 288 Marek, I. 9 Margaretha, P. 73 Marino, J.P. 84 Marquez, V.E. 263 Marra, C. 174 Marsaioli, A.J. 96 Marshall, J.A. 27, 154, 339, 340

AUTHOR INDEX

Marson, C.M. 55, 101 Martens, J. 366 Martin, N. 306, 310, 315 Martin, O.R. 50, 334 Martin, S.E. 103 Martin, S.F. 48, 49, 69, 299, 335 Martin, V.S. 174, 219, 251 Martinelli, M.J. 276 Martynov, A.V. 10 Maruoka, K. 3, 7, 17, 22, 34, 84, 99 Maryanoff, B.E. 144 Mas,T. 330, 339 Mascarenas, J.L. 92, 177 Masquelin, T. 370 Massa, A. 22 Massanet, G.M. 107 Matabe, H. 332 Mathew, J. 247 Mathey, F. 119, 208, 303 Matondo, H. 260 Matreeva, E.D. 265 Matsubara, S. 103 Matsuda, A. 247,262 Matsuda, T. 120 Matsui, M. 16 Matsukawa, S. 348 Matsumura, Y. 350 Matsuo, J. 367 Mattay, J. 307 Mauduit, M. 357 Maycock, C.D. 331,341 Mayoral, J.A. 61 Mayr, H. 275 Mayville, Jr., F.C. 359 Mazur, A.W. 54, 179 McAuliffe, J.C. 294 McClure, C.K. 75, 168 McElwee-White, L. 191 McKew, J.C. 84 McLaughlin, M. 186 McLeod, M.D. 345 McNulty, J. 248 McWhorter, Jr., W.W. 21, 101,334 McWilliams, J.C. 169 Mebane, R.C. 122 Medio-Simon, M. 86 Mehta, G. 117, 335, 337, 341,343

399

Meier, M.S. 310 Meier, P. 78 Meisenbach, M. 370 Menendez, J.C. 115, 345, 349 Meng, C.Q. 376 Meng, J. 176 9 Merino, P. 23, 193, 333 Merlic, C.A. 88, 286 Merour, J.-Y. 176, 198 Merschaert, A. 128 Mete, A. 50 Metz, W.A. 214 Metzner, P. 133 Meyer, C. 147,346 Mezzetti, A. 61 Mi, A.-Q. 28, 79 Micouin, L. 231, 251 Miesch, M. 64 Migihashi, C. 371 Mignani, S. 187 Mihailovic, D. 312 Mihovilovic, M.D. 150 Mikami, K. 31,172 Mikolajczyk, M. 126 Miljanic, O.S. 59 Milkiewicz, K.L. 140 Miller, B.L. 169 Miller, G.P. 306 Miller, M.J. 25,243, 331 Miller, R.A. 103 Miller, S.J. 14, 48, 225 Minakawa, N. 247,262 Minami, T. 29 Mineham, T. 82 Ming, Y.L. 354 Mingos, D.M.P. 288 Minnaard, A.J. 37, 126, 141 Minnikin, D.E. 339 Mino, T. 6, 79 Mioskowski, C. 46, 86, 109, 223, 230, 265, 269 Miranda, L.D. 84, 140 Mirkin, C.A. 326 Mislow, K. 276 Mitchell, M.O. 198 Mitchell, T.N. 272 Mitra, A.K. 188 Miura, K. 34, 272

400

Miura, M. 54, 80, 91 Miyamoto, H. 351 Miyano, S. 323 Miyashita, M. 42, 229, 253 Miyaura, N. 37, 83, 261 Mizuno, K. 61 Mizuno, N. 103 Mizuno, T. 271 Mlochowsld, J. 290 Moberg, C. 6, 366 Modarelli, D.A. 316 Moeller, K.D. 244, 330 Moghaddam, F.M. 158 Mohammadpoor-Baltork, I. 110, 216 Mohan, R.S. 216, 221,359 Mohri, K. 67 Mol, J.C. 48 Molander, G.A. 81,338 Moler, G.A. 181 Molina, P. 346 Molnar, A. 82 Moloney, M.G. 54, 160 Mongin, F. 80, 84 Mongin, O. 318 Monteiro, A.L. 55, 79 Monteiro, N. 210 Montero, J.-L. 207 Montgomery, J. 15,338 Monti, H. 334 Mootoo, D.R. 48 Moreau, J.J.E. 365 Moreau, V. 227 Moreno-Manas, M. 289 Mori, A. 80, 90, 375 Mori, K. 332, 345 Mori, M. 6, 90, 92, 94, 162, 181,. 334, 345 Morimoto, T. 142 Morimoto, Y. 343 Morken, J.P. 23, 113, 331 Moroder, L. 79 Morohashi, N. 323 Morris, R.H. 119 Mortier, J. 84 Motherwell, W.B. 12, 62, 96 Motterlini, R. 288 Mountford, P. 322

AUTHOR INDEX

Moustafa, A.H. 206 Movassagh, B. 267 Mukai, C. 51, 88,330 Mukaiyama, T. 13, 14, 32, 250 Mukherjee, D. 332, 337, 340, 343, 345 Mukhetjee, D. 333 Mukhopadhyay, S. 81 Mulchandani, A. 313 Mullen, K. 316 Muller, M. 113, 334, 338, 344 Muller, P. 60, 147 Muller, T. 268 Muller, T.E. 278 Muller, T.J.J. 58, 79, 190 Mulzer, J. 210, 298 a_5,339 Muniz, K. 113, 114 Murahashi, S. 40 Murai, T. 7 Murakami, M. 53,282 Murga, J. 342 Murphy, J.A. 48, 142, 171,333, 337 Murphy, P.J. 112, 192, 333 Murthy, K.S.K. 36 Murty, M.S.R. 237 Muthusamy, S. 61 Muzart, J. 283, 350 Myles, D.C. 335 Nadin, A. 87 Nadkarni, D. 119 Nagaiah, K. 216 Nagano, H. 40 Nagao, Y. 102 Nagaoka, H. 23 Nagasaka, T. 332, 339 Nagendrappa, G. 258 ' Naidu, B.N. 238 Nair, V. 23, 153, 198,203, 210, 292 Naito, T. 33, 40, 147, 151,347, 373 Najera, C. 21, 32, 221,364 Nakada, M. 21, 60, 118 Nakagawa, M. 31 Nakahara, S. 340, 345 Nakajima, M. 34

AUTHOR INDEX

Nakamura, E. 2, 5, 9, 308, 310, 311,350 Nakamura, K. 280, 363 Nakamura, M. 2, 5, 9 Nakano, H. 6 Nakata, M. 228 Nakayama, J. 67, 203 Nam, K.S. 200 Namy, J.-L. 31 Nan, F. 339 Nantermet, P.G. 48 Narasaka, K. 155, 161,162, 168 Narasimhan, S. 33 Naskar, D. 84, 87, 139, 372 Nassim, B.E. 377 Natale, N.R. 102 Natalini, B. 311 Neckers, D.C. 268, 316 Nefzi, A. 368, 369 Negishi, E. 58, 291 Neitzel, M.L. 367 Nelson, A. 89 Nelson, S.G. 96 Nemoto, H. 14, 49, 69 Nenajdenko, V.G. 285 Nepveu, F. 114 Neri, P. 322 Nettekoven, M. 372 Neumann, R. 103, 253 Neumann, W.L. 78 Newkome, G.R. 317 Nguyen, S.T. 61,243 Nicewonger, R. 369 Nicholas, K.M. 172 Nicolaou, K.C. 108,330, 334, 340 Nicolas, E. 364 Nieger, M. 113 Nielsen, P. 263 Nierengarten, J.-F. 307, 311, 316 Nierengarten, J.F. Nierhaus, K.H. 295 Nikolaropoulos, S.S. 105 Nishida, A. 49, 341 Nishida, M. 78 Nishida, Y. 226 Nishikido, J. 365 Nishimura, J. 301,306, 310, 325 Nishiyama, H. 61

401

Nishiyama, K. 45, 244 Nishiyama, S. 336, 337 Nishiyama, Y. 41,129, 266 Nishizawa, M. 84, 152, 222 Node, M. 103, 119 Noiret, N. 308 Nokami, J. 24 Nolan, S.P. 79, 84, 181,248 Noodleman, L. 205 Norrby, P.-O. 19 North, M. 21 Novikov, Y.Y. 26 Nozaki, K. 90, 167 Nubbemeyer, U. 284 Nudelman, N.S. 288 Nyerges, M. 162, 179, 334 O'Brien, P. 100, 112 O'Connor, S.J. 141 O'Donnell, M.J. 243,372 O'Neill, P.M. 111 O'Shea, D.F. 164 O'Shea, P. 79 Oba, M. 244 Occhiato, E.G. 87, 94 Ochiai, M. 201 Odinets, I.L. 214 Odom, A.I.,. 256 Oestreich, M. 268 Ogasawara, K. 335,344 Ogawa, A. 89, 259 Ogilvie, W.W. 48 Ogle, C.A. 36 Ogura, K. 232 Oh, C.H. 53, 86 Oh. T. 354 Ohe, K. 61, 63, 156, 161 Ohfune, Y. 278 Ohler, E. 298 Ohno, H. 63 Ohno, K. 85 Ohsawa, A. 185 Ohsugi, S. 103 Ohta, S. 338, 339 Ohta, T. 6, 129 Ohwada, T. 170, 194 Oi, S. 21, 37, 81 Ojima, I. 127 Oka, M. 180

402

Okamura, H. 335, 342 Okano, T. 6 Oku, A. 192 Okuma, K. 202 Olah, G.A. 76 Ollevier, T. 22 Olse, S.H. 333 Olsson, R. 370, 378 Oltra, J.E. 41, 119 Omae, I. 301 Onaka, M. 111 Opatz, T. 159 Ordonez, M. 23 Orfanopoulos, M. 308, 310 Organ, M.G. 87, 331 Oriyama, T. 22, 223 Orru, R.V.A. 189, 380 Ortar, G. 87 Ortuno, R.M. 133 Oshima, K. 10, 54, 58, 93, 95, 157, 163 Otera, J. 58 Overkleeft, H.S. 96, 217, 379 Overman, L.E. 96, 140, 237,259, 284, 330, 331,334, 337, 338 Owton, W.N. 158 Ozaki, S. 91 Ozawa, F. 93, 268 Padwa, A. 65, 70, 152, 167, 171, 178, 181,335, 338 Pagenkopf, B.L. 10, 21, 165 Pagliaro, M. 103 Paintner, F.F. 4, 69, 79 Paio, A. 377 Pak, C.S. 199 Pakulski, Z. 355 Pal, M. 76, 155, 222 Palacios, F. 136, 167 Palaniappan, S. 365 Palenzuela, J.A. 167 Paleo, M.R. 336 Palmieri, C. 28 Palmisano, G. 80 Pan, X. 40, 331 Panek, J.S. 216, 330, 340 Pannecoucke, X. 5 Pansare, S.V. 192 Paolucci, F. 311

AUTHOR INDEX

Paquette, L.Ao 67, 100, 262, 304, 312, 332, 338, 346 Pare, P.W. 15, 346 Park, H. 159, 242 Park, J.T. 312 Park, J.W. 328 Park, K. 80 Park, K.H. 331, 332, 335 Parker, K.A. 196 Parlow, J.J. 79, 376 Parmar, V.S. 249 Parrain, J.-L. 332, 335 Parsons, A.F. 40, 286, 357 Parsons, P.J. 25 Paryzek, Z. 125 Pascal, R. 299 Passarella, D. 330, 344 Patel, B.K. 105 Patel, M.V. 158 Patel, R.N. 120 Paterson, I. 176, 297, 332, 335, 339 Pattenden, G. 314, 340, 342, 345 Paugam, J.P. 61 Pearson, A.J. 36, 72 Pearson, W.H. 284 Pedrosa, R. 67, 73 Pei, J. 317 Pelinski, L. 20 Pellacani, L. 185 Pellissier, H. 276, 287 Peng, Z~ 315, 318 Percy, J.M. 113 Perdicchia, D. 122 Peregrina, J.M. 139 Perez, P.J. 91,252 Perez-Prieto, J. 60, 344 Periasamy, M. 76, 118 Pericas, M.A. 20 Peris, E. 114, 366 Perlmutter, P. 138 Perumal, P.T. 188, 357 Peters, D.G. 156 Petraglia, F. 294 Petridis. D. 327 Petrini, M. 76, 130 Pettus, T.R.R. 340 Peyrat, J.-F. 54

AUTHOR INDEX

PezzeUa, A. 80 Pfaltz, A. 125 Pfeiffer, W.-D. 206 Phanstiel, IV, O. 108 Piermatti, O. 150 Pietrusiewicz, K.M. 50 Pietruszka, J. 97, 333 Piettre, S.R. 67, 266 Pihko, P.M. 343 Pilkington, C.J. 127 Pilli, R.A. 330, 334, 336 Pindur, U. 76 Pinhas, A.R. 197, 240 Pinho e Melo, T.M.v.D. 67 Pinto, B.M. 344 Piras, P.P. 99, 336 Pirat, J.-L. 204 Pirrung, M.C. 375, 376 Piva, O. 151 Pizzo, F. 67, 150, 350 Plaquevent, J.-C. 276 Player, M.R. 369 Pie, N. 78 Plenio, H. 58, 79 Plietker, B. 113, 114 Plumet, J. 21,283 Podesta, J.C. 272 Podlech, J. 293 Pohmakotr, M. 146 Poirier, D., 241 Poletti, L. 355 Poll, G. 162 Pollini, G.P. 265 Pons, J.-M. 340, 343 Ponticelli, F. 184 Popik, V.V. 59 Poppe, L. 120 Popsavin, V. 341 Porco, Jr., J.A. 339, 342, 345 Portland, D.E. 379 Portlock, D.E. 372 Portnoy, M. 366 Porto, A.L.M. 120 Posner, G.H. 1, 148, 295 Postel, D. 285 Postema, M.H.D. 48 Pouli, N. 263 Pozharskii, A.F. 302

403

Prabhakar, S. 161,223, 344 Prajapati, D. 169, 349, 351 Prakash, G.K.S. 22, 76, 268 Prakash, I. 127 Prakash, O. 204 ................... Prandi, C. 94 Prasad, K. 58 Prashad, M. 238 Prato, M. 307, 311 Procopio, A. 248 Procter, D.J. 32, 37,363 Proenca, M.F. 169 Prunet, J. 294 Pu, L. 280 Pulido, F.J. 100 Punniyamurthy, T. 104, 105 Py, S. 32, 38, 343 Pyne, S.G. 334, 335 Qabar, M. 188 Qing, F.-L. 88,244, 245,263 Quan, M.L. 204 Quayle, P. 148 Queiroz, M.-J.R.P. 79, 83, 238 Quideau, S. 102 Quintero, L. 154 Raboisson, P. 262 Rachon, J. 272 Rad-Moghadam, K. 189 Rademann, J. 364, 373 Radius, U. 322 Radivoy, G. 120 Ragaini, F. 165 Raghavan, S. 153, 243, 245, 331, 336, 341,343, 368 Ragnarsson, U. 121 Rainier, J.D. 95, 98 Raja, R 288 Rajakumar, P. 222 Rajanbabu, T.V. 94 Raj ski, S.R. 258 Ram, V.J. 170 Ramachandraiah, G. 253 Ramachandran, P.V. 25 Ramachandran, U. 3 Ramamurthy, V. 277, 285 Ramesh, N.G. 280 Rampf, F.A. 125 Ramsden, C.A. 296

404

Ramsden, J.A. 119 Ran, C. 258 Rando, R.R. 341 Rangappa, K.S. 141 Ranu, B.C. 46, 126, 159, 169, 355 Rao, B.V. 216, 338, 342 Rao, H.S.P. 151 Rao, J.M. 222 Rao, K.D. 102 Rao, K.R. 215, 216, 230, 232 Rassat, A. 109 Ratovelomanana-Vidal, V. 119 Raubo, P. 148 Rault, S. 341 Rautenstrauch, V. 119 Ravikumar, V.T. 374 Ravina, E. 58, 370 Ravn, J. 373 Rawal, V.H. 335 Ray, J.K. 85, 128 Ray, S. 234 Rayner, C.M. 21 Read, R.W. 225 Reddy, C.S. 223 Reddy, G.O. 196 Reddy, K.L. 235 Reddy, P.S. 213 Reddy, V.V.N. 188 Reeder, M.R. 81 Reedijk, J. 241 Reetz, M.T. 127 Reid, D.H. 201 Reinaud, O. 319, 322, 323 Reiser, O. 61,341,343, 344 Reissig, H.-U. 32, 181, 194, 334 Remaud-Simeon, M. 249 Ren, R.X. 358 Renard, P.-Y. 265 Renaud, P. 41, 86, 87, 154, 277 Rey, A.W. 36 Rey, P. 109 Reymond, J.-L. 318 Rezaei, R. 368 Rhee, H. 107 Ricards, R.W. 334 Ricci, A. 26, 29, 289 Rice, K.C. 331 Richards, C.J. 21, 79

AUTHOR INDEX

Richeson, D.S. 259 Riera, A. 88, 329, 333, 344 Rigby, J.H. 65, 150 Risch, N. 169 Risitano, F. 196 Riva, R. 54 Rivalle, C. 334 Rivero, M.R. 88 Rivett, D.E.A. 343 Rizzacasa, M.A. 332, 333, 343, 344 Rizzo, C.J. 208 Robertson, A.A.B. 370 Robina, I. 244 Robins, M.J. 262 Rodrigues, A. 19 Rodriguez, J. 169 Rodriguez, J.B. 263 Rodriguez-Lopez, J. 315, 317, 319 Roesky, P.W. 278 Rogers, B.N. 199 Rogers, R. 305 Roglans, A. 53 Rokita, S.E. 57 Rolando, C. 86 Rolland, V. 244 Romao, C.C. 110 Romea, P. 12, 13 Romeo, G. 193 Romo, D. 334 Ronan, B. 334 Rosania, G.R. 379 Rossi, E. 196 Rossi, R.A. 165, 285 Rotello, V.M. 301 Roumestant, M.L. 243 Roush, W.R. 23, 24, 39, 69, 226, 333, 336 Rousseau, G. 179 Rovis, T. 35, 85 Rowan, A.E. 325 Rowlands, G.J. 22 Roy, S.C. 215 Rozen, S. 111,255,257 Ruano, J.L.G. 19 Rubin, Y. 306, 308 Ruchirawat, S. 99, 346 Ruedi, G. 101 Rutjes, F.P.J.T. 162, 294

AUTHOR INDEX

Ruveda, E.A. 332 Ruzziconi, R. 67 Rychnovsky, S.D. 8, 13, 22, 69, 174, 333, 335 Ryu, I. 138 Ryzhakov, A.V. 211 Saa, C. 70, 212 Saa, J.M. 21, 32 Sabitha, G. 116, 177, 188, 241, 346, 369 Sabol, J.S. 212 Sadighi, J.P. 125 Saeed, A. 342 Saeeng, R. 27 Sagar, A.D. 251 Sai, H. 45 Saidi, M.R. 21, 77, 264, 266 Saigo, K. 309 Saikia, A.K. 109 Sain, B. 108, 117, 134, 257 Saito, S. 27, 65 Saito, T. 165 Saitoh, T. 169 Sajiki, H. 126, 224 Sakai, N. 84 Sakamoto, M. 21,179, 304 Sakamoto, T. 166 Saksena, A.K. 159 Saladino, R. 367 Salama, T.A. 204 Salamonczyk, G.M. 319 Salaun, J. 138 Salehi, P. 137, 188 Salem, M. 205 Salunkhe, M.M. 354, 356, 360, 361 Salvadori, P. 61, 88 Salvatore, R.N. 264, 266 Samant, S.D. 253 Sames, D. 80, 177, 334 Sampson, P. 26 San-Felix, A. 263 Sanchez-Martinez, C. 94 Sander, W. 287 Sanders, J.K.M. 375 Sandford, G. 211,293 Sandhu, J.S. 351 Sanghvi, Y.S. 116 Sansone, F. 321

405

Santelli, M. 53, 57, 87 Santoyo-Gonzalez, F. 203 Sarabia, F. 346 Sarandeses, L.A. 36, 89, 94 Sarghi, H. 256 Sarkar, T.K. 67, 162 Sarm, J.C. 224 Sartillo-Piscil, F. 154 Sartori, G. 111 Sasai, H. 31, 111,149, 162, 364 Sasaki, M. 336 Sasson, Y. 81 Sato, F. 25, 42, 51, 55, 87, 92 Sato, K. 113 Sato, N. 84 S ato, Y. 94 Satoh, T. 15, 18, 35, 333 Sauer, D.R. 365 Sauers, R.R. 194 Saunders, M. 309 Sauvage, J.-P. 325, 326 Savelli, G. 354, 365 Savoia, D. 28 Scafato, P. 36 Scammells, P.J. 158, 166 Schafer, L.L. 240, 257 Scharer, O.D. 296 Schaus, S.E., JACS, 125, 12094. 25 Scheeren, H.W. 64, 314 Scheinmann, F. 331,338 Schirmeister, T. 136 Schlaf, M. 252 Schlitzer, M. 300 Schlosser, M. 84 Schmidt, B. 85, 176, 292 Schmidt, R.R. 222, 227 Schmitt, M. 78,245 Schmittel, M. 80 Schmitz, F.J. 342 Schneider, J.P. 242 Schneider, R. 121, 164 Schneller, S.W. 263 Schobert, R. 106 Schoffers, E. 279 Schon, U. 365 Schore, N.E. 345 Schreiner, P.R. 72, 276

406

Schrock, R.R. 292 Schubert, U.S. 213 Schultz, P.G. 78 Schulze, B. 211 Schurig, V. 229 Schwan, A.L. 270 Scialdone, M.A. 243 Scolastico, C. 48 Scott, A.I. 15 Scott, W.L. 372 Scriven, E.F.V. 303 Seddon, D. 305 Seebach, D. 196 Seebacher, W. 183 Seeberger, P.H. 114, 374, 378, 380 Seela, F. 263 Sefkow, M. 75, 297 Sega, A. 353 Segura, J.L. 315 Seifert, K. 337, 344 Seki, M. 26, 57, 331 Sekine, M. 262, 263 Seleque, J.P. 180 Selesto, J.P. 94 Selva, M. 237 Semple, G. 377 Senanayake, C. 276 Seneci, P. 377 Sengupta, S. 42 Sensfuss, U. 372 Serra, S. 153 Serwatowski, J. 267 Sessler, J.L. 212, 320 Sestelo, J.P. 36, 89 Seto, C.T. 20, 249 Sevenard, D.V. 50 Sewald, N. 243 Sezen, B. 80 Sha, C.-K. 339, 342 Shaabani, A. 192 Shabat, D. 319 Shackelford, S.A. 257 Shair, M.D. 13 Sharghi, H. 236, 250 Sharma, G.V.M. 222, 223, 331, 339 Sharma, P. 320 Sharpless, K.B. 205

AUTHOR INDEX

Shashidhar, M.S. 275 Shastin, A.V. 214 Shaughnessy, K.H. 78 Shawali, A.S. 209 Shchepinov, M.S. 304 Shea, K.J. 70, 312 Sheldon, R.A. 103 Shen, Y. 26 Sheng, S.-R. 116, 363 Sherbum, M.S. 69 Sheremetev, A.B. 210 Shevchenko, V.P. 380 Shevelev, S.A. 241 Shi, M. 14, 16, 28, 30, 31, 77, 119, 193 Shi, X. 321 Shi, Y. 61, 112, 231 Shi, Y.-L. 252 Shibasaki, M. 13, 18, 20, 26, 30, 34, 111,238, 330, 342 Shibata, N. 255 Shibata, T. 88 Shieh, W.-C. 237 Shigemasa, Y. 215 Shih, N.-Y. 4 Shiina, I. 233 Shim, S.C. 1, 168 Shimada, S. 76, 82 Shimazaki, M. 370 Shimizu, K. 33 Shimizu, M. 29, 41, 100, 149 Shimizu, S. 323 Shin, C. 118 Shin, D.-S. 199 Shindo, M. 66 Shing, T.K.M. 69, 112 Shinokubo, H. 10, 54, 58, 157, 163 Shioiri, T. 333, 341 Shipman, M. 7, 30 Shirakawa, E. 57, 92 Shirini, F. 216, 367 Shishido, K. 331,337 Shoda, S. 301 Shreeve, J.M. 255, 361 Shuto, S. 21, 132, 261 Shuttleworth, S.J. 373 Shvo, Y. 259

AUTHOR INDEX

Sibi, M.P. 39, 49, 66, 195,277, 286 Sieburth, S.McN. 268 Sigman, M.S. 102 Silva, A.M.S. 170 Silva, D.J. 142 Silveira, C.C. 91,170 Silverman, R.B. 344, 363 Simanek, E.E. 315, 318 Simas, A.B.C. 250 Simpkis, N.S. 338 Sinay, P. 47 Singaram, B. 239 Singer, R.A. 238 Singh, A.K. 202, 250, 312 Singh, G.S. 209 Singh, J. 118 Singh, V. 67 Singh, V.K. 27, 331,335 Sinou, D. 254, 346 Sirkecioglu, O. 251 Sisti, M. 80 Sivaram, S. 34 Six, Y. 63 Sizov, A.Y. 293 Sjoberg, S. 82 Skoda-Foldes, R. 290 Skrydstrup, T. 16, 40 ~ Sliwa, W. 300 Slomczynska, U. 377 Smith, B.D. 326 Smith, D.B. 370 Smith, D.K. 329 Smith, III, A.B. 8, 10, 334, 335, 338,342, 344 Smith, III, M.R. 231 Smith, K. 11, 77, 141 Smith, R.A. 372 Smithrud, D.B. 324 Smythe, M.L. 244 Snaith, J.S. 374 Snapper, M.L. 30, 48, 49, 167, 332 Snider, B.B. 91,336, 337, 342, 345 Snieckus, V. 48, 76, 88 Snyder, J.K. 167 Soai, K. 20 Sodeoka, M. 355

407

Soderberg, B.C.G. 163, 166 Soga, T. 313 Soheili, A. 57 Solladie, G. 123, 155 Solladie-Cavallo, A. 112 Soloshonok, V.A. 3, 244 Somfai, P. 67, 95, 136, 332, 334 Song, C.E. 259, 357 Song, M. 366 Song, S.J. 371 Sonnet, P. 344 Sonoda, N. 41,129, 266 Sosnovskikh, V.Y. 35, 158, 210 Souers, A.J. 163 Soufiaoui, M. 185 South, M.S. 376 Spanu, P. 12 Spencer, J.B. 238, 372 Spilling, C.D. 346 Spino, C. 285 Spitz, I.M. 294 Spivey, A.C. 57, 248, 370 Spring, D.R. 380 Springer, D.M. 103 Springfield, S.A. 169 Spur, B.W. 342 Srebnik, M. 36 Srikrishna, A. 48, 333, 337 Srinivas, P. 45, 103, 227 Srinivasan, K.V. 352, 356, 360 Srinivasan, P.C. 117 Srivastava, R.S. 241 Stachel, H.-D. 199 Stachulski, A.V. 226 Stack, T.D.P. 110 Stalinski, K. 140 Stanetty, P. 81 Stang, P.J. 293, 326 Stanovnik, B. 136 Stara, I.G. 85 Stary, I. 85 Stavber, S. 107,255 Steel, P.G. 243, 269, 341 Stefani, H.A. 152 Steglich, W. 330, 332, 337 Steinmetz, M.G. 74 Stella, L. 369 Stepanov, A.V. 303

408

Stephens, C.E. 258 Stevenazzi, A. 283 Stevens, R.W. 164 S tiffb a, S.-E. 60 Stockland, Jr., R.A. 79 Stockman, R.A. 136 Stoddart, J.F. 324, 325, 326 Stoermer, M.J. 67 Stoltz, B.M. 94, 97, 299, 339 Stratakis, M. 339 Strauss, C.R. 50 Strazewski, P. 262 Strazzolini, P. 104 Struber, F. 379 Studer, M. 89 Stuhr-Hansen, N. 224 Su, W. 271 Su, W.K. 270 Suades, J. 90 Suarez, E. 136, 197, 342 Suckling, C.J. 370 Sudalai, A. 110, 134, 260, 331 Suffert, J. 94 Suga, H. 133 Suga, S. 198 Sugai, T. 245 Sugi, Y. 89 Sugimoto, O. 21 Sugimura, T. 60 Sugiura, M. 163 Suh, J. 296 Suh, Y.-G. 18 Sulikowski, G.A. 69 Sun, C.-M. 368, 371 Sun, Y.-C. 112 Suslick, K.S. 319 S'utcliffe, J.A. 300 Sutherland, A.J. 367 Suzuki, H. 24, 257 Suzuki, K. 33, 64, 99, 196 Suzuki, T. 146, 179, 339 Suzuki, Y. 231 Sweeney, J.B. 146, 161,244 Szabo, K.J. 6, 24 S zoka, Jr., F.C. 274 Szymoniak, J. 62 Taber, D.F. 47, 50 Tabor, A.B. 245

AUTHOR INDEX

Tadano, K. 66, 339 Taddei, M. 360, 363 Tae, J. 48 Tagata, T. 78 Taguchi, T. 163,237 Taillades, J. 265 Taillefer, M. 129 Takacs, J.M. 66 Takagi, K. 83 Takaguchi, Y. 319 Takahashi, S. 147, 334, 341,343 Takahashi, T. 91,268, 339, 366, 375 Takahata, H. 170 Takai, K. 61 Takaki, K. 265 Takalds, I.M. 36 Takamura-Enya, T. 238 Takashi, T. 226 Takasu, K. 39, 143 Takata, T. 324 Takayama, H. 346 Takeda, K. 3 Takeda, T. 50, 159 Takemoto, Y. 4, 29, 34, 242 Takeya, K. 251 Takikawa, H. 330, 331 Tale, R.H. 121 Tamami, B. 118,216, 368 Tamaoki, N. 325 Tamaru, Y. 6 Tamura, O. 333 Tamura, R.A. 340 Tanaka, F. 14 Tanaka, H. 80 Tanaka, M. 82 Tanaka, T. 53, 63, 94, 162, 198, 256, 340 Tanemura, K. 257 Tang, C. 118 Tang, T. 62 Tang, Y. 134, 138 Taniguchi, N. 266 Tanji, K. 21 Tanner, D. 19 Tanyeli, C. I, 106, 249, 366 Tavani, C. 138 Taylor, D.K. I 13, 146, 151

AUTHOR INDEX

Taylor, E.C. 165, 172 Taylor, R. 306, 309 Taylor, R.E. 63, 285, 342 Taylor, R.J.K. 33, 93, 104, 330 Taylor, R.T. 367 Taylor, S.K. 75 Tejeda, J. 82 Tellitu, I. 84 Tepe, J.J. 186 Terashima, S. 136 Tesche, B. 80 Thanh, G.V. 48 Thayumanavan, S. 316, 317 Thebtaranonth, Y. 4 Theodorakis, E.A. 69, 224, 331, 334, 336 Therisod, M. 359 Thiel, W.R. 291 Thomas, A.W. 291,375 Thomas, E.J. 24, 98 Thomas, J.M. 288 Tian, W. 334 Tiecco, M. 146, 260 Tietze, L.F. 274, 294, 335, 378 Tilley, T.D. 135 Timari, G. 332 Tingoli, M. 253 Tirrell, D.A. 203 Tius, M.A. 41,101,285 Tobe, Yo 53 Togni, A. 40 Togo, H. 93, 106, 107, 201,366 Tois, J. 369, 380 Tokuda, M. 73, 182 Tokunaga, Y. 325 Tolstikov, A.G. 281 Toma, S. 239, 358 Tomao, K. 305 Tomasini, C. 196 Tomasni, C. 245 Tomioka, K. 28, 243, 339 Tomooka, K. 95 Toon, J. 320 Toone, E.J. 378 Tor, Y. 246 Torisawa, Y. 76 Toru, T. 26, 186 Toste, F.D. 230, 252

409

Tour, J.M. 57,308 Townsend, L.B. 262, 263 Toy, P.H. 367 Toyooka, N. 330, 343 Toyota, M. 98, 154 Trauner, D. 41, 50, 342, 345 Trehan, S. 28 Trenkle, W.C. 50 Tretyakov, Y.D. 277 Trifanov, A. 160 Trivedi, G.K. 71 Trofimov, A.V. 275 Trombini, C. 24 Troschutz, R. 169 Trost, B.M. 4, 7, 17, 29, 71, 150, 157, 173, 176, 248, 268, 330, 331,333, 338, 344 Trudell, M.L. 103, 110 Tsubaki, K. 79 Tsuboi, S. 76, 224 Tsubuki, M. 98 Tsuchida, E. 304 Tsuchimoto, T. 92 Tsuji, Y. 127 Tsukada, N. 92 Tsukade, N. 93 Tsutsumi, K. 269 Tu, S. 188 Tu, Y.-Q. 99, 131,239 Tucker, J. 367 Tumkevicius, S. 206 Tung, C.-H. 277 Tuntulani, T. 275, 323 Turner, N.J. 296, 365, 378 Tun'o, N.J. 327 Twieg, R.J. 239 Tye,-H. 180 Tykwinski, R.R. 59, 60, 102, 291 Tyrrell, E. 210 Uang, B.-J. 74, 80 Ueda, M. 315 Uemura, A. 54 Uemura, M. 79 Uemura, S. 2, 36, 61, 63, 77, 103, 156, 157, 161, 177, 232 Uenishi, J. 329 Ueoka, R. 324 Ukaji, Y. 139, 194

410

Ulijn, R.V. 362, 363 Umani-Ronchi, A. 39, 169 Uneyama, K. 7, 16, 31, 64 Ungaro, R. 321,329 Uozumi, Y. 102, 348 Urabe, H. 25, 42, 51 Urawa, Y. 232 Urpi, F. 12 Utesch, N.F. 57 Vaccaro, L. 241,350 Valla, A. 343 Vallee, Y. 30, 32, 38 Valls, N. 330 van Boom, J.H. 379 Van der Eycken, E. 349 van der Marel, G.A. 226 Van Dorsselaer, A. 307 van Koten, G. 48, 317, 378 van Maarseveen, J.H. 145 Van Nhien, A.N. 285 van Otterlo, W.A.L. 179, 302 van Vranken, D.L. 79, 96 Vankar, Y.D. 223 Vankelecom, I.F.J. 127 Vaquero, J.J. 28 Vargas-Berenguel, A. 57 Vatele, J.-M. 218 Vedejs, E. 240, 248 Vederas, J.C. 48, 74 Vedernikov, A.N. 134 Venkataraman, D. 264, 366 Venkateswaran, V. 340 Venkateswarlu, Y. 39 Venturello, P. 82 Venturi, M. 325, 326 Verdaguer, X. 88 Verdine, G.L. 375 Verkade, J.G. 3, 25, 34, 84, 238 Verma, R.P. 304 Vibhute, Y.B 253 Vicens, J. 322, 323 Vidal, A. 166 Vidal, J. 80 Vilar, R. 328 Villamizar, J. 333,335 Villemin, D. 229, 266 Virieux, D. 265 Virta, P. 374

AUTHOR INDEX

Viso, A. 186 Vivona, N. 203 Vlasov, V.M. 283 Vogl, N. 112 Vohlidal, J. 292 Volochnyuk, D.M. 169 Volonterio, A. 238, 185 Voronkov, M.V. 314 Vourloumis, D. 368 Vyvyan, J.R. 225 Wada, E. 148 Wade, P.A. 271 Wagenknecht, H.-A. 78 Wagner, A. 86, 223, 269 Wahala, K. 105 Waldmann, H. 363 Waldvogel, S.R. 80, 122, 253, 297 Wallace, D.J. 176, 236 Walsh, C.T. 299 Walsh, P.J. 20, 243, 279 Wan, Z. 251 Wandless, T.J. 346 Wang, D. 77 Wang, G.-W. 308, 310, 311 Wang, J. 15, 50, 95 Wang, K.K. 94, 168 Wang, L. 124, 129, 232, 349 Wang, M.-X. 228, 236 Wang, P.G. 379 Wang, Q. 180, 251 Wang, R. 20, 27 Wang, S. 165 Wang, T. 234 Wang, W. 160 Wang, Y. 108 Wang, Y.-G. 223, 369, 370 Wang, Y.-L. 132 Wang, Z.-X. 203 Wanner, K.T. 241 Wanner, T. 3 Ward, T.R. 126 Wardrop, D.J. 154, 329 Warren, S. 160 Wasserman, H.H. 299 Wasserschied, P. 356 Watanabe, T. 340 Wattanasin, S. 375 Weber, C. 371

AUTHOR INDEX

Weberskirch, R. 126 Wee, A.G.H. 95, 243 Wei, X. 33 Weigand, W. 199 Weigel, L.O. 231 Weinreb, S.M. 48, 232, 298 Weiss, R. 183 Weissleder, R. 75 Welch, J.T. 347 Welton, T. 359 Wender, P.A. 88, 119, 348 Wendisch, V. 36, 243 Wentworth, Jr., P. 336, 365 Werdrop, D.J. 144 Werner, H. 48 Wessig, P. 64 Wessjohann, L.A. 267 West, F.G. 71, 198 West, R. 305 Westermann, B. 278 Westman, J. 368 Whitby, R.J. 329 White, J.D. 152, 338 Whitehead, R.C. 45, 340 Whitener, G. 59 Whiting, A. 53 Wicha, J. 51 Widenhoefer, R.A. 92 Widlanski, T.S. 26 Wiemer, D.F. 48, 263 Wiesner, J. 300 Wiley, M.R. 363 WiNe, G. 288 Williams, C.M. 76, 283 Williams, D.B.G. 293 Williams, D.H. 296 Williams, D.R. 36, 334, 342, 345 Williams, J.M.J. 248, 349 Williams, L.J. 233 Williams, R.M. 138, 297, 298, 312, 332, 342, 344 Willis, C.L. 34, 174 Willis, M.C. 147, 251,263 Wills, M. 170 Wilson, S.R. 309 WinNer, J.D. 70 Winterfeldt, E. 67 Wipf, P. 27, 29, 152, 251

411

Wirth, T. 107, 147 Wisnoski, D.D. 362 Wittman, V. 364 Witulsld, B. 164, 166 Woerpel, K.A. 10, 334 Wolf, C. 79, 81, 83, 237, 254 Wolfe, J.P. 256 Wong, A. 165 Wong, C.-H., 233 Wong, H.N.C. 13 Wong, K.-T. 52 Wong, M.-K. 328 Woo, L.K. 50 Wood, J.L. 85, 299 Woodward, S. 36, 207 Wozniak, L.A. 284 Wu, G. 11,124 Wu, J. 93 Wu, M.-J. 127, 155 Wu, Y.-D. 14 Wu, Y. 366 Wu, Y.-C. 250 Wu, Y.-J. 269 Wu, Y.-Q. 185 Wu, Z. 368,369 Wuest, J.D. 327 Wulff, W.D. 93, 330 Wuthrich, K. 274 Wynne, J.H. 271 Xi, Z. 95, 157 Xia, C.-G. 90, 235, 238, 251,348, 351,357, 360 Xia, M. 184, 188 Xiao, J. 352, 366 Xu, D.-Q. 361 Xu, F. 270 Xu, J. 118 Xu, J.-H. 53 Xu, X. 21 Xu, Y.-C. 151 Xu, Z.-Y. 358 Xue, S. 21 Yabuta, G. 333 Yadav, A.K. 120 Yadav, J.S. 27, 40, 42, 135, 137, 167, 175, 199, 232, 252, 270, 330, 331,337,338, 351,354, 356, 359, 360, 361

412

Yadav, L.D.S. 149, 202, 262 Yadav, V.K. 12 Yakura, T. 154 Yamada, S. 100 Yamada, T. 31, 66, 118, 122, 126 Yamada, Y. 332, 335, 342 Yamago, S. 31 Yamaguchi, M. 77, 125,267 Yamaguchi, R. 239 Yamamoto, H. 13, 23, 106, 111 Yamamoto, K. 318 Yamamoto, T. 288 Yamamoto, Y. 67, 68, 69, 85, 92, 94, 129, 162, 203, 336 Yamashita, T. 239 Yamauchi, S. 340 Yamazaki, S. 169 Yanagisawa, A. 13 Yang, D. 6, 31,175 Yang, D.-Y. 159 Yang, L.-M. 221 Yang, R. 265 Yang, T.-K. 120 Yang, W. 78 Yang, Z. 93 Yang, Z.-Y. 61 Yannakopouiou, K. 328 Yao, C.-F. 40, 53 Yao, Q. 82, 356 Yao, S.Q. 376 Yao, z.-J. 244, 245 Yasuda, M. 239 Yavari, I. 177 Ye, T. 346 Yeleswarapu, K.R. 76, 155, 222 Yet, L. 299 Yeufig, C. 126 Yeung, C.H. 119, 126 Yi, C.S. 252 Yinghuai, Z. 306, 358 Yoakim, C. 264 Yoda, H. 130, 330, 332, 342 Yokokawa, Y. 338 Yoo, B.W. 123, 124 Yoon, C.M. 121,124, 125 Yoon, J. 115 Yoon, Y.-J. 199, 228, 257 Yoshida, H. 10, 79, 207

AUTHOR INDEX

Yoshida, J. 31, 82, 198, 376 Yoshida, M. 90 Yoshida, Y. 240 Yoshimitsu, T. 23, 341 Yoshimura, T. 255 Young, D.G.J. 59 Yu, B. 332 Yu, C.-M. 13, 25, 31 Yu, G. 253 Yu, J.-Q. 130 Yu, S. 79 Yu, W.-Y. 156 Yuan, C. 229 Yuan, D.-Q. 328 Yudin, A.K. 4, 239, 241 Yum, E.K. 181 Yun, H. 342 Yus, M. 11, 20, 120, 129, 222, 289 Yuste, F. 331 Zaidlewicz, M. 121,353 Zaleska, B. 190 Zambrano, J.L. 353 Zamir, L.O. 313 Zanda, M. 185,370 Zanka, A. 104 Zanoni, G. 276, 338, 343 Zapf, A., 291 Zard, S.Z. 40, 46, 98, 192, 340, 341 Zargarian, D. 268 Zaveri, N.T. 76 Zecchi, G. 214 Zechel, G. 370 Zefirov, N.S. 265 Zeni, G. 54, 58, 91,292 Zercher, C.K. 11, 51,342 Zeynizadeh, B. 118, 121 Zhai, H. 76, 254, 330, 341,345 Zhang, A. 13 Zhang, G. 76 Zhang, H. 1, 79, 185 Zhang, J. 139, 226 Zhang, L. 96, 374 Zhang, M. 79, 125 Zhang, R. 111, 112 Zhang, T.Y. 139 Zhang, W. 362, 365, 380 Zhang, X. 121,126, 149, 155, 343

413

AUTHOR INDEX

Zhang, X.P. 50, 61 Zhang, Y. 22, 27, 47, 153, 352 Zhang, Z. 28, 79, 92, 149 Zhao, C.-G. 112, 153 Zhdankin, V.V. 50, 102 Zheng, Q.-Y. 320 Zheng, S.-L. 333 Zheng, Z. 20, 119, 127, 366 Zhong, G. 230 Zhou, Q.-L. 36, 119 Zhou, W.-S. 339, 344

Zhou, Y.-G. 123 Zhou, Z. 314 Zhu, G. 81 Zhu, J. 191,210, 245, 251,344 Zhu, S. 161, 165, 203, 259 Zimmerman, S.C. 319 Zolfigol, M.A. 108,250, 257, 365 Zou, G. 57, 82 Zunino, F. 76 Zwierzak, A. 260 Zyk, N.V. 302

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