Annual Reports in Organic Synthesis (2003), Volume 2003 (Annual Reports in Organic Synthesis)

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annual reports

in or_ganic synthes~s- 2003

This Page Intentionally Left Blank

annual reports in organic synthesis- 2003 by

Philip M. Weintraub

A ventis Pharmaceuticals Bridgewater, New Jersey

Jeffrey Sabol

A ventis Pharmaceuticals

Bridgewater, New Jersey

Kenneth Turnbull Wright State University Dayton, Ohio

Peter Norris

Youngstown State University Youngstown, Ohio

ELSEVIER ACADEMIC PRESS

Amsterdam Boston Heidelberg London New York Oxford Paris San Diego San Francisco Singapore Sydney Tokyo

ELSEVIER Inc. 525 B Street, Suite 1900 San Diego, CA 92101-4495, USA 9 2003 Elsevier Inc. All rights reserved. This work is protected under copyright by Elsevier Inc., and the following terms and conditions apply to its use: Photocopying Single photocopies of single chapters may be made for personal use as allowed by national copyright laws. Permission of the Publisher and payment of a fee is required for all other photocopying, including multiple or systematic copying, copying for advertising or promotional purposes, resale, and all forms of document delivery. Special rates are available for educational institutions that wish to make photocopies for non-profit educational classroom use. Permissions may be sought directly from Elsevier's Rights Department in Oxford, UK: phone (+44) 1865 843830, fax (+44) 1865 853333, e-mail:[email protected]. Requests may also be completed on-line via the Elsevier homepage (http://www.elsevier.com/locate/permissions). In the USA, users may clear permissions and make payments through the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, USA; phone: (+1) (978) 7508400, fax: (+1) (978) 7504744, and in the UK through the Copyright Licensing Agency Rapid Clearance Service (CLARCS), 90 Tottenham Court Road, London W1P 0LP, UK; phone: (+44) 20 7631 5555; fax: (+44) 20 7631 5500. Other countries may have a local reprographic rights agency for payments. Derivative Works Tables of contents may be reproduced for internal circulation, but permission of the Publisher is required for external resale or distribution of such material. Permission of the Publisher is required for all other derivative works, including compilations and translations. Electronic Storage or Usage Permission of the Publisher is required to store or use electronically any material contained in this work, including any chapter or part of a chapter. Except as outlined above, no part of this work may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without prior written permission of the Publisher. Address permissions requests to: Elsevier's Rights Department, at the fax and e-mail addresses noted above. Notice No responsibility is assumed by the Publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made. First edition 2003 ISBN: 0-12-040833-3 ISSN: 0066-409X The paper used in this publication meets the requirements of ANSI/NISO Z39.48-1992 (Permanence of Paper). Printed in The Netherlands.

CONTENTS P R E F A C E ............................................................................................................... xi LIST OF J O U R N A L S A B S T R A C T E D ................................................................ xv G L O S S A R Y OF A B B R E V I A T I O N S ................................................................. xvii

CARBON-CARBON BOND FORMING REACTIONS A.

B.

C.

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 ..................... 3 3. Alkylations of ~-Dicarbonyl, [3-Cyanocarbonyl Systems, and Other Active Methylene C o m p o u n d s ...................... 6 4. Alkylations of N-, P-, S-, Se & Similar Stabilized Carbanions ..................................................................................... 8 5. Alkylations of Organometallic Reagents (see also: I.B.3., I.B.4., I.F., I.G.) ................................................. 10 6. Other Alkylation Procedures ........................................................ 13 7. Nucleophilic Addition to Electrophilic Carbon ........................... 14 a. 1,2-Additions ......................................................................... 14 (1) Aldol-Type 1,2 Additions ........................................... 14 (2) Addition of N, P, S, Se & Similar Stabilized Carbanions .................................................................. 21 (3) Addition of Organometallic and Related Species ...... 21 (4) Other 1,2-Additions .................................................... 33 b. Conjugate Additions .............................................................. 35 (1) Enolate-Type Carbanions ........................................... 35 (2) Organometallic and Related Reagents ....................... 37 (3) Other Conjugate Additions ......................................... 40 8. Other Carbon-Carbon Single Bond Forming Reactions .............. 42 Carbon-Carbon Double Bonds (See also: I.E.1) ................................ 45 1. Wittig-Type Olefination Reactions .............................................. 45 2. Eliminations ................................................................................. 47 a. Alcohols and Derivatives ....................................................... 47 b. Halides ................................................................................... 48 c. Other Eliminations ................................................................. 48 3. Olefin Metatheses ........................................................................ 49 4. Other Carbon-Carbon Double Bond Forming Reactions ............. 52 5. Vinylations ................................................................................... 55 6. Allene Forming Reactions ........................................................... 58 Carbon-Carbon Triple Bonds ............................................................. 59

vi

CONTENTS

D.

C y c l o p r o p a n a t i o n s .............................................................................. 62 1.

C a r b e n e or C a r b e n o i d A d d i t i o n s to a M u l t i p l e B o n d ........................................................................... 62

2. E.

1.

F.

O t h e r C y c l o p r o p a n a t i o n s ............................................................. 63

T h e r m a l and P h o t o c h e m i c a l R e a c t i o n s .............................................. 66 C y c l o a d d i t i o n s ............................................................................. 66

2.

O t h e r T h e r m a l R e a c t i o n s ............................................................. 75

3.

P h o t o c h e m i c a l R e a c t i o n s ............................................................. 75

A r o m a t i c Substitutions F o r m i n g a N e w C a r b o n - C a r b o n B o n d .......................................................................... 77 1.

F r i e d e l - C r a f t s T y p e A r o m a t i c Substitution

2.

R e a c t i o n s ...................................................................................... 77 C o u p l i n g R e a c t i o n s to F o r m an A r o m a t i c C a r b o n - A r o m a t i c C a r b o n B o n d ................................................... 80

3. G.

1. 2. H.

II.

O t h e r A r o m a t i c Substitutions and P r e p a r a t i o n s ........................... 84

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 ........................................................... 88 Synthesis via O r g a n o b o r a n e s ....................................................... 88 C a r b o n y l a t i o n R e a c t i o n s .............................................................. 90

3. O t h e r S y n t h e s e s via O r g a n o m e t a l l i c s .......................................... 93 R e a r r a n g e m e n t s .................................................................................. 97 1. Claisen, C o p e and S i m i l a r P r o c e s s e s ........................................... 97 2. O t h e r R e a r r a n g e m e n t s ................................................................ 100

OXIDATIONS A. C - O O x i d a t i o n s ................................................................................ 104 1. A l c o h o l ~ K e t o n e s , A l d e h y d e s ................................................. 104 2. A l c o h o l s , A l d e h y d e s ~ Acids, Esters ....................................... 107 B.

C - H O x i d a t i o n s ................................................................................ 108 1. C - H ---~C-O ............................................................................... 108 2. C - H --~ C - H a l ............................................................................ 110

C.

C - N O x i d a t i o n s .................................................................................

D.

A m i n e O x i d a t i o n s ............................................................................. 110

110

110

E.

Sulfur O x i d a t i o n s ..............................................................................

F.

O x i d a t i v e A d d i t i o n s to C - C M u l t i p l e B o n d s ................................... 112 1. E p o x i d a t i o n s .............................................................................. 112 2. H y d r o x y l a t i o n s ........................................................................... 114 3.

O t h e r O x i d a t i v e A d d i t i o n s to C - C M u l t i p l e B o n d s .........................................................................................

115

G.

P h e n o l - Q u i n o n e O x i d a t i o n ............................................................... 116

H.

D e h y d r o g e n a t i o n s ............................................................................. 116

I.

O t h e r O x i d a t i o n s .............................................................................. 117

CONTENTS

III.

vii

REDUCTIONS A.

C - - O R e d u c t i o n s (see also III.F.1) ................................................... 119 1. A l d e h y d e s , K e t o n e s --> A l c o h o l s .............................................. 119 2. Acids, Esters, A m i d e s --> A l d e h y d e s ........................................ 123

B.

3. Acids, Esters, A m i d e s --> A l c o h o l s ........................................... 4. Acids, Esters, A n h y d r i d e s --> O t h e r .......................................... C - N M u l t i p l e B o n d R e d u c t i o n s ....................................................... 1. I m i n e R e d u c t i o n s ....................................................................... 2. R e d u c t i o n o f H e t e r o c y c l e s .........................................................

C.

R e d u c t i o n o f Sulfur C o m p o u n d s ...................................................... 125

D. E.

N - O R e d u c t i o n s ............................................................................... 125 C - C M u l t i p l e B o n d R e d u c t i o n s ....................................................... 126

F.

1.

C - - C R e d u c t i o n s ........................................................................ 126

2.

C-C

IV.

R e d u c t i o n s ........................................................................ 129

H e t e r o B o n d R e d u c t i o n s ................................................................... 130 1. 2.

G.

123 124 124 124 125

C - O ---> C - H ............................................................................... 130 C - H a l ---> C - H ............................................................................ 131

3. C - S --->C-H ............................................................................... 131 R e d u c t i v e C l e a v a g e s ........................................................................ 132 1.

O x i r a n e s .....................................................................................

2. 3.

N ~ O C l e a v a g e s ........................................................................ 132 O t h e r R e d u c t i v e C l e a v a g e s ........................................................ 133

132

H.

R e d u c t i o n o f A z i d e s ......................................................................... 133

I.

O t h e r R e d u c t i o n s .............................................................................. 134

SYNTHESIS OF HETEROCYCLES A. B C. D. E. F. G.

O x i r a n e s , Aziridines, and T h i i r a n e s ................................................. O x e t a n e s , A z e t i d i n e s , and T h i e t a n e s ................................................ L a c t a m s ............................................................................................. L a c t o n e s ............................................................................................ F u r a n s and T h i o p h e n e s ..................................................................... P y r r o l e s , Indoles, etc ........................................................................ Pyridines, Q u i n o l i n e s , etc .................................................................

135 139 139 145 150 158 166

H.

P y r a n s , P y r o n e s , and S u l f u r A n a l o g u e s ........................................... 174

I.

O t h e r H e t e r o c y c l e s w i t h O n e H e t e r o a t o m ....................................... 180

J.

H e t e r o c y c l e s with a B r i d g e h e a d H e t e r o a t o m ................................... 182

K.

H e t e r o c y c l e s with T w o or M o r e H e t e r o a t o m s ................................. 184 1.

H e t e r o c y c l e s with 2 N ' s ............................................................. 184 a.

5 - M e m b e r e d ......................................................................... 184

b.

6 - M e m b e r e d ......................................................................... 188

c.

7 - M e m b e r e d ......................................................................... 191

viii

CONTENTS

L. M.

Vo

192 194 200 202 203 205 206 206 208

PROTECTING GROUPS A. B. C. D. E. F.

VI.

2. Heterocycles with 2 O ' s or 2 S's ............................................... 3. Heterocycles with 1 N and 1 0 .................................................. 4. Heterocycles with 1 N and 1 S ................................................... 5. Heterocycles with 1 0 and 1 S ................................................... 6. Heterocycles with 3 or more N ' s ............................................... 7. Heterocycles with 2 N ' s and 1 0 ............................................... 8. Heterocycles with 2 N ' s and 1 S ................................................ Other Heterocycles ........................................................................... Reviews ............................................................................................ A l d e h y d e and Ketone Protecting Groups ......................................... A m i n o Acid Protecting Groups ........................................................ A m i n e Protecting Groups ................................................................. Carboxyl Protecting Groups ............................................................. H y d r o x y l Protecting G r o u p s ............................................................. Other Protecting Groups ...................................................................

215 218 219 221 222 226

USEFUL SYNTHETIC PREPARATIONS A.

B. C. D. E. F. G. H.

Functional Group Preparations ......................................................... 1. Acetals and Ketals ................................................................... 2. Acids and Anhydrides ............................................................. 3. Alcohols and Related Species (see also: II.B.1, III.A., V.E., VI.A.9) ................................................................ 4. Aldehydes and Ketones (see also: I.A.I., I.G.2., II.A. 1) ...................................................................................... 5. Amides and Related Species ................................................... 6. Amines ..................................................................................... 7. A m i n o Acid Derivatives .......................................................... 8. Azides ...................................................................................... 9. Carbohydrates .......................................................................... 10. Esters (see also: I.G.2., IV.D., V.D., VI.A.3) ..................................................................................... 11. Ethers ....................................................................................... 12. Halides (see also: II.B.2.) ........................................................ 13. Nitriles and Imines .................................................................. 14. Other N-Containing Functional Groups .................................. Additions to Alkenes and Alkynes ................................................... Boron C o m p o u n d s ............................................................................ Nucleosides, Nucleotides, etc ........................................................... Phosphorus, Selenium and Tellurium C o m p o u n d s .......................... Silicon C o m p o u n d s .......................................................................... Sulfur C o m p o u n d s ............................................................................ Tin C o m p o u n d s ................................................................................

227 227 229 230 232 2~4 238 242 246 247 248 252 253 256 258 260 262 263 265 267 268 272

CONTENTS

VII.

REVIEWS A. B. C. D. E. F.

VIII.

ix

T e c h n i q u e s ........................................................................................ 274 A s y m m e t r i c Synthesis and M o l e c u l a r R e c o g n i t i o n ......................... 276 Reactions .......................................................................................... 281 Reactive Intermediates ..................................................................... 286 O r g a n o m e t a l l i c s and Metalloids ....................................................... 288 H a l o g e n C o m p o u n d s and H a l o g e n a t i o n (see also: VI.A. 11.) ........................................................................... 293 G. Natural Products ............................................................................... 294 H. Others (see also: IV.M, VIII.A.5, VIII.C.6, VIII.F.7) ...................... 301 SELECTED TOPICAL AREAS A. F u l l e r e n e C h e m i s t r y ......................................................................... 305 1. D i e l s - A l d e r T y p e Cycloadditions .............................................. 305 2. Other Cycloadditions ................................................................. 305 3. P h o t o c h e m i c a l Reactions ........................................................... 306 4. Other F u l l e r e n e C h e m i s t r y ......................................................... 306 B. Taxol and Related T a x a n e C h e m i s t r y .............................................. 310 C. D e n d r i m e r s , Calixarenes and Other Unnatural Products ................. 312 1. D e n d r i m e r s ................................................................................. 312 a. D e n d r i m e r Synthesis ............................................................ 312 b. D e n d r i m e r Catalysts ............................................................ 316 c. H e t e r o - C o n t a i n i n g & M i s c e l l a n e o u s D e n d r i m e r s ............... 316 2. Calixeranes ................................................................................. 317 a. Calixarene Receptors ........................................................... 317 b. Synthesis of Calixirane ........................................................ 319 c. Synthesis on Calixiranes ...................................................... 321 d. Calixirane Isolation, C o n f o r m a t i o n , etc .............................. 323 3. R o t a x a n e s ................................................................................... 323 4. S u p r a m o l e c u l e s .......................................................................... 324 5. C y c l o p h a n e s ............................................................................... 327 6. Other ........................................................................................... 329 7. R e v i e w s ...................................................................................... 330 D~ Total Syntheses of Selected Natural Products (see also: VIII.B and VIII.C) ............................................................ 332 Eo Reactions in Polar M e d i a .................................................................. 347 1. Reactions in A q u e o u s M e d i a ..................................................... 347 2. Reactions in Ionic M e d i a ........................................................... 350 F~ C o m b i n a t o r i a l C h e m i s t r y ................................................................. 355 1. Supports, Linkers and Protecting G r o u p s .................................. 355 2. Supported Reagents, Catalysts, Ligands and Scavengers .............................................................................. 357 3. Solid-Phase Heterocyclic Synthesis ........................................... 359

x

CONTENTS

4. 5. 6. 7.

Solid-Supported Organic Reaction Processes ............................ Targeted Library Synthesis ........................................................ Novel Techniques in Combinatorial Chemistry ......................... Reviews ......................................................................................

A U T H O R I N D E X ................................................................................................

363 367 371 372 375

PREFACE 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 synthetic 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 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. II.A. 1-2: "similar solvent free oxidation using CrO3"and IV.D-l: "also with allyl 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

xii

PREFACE

II.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 2002. Any references from 2001 (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. In producing Annual Reports in Organic Chemistry-2003 we have abstracted 44 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 function. Chapters I-III 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 beating multiple heterocyclic tings 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 Chapter IV; Selected topical reviews are in VIII.C.7. Selected Topical Areas, consists of topical areas we felt are "hot" 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 (VIII.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 added a section on Carbohydrates (VI.A.9) to the Useful Synthetic Preparations chapter. We maintain the section divisions on Combinatorial Chemistry

PREFACE

xiii

(VIII.F): 1. Supports, Linkers & Protecting Groups; 2. Supported Reagents, Catalysts Ligands & Scavengers; 3. Solid-Phase Heterocyclic Synthesis; 4. SolidSupported 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-2003 to be, we made further changes to the formatting 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. 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 AA ACR ACS AG(E) AJC BCJ BMCL CC CCC CEJ CI(L) CJC CL CPB CRV CSR EJOC EJOC H

HCA JACS JCR(S) JCS(P1) JCS(P2) JHC JMC JOC JOM M OL OM OPP OS PAC RCR S SC SL

Aldrichimica Acta Accounts of Chemical Research Acta Chemica Scandinavia Angewandte Chemie International Edition in English Australian Journal of Chemistry Bulletin of the Chemical Society of Japan B ioorganic and Medicinal Chemistry Letters Journal of the Chemical Society Chemical Communications Collection of Czechoslovakian Chemical Communications European Journal of Chemistry Chemistry and Industry (London) Canadian Journal of Chemistry Chemistry Letters Chemical and Pharmaceutical Bulletin Chemical Reviews Chemical Society Reviews European Journal of Medicinal Chemistry European Journal of Organic Chemistry Heterocycles Helvetica Chimica Acta Journal of the American Chemical Society Journal of Chemical Research (S) Journal of the Chemical Society (Perkin I) Journal of the Chemical Society (Perkin II) Journal of Heterocyclic Chemistry Journal of Medicinal Chemistry Journal of Organic Chemistry Journal of Organometallic Chemistry Monatschefte fiir Chemie Organic Letters Organometallics Organic Preparations and Procedures International Organic Synthesis Pure and Applied Chemistry Russian Chemical Reviews Synthesis Synthetic Communications Synlett XV

xvi

ST T TA TCC TL Z

LIST OF JOURNALS ABSTRACTED

Steroids Tetrahedron Tetrahedron Asymmetry Topics in Current Chemistry Tetrahedron Letters Zeitschrift f~ir Naturforschung, Teil B

GLOSSARY OF ABBREVIATIONS 4-PP 9-BBN

pyrrolidinopyridine 9-borabicyclo[3.3.1 ]nonane 18-Cr-6 = 8-C-6 18-crown-6 AA amino acid Ac acetyl acac acetonylacetone ad adamantanyl ADC 9,10-anthracene dicarbonitrile ADDP 1,1 '- (az adic arbonyl)dipiperidine AIB N azobisisobutyronitrile ALB aluminum lithium bis(binaphthoxide) All allyl Alloc = ALOC allyloxycarbonyl An p-anisyl APC allyl palladium dimer APSG aminopropylated silica gel aq aqueous Ar aryl ATD aluminum tris

BER BICP BIH

AZMB BARF

BCN

BDPP

bis(sym-collidine)

iodine(I)hexafluoro phosphate BINAL-H LiA1H4/ethanol/1,1'bis-2-naphthol complex BINAP = DINAP 2,2'-bis(diphenylphosphino)1, l'-binaphthyl BINAS 6-fold sulfonated 2,2'bis(diphenylphosphinomethyl)- 1, l'-binaphthyl Bip biphenyl-4-sulphonyl BLA Bronsted acid assisted chiral Lewis Acid bmin 1-butlyl-3-methylimidazolium cation Bn benzyl BNAH 1-benzyl- 1,4-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= O,N-bis-trimethylsilyl acetamide Bt 1- or 2-benzotriazolyl BTAC benzyl triethylammonium chloride

(2,6-di-tert-butyl-4-

ATPH

borohydride exchange resin (R,R) 2(R)-2'(R)-bis(diphenylphosphino)1(R), l'(R)-dicyclopentane

methylphenoxide) aluminum tris(2,6diphenylphenoxide) 2-(azidomethyl)benzoyl tetrakis[3,5-bis (trifluoro-methyl) phenyl]borate N-benzyloxycarbonyloxy-5-norbornene-2,3dicarboximide (2R, 4R) or (2S, 4S) 2,4bis(diphenylphosphino)pentane xvii

xviii

BTF Bth BTI BTI BTEAC BTFP BTMA BTS BTSA BTSP Bu Bus Bz CAN cat. Cbz CCE CHD CHP Chx2BI CMHP CMMP cod cot Cp CPTS Cr-PILC CRA CSA CTAB CTAC1

GLOSSARY OF ABBREVIATIONS

benzotrifluoride benzothiazole PhI(OzCCF3) 2 [bis(trifluoroacetoxy) iodo]benzene benzyl triethylammonium chloride 2-bromotrifluoroisoprene benzyltrimethyl ammonium bis(trimethylsilyl) sulfate bis-trimethylsilyl chromate bis(trimethylsilyl) peroxide butyl te rt-butylsulf on yl benzoyl ceric ammonium nitrate catalyst benzyloxycarbonyl constant current electrolysis cyclohexadiene cumene hydroperoxide dicyclohexyl iodoborane cumene hydroperoxide cyanomethylenetrimethyl phosphorane 1,5-cyclooctadiene cyclooctatriene cyclopentadienyl collidinium-p-toluenesulfonate chromium-pillared clay catalyst complex reducing agent camphor sulfonic acid cetyl trimethylammonium bromide cetyl trimethylammonium chloride

CTMS=TMCS chlorotrimethyl-silyl 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-tert-butylazodicarboxylate DBH di-tert-butyl hyponitrite DBI dibromoisocyanuric acid DBn p-dodecyloxybenzyl dbpp 1,3-bis(dibenzophospholyl)propane DBPO Di-tertbutyl peroxyoxalate DBS dibenzosuberyl DBSA dodecylbenzylsulfonic acid DBTA dibenzyl L-tartramide DBU 1,5-diazabicyclo [5.4.0]undec-5-ene DCA 9,10-dicyanoanthracene DCB dichlorobenzene DCC dicyclohexyl carbodiimide DCE 1,2-dichloroethane DCN 1,4-dicyanonaphthalene Dcpm dicyclopropylmethyl DDQ 2,3-dichloro-5,6dicyano-benzoquinone de = d.c. diastereomeric excess DEAD diethyl azodicarboxylate DEPC diethyl cyanophosphoridate

GLOSSARY OF ABBREVIATIONS

DET DHAP

diethyl tartrate dihydroxyacetone phosphate DHP dihydropyran DHQD dihydroquinidine DIAD diisopropylazodicarboxylate DIB (diacetoxyiodo) benzene DIBAH = DIBAL diisobutylaluminum hydride DIM 2-(hydroxyethyl)- 1,3dithiane DIOP 2,3-O-isopropylidene-2,3dihydroxy- 1,4-bis(diphenylphosphino)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 m-dimethoxybenzene Dmb 2,4-dimethoxybenzyl DMB 2,3-dimethylbuta- 1,3diene DMD dimethyl dioxirane DME dimethoxyethane DMF dimethylformamide DMG directed metalation group DMI 1,3-dimethylimidazolidin2-one DMM dimethoxymethane DMN 1,5-dimethoxynaphthalene DMP Dess Martin Reagent DMP 2,6-dimethylphenol DMPS dimethylphenylsilyl

xix

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 dpba 2-(diphenylphosphino)benzoic acid DPC diphenylphosphoro chloridate DPDC diisopropyl peroxy di-carbonate DPDM diphenyl diazomethane DPEDA 1,2-diphenylethane- 1, 2-diamine DPPA diphenylphosphorazidate dppb bis(1,4-diphenylphosphino)butane dppe- DPPE bis(diphenylphosphino)ethane dppf dichloro [ 1, l'-bis(diphenylphosphinoferrocene)] dppp 1,3-(diphenylphosphino)propane DPS t-butyldiphenylsilyl DPTC O,O'-di(2-pyridyl) thiocarbonate dr diastereomeric ratio ds diastereoselectivity DTBAD = DBAD di-tert-butylazodicarboxylate DTB B 4,4'-di-tert-butylbiphenyl DTBP 2,6-di-t-butylpyidine dtBPF 1,1'-bis(di-tertbutylphosphino) ferrocene DTE dithioerythritol DTPM [ 1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidine]methyl

xx

E EDAC

general electrophile ethyldimethylaminopropylcarbodiimide EDC 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide 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 group Fc ferrocenyl FDP fructose- 1,6-diphosphate Fe(dbm)3 tris(dibenzoylmethido) iron(Ill) FePHEN tris(1,10-phenanthroline)iron(III)hexafluorophosphate Fe(Epp) iron(Ill) tetraphenylporphyrin fl flavin 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

GLOSSARY OF ABBREVIATIONS

Gr GSNO h Hap HDNIB

graphite nitrosoglutathione hours hydroxyapatite [hydroxy(2,4-dinitrobenzenesulfonyloxy) iodo]benzene hfacac hexafluoroacetylacetone HFIP hexafluoro-2-propanol HGK 4-hydroxy2-ketoglutarate HLADH horse liver alcohol dehydrogenase HLE horse liver esterase Hmb 2-hydroxy-4-methoxybenzyl HMDS 1,1,1,3,3,3hexamethyldisilazane HMPA = HMPT hexamethylphosphoramide HMS hexagonal mesoporous silica HMTAB hexamethylenetetramine bromide HNIB [hydroxy(p-nitrobenzenesulfonyloxy)iodo] benzene hv irradiation with light HPA heteropoly acid 3-HQD 3-hydroxyquinuclidine HTIB [hydroxy(p-tolyl- sulfonyloxy)iodo]benzene IBDA iodobenzene diacetate IBX o-iodoxybenzoic acid IDCP iodonium dicollidine perchlorate INOC Intramolecular Nitrile Oxide Cycloaddition Ipc2 diisopropylcamphyl IPr 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene K- 10 a Montmorillonite clay

GLOSSARY OF ABBREVIATIONS

KMBA

potassium N-methylbutyramide KSF a Montmorillonite clay LA Lewis acid L-selectride" lithium tri-Sbutylboro hydride L.R. Lawesson's reagent LAH lithium aluminum hydride LDA lithium diisopropylamide LDBB lithium 4,4'-%utylbiphenylide LDE lithium diethylamide LDPE lithium perchloratediethyl ether LICKOR BuLi/tBuOK liq. liquid LR Lawesson' s reagent LTMP lithium 2,2,6,6-tetramethylpiperidide MABR methylaluminum bis (4-bromo-2,6-ditbutyl-phenoxide) MAD methylaluminum bis-(2,6-di-%utyl-4methyl-phenoxide) MAPh methylaluminumbis (2,6-diphenoxide) MBDA magnesium bis(diisopropylamide) MBT 2-mercaptobenzothiazole MCPBA m-chloroperbenzoic acid MCM-41-TBD hybrid organic/ inorganic reusable catalyst Me methyl Mek methyl ethyl ketone MEM [3-methoxyethoxy-methyl MEPY methyl 2-pyrrolidone5(S)-carboxylate

xxi

Mes = mesityl 2,4,6-trimethyl-phenyl MMPP magnesium monoperoxyphthalate Mmt 4-methoxytrityl MOM methoxymethyl MPD 1-methylpyrrolidone MPM methoxy(phenylthio)methyl Mpm = PMB p-methoxybenzyl MPPC N-methyl piperidine chlorochromate MS molecular sieves Ms methanesulfonyl MSA methanesulfonic acid MSH o-mesitylenesulfonyl hydroxylamine Mspoc 2-methylsulfonyl-3phenyl- 1-prop-2enyloxy-carbonyl MTO methyltrioxorhenium (MeReO 3) MTPA methoxy-a-trifluoromethylphenylacetyl MV 2+ methyl viologen MVK methyl vinyl ketone mw = laW microwave NaBMGS sodium butylmonoglycosulfate NAP naphthylmethyl Naph = Np naphthyl NBS N-bromosuccinimide NCS N-chlorosuccinimide NDMS 2-norbornyldimethyl silyl Nf nonaflate Nf nonafluorobutylsulfonyl NfF nonafluorobutane sulfonyl fluoride NFOBS N-fluoro-O-benzenedisulfonimide NHPI N-hydroxyphthalimide NIS

N-iodosuccinimide

xxii

NISac NMM NMO

N-iodosaccharin N-methyl morpholine N-methylmorpholineN-oxide NPM N-phenylmaleimide N-PSP N-phenylselenophthalimide NR no reaction Ns 2-nitrobenzenesulfonyl Nuc. general nucleophile [O] general oxidation ODCB o-dichlorobenzene ONf nonaflate = nonafluoro1-butanesulfonyl 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 PhTRAP 2,2'-bis[1-(diphenylphosphino)ethyl]- 1, l'-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

GLOSSARY OF ABBREVIATIONS

PMP

1,2,2,6,6-pentamethylpiperidine PMP p-methoxyphenyl p-nitrobenzyl PNB PNP dimer cis, exo-2-phenylnorbornylpalladium C1p-nitrobenzyloxycarbonyl PNZ PPA polyphosphoric acid PPE ethyl polyphosphate pyridinium polyhydrogen PPHF fluoride PPI 2-phenyl-2- (2-pyridyl) imidazole pig pancreatic lipase PPL poly(p-phenylene) PPP polyphosphoric acid PPSE trimethylsilyl ester pyridinium PPTS p-toluene-sulfonate Pr propyl Proc propargyloxycarbonyl PSCBH poly supported cyanoborohydride poly[4-(diacetoxy) PSDIB iodostyrene] phenylsulfonylethylidene PSE pounds per square inch psi phenyltrimethylPTAB ammonium perbromide phase transfer catalysis PTC (2-phenyl-2-trimethylPTMSE silyl)ethyl p-tolylsulphonate PTS p-toluenesulfonic acid PTSA phenyltrimethylPTT ammonium tribromide pyridine pyr quinolinium QFC fluoro-chromate quinoxalinium dichromate QxDC racemic rac Raney nickel RaNi

GLOSSARY OF ABBREVIATIONS

perfluorinated alkyl ring-opening metathesis room temperature rt N,N'-ethylenebisSalen (salicylideneiminato) SAMP (s)- 1-amino2-methoxymethylpyrrolidine SBER sulfurated borohydride exchange resin SC CO2 super critical CO 2 SDS sodium dodecylsulfate SEM = TEOC ~-trimethylsilylethoxymethyl SES 2-[(trimethylsilyl) ethyl]-sulfonyl Sia Siamyl Si-BEZA O-(trisubstituted silyl) benzamide SMEAH sodium bis (2-methoxy-ethoxy) aluminum hydride SPB sodium perborate SPC sodium percarbonate T3p| propane phosphonic acid anhydride TABCO 2,4,4,6-tetrabromo-2, 5-cyclohexadienone TADDOL 2,2,-dimethyl-t~,t~,ct1,ctltetraaryl- 1,3-dioxolan-4, 5-dimethanol TASF tris(dimethylamino)sulfur(trimethylsilyl)difluoride TBAB tetrabutylammonium bromide TB AF tetrabutylammonium fluoride TB AHS tetra-n-butylammonium hydrogen sulfate TB ATB tetrabutlyammonium tribromide Rf

ROMP

xxiii

TBATFA tetrabutylammonium trifluoroacetate TBATFA tetrabutylammonium trifluoroacetate TBCO tetrabromocyclohexadienone TBDMS = TBS t-butyldimethyl-silyl TBDPS butyldiphenylsilyl Tbfmoc Tetrabenzo[a,c,g,i] fluorenyl- 17-methyloxycarbonyl TBH di-tert-butyl hypochlorite TBHP %utyl hydroperoxide TBME %utyl methyl ether TBP tributylphosphine TBST triphenyl silanethiol Tbs 4-methoxy-3-t-butylbenzenesulphonyl TBSOP N-tbutylcarbonyl-2 (tbutyldimethylsiloxy)pyrrole TBTH tributyltin hydride TBTSP t-butyl trimethylsilyl peroxide TCAA trichloroacetyl anhydride TCCA trichloroisocyanuric acid TCF trichloromethyl chloro-formate TCNE tetracyanoethylene TCNEO tetracyanoethylene oxide TDTAP tetradecyl trimethylammonium permanganate TCPC TFE (tetrakis(2,2,2-trifluoroethoxycarbonyl)palladium cyclopentadiene TDS dimethyl thexylsilyl TEA triethylamine TEAA tetraethylammonium acetate TEAP tetraethyl ammonium perchlorate

xxiv

TEBA

Benzyl trimethylammonium chloride TEOC = SEM [3-trimethylsilylethoxymethyl TEP triethylphosphite TES triethylsilyl Tf trifluoromethanesulfonyl TFA trifluoroacetic acid TFAA trifluoroacetic anhydride TFE trifluoroethanol TFMSA trifluoromethanesulfonic acid TFP 1,1,1-trifluoro-2-propanol TFP tris (2-furyl)phosphine TFPZ trifluoroisopropenyl zinc THAB tetrahexylammonium bromide THAH tetrahexylammonium hydrogen fluoride thexyl 2,3-dimethylbutly THF tetrahydrofuran THP tetrahydropyranyl TIBA tri(isobutyl)aluminum TIBAL tri-iso-buylaluminum TIPPSe-Br (2,4,6-triisopropylphenyl)selenium bromide TIPS tri-ipropylsilyl TMABr tetramethylammonium bromide TMACC trimethylammonium chlorochromate TMAF tetramethylammonium fluoride TMAO= TMANO trimethyl-amine N-oxide TMATB trimethylammonium tribromide TMEDA tetramethylethylenediamine TMG 1,1,3,3-tetramethylguanidine Tmob 2,4,6-trimethoxybenzyl

GLOSSARY OF ABBREVIATIONS

TMP

2,2,6,6-tetramethylpiperidine TMS trimethylsilyl TMSA trimethylsilyl azide = azido trimethylsilane TMSDEA N,N-diethyltrimethylsilylamine TMU tetramethylurea TNM tetranitromethane Tol tolyl Tos = Ts p-toluenesulfonyl Tp trispyazole borate TPCD tetrapyridine cobalt(II) dichromate TPP Tetraphenylporphyrin TPP triphenyl phosphine TPP triphenylphosphate TPPB tris(pentfluoro-phenyl) borane TPPTS m-sulfonated triphenylphosphine Tr= trityl triphenylmethyl Ts-MIC tosylmethyl isocyanide TSE 2-(trimethylsilyl)ethyl TTBP 2,4,6-tri-tert-butylpyridine TT Co(II) Pc tetrabutylammonium cobalt(II) phthalocyanine5,12,19,26-tetrasulfate TTMPP tris(2,4,6-trimethoxyphenyl)phosphine TTMSS tris(trimethylsilyl)silane UHP urea-hydrogen peroxide complex wk week Z benzyloxycarbonyl (~ ~( *

_ ~ -

polymeric support US ultrasound Denotes asymmetric center

I CARBON-CARBON

I,A, C a r b o n -

BOND

FORMING

REACTIONS

Carbon Single Bgads

(see also:

I.E., I.F., I.G., I.H.)

I,A,1, Alkylations of Aldehvdes, Ketones and Their Derivatives I.A.I-1 Ender, D.; Voith, M. S, 1571; Enders, D. et al. S, 1775; Quirion, J.-C. et al. SL, 1669; Okano, T. et al. OL, 4, 1571. OlVle t t ~

1. tBuLi, R-X,THF,-100~ -~ rt O~O

2.03, CH2C12,-70~

~ .

Jb, I

(~O

-

R

61-87% ee = 90-94% I.A.1-2 Trost, B.M. et al. AG(E), 41, 3492; Tanyeli, C.; Ozdemirhan, D. TL, 43, 397; Yamamoto, Y. et al. TL, 43, 2903. n -k ~ ' x . IOAc NaHDMS, (~13-C3HsPdCI)2,DME ~

O

ePhze h z P ' ~ ~

~~N-% 9 ~ "="

~

"~

77.95 cr~

ee = 84-92%

I.A.1-3 Yamaguchi, M. et al. OL, 4, 2209; Matsuda, I. et al. JACS, 124, 9072. TMS~)A --r...~.xx/R + Ct

~

1. GaCI3, Ph-CI, c-C6H11Me, -40~ TMS . . . . . . . . . . . . . . . 2. H2SO4, MeOH

r L ~

R 40-95%

2

ORGANICSYNTHESISm2003

acl2

I . A . 1 - 4 0 s h i m a , K. et al. BCJ, 75, 2049; Baba, A. et al. JACS, 124, 7440; see also: Yamamoto, H. et al. JOC, 67, 5124; Cho, C.S.; Shim, S.C. et al. TL, 43, 7987. 1. MeLi

2. GaCI3~

xLc~ nl

CO2R1

BEt:~ 02 : 7-76%

I.A.1-5 Dominguez, E. et al. OL, 4, 1591. A r

R ~ B r

+ ~~A r R2 r1

Pd(OAc)2, PPh3, Cs2CO3 = ~

Arl

R2

DMF, 150"C, 0.5-1h

R1 12-80%

"~O+ ~-],/NR1R2

I.A.1-6 Nagasawa, K. et al. TL, 43, 2935.

EtO2C/

"~\'~R

~O~j/NRIR2

HCHO

AcOH, 800C EtO2C" v

"~\R

0-89% I.A.1-7 Campos, K.R. et al. TL, 43, 6957; Yee, N.K. et al. JOC, 67, 8688; Cerichelli, G. et al. CEJ, 8, 5204. 1. LDA, THF 2. E +, DMPU,-45~

E 75-90% de = 98 %

I . A . I - 8 Takahashi, T. et al. SL, 97.

___NC q

,,

LiHMDS

!~

dioxane, reflux

XO OY

XO OY

17-52%

CARBON-CARBON BOND FORMING REACTIONS

I.A.2.

Alkylations

of Nitriles.

3

Acids

and

Acid

Derivatives

I.A.2-1 Wang, B. et al. T, 58, 7663; Gurjar, M.K.; Chaudhuri, S.R. TL, 43, 2435. G12.LHDMS, . THF, -95--,-78~ R-X P

PG 19-83% de = 84-93%

I.A.2-2 Molander, G.A. et al. JOC, 67, 3459. 0

I

R~~M~,~a

SmI2

I

)n

-~ HOR.~ ...... 39-90%

I.A.2-3 De Mong, D.E.; Williams, R.M. TL, 43, 2355; Papini, A.M. et al. EJOC, 2736. Ph Ph ~ % 1. TiC,4, TEA ~ % Ph O ,'- Ph O CbzN__~ 2. HC(OMe)3,CH2CI2,-78~ CbzN--<..

~ --OMe

MeO

94%

I.A.2-4 Najera, C.; van Koten, G. et al. TA, 13, 2181; Najera, C. et al. TA, 13, 927; Maruoka, K. et al.'AG(E), 41, 1551; Jew, S.; Park, H. et al. CC, 1244; Nagasawa, K. et al. AG(E), 41, 2832; Takemoto, Y. et al. JOC, 67, 7418; Lygo, B. et al. TL, 43, 8015. ph,,~N,,,/co2ipr

Bn-Br, -20~

aq~MeOH/Ph-Me/CHCI3 - Ph.~N~CO2ipr

Ph

// iX,,. Y

..,oti,.t~ ~

W

OR

Ph Bn 70-98% ee = 28-76%

4

ORGANIC SYNTHESIS--2003

I.A.2-5 Liebscher, J. et al. EJOC, 369.

~

Me~ _7,Co(CO)31. KOH, DMSO F[ ~ / / " or LDA Me 2. hv, Et20, rt COzMe

R R1 •

L

R

R~1 R

"CO2Me 60-97% dr = 1.27-19:1

(also with ketones)

Me

I.A.2-6 Trost, B.M.; Dogra, K. JACS, 124, 7256.

R ~

+

Ar

Ph

~CO2Me LiHMDS,Mo(CO)3C7H8 r ~ ~ CO2Me -THF, 60~ A R4""NHBz ~r~ -~~ 76-92% Off"N.n ,m~'~O dr = 24-49:1 ee = 85-99%

I.A.2-7 Solberghe, G.F.; Marko, I.E. TL, 43, 5061.

~iCO2Et

M-HMDS,R-X ,

(EtO)2P~O

THF, 0~ or -20~

~CO2Et (EtO)2P~oR 50-75%

I.A.2-8 Davies, S.G. et al. TA, 13, 647; Kim, T.H. et al. TA, 13, 9; Romea, P.; Urpi, F. et al. OL, 4, 4651. R1

LDA, E+

THF;-780c33-80% de = 89-96% I.A.2-9 Greenhalgh, D.A.; Simpkins, N.S. SL, 2074.

4• O~

"N"

E+ "O

> 4"F'Pho~N~ ,,E O

Ph

.~--NLiL i ~ 4 P~

Ph

Ph

40-87 %

ee = 74.97%

CARBON-CARBON BOND FORMING REACTIONS

5

I.A.2-10 Manthorpe, J.M.; Gleason, J.L. AG(E), 41, 2338; Romo, D. et al. OL, 4, 2645. 1" LDBB' THF' "78~ ~. 2. RI-x

H

~de 59-89% de = 88-95%

I.A.2-11 Simig, G. et al. S, 595. R1

yOH

O§

R1

H

RaN, 150-220~

-

0 H 82-98%

I.A.2-12 Kim, S. et al. JACS, 124, 14306. 9_TBS

R-I + ~ N

,-OTBS Cbz

AIBNor (Me3Sn)2 Ph-H

--

NHCbz 60-84 %

I.A.2-13 Procter, D.J. et al. OL, 4, 4583. MO~Me~ Ph

1. LDA, LiCI, Bn-Br, THF _-

2. ~ L i

n 60% ee = 90%

I.A.2-14 Donohoe, T.J. et al. JCS(P1), 1748. ~TMS MS ...~---OMe Na, NH3, R-X O ~OMe

~

.=--OMe

= \ RO~o ~OMe 68-93% de = 94%

Me H

6

ORGANIC SYNTHESIS--2003

I.A.2-15 Zaragoza, F. JOC, 67, 4963. R/'OH

1. iPr2NEt, EtCN, 97"C 2. H20, 97"C

+ Me3P + ~ C N I"

35-79%

I.A,3, Alkvlations of [I-Dicarbonyl. D-Cyanocarbonyl and Other Active Methy!enf Compoun~ls

Sv~tfm~

I.A.3-1 Malmstrom, E.; Moberg, C. et al. JOC, 67, 8197; Hou, X.-L. et al. JOC, 67, 4684; Guiry, P.J. et al. JOC, 67, 4209; Tomioka, K. et al. JOC, 67, 5864; Daran, J.-C. et al. TA, 13, 1097; Carretero, J.C. CC, 2512; Ding, K. et al. TA, 13, 1291; Pericas, M.A.; Muller, G. et al. CEJ, 8, 4164; Gong, L. et al. TA, 13, 809; Dieguez, M.; Gomez, M. et al. CC, 1132; Tietze, L.F.; Lohmann, J.K. SL, 2083; Zheng, Z. et al. TL, 43, 9179 and TA, 13, 1687; Morales-Morales, D. et al. JOM, 654, 16; see also: Moyano, A. et al. JOM, 660, 62. ~ . ~ MeO2C~CO2Me Ac CH2(CO2Me)2 Ph Ph ~ Ph~"'~"'x" Ph dendromer ~ dendromer 10-99% P ,IPh ee = 81-94%

I.A.3-2 Trost, B.M.; Andersen, N.G. JACS, 124, 14320.

MeO2 .

NaoAoM: Boc

Mo(CO)3(C7Hs), lig. THF, 67~ BocN,. 02

M e O 2 ~ Me02C

y

BocN..

I.A.3-3 Song, C.E.; Han, H. et al. AG(E), 41, 3852; Hegedus, L.S. et al. JOC, 67, 3788; Jin, M.-J. et al. TL, 43, 7409; Schultz, E. et al. TL, 43, 4907; Lloyd-Jones, G.C. et al. CEJ, 8, 4443. "Heterogeneous Pd-Catalyzed Asymmetric Allylic Substitution Using Resin-Supported Trost-Type

Bisphosphine Ligands."

CARBON-CARBON BOND FORMING REACTIONS

7

Trost, B.M.; Hughes, D.L. et al. AG(E), 41, 1929. H,. ~H(C O2Me)2 ph~-"~/~'OCO2Me + NaCH(CO2Me)2 Mo(CO)3(CTHs)~ Ph~ or ?CO2Me ~N N~ 90%

I.A.3-5

o/y_~m~_~o

I.A.3-6 Moloney, M.G. et al. TL, 43, 3407. e

e

ee=99%

_

~

,OMe

1,10-phenanthrene

+

CHCi3

,

99%

Pb(OAc)3

I.A.3.7 Matsumura, Y. et al. TL, 43, 3229. Cu(OTf) ~., + CH2(CO2Me)2 P]I ~..~OPh ..,,,(CO2Me OMe -. O"~ O ~ R CO2Me 34-78% ee = 41-53% I.A.3-8 Trost, B.M. et al. AG(E), 41, 1059. ~.X~/ + N C ~ }

[~5-C5Me5)Ru(MeCN)3]PF6 n

Bu3N, rt 85-98% branch:linear = 13-100:1

I.A.3-9 Kim, J.N. et al. TL, 43, 6597. ACR~

+

K2CO3 DMF, 70~

I

R ~ O H 71-76%

8

ORGANIC SYNTHESIS--2003

I.A.3-8 Shibatomi, K.; Uozumi, Y. TA, 13, 1769.

~,~ L 02Me [~,.,~OCO2Me [0]3C3H~jPdCI]2 , ~ .,~ .,CO2Me }n + NaCH(CO2Me)2 I , ~ % ~86.99% In ee = 82-89% X ' ~

PPh2

I.A.3-4 Belda, O.; Moberg, C. S, 1601. "Substituted Pyridylamide Ligands in Microwave-Accelerated Mo(0)-Catalyzed Allylic Alkylations." I.A,4, Alkvlation~ of N-. P-. S., Se aod Similar Stabilized Carbanions I.A.4-1 Enders, D. et al. AG(E), 41, 109.

R~ ~

SO3R* THF,BULi-'90~ ~ ~>~o~,.~:o~

R*=

,

,

.

.

.

.

.

.

.

SO3R* de94-98% =89-93%

,

I.A.4-2 Beletskaya, I.P. et al. TL, 43, 2539; Chou, S.-S.P.; Liang, P.W. TL, 43, 4865; Zhu, Y.; Drueckhammer, D.G. TL, 43, 1377; Najera, C. et al. JOC, 67, 5216.

9 O2Ph Nail, Pd2(dba)3.CHCl:~PPh3 ~,,O2Ph EWG + Ar.Br -- EWG" "Ar dioxane 25-90%

I.A.4-3 Azzena, U. JCS(P1), 360.

C'~

1" P Li E-X ~h K' C10H8' 2 . THF-

HO,.,,,,,..~ 23-25%

CARBON-CARBON BOND FORMING REACTIONS

9

I.A.4-4 Volonterio, A.; Bravo, P.; Zanda, M. TL, 43, 6537; Metzner, P. et al. JOC, 67, 6852. ./R

B uLi, R1-X

Z,,.. l~)

R

NHMe HMPA/THF, -78~

O

62-95% de = 5-94 %

I.A.4-5 Marr, F.; Hoppe, D. OL, 4, 4217; Toru, T. et al. EJOC, 1690; see also: Tyrrell, E. et al. SL, 1073; Smith, A.B., III et al. JACS, 124, 14516.

(k

/~S

N(/er)2

SBuLi' E'X

TMEDA/Ph.Me/Et20/THF

/(~~ k/,~" ~S ~'~NiPr2 "

" E

58-99%

I.A.4-6 Coldham, I. et al. AG(E), 41, 3887; Katritzky, A.R. et al. JOC, 67, 8230. 1. BuLi, HexlEt20, 22~ . ~ 2. BuLi, lig., Et20 .~ SnBu3 3. E +,-10~ ~ '"'E ZBu tBu ~.~ 54-75% NMe er 24.32.3:1 lig= I ?~---"/ I.A.4-7 Florio, S. et al. OL, 4, 2445; Malacria, M. et al. SL, 553; Uneyama, K. et al. OL, 4, 173; Schmalz, H.-G. et al. AG(E), 41, 2525; Hoppe, D. et al. S, 381; Hodgson, D.M.; Gras, E. AG(E), 41, 2376. ph.~ SBuLi' E+ I~ THF,.98o C -- ph~",~ 40-95% er = 49:1

10

ORGANIC SYNTHESIS--2003

I.A.5.

A l k vv l a t i o n s

of O r ~_ a n o m e t a l l i c

R e a g_ e n t s

(see also" I.B.3., I.B.4., I.F., I.G.) I.A.5-1 Dvorak, D. et al. TL, 43, 7867.

R~

]I1 i~r(CO)5

OCOR2 + .CH2__~Cr(CO)5 Pd(PPh3)4 R ~ I ~ ~ N M e 2 NMe2 THF 48-81%

I.A.5-2 Bondarev, O.G. et al. TA, 13, 1587; see also: Weissensteiner, W.; Widhalm, M. et al. JOC, 67, 2206; Widhalm, M.; Calhorda, M.J. et al. OM, 21, 315; Konno, T. et al. JOC, 67, 1768.

Ph~ ~ c P h

NaTs,[Pd(C3H5)CI]2,THF, rt ,

Ph~

MeM~ tO -%

Ph

57% ee= 92%

Me Et

I.A.5.3 Demuth, M. et al. JOC, 67, 1167; Oshima, K. et al. A G(E), 41, 4137. R1 R ~ ~ 4-R-Ph-CH2MgCI,Pd(PPh3)4. e THF, rt 49-94%

~ /

I.A.5-4 Kishi, Y. et al. OL, 4, 4427; Otaka, A.; Fujii, N. et al. JOG, 67, 6152, 6162.

Trisyl

/R OH

DME, -78~

~

R Me OH 92%

I.A.5-5 Kobayashi, Y.; Matsuumi, M. TL, 43, 4361; Kobayashi, Y. et al.

JOC, 67, 7110. H ~ O A c

CIMg(CH2)sOTBDPS' .............. THF, -18~

CuCN _- H ~

....,(CH2)sOTBDPS 84%

CARBON-CARBON BOND FORMING REACTIONS

11

I.A.5-6 Funabiki, K.; Matsui, M. et al. SL, 1134. C ~ F3 F

OTs

R-MgBr _ F 2 ~ THF, reflux F

t

R

14.85% I.A.5-7 Miyashita, M. et al. CC, 1970; Yamazaki, T. et al. CC, 2670; see also: Burova, S.A.; McDonald, F.E. JACS, 124, 8188; see also: Ruano, LEG.; Castro, A.M.M. et al. TA, 13, 1321. R

Me2Zn, CuCN H R ~ C _ , ~ O t DMF,"230C 2E

~

/Me \

,~

H(~__.(Me R

CO2Et 75-99% 11.5-49:1

I.A.5-8 Ernst, M.; Helmchen, G. AG(E), 41, 4054. B~.

I=I

_H

RO2C(CH2)7CuZn(CN)Br -

,

,

,

THFI iiD78 OC ~I

~ % 0

-

I

RO2C~) 7 ~I 97%

I.A.5-9 Kobayashi, Y. et al. TL, 43, 4829. ,CO2Me .._ ~ O 2 Me AcO,..,~,,~ Bu-MgBr, CuCN \__/ "CO2Me Et20,.45oc - \\ ..../ "CO2Me Bu 63% I.A.5-10 Kambe, N. et al. JACS, 124, 4222. NiCI2, 1,3-C4H6 R-X + R1-MgX THF, rt I.A.5-11

R.R x

56-99%

Knochel, P. et al. AG(E), 41, 351. EtO2C

I

THF,-40~

EtO2C E 52-92%

CO2Et

12

ORGANIC SYNTHESISm2003

I.A.5-12 Sato, F. et al. TL, 43, 6511.

R

E 65-88%

I.A.5-13 Backva11, J.-E. et al. JOC, 67, 2136. 2

R1

~

THF,0 C

tPhMezSi

OP(~

R1

2CuJ

R2

R/-3--~R4 51-94%

I.A.5-14 Lipshutz, B.H. et al. S, 2110. ,~iMe2

R~

4- k.~...RI CI

~ R

2

Ni/C THF,rt

R1 R R2

I.A.5-15 Dahanukar, V.H.; Zavialov, I.A. et al. TL, 43, 6121. MeO~OMe

~~,~OMe

Me'-NJ 1. HexLi, THF,-20~

....OH 2. CIP(O)(OPh)2 3. C~OMe

v l~Ie ~ ~ M ~ OMe

75% MgBr

I.A.5-16 Revell, J.D.; Ganesan, A. JOC, 67, 6250. ~-~

LICKOR'R'X 78-~ ~" ~ 62-76%

R

CARBON-CARBON BOND FORMING REACTIONS

13

I.A.5-17 Clayden, J. et al. JCS(P1), 901; Uemura, M. et al. JOC, 67, 1929. C~,,Nipr2 R

SBuLi, E+ THF, -78~ 51-99% 1-56.7:1

I.A.5-18 Larock, R.C.; Reddy, C.K. JOC, 67, 2027. R1

~O

R2-I,Pd(OAc)2, PPh:~ Bu4NCI

[ [

iprNEt2, DMF, 80~

\

R

23-75% I.A.5-19 Dolbier, W.R., Jr. et al. OL, 4, 4671. 02 ((S~]o 1. CF31,(Me2N)2C=C(NMe2)2 HO~ TH v, -20"C-~ rt M~" 2. aq H2SO4 M~ v

\CF 3 43% ee = 99 %

I.A.5-20 Nelson, S.G. et al. JOC, 67, 4680.

Q~.---~

R-MgBr, CuBr R1

.:R HO2C,,,/~ R1 74-94%

[,A.6. Other AIkylation Procedures I.A.6-1 Yoshimatsu, M. et al. JOC, 67, 1078.

PhX

OEt OEt

Nuc', Lewis acid ~- PhX CH2Ci2

OEt Nuc 60-84%

14

ORGANIC SYNTHESIS--2003

I.A.6-2 Takacs, J.M. et al. OL, 4, 3843. CH2(CO2CH2CF3)2 ,

,

R-OH, DEAD or ADDP, PPh3 ......

Ph-Me, rt

,,

R-CH(CO2CH2C F3)2

40-82%

,

I.A.6-3 Huang, Z.-T. et al. S, 523. H

H

X

(

N

X

K2CO3 = ( n MeCN, reflux

+

MeO2~

79-85% I.A.6-4 Katritzky, A.R. et al. JOC, 67, 8239. Cl~k~

H BtH,TEA

CI Rf~Ph

()

Bt~HN~

Ph

Nuc" =

Nuc~HN~

() 32-73%

I.A.6-5 Quan, J.G." Cha, J.K. JACS, 124, 12424. I

Pd(OAc)2, dppp, TEA . . . 80~ . . . . . //"~C6HI 3 DMF/H20, iPr2S~1~ C 6 H I ipr2SZr--OH 3

68-73%

I,A,7, Nueleophilir

A~ldition t9 Elr162

I,A,7.a.1, Aldol-Tvoe

Carbon

1.2-Additions

I.A.7.a.l-1 Starkmann, B.A.; Young, D.W. JCS(P1), 725. "Double Stereodifferentiation in Aldol Reactions of Pyroglutamic Esters."

Ph

CARBON-CARBON BOND FORMING REACTIONS

15

I . A . 7 . a . l - 2 Ragoussis, V. et al. JOC, 67, 4615; Schneider, C.; Hansch, M. CC, 1218. pH 7.8 R~ ! + R1-CHO -~ CO2K H20, 60~ 6h 75-90% R1

I . A . 7 . a . l - 3 Mukaiyama, T. et al. CL, 698; Hashimoto, S.; Kikuchi, S. CL, 126.

R•I Me

1. 9-BBN, 2,6-1utidine 2. R1-CHO

=-

R1

Me 90-97 % syn:anti = 7.3-99:1

l.A.7.a.1-4 Dias, L.C. et al. OL, 4, 4325; Romea, P. et al. TL, 43, 6145; Paterson, I.; Coster, M.S. TL, 43, 3285; De Brabander, J.K. et al. OL, 4, 481; Righi, G. et al. TL, 43, 4737; see also: Hosomi, A. et al. JACS, 124, 536; Denmark, S.E.; Fujimori, S. OL, 4, 3473; Wang, D.; Li, C.-J. et al. CC, 2994; Woerpel, K.A. et al. JOC, 67, 2056; Li, W.-D.Z.; Zhang, X.-X. OL, 4, 3485. _PMP _PMP .

c

Me Me

Et20, -78~

Me

Me

Me 75-89 dr - 19:1

I . A . 7 . a . l - 5 Kobayashi, S. et al. JACS, 124, 3292; Evans, D.A. et al. OL, 4, 3375; Denmark, S.E.; Fan, Y. JACS, 124, 4233; Demark, S.E. et al. JACS, 124, 13405; Harada, T. et al. SL, 972; Fujisawa, H.; Mukaiyama, T. CL, 182; Kiyooka, S. et al. TL, 43, 5377; see also: Moser, W.H. et al. OL, 4, 1981. MS 3 Zr(OR )4Pr-OH/H20/Ph-Me, 0~ ~ RO2 R2 R + R2"CHO R1 on 61-96 % on syn:anti = 1:5.67-24 ee = 89-99 % x v -,~ -i

~

16

ORGANIC SYNTHESIS--2003

I.A.7.a.l-6 Enders, D.; Ince, S.J. S, 619; Enders, D. et al. SL, 962; Shibasaki, M. et al. JOC, 67, 2556; see also: Patonay, T. et al. EJOC, 285. 1. Cy2BCI,TEA, Et20 OBuO~

2. R-CHO, Et20

OBuO~ 60-87 % de = 96 %

I . A . 7 . a . l - 7 Jiang, B. et al. TL, 43, 6819. MeO2

T M c ~ ST +M O S ~' AO T f F -C~~A R r CH2CI2,0~ MeO2 r F F F 23-91%

l.A.7.a.1-8 Shinada, T.; Ohfune, Y. et al. TL, 43, 6755; Velazq[aez, F.; \ Olivo, H.F. OL, 4, 3175. + OHC-Ar

ip

TEA, Ac20 ~rt i Ar 15-76%

R

R

I.A.7.a.l-9 Ellman, J.A. et al. JACS, 124, 6518; Jorgensen, K.A. et al. CEJ, 8, 5652. tBur S"N

LDA, MgBr2 or ZnBr2 t B u r .~H Ph" v ~""R phl~'.-Me + OHC-R THF, -78~

64-88% dr = 6.14-49:1

I.A.7.a.l-10 Mangeney, P. et al. JOC, 67, 8928; see also: Fleming, F.F. et al. JOC, 67, 9414. Bn LDA u/N--~ + OHC-R tB CN THF, -80~

Bn, tBu/

t~ "",OH CN

20-90%

anti:syn = 2-19:1

CARBON-CARBON BOND FORMING REACTIONS

17

I . A . 7 . a . l - l l Abiko, A. et al. TL, 43, 8297 and JACS, 124, 10759 and JOC, 67, 5250; Hulme, A.N.; Rosser, E.M. OL, 4, 265; lithium enolates: Ley, S.V. et al. S, 1973; Enders, D. et al. S, 515; silicone enolates: Huang, X.-T.; Chen, Q.-Y. JOC, 67, 3231; Evans, D.A. et al. JACS, 124, 392; titanium enolates: Ghosh, A.K.; Kim, J.-H. TL, 43, 5621; Hitchcock, S.R. et al. OL, 4, 3739; Guz, N.R.; Phillips, A.J. OL, 4, 2253; Olivo, H.F. et al. TL, 43, 6439; Koch, G.; Loiseleur, O. et al. OL, 4, 3811.

Me + OHC.R

Bu2BOTf,TEA

=

~

~

Bn

~H " R O

71-98% I.A.7.a.l-12 Hassfeld, J.; Kalesse, M. TL, 43, 5093 and SL, 2007. ~TBS

MeO~~

TBS~

+ Me

OH~

. lVle

_OH ~TBS MeOzC~~~: _ Me _ iprOH/Et20~ Me 76% TPPB

I.A.7.a.l-13 Dolbier, W.R., Jr. JOC, 67, 72.

EtO2C~Br + % R 1 F R

Zn, CeCi3"7H20 EtO2~ stOH _-)--.~R 1 THF, rt F R 60-95%

I.A.7.a.l-14 Bellassoued, M. et al. JOC, 67, 5611.

~

~ ~ R 1 R I'BuLi'THF"70~ I + .. ~ R" 2. H3O+ ~ ~R2 CO2TMS CO2H 61-97%

I.A.7.a.l-15 Staas, D.D. et al. JOC, 67, 8276; Petrini, M. et al. J O C , 67, 4530. R O

EtOeC~ZnBr F F

+

R~I

N,...,,O

tB~u

THF

~

EtO,~N...~ F F H 51-82%

dr = 4-19:1

tBu

18

ORGANIC SYNTHESISm2003

I.A.7.a.l-16 Yu, C.; Hu, L. JOC, 67, 219; Li, G. et al. CC, 1856, 2412; Ramachandran, P.V. et al., JOC, 67, 5382; Goodman, J.M. et al. TL, 43, 8219; Kisanga, P.B.; Verkade, J.G. JOC, 67, 426; Rayner, C.M. et al. CC, 968; Gatri, R.; E1 Gaied, M.M. TL, 43, 7835; Batra, S. et al. JOC, 67, 5783; Hayashi, Y. et al. TL, 43, 8683; see also: Li, G. et al. SC, 32, 1765 and OL, 4, 3691. H2

+ OHC-Ar

DABCO . H2 H20/dioxane, rt

r 61-99%

I.A.7.a.l-17 Kamimura, A. et al. T, 58, 9817; Feringa, B.L. et al. JOC, 67, 7244; Hayashi, T. et al. JACS, 124, 10984. OH PhXMgBr R~co2tBu R ~ C O 2 tBu + OHC-R1 , CH2C!2,-780C-~ rt R 9 "XPh 24-99% I.A.7.a.l-18 Krische, M.J. et al. JACS, 124, 15156; Shinokubo, H.; Oshima, K. et al. OL, 4, 3 l 11; Deslongchamps, P. et al. JOC, 67, 5669; Brimble, M.A.; McLeod, M. et al. JCS(P1), 924. Ar~l

fCHO

H2, Rh(cod)2OTf,P(4-CF3Ph)3 KOAc, DCE, 25~ 70-90% 5-19:1

I.A.7.a.l-19 Shimizu, M.; Sahara, T. CL, 888. EtO2C~OTMS N"Ar TiI4 EtO2~~__(NHAr +

II

R/

-

EtCN, 0~

HO

R

14-83% anti:syn = 1.23-3.54:1 l.A.7.a.l-20 Katritzky, A.R. et al. JOG, 67, 4957. tBuO2C~ ~HCbz LDA t B u O 2 C ~ NHCbz R]

+ Bt/~

R1

~THF,-78~

1~

"R1

35-73%

CARBON-CARBON BOND FORMING REACTIONS

19

l.A.7.a.l-21 Trost, B.M.; Yeh, V.S.C. AG(E), 41, 861; Misumi, Y.; Matsumoto, K. AG(E), 41, 1031; Ma, D. et al. TL, 43, 9401; Reiser, O. et al. TL, 43, 7503; Jorgensen, K.A. et al. JOC, 67, 4875. 4,~ MS, THF,-78 to-35"C O21W"~.. R O2N-Me + OHC-R

6.

56-90% ee = 78.93

%

Me

I.A.7.a.l-22 Northrup, A.B.; MacMillan, D.W.C. JACS, 124, 6798; Barbos, C.F., III et al. JOC, 67, 301; Shimizu, K. et al. TL, 43, 9073; Dickerson, T.J.; Janda, K.D. JACS, 124, 3220; Jorgensen, K.A. et al. CC, 620; Loh, T.-P. et al. TL, 43, 8741. O H % + RI.CHO L-Proline_ OHC~ \/'OH R DMF, 4oC R R1 75-88% anti:syn = 3-24:1 ee = 91-99%

I.A.7.a.1-23 Kobayashi, S. et al. CEJ, 8, 4185 and OL, 4, 3395; Liotta, D.C. et al. S, 2075; Wenzel, A.G.; Jacobsen, E.N. JACS, 124, 12964; Murahashi, S.-I. et al. JACS, 124, 2888. TlVI~ H PhO ~/ + Me

Zr(OtBu)4, BINOL NMI, CH2C12

H ~ ~" H ": R1 PhOzC~R Me 54-96% syn:anti = 1"2.45-49 ee 80-96 %

I.A.7.a,l-24 Lectka, T. et al. JACS, 124, 67; Kobayashi, S. et al. JACS, 124, 5640; Ranu, B.C. et al. T, 58, 983; Enders, D,; Oberborsch, S. SL, 471. ,~iR

% chiral transition ~,. /]NHTs 3 EtO2 metal-phosphine complex R~- ~ + "CO-,Et N'-Ts THF or CH2C!2,-78-0~ ~ R1-- v 65-97% ee = 67-98%

20

ORGANICSYNTHESIS--2003

l.A.7.a.l-25 Loh, T.-P.; Chen, S.-L. OL, 4, 3647. R-CHO + R1-NH2 +

/OTIS

,-R3 \R 4

InCl

MeOH, rt--

R4

40-80% dr = 3-99:1 I.A.7.a.l-26 Hou, X.-L. et al. JCS(P1), 1487. yTs j~tBu ~HTs + a~ LDA R2,~CHO R2

R

R1

R

~HTs + R 2 " ~ CHO 1~ "R1 61-82% 1:1.5-11.5

I.A.7.a.1-27 List, B. et al. JACS, 124, 827. M

e& OH

+ PMP-NH2 + OHC-R

.~HPMP

(s)-Proline DMSO, rt

Me" v . ] -R -2 OH 57-92% dr = 3-20:1 ee = 61-99%

I.A.7.a.l-28 Balan, D.; Adolfsson, H. JOC, 67, 2329; Shi, M.; Zhao, G.-L. TL, 43, 9171; Shi, M.; Xu, Y.-M. TA, 13, 1195. Oz R.. EWG Ti(Oier)4, 3-HQD R,.S,,.NH Ar-CHO + ~O2 + -~ NH2 4A,MS, iprOH, rt A r / X ~ EWG 12-94% I.A.7.a.l-29 Mikami, K.; Ohmura, H. CC, 2626; Pinheiro, S. et al. TA, 13, 1157; Tsukamoto, T. et al. JOC, 67, 7365.

(

CHO CHO

/ ~ SiR3 + " - I Me + MeNH2

BF3.Et20 CHxCi2,-78~ -~ rt

M

~

~

O 18-40%

CARBON-CARBON BOND FORMING REACTIONS

21

I.A.7.a.2. Addition of N-. P,. S-. Se and Similar Stabilized Carbanions I.A.7.a.2-1 Aggarwal, V.K.; Esquivel-Zamora, B.N. JOC, 67, 8618, fi.,,~ci-io

) ~ I

q

~~

NaHMDS pYr/THF'0*C ~ I ~O /

+

n

O

89%

l.A.7.a.2-2 Mitzel, T.M. et al. JOC, 67, 136.

R-CHO +

Arl~ C

In

-~

A~_~. ~ 46-87%

I.A.7.a.2-3 Gais, H.-J. et al. JACS, 124, 7789, 10427.

R1/~

1. BuLl,THF,-78~ zNMe 2. ClTi(Oipr)3 RO2SH~ O, CNMe " ~ S ~ . p h ~Ph 3. EtOzCCH=NSOzR EtOz 4. (NH4)2CO3 59-82 dr = 49:1

I.A.7.a.2-4 Kirschning, A. et al. SL, 525.

,OMe R-CHO + PhzP ~ Li OMe THF,-ll0~

41-89%

l.A.7.a.3. Addition of Oreanometallic and Related Soecies w

l.A.7.a.3-1 Ishino, Y. et al. SL, 2116; Beak, P. et al. JOC, 67, 6797.

R..q Zn, TMS-C! ~n H )n + R1-CItO " X THF/DMAor NMP R1 12-75%

22

ORGANIC SYNTHESIS--2003

I.A.7.a.3-2 Chong, J.M. et al. OL, 4, 3553; Bolm, C.; Rudolph, J. JACS, 124, 14850; Kabalka, G.W. et al. T, 58, 3243; see also: Wipf, P.; Wang, X. OL, 4, 1197; Braga, A.L. et al. S, 2338; Wolf, C. et al. TA, 13, 1733; Frejd, T. et al. JCS(P1), 645; Nugent, W.A. OL, 4, 2133; Wolf, C.; Hawes, P.A. JOC, 67, 2727; Walsh, P.J. et al. JACS, 124, 10970; Singleton, D.A.; Vo, L.K. JACS, 124, 10010; Heckel, A.; Seebach, D. CEJ, 8, 559; Lasperas, M. et al. TA, 13, 357; Molina, P. et al. TA, 13, 5; Martinez, A.G.; Vilar, E.T. et al. TA, 13, 1; Bauer, T. et al. TA, 13, 77; Pale, P. et al. TA, 13, 119; Sebesta, R.; Salisova, M. CCC, 67, 1700; Kim, T.-J.; Jeong, J.H. et al. JOM, 649, 258; Hu, Y. et al. TL, 43, 8367; Bercot, E.A.; Rovis, T. JACS, 124, 174; Pu, L. et al. TL, 43, 8831; Soai, K. et al. TA, 13, 805; Yamano, T. et al. OL, 4, 3051. R~-CHO + R2Mg

OH

"

?h ~ Me"N ~ ' I H

% - - R1 34-77%

er = 2.57-10:1

l.A.7.a.3-3 Poupat, C. et al. T, 58, 4201; Couture, A. et al. JOC, 67, 3601; Jurczak, J. et al. TA, 13, 2133; Murai, S. et al. AG(E), 41, 2779. tBu~

LDA

THF, -78~

,/ S-~y~ OH 99%

I.A.7.a.3-4 Motherwell, W.B.; Storey, L.J. SL, 646; Dolbier, W.R., Jr. et al. TL, 43, 4317. R~O R1

TMS~ph+

CsF

F3C -NMe2 THF,reflux

. ~HF3 Rx 41-92%

l.A.7.a.3-5 Steurer, S.; Podlech, J. S, 945; see also: Delgado, A. et al.

JOC, 67, 308; see also: Basavaiah, D. et al. JOC, 67, 7135. PhHN: ~ R~ CHO +

In /CO2Me ..... H20/EtOH, rt

PhH_N RO ~ ~ H

"CO2Me

72-89% syn:anti = 1-1.22-4.56

CARBON-CARBON BOND FORMING REACTIONS

23

I.A.7.a.3-6 Murakami, T.; Furusawa, K. T, 58, 9257; Behar, V. et al. JOC, 67, 1947; Mohr, P.J.; Halcomb, R.L. OL, 4, 2413; Sato, F. et al. TL, 43, 4373.

"~~--N.. Boc O~~CHO

R

+ CICp2Zr~

ZnBr2 THF, 0*C--,rt

~'~--N. Boc _-- ~ ~ . . ~ R OH 58-74% anti:syn = 5-20:1

l.A.7.a.3-7 Takai, K. et al. CC, 1128; Takeda, T. et al. CC 1974. R~CO2Me CrCI2 _ R ~ C13 + R1-CHO DMF/THF -

t R1

CI 46-84% l.A.7.a.3-8 Baba, A. et al. OL, 4, 301; Medebielle, M. et al. S, 2601; Orsini, F.; Caselli, A. TL, 43, 7255, 7259.

2.f 'X

R

+ R-CHO

Li(Bu2SnI3) HMPA

R

O OH 9-93% syn:anti = 4-19:1

O

I.A.7.a.3-9 2345.

Hamada, Y. et al. TL, 43, 4695; Procter, D.J. et al. OL, 4,

P%.

1 ~ % M e , ~ OH Ts

~

R

SmI2 -55~ HMPA/THF, -78 to

~ O H Ts 75% 32.3"1

l.A.7.a.3-10 Goldberg, S.D.; Grubbs, R.H. AG(E), 41, 807. QH Q 1. RCH=CH2, cat., CH2CI2,40~ f~,jB---~___ 2. RICHO, rt

cat.

=

Mes-/~N-Mes Ck !

/Ph

cr,r~u=-" PCY3

:- ~ , , , , , ' , , ~ R1 R 44-79% anti:syn = 4-20:1

24

ORGANIC SYNTHESISm2003

I.A.7.a.3-11 Pansare, S.V. et al. T, 58, 8985. Me ~ O Me

Me

Ph 1. RMgX, ....... Et20/CH2CIz, -78"C _... M e ~ " ~ 2. TMS-CH2CH=CH2,TiCL4

O

Ph

45.57%

dr = 95% l.A.7.a.3-12 Yu, C.-M. et al. AG(E), 41, 161. ~T R-CHO + Bu3S

[(R.BINOL)TilV(ocH(CF3)212 MS

iprSBEt2,--CH2Cl2

TMS

69-97% ee = 90-97 %

A.7.a.3-13 Thadani, A.N.; Batey, R.A. OL, 4, 3827; Andrade, C.K.Z. et al. S, 928; Wessjohan, L.A. et al. JOC, 67, 1975; Denmark, S.E.; Fu, J. OL, 4, 1951. R-CHO + I ~ ~ B R~

F3"K+ . . . . Bu4Nl : RR ~ , R 2 H20/CH2CI2, rt 94-99% dr = 49:1

I.A.7.a.3-14 Kumar, S. et al. SL, 573; DiMauro, E.F.; Kozlowski, M.C. OL, 4, 3781. HO2C~O + R1 ~ , , x , / B r

H20/THFIn> H O 2 ~ 66-96% 6.14-49"1

I.A.7.a.3-15 Loh, T.-P. et al. OL, 4, 2715; Mori, M. et al. JOC, 67, 656. R-ClIO +

C

tZn, Niacac,~ TItF, rt

55-92% syn:anti = 1.38-2.57:1

CARBON-CARBON BOND FORMING REACTIONS

25

l.A.7.a.3-16 Schmidt, B.; Wildemann, H. JCS(P1), 1050; Ishino, Y. et al. TL, 43, 6601; Namy, J.-L. et al. TL, 43, 8007.

~,,,,..,, MgBr 02

Et20' '78*C~ ~ . ~ R

R

R

1

64-96%

l.A.7.a.3-17 Alcaide, B. et al. JOC, 67, 1925. x

II

~

,,,%/o

Zn or In

§ o:_Na

II on

O~--NR 9-62%

X I.A.7.a.3-18 Jeong, I.H. et al. TL, 43, 7171.

a,: 2 a

~Me

CFaC-CLi + R1R2NH + " t ~ N'Me

R

THF, -78 to 0~

O 31.98% Z:E = 3-100:1

I.A.7.a.3-19 Srebnik, M. et al. SL, 61. @P(OEt)2 Zr Cp/ ~Cp

+

~__~/P(OEt)2

R~O R~

R2 OH 75-87%

I.A.7.a.3-20 Kang, S.-K. et al. JOC, 67, 4376 and AG(E), 41, 343 / ( ~ O A r -+I R

In, Pd(OAc)2,DMF, 80"C P~)a

"

t-hR'OH 63-84%

26

ORGANIC SYNTHESIS--2003

I.A.7.a.3-21 Leighton, J.L. et al. JACS, 124, 7920; Carreira, E.M. et al. CC, 2560; Hayashi, T. et al. OL, 4, 2799; Walsh, P.J. et al. A G(E), 41, 3697; Kurosu, M.; Lorca, M. TL, 43, 1765; Cunningham, A.; Woodward, S. SL, 43; Shibasaki, M. et al. JACS, 124, 6536 and S, 1956; Liu, L.; Guo, Q.-X. et al. TL, 43, 9373; Jurczak, J. et al. TA, 13, 1103; Radetich, B.; Corey, E.J. OL, 4, 3463; Watahiki, T.; Oriyama, T. TL, 43, 8959; see also: Mohan, R.S. et al. TL, 43, 4597. Ph,..

_,

-'["- XcSix M e ~ " " N e CI

+ R-CHO

' -Ph-Me,-10"C

59-85% ee = 78-96 %

I.A.7.a.3-22 Mori, M. et al. JOC, 67, 9310 and CL, 18.

//

X ~----CHO

R3Si-H, Ni(cod)2 X ~ ~ O S ~ ; Ph

e

22-88%

ee = 10.73 %

I.A.7.a.3-23 Montgomery, J.; Song, M. OL, 4, 4009.

Xx_c. ~

R2Zn, Ni(cod) 2

/'-~..'

R

52-77%

I.A.7.a.3-24 Pu, L. et al. OL, 4 4143; Moore, D.; Pu, L. OL, 4, 1855; Xu, M.-H.; Pu, L. OL, 4, 4555; Carreira, E.M. et al. OL, 4, 2605; Jiang, B. et al. CC, 2098 and OL, 3451; Braga, A.L. et al. T, 58, 10413; Chan, W.L.; Chan, A.S.C. et al. CC, 172; Auge, J. et al. TL, 43, 5255; Yadav, J.S. et al. TL, 43, 5437; Yokozawa, T. et al. T, 58, 245; Brisdon, A.K.; Crossley, I.R. CC, 2420; Taber, D.F.; Storck, P.H. JOC, 67, 8273; Jiang, B.; Si, Y.G. TL, 43, 8323. R-C---C + R1-CHO

Et2Zn, Ti(OiPr)4, rt on

~ R

/OH _(,R1

58-99 % ee = 91-99%

CARBON-CARBON BOND FORMING REACTIONS

27

I.A.7.a.3-25 Snapper, M.L.; Hoveyda, A.H. et al. AG(E), 41, 1009; Liang, S.; Bu, X.R. JOC, 67, 2702; Vachel, P.; Jacobsen, E.N. JACS, 124, 10012; Lin, G. et al. JOC, 67, 8251; Najera, C.; Saa, J.M. et al. OL, 4, 2589; Jenner, G. et al. TL, 43, 9167; Somanathan, R.; Walsh, P.J. TA, 13, 149; Feng, X.; Jiang, Y. et al. SL, 793, 1353; Uang, B.-J. et al. CC, 54; Yadav, J.S. et al. TL, 43, 9703; Verkade, J.G. et al. JOM, 646, 161; Shreve, J.M. et al. CCC, 67, 1296; Shibasaki, M. et al. AG(E), 41, 3636 and TL, 43, 2919, 2923; Johnson, J.S. et al. OL, 4, 2957; Jursic, B.S. et al. TL, 43, 5361; Takamura, H. et al. CPB, 50, 1118; Bandini, M.; UmaniRonchi, A. et al. EJOC, 3243. TMS-CN, Al(O/Pr)3, 3,~ MS R~O MeOH/Ph.Me, -78~ .,,OTMS ,, al

Me

O~~N~,H ~on

~ _= o

o~

gl

N~CO2Me

a

66-98%

ee =

80-95 %

NHTr

I.A.7.a.3-26 Baker, R.W. et al. TL, 43, 9319. R2

+R OR R3 R" 45-95%

I.A.7.a.3-27 Davis, C.E.; Coates, R.M. AG(E), 41, 491. TiCi4 Me'""

CH2C!2' "78~

Me'""

OH 72% cis:trans = 8:1

C

I.A.7.a.3-28 Semmelhack, M.F. et al. TL, 43, 4947. n ...,CHO

CrCI3, NicI 2

47%

28

ORGANIC SYNTHESISm2003

I.A.7.a.3.29 Szymoniak, J. et al. S, 1115. R ~ N R 2 1. EtMgCI, Cp2ZrCI2, T H F R1

2. E +, 0 - , rt

E

50-69%

Pericas, M.A. et al. OL, 4, 2381. Et2Zn, Ph-Me, -10*C, 4h R'--~--[-- CHO Ph Co2(C0)6

I.A.7.a.3-30

Et Co2(CO)6 51-83%

Ph

ee = 96-99 % L

.

.

.

.

.

I.A.7.a.3-31 Yus, M. et al. JOM, 663, 21. I'BuLi,'IO0~ 2. RCOR 1

Br.~/:~ ..../ ~ L - - C I

H

1 ~ ~

u.. y

3. Li, CsH10 4. Et2CO,-78~

(EoH 45-85%

Et

I.A.7.a.3-32 Masson, G.; Py, S.; Vallee, Y. AG(E), 41, 1772. "O'N-Bn !~) SmI2 HO~ a 2 R~." + ~ ~ R/ (R 3 R1 R R3 THF, -78~ R1 OH 69-98% dr = 1:1-2.33

=oEt2 LDA' tO2

l.A.7.a.3-33 Kraus, G.A.; Choudhury, P.K. OL, 4, 2033.

+ OH -.~

"CO2Et THF,-78~ -~ R / ~ R 1

30-65%

'
I.A.7.a.3-34 Li, Z.; Zhang, Y. T, 58, 5301. 0

+

BrSm v H (similarly with lactones)

TItF, rt 85-95%

0-48%

CO2Et

CARBON-CARBON BOND FORMING REACTIONS

29

l.A.7.a.3-35 Shintani, R.; Fu, G.C. AG(E), 4, 1057. Ph-MgCI, (-)-sparteine ,. O

"'~',.ICO2H

Ph-Me, -78~

Ph 51-91% ee = 87.92%

I.A.7.a.3-36 Goosen, L.J.; Ghosh, K. EJOC, 3254; Yamamoto, A. et al. BCJ, 75, 1333; see also: Liu, J.; Ikemoto, N. et al. TL, 43, 8223; Yoo, B.W. et al. TL, 43, 4813. (tBuCO)20, Pd(OAc)2,P(2-MeOPh)3 I ~ O R-CO2H + Ar-B(OH)2 H20,60"C, 16h Ar 1-96% I.A.7.a.3-37 Shi, M.; Zhao, G.-L. TL, 43, 4499; Azizi, N.; Saidi, M.R. TL, 43, 4305; see also: Keck, G.E.; Welch, D.S. OL, 4, 3687; Pare, P.W. et al. TL, 43, 5677. P h2P-..

[ff~CO2Me PPh3 +

p h21~ r~

MeCN -

"Ar

A

"a

~.COzMe 77-99%

l.A.7.a.3-38 Enders, D. et al. S, 2737. tHexMe2Si~

1. LDA, TMS-CI,HMPA/THF t H e x M e 2 S i @ ~ . R

R1 2. MeOCHzNBn2, BF3oEt2 O

R

R1

93-95% ee = 96% I.A.7.a.3-39 Toru, T. et al. TA, 13, 1509. ,0

~

N,,R1

. R..~O~HR1

R2.Li THF' "78~ ~ ~

~R2 72-98% dr - 49:1

NBn2

30

ORGANIC SYNTHESIS--2003

I.A.7.a.3-40 Lete, E. et al. TA, 13, 311. iPr2NC~_..~ Ph

ipr2N~3~ + N-PMpCPh.SBuLi,(.).sparteine ...

Ar

NHPMP 13-84%

Ar

ee = 15-96% I.A.7.a.3-41 Katritzky, A.R. et al. S, 199. R4 B~ + NRIR2 R MgBr R Ph-Me, rt-50~

R4 R ~

NRIR2

R 82.94%

I.A.7.a.3-42 Carda, M.; Marco, J.A. et al. SL, 711. "O-.N+'Bn HO,.N~Bn h~~./OTPS R'MgX'ZnBr2 = ~ O T P S ~O THF' "78~ ~O 72-85% dr = 4-19:1 I.A.7.a.3-43 Carreira, E.M. et al. A G(E), 41, 3054; Wei, C.; Li, C.-J. JACS, 124, 5638 and CC, 268. +

J-R 1

1. Zn(OTf)2 2. NH2OH

HOH3 R

-~

R1

54-85%

l.A.7.a.3-44 Enders, D.; Schaadt, A. SL, 498; Palmieri, G. et al. TA, 13, 2011; Saidi, M.R.; Azizi, N. TA, 13, 2543; Moody, C.J. et al. SL, 1730. 1. R1-Li,CeCI3,THF,-100~ R NHCbz M e O ' % / . . ~ 2. BF3.THF, THF, reflux StBu

N" N . ~

3. Cbz-CI,K~,CO3 H20/CH2CI2, reflux

tBu

28-61%

de, ee = 96%

CARBON-CARBON BOND FORMING REACTIONS

31

I.A.7.a.3-45 Yadav, J.S. et al. TL, 43, 6245; Akiyama, T.; Onuma, Y. JCS(P1), 1157; Choudary, B.M. et al. SL, 1694; see also: Andrade, C.K.Z.; Oliveira, G.R. TL, 43, 1935. LiCIO4 R-CHO + R1-NH2 + Bu3SnCH2CH:CH2 L----",rt--MeldlN

~ HR 1

75-90% l.A.7.a.3-46 Knochel, P. et al. S, 2143. .NEt2 ~Et2 Tf20 ph~..-'~...~NEt2 + Ar-MgBr THF, NMP',-65:C = ph~~~~[,,.A r 50-81% I.A.7.a.3-47 Fan, X.; Zhang, Y. TL, 43, 5475. Ar.,~N-OH R

Ar' H

~,,.~SmBr THF, rt

59-93% I.A.7.a.3-48 Alexakis, A.; Amiot, F. TA, 13, 2117.

--

CIC02Me, Bu-Li, sparteine ~ Ph-Me, -80~

+

CO2Me

_/ O2Me Bu 85% 7:3 ee = 57%

\__ CO2Me

I.A.7.a.3-49 Burger, K. et al. S, 2579; Wang, Y.; Zhu, S. S, 1813. Fc3~Ci R-MgBr F3C~R NHPG THF,-78 to-10~

NHPG 64-89%

l.A.7.a.3-50 Akiyama, T. et al. OL, 4, 3967. T s H ~ N ) _ ~ R1 ~Ts + (OC)sCr<~/OMe R"

CH2RI DCE, reflux

OMe 63-81%

R

32

ORGANIC SYNTHESIS--2003

l.A.7.a.3-51 Chong, J.M. et al. JOC, 67, 3625. tBuS1"" I~lBoc tBuS""" blBoc BuLi " + Ar-CHO ' :SnBu3 Et20/THF, -78"C

>-yAr OH

58-79%

anti:syn =

2:1

I.A.7.a.3-53 Dahmen, S.; Brase, S. JACS, 124, 5940; Brase, S. et al. AG(E), 41, 3692; Petrini, M. et al. JOC, 67, 2989. A?

NH ~CHO

T

EI2Zn, hex,-15-20~

~

Ar~ Et

N" ~ Ph i

..,,I~H 'CHO

90-99 %

~OH

ee =

70-95 %

I.A.7.a.3-54 Roland, S. et al. TA, 13, 2205; Di Fabio, R.; Alvaro, G. et al. JOC, 67, 7319. Ph~ MeO_.~

//--CO2 Et

R-ZnBr, ZnBr2

N

Et20 or CH2C12

Ph~._..NH/-~--C 0 2Et MeO --j

50-68 %

dr = 13.3-19:1

I.A.7.a.3-55 Saidi, M.R.; Azizi, N. SL, 1347. 1~ ~0 R1

+ R2-NH2 + P(OR3)3

LiCi04, TMS-Cl Et20, rt

R

~ HR2

"~~I~(OR3) 2

R1 O

85-98%

I.A.7.a.3-56 Hiemstra, H. et al. OL, 4, 3497; Oba, M.; Koguchi, S.; Nishiyama, K. T, 58, 9359; Schuch, C.M.; Pilli, R.A. TA, 13, 1973. R2

R

\R 2

MeCN, 0~ -, rt 42-87%

CARBON-CARBON BOND FORMING REACTIONS

33

I.A.7.a.3-52 Prakash, G.K.S.; Mandal, M. JACS, 124, 6538; Senanayake, C.H. et al. TL, 43, 923; Krishnamurthy, D.; Senanayake, C.H. et al. TL, 43, 2331; Shimizu, M. et al. T, 58, 9621; Plobeck, N.; Powell, D. TA, 13, 303; see also: Wynne, J.H.; Stalick, W.M. JOC, 67, 5850; Haroutounian, S.A. et al. S, 111.

tBuS.. ~) N ~ N B u 2 R

TMS-CF3,Me4NF = THF, -35~

tB

{~F3

N~NBu2 H 60-86 %

de - 4-99:1 I.A.7.a.4

Other

l.2-Additions

I.A.7.a.4-1 Jung, M.; Groth, U. SL, 2015; Yoda, H. et al. TL, 43, 4667; Shimizu, M. et al. OL, 4, 4097.

P~

1. TMS-CI,Mn, CrCi2 _ ~ ~OH + R1 2. TBAF,THF

R + 1 ~ H

52-75% syn:anti - 1:3.55-49"1 I.A.7.a.4-2 Enders, D.; Kallfass, U. AG(E), 41, 1743.

tBuOK, THF (~ Ar ~~N~/~N+.Ph" Ar~'~'LOH

Ar-CHO

By,-

8-83% ee = 8 0 - 9 5 %

,Bu

I.A.7.a.4-3 Hasegawa, E. et al. TL, 43, 5067. o

CO2Et SmI2 _

O

w

~

R

THF

R 44-60%

I.A.7.a.4-4 Nagasawa, K. et al. TL, 43, 5751.

H

NMe2

EWG.CH2CO2R1

~ N M e 2 ~ EWCt--k H20/MeCN, 80~ "CO2R l 50-98%

R 1

34

ORGANIC SYNTHESIS--2003

l.A.7.a.4-5 Ruck, R.T.; Jacobsen, E.N. JACS, 124, 2882. CHO + ~ BaO'Me2CO~ = X X 26-97% 9 , , ~ ~ ' ~ ] r "s" ee = 70-96 % "07,-o - ' ~

R

tBu ,|

,

|

I.A.7.a.4-6 Procter, D.J. et al. OL, 4, 2345; Lee, D. et al. OL, 4, 3959; Nguyen, T.M.; Lee, D. TL, 43, 4033. I

,.,,,Me

....

Me

.

HMPA/tBuOH --COzEt 65% L

Sml2

~

.,,Me

~r..._COzEt THF/MeOH

CO2Et 45%

I.A.7.a.4-7 Zhang, X. et al. TL, 43, 4711. X. . . .

~O~NHA

1. N204 c 2. LiOH, THF, reflux

~ V/ ~~ :h 45-80%

I.A.7.a.4-8 Kalbaka, G.W. et al. OL, 4, 3415, 1491. R-CHO + R1-C---C

TiX4 CH2CI2' 0~

--

R

40-68%

I.A.7.a.4-90shima, K. et al. SL, 978. ~.~

R1-CHO,TiCI4,TBAI R~1~R. . , . ~ CH2Cl2 I 51-78%

I.A.7.a.4-10 Chen, J.; Cunico, R.-F. TL, 43, 8595. R"

NMe2

R NMe2 0-92%

X

CARBON-CARBON BOND FORMING REACTIONS

35

l.A.7.a.4-11 Huang, X.; Xie, M. JOC, 67, 8895. R m

~ O

Ts +

+ PhSe-MgBr

R"

R•H R2

CH2CI2/THF, -20"C PhSe/ Ts 60-89%

Z:E = 24-99:1

I.A.7.a.4-12 Cha, J.K. et al. oLI 4, 3707; Keller, B.M.; Leumann, C.J. S, 789.

Bu3SnH, AIBN :

~'--~O H[

OMe Br

OMe 84-99%

I.A.7.a.4-13 Aggarwal, V.K. et al. JACS, 124, 10300. 1. BuLi, THF, .78"C tOTMS R-CHO + TMS-CH=Nz 2. MeOH ~ R--~ 3. Rh2(OAc)4 70-84%

]~.A,7,b Coniueate ].A.7.b.1

Additions

E n o l a t e . T v o e .. Carbanions _

_

I . A . 7 . b . l - 1 Pedro, J.R. et al. TL, 43, 8463. H tBuX

,~

LDA HMPA =-

O H + R~ ~ ~ j ~ R 1 Ph

,

tB30r

H ,O....//~ Ph 74-85% 100-0:0-100

i

l.A.7.b.l-2 Amat, M.; Bosch, J. et al. OL, 4, 2787. Ph ~ 7

CO2Et +

R1

}

~~ "',lO Et

Ph

LDA THF EtOeC

Et 52%

36

ORGANIC SYNTHESISm2003

l . A . 7 . b . l - 3 Jorgensen, K.A. et al. JOC, 67, 8331; Itoh, K.; Kanemasa, S. JACS, 124, 13394; Pereira, V.L.P.; Costa, P.R.R. et al. TA, 13, 1025; Ballini, R. et al. SL, 1706 and S, 2725.

0 2

R2 +

R1

I...NMe N.~,~CO2 H -

Bn

,,,

,

" ~ "R 1 50-99% ee = 34-86% R"

[]

,

I . A . 7 . b . l - 4 Beak, P. et al. OL, 4, 2747; Lim, S.H.; Beak, P. OL, 4, 2657. R1 O2N\__

+R,~~

XR1

BuLi, (.).sparteine _ O

Ar IN'Boc

Ph-Me, -78~

2

-

~ RAr/N'Boc 73-90% dr = 5.25-49:1 ee = 24-32.3:1

I.A.7.b.1-5 Jackson, R.F.W. et al. SL, 1700; Prabagaran, N.; Sundararajan, G. TA, 13, 1053; Shibasaki, M. et al. T, 58, 2585 and TL, 43, 4661; Muthusamy, S. et al. SC, 32, 3247; Wang, J. et al. AG(E), 41, 2773. + CH2(CO2Bn)2

c'C6H 1t 02C~

tlo

f O 2c'C6H1z

on

~" 89%

ee = 58%

I.A.7.b.1-6 Zhou, J.; Tang, Y. JACS, 124, 9030; Pirrung, M.C. et al.

JOC, 67, 8374.

Ar,

H

A

O2Et

tP-3"

JPr

?o J- o ~ 0 ~

"

,CO2Et

73-99% ee = 60-93% tPr

CARBON-CARBON BOND FORMING REACTIONS

37

I . A . 7 . b . l - 7 Enders, D. et al. S, 1945; see also: Meyers, A.I. et al. T, 58, 207. NO2 BuLi, THF,-950C , ,

+ ,"-/

ff'~~~"'~NO2 l l

l

R"

i

84-99% ds = 84-99 %

I.A.7.b.l-8 Motoyama, Y. et al. CEJ, 8, 2968; Grossman, R.B. et al.

JOC, 67, 3149.

N OH

+M

Ph-Me

CO2 R

~

OHC

R ee = 69-85%

I.A.7.b.l-9 Shibasaki, M. et al. TL, 43, 9539; Arai, S.; Tsuji, R.; Nishida, A. TL, 43, 9535; Verkade, J.G. et al. JOC, 67, 3555 Ph'~~"CO2tB"

+ ~

Ph

,Cs2C03

.

P h ' ~ , ~ N V CO2tBu

"CO2Me 1 ~ / ~

N'Me(CII,Ar)2 Rl~O'J" 2 ~ N§Me(CH2Ar)2

Ph

~

C O2M e 67-94 % ee = 23-64 %

.I..A.7.b.20reanometallic and Related Rea2ents

I.A.7.b.2-1 Fleming, F.F. et al. JOC, 67, 5953 and OL, 4, 2493. H

CN R3"MgX' tBuMgCI 17,"1

IR2

H( ~ / ~

R1 - R3

....CN

THF,-780C 51-86%

l.A.7.b.2-2 Marek, I. et al. TL, 43, 6009. O

1. ipr-MgBr ............

2. Iz

74%

38

ORGANIC SYNTHESISm2003

I.A.7.b.2-3 Hoveyda, A.H. et al. JACS, 124, 13362, 779; Kim, Y.H. et al. TA, 13, 801; Madsen, U. et al. S, 31; William, A.D.; Kobayashi, Y. JOC, 67, 8771; Rodriguez, A.R.; Spur, B.W. TL, 43, 4575; Braga, A.L. et al. TL, 43, 7329; Harris, J.M.; Padwa, A. OL, 4, 2029; Chan, A.S.C. et al. OL, 4, 3799; Shintani, R.; Fu, G.C. OL, 4, 3699; Krause, N. et al. TL, 43, 7887; Kawanami, Y. et al.T, 58, 8095; Hanzawa, Y.; Taguchi, T. et al. T, 58, 10429; Oi, S.; Inoue, Y. et al. T, 58, 91; see also: Shibata, I.; Baba, A. et al. AG(E), 41, 1389; Yadav, J.S. et al. TL, 43, 9695; Pellissier, H.; Santelli, M. et al. TL, 43, 4339. ~ R 1

R2Zn'Ph'Me'0~ 1 ~ : R

K 42.85%

~ ~ .NHBu I~~"r"-N- ~lr rrh2

0

a n t i : s y n = 13-25:1 ee = 9 4 - 9 7 %

I.A.7.b.2-4 Hayashi, T. et al. OS, 79, 84; Tomioka, K. et al. JACS, 124, 8932; Pucheault, M.; Darses, S.; Genet, J.-P. EJOC, 3552; Genet, J.P. et al. TL, 43, 6155.

~:=

O

PhB(OH)2,Rh(acac)(C2H4,2,(R)-BINAP H20/dioxane, 100~

_~

~:=

O

Vl~ 83% ee =98% I.A.7.b.2-5 Pinheiro, S. et al. TA, 13, 2513; Meyers, A.I. et al. S, 2064; Chiacchio, U.; Romeo, G. et al. TA, 13, 1915; Li, C.-J. et al. CC, 2440; Simpkins, N.S. et al. JOM, 658, 21.

,,,,,..~)n

O ~

R1 R2CuLi Et20, -30~

R*O2C~~_:R1 + R*O2C~'~ R1 R

'R 85-90% dr = 2 . 3 3 - 9 9 : 1

l.A.7.b.2-6 Schneider, C.; Reese, O. CEJ, 8, 2585.

M

THF, -78-+ .40~

Me" v "'OH 41-77% ds = 19:1

CARBON-CARBON BOND FORMING REACTIONS

39

l.A.7.b.2-7 Feringa, B.L. et al. T, 58, 5773; Alexakis, A. et al. JACS, 124, 5262; Waldmann, H. et al., CEJ, 8, 4767; Ohe, T.; Uemura, S. TL, 43, 1269; Rimkus, A.; Sewald, N. OL, 4, 3289; Luchaco-Cullis, C.A.; Hoveyda, A.H. JACS, 124, 8192. JO2 R2Zn,Cu(OTf)z ~JO2

R1

~

r~Me

o~ o/ .M-M, P'-N

R1 100%conversion ee = 48-77%

Pg

l.A.7.b.2-8 Nicolaou, K.C. et al. AG(E), 41, 2107.

~_

/ ~ Bn ~ - " ' , . y ~ . "'', H OSEM ~

.HO~

Ni(cod)2,NaI' ,. DMF, 80~

Br

Bn

H OSEM -"

55% dr = 12:1

l.A.7.b.2-9 van Bergen, M.; Gais, It.-J. JACS, 124, 4321.

?q

7u3 Y

C u " , l ~~

EtzO/THF, -60~

~

.-"

OTBDMS

N..."-NTs

N'-NttTs 80%

,•CsHll .

OTBDMS

l.A.7.b.2-10 Lozanov, M.; Montgomery, J. JACS, 124, 2106.

OH% R

R1

II +.. + R2

TMS-CI, Ni(acac)2, DIBAL . . . . SnBu3

OH

3

RE R 49-69%

40

ORGANIC SYNTHESISm2003

l.A.7.b.2.11 Baldwin, J.E. et al. SL, 820.

I MeO2C..~/-

1. Mg, Br~ THF

3. MeO2CC--CCO e, Tar,-60"C

MeO2C

4. I2, THF, -70"C

I.A.7.b.2-12 Gasco, A. et al. JOM, 650, 77.

~

R-MgX

P(OEt)2

86 %

ur

o,

,P(OEt)2

(~P(OEt)2 THF, -15~

R

~/P(OEt)2 64-92%

I.A.7.b.3.

Other

Coniu~ate v

v

Additions

I.A.7.b.3-1 Paras, N.A.; MacMillan, D.W.C. JACS, 124, 7894.

R2X__~R /:

~,

__ /CHO CH2C!2or CHCI3

R1

p ~-N2cle I k ~ N.,~,Bu

n

~~R2 1 , B1 X'-2t~

CHO

ee = 84-99% 6 5 - 9 7 %

,,,,

I.A.7.b.3-2 Alexakis, A.; Andrey, O. OL, 4, 3611; Enders, D.; Seki, A. SL, 26. NO2 CHCI3 R ~ NO2 % p hR/ -1' - ' / R+ 'Pr

I.A.7.b.3-3 Prunet, J. et al. TL, 43, 7477. Ts

Ph-CHO, tBuOK THF

46-99% syn:anti = 3-19:1 ee = 29-85% Ph R ~ , , ~ , , ~ Ts 60-80% syn:anti = 19:1

CARBON-CARBON BOND FORMING REACTIONS

41

I.A.7.b.3-4 Bandini, M.; Umani-Ronchi, A. et al. S, 1110; Cozzi, P.G.; Umani-Ronchi, A. et al. JOC, 67, 3700; Krawczyk, H.; Sliwinski, M. S, 1351; Yoshida, J. et al. JACS, 124, 30. 02

NO2

R1 InBr3

H20/THF, rt H

H

44-99% l.A.7.b.3-5 Sibi, M.P.; Manyem, S. OL, 4, 2929; Sibi, M.P.; Hasegawa, H. OL, 4, 3347; Sibi, M.P.; Miyabe, H. OL, 4, 3435; Sibi, M.P.; Sausker, J.B. JACS, 124, 984; Sibi. M.P. et al. JACS, 124, 2924. ipr-l, Bu3SnH, Ln(OTf)3, Et3B i P r Q( ~ 'th 02, 4A MS, CH2C!2,-78~ . . . . ,Ph Ph

~

Ph

63%

H

ee = 9 2 %

I.A.7.b.3-6 Roush, W.R. et al. JACS, 124, 2404 and OL, 4, 3157; Krische, M.J. et al. JACS, 124, 2402; Murphy, P.J. et al. TL, 43, 8707; Overman, L.E. et al. OL, 4, 79; see also: Tomioka, K. et al. TL, 43, 4355; Rovis, T. et al. JACS, 124, 10298. . ,CHO PMe3 = ~ ~ . ~ C H ~ ~

R

tAm'OH

R 45-47% 19"1

l.A.7.b.3-7 Renaud, P. et al. AG(E), 41, 4323. /~--/"R

~/O Ph

Bu3SnH,AIBN Ph-Me, ll0~

O

~ R-'-~ 36-67%

l.A.7.b.3-8 Carreno, M.C. et al. CEJ, 8, 208. s

/~OTMS + \\

//

TBAF ca2cl2, rt

X +

X

s

s

56-70%

42

ORGANIC SYNTHESIS--2003

l.A.7.b.3-7 Sato, F. et al. AG(E), 41, 3671; Gansauer, A. et al. AG(E), 41, 3206.

~

~,,Tol iPr-MgCi,Ti(OiPr)4 0 .78- -.:c:,

"~R1

R1 40-70% er = 11.5-19:1

I,A,8, Other Carbon-Carbon Sinele Bond Formin~ Reactions I.A.8-1 Parsons, A.F. et al. SL, 1069; Snider, B.B.; Smith, R.B. T, 58, 25; Ishii, Y. et al. JOC, 67, 970; see also: Davies, H.M.L. et al. JOC, 67, 4165 and TL, 43, 4981. R ~ R I ~~"R2 +u O ~ Mn(OAc)3'Cu(OAc)2~ R I " ,,4 R3 CH2C12,reflux

R2

tr-- XR3 81-97% I.A.8-2 Waldvogel, S.R. et al. A G(E), 41, 2981; Wang, X.; Zhang, Y. TL, 43, 5431; Nishino, T.; Nishiyama, Y.; Sonoda, N. TL, 43, 3689 and JOC, 67, 966; van der Donk, W.A. et al. JOC, 67, 832; Grignon-Dubois, M. et al. JOC, 67, 4696; Csaky, A.G. et al. TA, 13, 753; Hayashi, T. et al. JOC, 67, 3355; see also: Kise, N. et al. JOC, 67, 8305; Hirao, T. et al. CC, 3048. M e ~ R MoCls 1Vie

R CH2C!2,0~ or reflux

@OMe

MeO" .,,/i

MeO/

OMe

X

R

30-76%

I.A.8-3 Gross, P.H. et al. JOG, 67, 7662; Yadav, J.S.; Reddy, B.V.S. S, 511; Cristoph, G.; OL, 4, 2189, 2193. R , ~ TMS-CN,Hg(CN)2,HgBr2 R ( ~ O ' ~ CN R10,'"

THF, rt OR2

R10,,"~ 52-65% ~:[3= 1-20:4:1

CARBON-CARBON BOND FORMING REACTIONS

43

I.A.8-4 Tius, M.A. et al. JACS, 124, 10091; Tius, M.A.; Grimmes, S.; Hoppe, D. et al. AG(E), 41, 1532; Schafer, H.J. et al. TL, 43, 2683.

~ ~ O Ng,, f,

- ~I,"'H + R[ l ~ ~ S

O

= H O ~

g

a

a ~ - "R 1 33-84 % ee = 55-90 %

I.A.8-5 Malacria, M. et al. AG(E), 41, 3284; Uguen, D. et al. TL, 43, 3181; Cohen, T. et al. JACS, 124, 12106; Landais, Y.; Renaud, P. et al. OL, 4, 4257. Me MeO H 1. Ph3SnH, AIBN, Ph-H, A _

" A ~-

"

v

2. KF, KHCO3, H202

H 45%

I.A.8-6 Yamada, S.; Morita, C. JACS, 124, 8184. MeO2C~R 1 ~Re.

~

+ R2x~'Rlll[

CICO2Me .

9

MeO""~OTMS

~

~ R"" MeO2C 56-94% de = 99%

I.A.8-7 Ferraz, H.M.C. et al. JOC, 67, 3518. R~HO l 2 OH

R1 20-71%

Tl(NO2)3

TI(NO2)3

aq a O A c

aq

R1

~

HCIO4

H

R2 ,o

R1 58-75%

44

ORGANIC SYNTHESIS--2003

I.A.8-8 Shinokubo, H.; Oshima, K. et al. OL, 4, 2795. e X +

~ R

(

1

CrMgCi /4

=

X

THF, 0*C

I

67-91%

I.A.8-9 Widenhoefer, R.A. et al. JOC, 67, 2778. ~)~

....

Et3SiH'Bs(C6F5)3' ~ i /fiN-EPh'Me' Ph t 11O~ 3 CP r- ~h

-

)--x

Me

Me

.

82%

Z:E = 26:1

I.A.8-10 Yoshida, M.; Sugimoto, K.; Ihara, M. T, 58, 7839.

! II

TM,

R2 Ar-l, Pd(PPh3)4, Ag2CO3 R1

Ar

Ph-Me, 80~

R

R

20-81%

I.A.8-11 Hoveyda, A. et al. OL, 4, 395. I OTs rac-(ebthi)ZrCl2, Bu-MgC!

_Me

THF, 55~ 14h ip~ 62% syn:anti = 12"1

CARBON-CARBON BOND FORMING REACTIONS

I.B.

Carbon-Carbon

Double

45

Bonds

(see also: I.E. 1) I.B.1.

W i t t i ~ - T v o_e_

Olefination

Reactions

I.B.I-1 Tang, Y. et al. JOC, 67, 3096 and CC, 1384; Huang, Z.-Z.; Tang, Y. JOC, 67, 5320; Kurihara, T. et al. S, 1072; Wang, Y.; West, F.G. S, 99; Ishibashi, H. et al. JOC, 67, 3156; Enders, D.; Voith, M. SL, 29. R-CHO +

B CO2R20=PPh3 or NaHSO3 r,,~. : R1 K2CO3, H20/THF R

/CO2R2 R1

65-99% E:Z = 1.38-99:1

I.B.1-2 Dai, W.-M. et al. TA, 13, 2187; see also: Iguchi, M.; Tamioka, K. OL, 4, 4329.

~

A

+,~ CO2Me sph

KHMDS _ R ~ ~ C O 2 M e THF, -10~

R ~ O

48-76% ee = 28-41%

I.B.1-3 Taylor, R.J.K. et al. SL, 215 and TL, 43, 6185; Runcie, K.A.; Taylor, R.J.K. CC, 974. MnO2, RCH2P+Ph3Br" THF, reflux ..___ssR R1.CH2OH ,. 54-92%

Me

I.B.1-4 Hatanaka, M. et al. S, 739 and SL, 124.5; Tanaka, K. et al. TA, 13, 721,729.

Ph3

Me + M

R O

'B ,i THF, -78~

-

R

M 33-63%

46

ORGANIC SYNTHESISm2003

I.B.1-5 Deslongchamps, P. et al.. JOC, 67, 5437.

BuLl

Me~ .0 /N-"~.__/R THF, -78"C MeO r R~

~) ~,~ (CF3CH20)2~R1 ~/-Me + R-CHO OMe

70-89% E:Z = 7-20:1 I.B.1-6 Huang, X. et al. JOC, 76, 8261 and TL, 43, 6823.

R-CHO +

Nu" Ph3

I+Ph BF4" CH2C!2,rt

u 61-97% Z:E = 5.67-100:1

I.B.1-7 Lievre, C. et al. TL, 43, 1847.

OH

Br2CHP+Ph3Br', Zn ._ dioxane, reflux, lh

HO"

bOH..~ Ph HO" 44-90%

I.B.1-8 Sano, S. et al. CPB, 50, 1300, 706; Sano, S.; Teranishi, R.; Nagao, Y. TL, 43, 9183; Huang, Z.-Z.; Wang, L. SL, 1281, 0 = ~ ~ 1 Sn(OS02CF3)2 M e O 2 ~ ~ / R (CF3CH20)2R,,,/CO2Me + ] CN-Et " Mer "17,1

Me

0-86 % E:Z = 1:32.3-2.7:1

I.B.1-9 Edwards, M.G.; Williams, J.M.J. AG(E), 41, 4740. R2 Cs2CO3,IrCl(cod)2, dppp I~ / R2 R/~ 1 Ph3P~/ ~ / OH+ Ph-Me, 150~ R 14-71% I.B.I-10 Kinoshita, H. et al. BCJ, 75, 2517.

N~ R1.CHO + R..

H

R1 Na2CO3'PBu3'Bu4NBr % R.. CO2Et THF or Ph-Me CO2Et H 25-96% Z:E = 5-99:1

CARBON-CARBON BOND FORMING REACTIONS

47

I . B . I - l l Kojima, S. et al. JOC, 67, 4093; Van Vranken, D.L. et al. JOC, 67, 6711; Rossiter, S. TL, 43, 4671; Lebel, H.; Paquet, V. OL, 4, 1671; Kwan, M.L.; Battiste, M.A. TL, 43, 8765. .COX KHMDS /COX R1.CHO + R3S'r- - / : --THF, -78~ R it' 47-97% Z:E = 1-32.3:1

I.B.2.

Elimination~

I.B.2.a. Eliminations of Alcohols and Derivatives l.B.2.a-1 Fleming, F.F.; Shook, B.C. JOC, 67, 3668; Marcantoni, E. et al. JOC, 67, 9111; Concellon, J.M.; Huerta, M. T, 58, 7775; Yokokawa, F.; Shioiri, T. TL, 43, 8679; Pourjavadi, A.; Marandi, G.B. JCR(S), 378, 552. HOk

R~-

/CN Me.MgCI

R/1 ~'R

R~~_(CN Me-MgBr,MgBr2 R ~ , CN --~ O+ ( " reflux > R 1 THF R" THF, R Li 61-92%

I.B.2.a-2 Uneyama, K.; Welch, J.T. et al. TL, 43. 6099; Kulinkovich, O.G. et al. SL, 443. R ~ F

F

Ph

1. Mg, TMS-CI, THF, 0~ 2. aq HCI

R ~ Ph F 61-73% E:Z = 1:95

I.B.2.a-3 Kruchok, I.S. et al. S, 71.

E t ~

R

CN OTMS

H2SO4 rt

NC~~

R O 44-73%

48

ORGANIC SYNTHESIS--2003

I.B.2.b.

Eliminations

of

Halides

I.B.2.b-1 Mioskowski, C.; Falck, J.R. et al. TL, 43, 959; Taguchi, T. et al. TL, 43, 5845. CrCi2 /---CCi 3 R THF R/"~CI 83-97% I.B.2.c. O t h e r

Elimination~

I.B.2.c-1 Panza, L. et al. T, 58, 4425; Tani, K. et al. SL, 239. OMPM OMPM Et

KHMDS CHO + ~tN~ltN "\N "N" O 2 ~ )12 DME, -55"C Ph

Et

Me

x__~Me}12 E ~

Et

O

52%

E:Z = 4:1

I.B.2.c-2 Cao, X. et al. JCS(P1), 2485 and T, 58, 1301; Ohnishi, Y.; Ichikawa, Y. BMCL, 12, 997. R

O2~/

.....

R

KOH/AI203 " S .R1 CH2Ci2/CBr2CF2 [ [ ~ R1 87-95% E:Z - 1-1.33:1

I.B.2.c-3 Wong, C.-H. et al. TL, 43, 3447; Gautier, A.; Piettre, S.R. et al. TL, 43, 4959.

f,-~

i Ph-Me, A

R 62-87%

XR

I.B.2.c-4 Jacobsen, M.A.; Williard, P.G. JOC, 67, 3915. H

~"'x'~

N" SiR3

BuLi

THF, rt

Li

~"'~" N" SiRa 100% conversion

CARBON-CARBON BOND FORMING REACTIONS

49

I.B.2.c-5 Ranu, B.C. et al. TL, 43, 5993; Reutrakul, V. et al. TL, 43,

2285.

RI%cx3 R

In . DMF, reflux

/ R

X X

60-97%

I.B.2.c-60lsson, R. et al. OL, 4, 4333. R~7

1. MgI2 or Et2ALI i ~ ) THF rt-80~ --+ R1-CHO + R2R3NH 2. tBuOK

R2R3

37-79% E:Z = 1-6:1

I.B.2.c-7 Hodgson, D.M. et al. SL, 310; see also: Florio, S. et al.

JOC, 67, 8351.

Bus

N~

O

R-Li Et20, -78~

B u s H ~ R 44-72%

I,B.3.

Olr

Metatheses

I.B.3-1 Blechert, S. et al. AG(E), 41, 3835; Wakamatsu, H.; Blechert, S. AG(E), 41,794, 2403; Maishal, T.K.; Sarkar, A. SL, 1925; Nolan, S.P. et al. OM, 21,442; De Clercq, B.; Verpoort, F. TL, 43, 9101; Moise, C. et al. JOM, 643-644,231; see also: Nolan, S.P. et al. OM, 21, 671; Akiyama, R.; Kobayashi, S. A G(E), 41, 2602; see also: Fogg, D.E. et al. OM, 21, 3335. "A Self-Generating Highly Active, and Recyclable OlefinMetathesis Catalyst." I.B.3-2 Micalizio, G.C.; Schreiber, S.L. AG(E), 41, 3272, 152; Miyaura, N. et al. SL, 128. 6,70C

50

ORGANIC SYNTHESIS--2003

I.B.3-3 Boulet, S.L.; Paquette, L.A. S, 895; Alexakis, A.; Croset, K. OL, 4, 4147; Neipp, C.E.; Martin, S.F. TL, 43, 1779; Sinay, P. et al. TA, 13, 2553; Ibrahim, Y.A. et al. TL, 43, 6421, 6971; Iqbal, J. et al. TL, 43, 6467, 6473, 6479; Mehta, G.; Umarye, J.D. OL, 4, 1063; van Boom, J.H. et al. JCS(P1), 2370; Mascarenas, J.L. et al. CEJ, 8, 2923; Hong, J.H. et al. JOC, 67, 6837; Shishido, K. et al. TL, 43, 2047; Le Merrer, Y. et al. TL, 43, 245; Bertozzi, C.R. et al. OL, 4, 1359; Burke, S.D. et al. JOC, 67, 8489; Riera, A. et al. JOC, 67, 6896; Perez-Castells, J. et al. TL, 43, 4765; Abell, A.D.; Gardiner, J. OL, 4, 3663; Nakagawa, M. et al. JCS(P1), 959; Ogasawara, M.; Nagano, T.; Hayashi, T. JACS, 124, 9068; Du, Y.; Wiemer, D.F. JOC, 67, 5701; Maier, M.E. et al. JOC, 67, 6260; Toyooka, N.; Okumura, M.; Nemoto, H. JOC, 67, 6078; Diver, S.T. et al. OL, 4, 2051; Louie, J.; Grubbs, R.H. OM, 21, 2153; Chen, G.; Kirschning, A. CEJ, 8, 2717; Blechert, S. et al. JOC, 67, 4325; Kiessling, L.L. et al. OL, 4, 2293; Florent, J.-C. et al. JOC, 67, 4399.

PhCH=Ru(PCy)2CI2.

H

CH2C!2,rt

HO,../[~

O~ --/ ~

97% I.B.3-4 Danishefsky, S.J. et al. TL, 43, 6107 and CC, 2759; Postema, M.H.D.; Piper, J.L. TL, 43, 7095; Langer, P.; Holtz, E. SL, 110; Marciniec, B. et al. OM, 21, 840. R10 OAc

~

Ac

Rq

OA~_c~)

,f-.....fC O2Bn PhCH=Ru(PCy)2CI2

NHFmoc

CH2C12,40~

~"

n OAc "~ /~ (,

C~O2 Bn

~... NHFmoc

66-70% I.B.3-5 Cossy, J. et al. TL, 43, 6715; Borsting, P.; Nielsen, P. CC, 2140.

H2,CH2C!2,reflux

~SiPh3 53.75%

Mes

CARBON-CARBON BOND FORMING REACTIONS

51

I.B.3-6 Hagiwara, H. et al. T, 58, 6651; see also: Hanson, P.R. et al.

~

TL, 43, 917; Slugovc, C. et al. CC, 2572.

PhCH=Ru(PCy)2CI2 = /ff ....

I

cHz=cH2, CH2C!2,rt .

)0-1

H 48-81%

OR

I.B.3-7 Danishefsky, S.J. et al. JOC, 67, 7737; Nicolaou, K.C. et al. CC, 2480; Aggarwal, V.K.; Daly, A.M. CC, 2490.

"~~/'~t

O

" ~ ~ 9CH2C12 =

y

Y/

jr'~ O -

y

I""NilesCr

"OTES

"OTES

55-58%

I.B.3-8 Roy, R. et al. OL, 4, 2723; Grubbs, R.H. et al. AG(E), 41, 4035 and OL, 4, 1939; Chatterjee, A.K.; Grubbs, R.H. A G(E), 41, 3172; Zhang, L.; Herndon, J.W. TL, 43, 4471; Vasbinder, M.M.; Miller, S.J. JOC, 67, 6240. Bn

OBn

~

,

x

.... , L

Bn

re. _,,

OBn

~

/~" R,tr"PCY3

~.~ OBn

~'~ ci ct

20-75 % E:Z = 4-20:1

I.B.3-9 Hoveyda, A.H. et al. JACS, 124, 2868, 4954; Hoveyda, A.H.; Schrock, R.R. et al. AG(E), 41, 589; Me2 Me2 Ph-H,

J

rt

_

9

"

9

~1~,~ Alk V -

.~

"SR,,, ~ Me

*

O

Me

4"SR1

tBu Me

87-99% ee = 66-94 %

52

ORGANIC SYNTHESISm2003

I.B.3-10 Boyer, F.-D.; Hanna, I. TL, 43, 7469.

~O2Me

rr ip

~

Me

CHzCi2, Mes .Ph reflux - r I~ ip

OTiS

~

~ s

~cl cl

93%

I.B.3-11 Grubbs, R.H. et al. AG(E), 41, 3839 and JACS, 124, 3224; Minger, T.L.; Phillips, A.J. TL, 43, 5357; Arjona, O.; A.J.; Plumet, J. et al. JOC, 67, 1380.

Q

Mes .rh

k " "n

69 99%

" "n In/2

MCI C!

I,B,4, Other Carbon-Carbon Double Bond Formin~ Reactions I.B.4-1 Danishefsky, S.J. et al. AG(E), 41, 2!85; Shi, D. et al. JCR(S), 344; Fan, X.; Zhang,~ Y. JCR(S), 439; Yoshimatsu, M.; Timura, Y. JOC, 67, 5678. EtO2C~ " H ~ O 1. MCPBA, CH2C12,0~

2. NaOEt,EtOH,50~

i p f r~4e'~ Me 71%

I.B.4-2 Xu, X.; Zhang, Y. T, 58, 503.

A % O + O==(Arl R2N

Sm, SmI2 ~

Ar2 THF,reflux

ArN~rx R2

r2

0-83% I.B.4-3 Menichetti, S.; Stirling, C.J.M. JCS(P1), 28. TM

$O2Ph + O ~

BuLi THF, -78~

• Ph

1 OTMS 67-86% E:Z = 1.27-49-1

CARBON-CARBON BOND FORMING REACTIONS

53

I.B.4-4 Wang, J.-X. et al. AG(E), 41, 2757. NiCi2(PPh3)2, TMS-CI Ar-CHO + RCH2-ZnX THF

___/R

A/ 54-92%

I.B.4-5 Shi, M.; Xu, B. JOC, 67, 294; see also: Sierra, M.A. et al. CC, 1842. R - - ( ' [ ~ ' A _ P+Ph3' O2,VO (acac)2, K2C0 3 . J X" 18-Cr-6,Ph-Me, 60-70~

R - ~ ~ _ _ R

51-93% Z:E = 1.3-49:1

I.B.4-6 Harmata, M.; Lee, D.R. JACS, 124, 14328.

tBuOj

TFE R

tBu 42-69%

R tBuO''~ ~ C F 3 7-12%

I.B.4-7 Sato, F. et al. CL, 4. Ti(Oipr)4, ipr-MgCI

OH

.500C R1 47-91%

I.B.4-8 Nenajdenko, V.G. et al. JCS(P1), 883. P~= CX4, CuCl ~ X NNH2 R DMSO, rt R X 23-92%

I.B.4-9 Viswanathan, G.S.; Li, C.-J. TL, 43, 1613; Shindo, M. et al.

JACS, 124, 6846. Ph.... .

ln(OTf)3 or GaCI3 R1 + R-CHO ~ PhI CH2CI2

C2-R1 C!

, R" 18-65%

R +

R

0-24%

54

ORGANIC SYNTHESISm2003

I.B.4-10 BaUini, R. et al. S, 681.

R~.._NO2 + ( CO2Me I'DBU'MeCN ..... ,. R~~_.~CO R= ...2cHo2H R CO2Me 2. NaOH, EtOH, reflux 71-95% I.B.4-11 Matsubarg, S. et al. AG(E), 41, 2837. RI~~OH

CH2(ZnI)2

~ _ OH

0-~ 20"C

R1 10-75%

I.B.4-12 Oshima, K. et al. TL, 43, 2399. MDPS,~/MDPS 1. BuLi, THF, .78"C

A C! C!

= MDPS,,,/MDPS i

2. R1CH=C(MgBr)R, CuCN.2LiCi 3. E +, -78~ 0~

i

~.1~/E

55-83% I.B.4-13 Takeda, T. et al. CC, 2218 and TL, 43, 5755.

5

T R

R2

+

4

R3

R5 1. R3CO-Cu 2. TBAF, H20

5 4

4

~

+

R,~ ~:~3 13-80%

R2 R3 4-69%

I.B.4-14 Trost, B.M.; Rudd, M.T. JACS, 124, 4178; Trost, B.M.; Toste, F.D. JACS, 124, 5025; Trost, B.M.; Pinkerton, A.B. JACS, 124, 7376; Trost, B.M. et al. CEJ, 8, 2341; Chatani, N. et al. JACS, 124, 10294; Ikeda, S. et al. JACS, 124, 12060; ~

R Me2CO, rt R1 = ( ...... OH Ru(Cy)(MeCN)3+BF4" ( n .
R

R 2" "-R 1 60-99%

CARBON-CARBON BOND FORMING REACTIONS

55

I.B.4-15 Doyle, M.P.; Yan, M. JOC, 67, 602.

~/CH=N2 A/

Rh2(OAc)4 A / i ' ~ ' ~ ' ~ ' ~ ~ ' A r CH2C!2,0~ A/r'~~~--/~i"Ar 50-65%2.1-49:1

I.B.5. Vinvlations _

I.B.5-1 Chattopadhyay, S.K. et al. TL, 43, 5079; Cai, M.-Z. et al. SC, 32, 3419; Rathore, R. et al. JACS, 124, 14832; Guiso, M. et al. TL, 43, 597; Prashad, M. et al. TL, 43, 8559; Feuerstein, M.; Doucet, H.; Santelli, M. TL, 43, 2191; Desmaele, D. et al. TL, 43, 4107; Reissig, H.-U. et al. EJOC, 3646; Harrowven, D.C. et al. TL, 43, 9327; Hosokawa, T. et al. TL, 43, 9323; Caddick, S.; Kofie, W. TL, 43, 9347. I ~~'~O~

.CO2R1 Pd(OAc)2,P(Tol)3 r

CO2R1

+ ===(NHR TEA, MeCN,reflux-" ~] ~ O ~

HR 87-91%

I.B.5-2 Brown, J.M. et al. AG(E), 43, 169. ~ I X--

B(OH)2 +

/CO2tBu [Ru(p.cymene)Cl2]2 X _ _ ~ Cu(OAc)2,Ph.Me, rt 63-96%

f

co2tBu

I.B.5-3 Oshima, K. et al. JACS, 124, 6514. R-X + ~"'Ar TMS-CH2MgCI,CoCl2(dpph) R~-"....Ar EtzO 67-90% I.B.5-4 Myers, A.G. et al. JACS, 124, 11250; Goosen, L.J.; Paetzold,

J. AG(E), 43, 1237.

d~[ ~ C O 2 H R"-I~ +

/al

Pd(O2CCF3)2, Ag2CO3 DMSO/DMF,120~ "

f~"] ~ R'--t'~ 42-99%

R1

56

ORGANIC SYNTHESISm2003

I.B.5-5 Xu, J.; Burton, D.J. TL, 43, 2877; Burton, D.J. et al. CCC, 67, 1247; Cho, C.-G. et al. TL, 43, 5591; Sherburn, M.S. et al. OL, 4, 1955; Moloney, M.G. et al. SL, 1871.

Bu3Sn~/. Y .Cul,Pd(PPh3)4 ~ [ 1 ~ / L DMF,rt X/.~ ~

X

Y J~[~// 52-73% Z:E= 6.6-49:1

I.B.5-60cchiato, E.G.; Prandi, C. et al. JOC, 67, 7144; Carboni, B. et al. TL, 43, 4935; Ishiyama, T.; Miyaura, N. et al. JACS, 124, 8001; see also: Miller, J.A. TL, 43, 7111.

RO2C.~ R1 R3/~R3

RO2C,,~ Pd(PPh3)2CI2,NaHCO3 R1~ ( ~ ) n THF,500C R~R 3 Tf~ 45-81%

I.B.5-7 Yamaguchi, M. et al. S, 138.

OTMS +

R__~

TMS

O __R ~ ~ H 36-90%

I.B.5-8 Jin, Z. et al. OL, 4, 691; Anikumar, R.; Burton, D.J. TL, 43, 2731.

~ S M e 1.tB_uLi,Et20 ~ Br 2. ZnCI2

SMe Pd(OAc)2,PPh3 Me~~2R1 ZnCI Br R~OR 2 70-91%

I.B.5-9 Denmark, S.E. Yang, S.-M. JACS, 124, 2102.

Me2 Si~ _APC,TBAF ( ~ n

HO 55-72%

CARBON-CARBON BOND FORMING REACTIONS

57

I.B.5-10 Sames, D. et al. JACS, 124, 11856.

~OMe ' ~

[~OMe

ff'B(OH)2

OMe

PdCI2 N~

AcOH

MeO,. ~OMe~.

""Pd ~

Ag20,DMF ~

Me ' / ~

OMe

~--.SMe~

ip 86%

~.~

OMe

I.B.5-11 Fiandanese, V. et al. T, 58, 9547; Duchene, A. et al. TL, 43, 4703; Braga, A.L. et al. TL, 43, 4399. II T M ~ Pd(PPh3)2CI2,Cul T M ~ x I + X TEA,MeCN, rt

R

I

R

61-84% I.B.5-12 Zheng, F.; Negishi, E. OL, 4, 703; Farhat, S.; Marek, I. AG(E), 41, 1410; Oshima, K. et al. OL, 4, 2993. R~ x.-- v Br-- ~

1. HZrCp2CI, THF 2. Pd(PPh3)2CI2, DIBAH + ZnCI2, THF . TMS 3. K2CO3,MeOH

.

~

.

._

~

73-78%

I.B.5-13 Thadani, A.N.; Rawal, V.H. OL, 4, 4317; Lee, P.H. et al.

JOC, 67, 8265.

+ R ~ X

' R1

1. PdBr2(PhCN)2, THF

-"2. RaB(OH)2, PtBu3, Cs2CO3

R1 3

I.B.5-14 Hilt, G.; Luers, S. S, 609; Park, H.; RajanBabu, T.V. JACS, 124, 734; Leitner, W. et al. JACS, 124, 736. CH2C!2, rt

FG 34-99%

58

ORGANIC SYNTHESISm2003

I.B.6.

Formin~

Allene

Reactions

w

I.B.6-1 Satoh, T. et al. T. 58, 2533 and TL, 43, 2043; Fensterbank, L.; Malacria, M. et al. "k ~.Tol Pl!k__/~ O

Et-MgBr

H

H

. . . . . . . .

AcO \ H"~

THF,-78~

10min -

Pd

~-"Ph ee

87% = 48%

Ph

I.B.6-2 Tanaka, T. et al. JOC, 67, 1359; see also: Baird, M.S. et al. T. 58, 1581. R1

Et2Zn, Pd(PPh3)4 THF, rt

Br

~

/

R

"

/

47-90%

I.B.6-3 Ma, S. et al. S, 1643; Uang, B.-J. et al. JOC, 67, 1308. *P~

(HCHO)n' CuBr'ipr2NH -- R.--~"

HO

dioxane, reflux

"

OH 69-79% ee = 8 0 - 9 8 %

I.B.6-4 Fensterbank, L.; Malacria, M. et al. SL, 923. /

<~

Me2Si--~

1. Bu3SnH, AIBN, Ph-H, reflux 2. MeLi 3. CICO2Me

Br

MeO2CO--~ TMS - - /

66 %

Et

I.B.6-5 Lee, P.H. et al. AG(E), 41, 3901. R1

+ Rt

,,~

R2 \R3Br

In, Pd(PPh3)4, LiI .... -'-

D

rtl00O

80-96%

I.B.6-6 Tomioka, K. et al. T, 58, 83. "Synthesis of Allenes by Double H o r n e r - W a d s w o r t h E m m o n s Reaction."

R2

CARBON-CARBON BOND FORMING REACTIONS

59

I.B.6-7 Mann, A. et al. TL, 43, 1453.

_~HCO2R

/TMS BF3.Et20 :

R-CHO + NH2-Cbz +

MeCN

63-82% I.B.6-8 Konno, T. et al. CCC, 67, 1421. MsO) --., R1 R-ZnCI,Pd(PPh3)4 Rf

R1

Rf 0-89%

I.C, C a r b o n - C a r b o n

Triole _

R

Bonds

I.C-1 Brisbois, R.G.; Grieco, P.A. et al. OL,4, 3199; Eberhard, M.R. et al. CC, 818; Molander, G.A. et al. JOC, 67, 8416; Najera, C. et al. TL, 43, 9365; Blum, J. et al. JOC, 67, 6287; Gottardo, C.; Aguirre, A. TL, 43, 7091; Failer, J.W.; Kultysheu, R.G. OM, 21, 5911; Leung, M. JOC, 67, 1501; Yang, C.; Nolan, S.P. OM, 21, 1020; Panek, J.S. et al. JOC, 67, 6812; Halbes, U.; Pale, P. TL, 43, 2039; Wada, A. et al. SL, 1061; Tanmer, G.K.; Tam, W. S, 1675; Yamashita, Y. et al. JOC, 67, 7813; Faller, J.W.; Crabtree, R.H. et al. OM, 21, 700. 1. CuI, Pd(PPh3)2CI2 R/~~-- I + TMS' TEA' Ph'H' rt ~ RSVP-~ "--" ~ / x . 2. DBU,H20, rt R1 ~_~~R

1

61-90%

I.C-2 Meffre, P. et al. T, 58, 5159. Ig'(~N/~HocO +

N3+ ~ ~P(OMe)2 O" -Me

K2CO3 CHCi3/MeOH,0-10~

NHAc

l~..f_~y~/O~N / \ Boc 78%

I.C-3 Zard, S.Z. et al. SL, 1257.

a3 -" Rl k 9 2. NaNO2,FeSO4,H20/AcOH R2

, a

R1 ..~

R 31-75%

60

ORGANIC SYNTHESISm2003

I.C-4 Hlavaty, J. et al. JCS(P1), 705. ( )2 \ l'tBuOK'THF"78*C ) 3T/ ,\ r ' , I / CI" C l 2. I2, THF,-40"C 64% I.C-5 Shuto, S. et al. AG(E), 41, 4748.

R ~/Io1 R2

R1

1. Et3B, Ph-Me, rt

SiMe2 2. TBAF, Ph-Me, rt

R2

36-88%

I.C-6 Thadani, A.N.; Rawal, V.H. OL, 4, 4321; Abraham, E.; Suffert, J.

SL, 328.

1. CH2=CHCH2Br, PdBr2(PhCN)2 R.... "--- R 1 " ~ 2. R2C-CH, PtBu3, Cul, iprzNH

R R1 ~"~

J

73-87%

R2

I.C-7 Hsung, R.P. et al. OL, 4, 2417. Me-'-( Ph o = ~ N - ~ '% R

tBuOK THF, rt -~

M e ' - ( Ph O==(N ---- Me R 50-83 %

I.C-8 Boutillier, P.; Zard, S.Z. CC, 1304. ~CO2E~t C_~ EtO2 R S--~S R ...... 9 R Alkynyl Radical Equivalent

Et R ~. \\ : S Propargyl Radical Equivalent /

,

1

1

I.C-9 Grela, K.; Ignatowska, J. OL, 4, 3747. ''"

Mo(CO)6, F-Ph-2-OH Ph-CI, reflux

I 79%

CARBON-CARBON BOND FORMING REACTIONS

61

I.C-10 Vallee, Y. et al. OL, 4, 1463. R1 _

R

R1

+

/O

~R

2

Et2Zn

R----

Ph-Me,rt

(

,N-OH R2 42-99%

I.C-11 Otera, J. et al. CEJ, 8, 2000, 2005. '~SO2Ph 1. O=PCI(OEt)3, LHMDS, THF = @ "CHO

2. LDA, -78~ 61%

I.C-12 Zhang, X. et al. JOC, 67, 1969. Pd(PPh3)2Ci2, CuI, iPr2NEt R THF, rt

R '

R 47-99%

I.C-13 Aitken, R.A. et al. JCS(P1), 533. R2

R102C,.s ~ O

FVP _--

EtO2C "-PR3

P~

R102C-NH

I.C-14 Yoshimatsu, M. et al. JCS(P1), 1413. R

:

.... SO2Ar

A

=

R ~

,--7, CO2Et 10-49%

.... .

/SO2Ar \\ ~\ ----" IIR / A~: 24-99%

I.C-15 Hidai, H.; Uemura, S. et al. JACS, 124, 11847. R~X~

+ HO~R,1 '

' Ru2CI2Cp2(SMe)2' 60D ~CE,lhNH4BF4~ R ~ ~ R I / / 51-94%

62

I.D.

ORGANIC SYNTHESISn2003

Cvclovrovanations _

_

I.D.I. Carbene or Carbenoid Additions to a Multiple B o n d

I.D.I-1 Charette, A.B. et al. JACS, 124, 12168; Charette, A.B.; Wilb, N. SL, 176; see also: Charette, A.B.; Lacasse, M.-C. OL, 4, 3351; Mori, A. etal. TA, 13, 13.

R1 ~ ~ R 2 OH Zn(CH21)2'4~kMS' CH2Ci2 RI~R2 OH R Pl~,,Ph R q~rO~tO"--~'l't't~Et~r', 56-90% ,prff~o...,~6 Et

er = 3-32.3:1

PhI "Ph

I.D.1-2 Charette, A.B. et al. JACS, 124, 386.

Bn~OBn

1. Et2Zn,CHI3, CH2C!2 t ~ OBn - Bn 2. E+ 64-94%

I.D.1-3 Concellon, J.M. et al. AG(E), 41, 1917.

R~ _/ ~-NR2 R2~\R 3

Sm, CH212

~--NR2 R2 V "R3 66-85%

I.D.1-4 Barluenga, J. et al. OL, 4, 4273; Harvey, D.F. et al. JOC, 67, 8675; Hossain, M.M. et al. OM, 21, 2596.

: R

+

~ :R2 = . A .'NR2 (CO)SC--cO2R1 Ph-Me,ll0~ R2 CO2R1 30-70%

I.D.1-5 Perez-Prieto, J.; Lahuerta, P. et al. OM, 21, 1667; Doyle, M.P. et al. OM, 21, 1747; Nagashima, T.; Davies, H.M.L. OL, 21, 1989; see also: Woo, L.K. et al. OM, 21, 4490; see also: Zhang, X. et al. TL, 43, 3075. "Chirai Dirhodium(ll) Catalysts with ortho.methylated Arylphosphine Ligands: Synthesis and Application to the Enantioselective Cyclopropanation of a-Diazo Ketones."

CARBON-CARBON BOND FORMING REACTIONS

63

I.D.1-6 Srikrishna, A.; Anebouselvy, K. TL, 43, 2769; Taber, D.F. et al. JACS, 124, 13120; see also: Marko, I.E. et al. TL, 43, 2317. hv

""W""

N2

c-C6H12preflux, 5h

:

O

." 56%

I . D . 1 - 7 0 h e , K.; Uemura, S. et al. JACS, 124, 5260. h

_It'^ I..

O + fR

Cr(CO)s(THF),. f'~"v ~ R

40-99% cis:trans = 1:1-100

I.D.1-8 Xu, W.; Chen, Q.-Y. JOC, 67, 9421. R ---

I

TMSO2CCF2SO2F,NaF

FR~

diglyme, A

I 69-82%

I.D,2, Othr

Cyclovroaanations

I.D.2-1 Tang, Y. et al. JACS, 124, 2432; Patzel, M. et al. T, 58, 10485; Ma, Y. et al. OPP, 34, 194.

~.Me

WG

TMS EWG

OH

+ R"

tBuO K

THF, .780C

R

20-85% TMS

ee = 9:~-99%

I.D.2-2 Takeda, T. et al. TL, 43, 5641.

/SPh SPh

+

Ti(Cp)2[P(OEt)a]2 Rr"

V--RI

27-77%

64

ORGANIC SYNTHESIS--2003

I.D.2-3 Villar, H.; Guibe, F. et al. TL, 43, 9517; Stevens, C.V. et al. SL, 1089; see also: Takeda, T. et al. CL, 290. ~ C O 2 B n R

R R

SmIz, ,,,.. HR10 ~ tBuOHfrHF

CO2Bn

R R 60-90%

I.D.2-4 Yang, D. et al. OL, 4, 3271; Barluenga, J. et al. OL, 4, 2719. 60-90%

{

CO2Me 12,Mg(CIO4)2,TEA ( f ' ~ ~ ~ R1 CH2C!2 ~

~

R2

R

R,~

34-92%

I.D.2-5 Cha, J.K. et al. AG(E), 41, 2160; Bertus, P.; Szymoniak, J. JOC, 67, 3965; de Meijere, A. et al. SL, 879. i RICO2R2'Ti(OiPr)4' c'CSH9MgCl [ ~ ~ O R THF, rt H

H R

42-68% dr - 3.5-12.2:1 I.D.2-6 Barluenga, J. et al. OL, 4, 2225. 2y.. R

R1

3 Br

R

~ ~ 2 R .---

tBu-Li, (-)-sparteine ~ R - y ~ " - . !

O~~R1 R

Ph-Me,-78-, 20~

R 57-82% ee = 81-86%

I.D.2-7 Florio, S. et al. JOC, 67, 759.

"O

THF/Ph-Me,-98~

~N,,) %

CARBON-CARBON BOND FORMING REACTIONS

65

I.D.2-8 Kirwin, S.K.; et al. OL, 4, 4543. H ( 'NN --"

Ph + O

H

.... neat, 100*C Ph 28%

I.D.2-9 Marek, I. et al. SL, 423; Kimber, M.C.; Taylor, D.K. JOC, 67, 3142. R1 I ~ ~ RI-Li, !-)-sparteine R ~ ~ /O~O /\

hex, .IO*C

oyez,

45-70% ee = 50-83%

I.D.2-10 De Kimpe, N. et al. TL, 43, 599. NaBH4

C! MeOH,0~ 2h

R C! 92-99%

I.D.2-11 Alexakis, A.; March, S. JOC, 67, 8753. f~

Jon, _...o.

1. R2Zn, CuX, fig., CH2CI2, -300C T M S ~ . . ~ 2. TMS-OTf 3. CH212

~

R 91-97% de = 60-84% ee = 89-98 %

I.D.2-12 Fensterbank, L.; Malacria, M.; Marco-Contelles, J. et al.

AG(E), 41, 2132.

,...OAc

H PtC!2

Ac

Ph-Me, rt "'J H 66%

66

ORGANIC SYNTHESISm2003

I.D.2-13 Oshima, K. et al. BCJ, 75, 841. ~G

a '~-'2 "- +

X~R.

1

Y

BEt~'O2 : 0-79%

(also with indium reagents)

I.D.2-14 Diez, D. et al. SL, 355; Shuto, S. et al. JOC, 67, 1669. TI-IP ~OTI-I[P I~SO2Ph LDA = THF, -78"C ~so2eh 94% 7:3 I.E. Thermal and Photochemical Reactions I.E.1. Cvcloaddition~ I.E.I-1 Schmalz, H.-G. et al. AG(E), 41, 1524; Fleming, J.; Dolphin, D. TL, 43, 7281; see also: Khlebnikov, A.F. et al. JCS(P1), 1628. ~TBS ghz OAc,4

MeO-Me~O v ~ -

M

TBS

TMS Ph-H,reflux MeO MeOX[ TMS

O~,,~N2

i\O 62% dr = 14:1

I:E.1-2 Lallemand, J.-Y. et al. EJOC, 503. H

Me

1. neat, 80oc, 16h

+ II tt'CO2Me 2. Ph-H, rt, 4h ~_~

0 tlC/'--~ OBn

~,.

OBn

u,"~ Me_

~ .~

,r~ R

( CO2Me 33-50%

CARBON-CARBON BOND FORMING REACTIONS

67

I.E.1-3 Shen, Q.; Hammond, G.B. JACS, 124, 6534; Ghosez, L. et al. CEJ, 8, 3411; Lu, X. et al. JOC, 67, 8901. TIPS ~

F

Mo(CO)6 DMSO/Ph-Me, IO0*C R

72-92%

R

LE.1-4 Dulcere, J.-P. et al. SL, 1883; Gomaa, M.A.-M. JCS(P1), 341; see also: Taguchi, T. et al. JOC, 67, 922. o,

~R ~R

, + II

02

CO2Me Triton B ~ THF CO2Me

R1,.... M

2Me 47-80%

I.E.1-5 Itoh, K. et al. JACS, 124, 6844. / \

X

_i~ R

I~ ~ EtO2

RuCp(cod)CI ' COzEt DCE,90~

O

EtO2C "CO2Et 46-75% I.E.1-6 Corey, E.J. et al. JACS, 124, 3808, 9992; Roush, W.R. et al. OL, 4, 1543; Rawal, V.H. et al. JACS, 124, 5950 and OL, 4, 1163; Carmona, D. et al. OM, 21, 5100; Liao, C.-C. et al. JOC, 67, 6493, 8157. Me CHO t ~ ~ / p ~,HO ~ + I~ CH2CI2"'95~ ~ e

<X..r~. B;o Tin- H r oi

97% exo:endo = 10:1 ee = 96%

I.E.1-7 de Meijere, A. et al. CEJ, 8, 2350.

R"" R" 35-59%

R1

68

ORGANIC SYNTHESIS--2003

I.E.1-8 Northrup, A.B.; MacMillan, D.W.C. JACS, 124, 2458; Tanaka, F.; Barbas, C.F., III et al. TL, 43, 3817. ~[~ +

EtOH, HCIO4, -30"C Et

O

Me

-

n,CJ~Nx~o I~

Me

Et

X

O

78-92%

endo:exo - 100:1 ee = 85-98 %

I.E.1-9 Nakano, H. et al. JOC, 67, 5011; van der Eycken, J. et al. TA, 13, 1673; Kiesman, W.F.; Petter, R.C. TA, 13, 957; Lakner, F.J.; Negrete, G.R. SL, 643; Baldovini, N.; Solladie, G. TA, 13, 885; Palomo, C. et al. JACS, 124, 10288; Kita, Y. et al. CEJ, 8, 4255; Takadoi, M. et al. BMCL, 12, 3271; Harwood, L.M. et al. EJOC, 3589; Kraus, G.A.; Cui, W. JOC, 67, 9475; Haufe, G. et al. JOC, 67, 4715; Dhimane, H.; Lhommet, G. et al. TL, 43, 1645; Dias, L.C. et al. SL, 100; Jung, M.E.; Davidov, P. AG(E), 41, 4125; Piettre, S.R. et al. TL, 43, 4963; Mancini, P. et al. TL, 43, 4601; Ohkata, K. et al. CC, 2096; Kende, A.S. et al. TL, 43, 5237; see also: Stevenson, P.J. et al. JCS(P1), 69; Spyroudis, S.; Xanthopoulou, N. JOC, 67, 4612; S ingh, V. et al. CC, 2050.

0 H

PAr 2

30-92 % endo:exo = 3-24:1 ee = 16.93 %

I.E.1-10 Mural, A. et al. SL, 399, 403. ~

Cbz

e6t~

(-)-siam.Cu(SbF

Cbz_ 89%

exo:endo = 15.7:1

I . E . I - l l Diaz-Ortiz, A. et al. SL, 2037.

["N~ "CHBr2 +

DMF"90~ -~ R

R 38-43 %

CARBON-CARBON BOND FORMING REACTIONS

69

I.E.l-12 Gonzalez-Gomez, J.C.; Uriarte, E. SL, 2095; Uriarte, E. et al. S, 43, 475

~~O~

OR

N~ CO2Me N

TsOH dioxane,reflux

N~ N

50-75% CO2Me

I.E.l-13 Sarkar, T.K. et al. TL, 43, 1341; Ruano, J.L.G.; Ramos, J.H.R. et al. JOC, 67, 2919. O~

C!

Ph

~CO2Me +

CI

!"C02Me

(C4F7CO)20, TsOH C Ph.Me, reflux, lh

CO2Me /N~~~CO2M C! Ar 33-40% I

Ar

e

I

I.E.I-14 Hilt, G. et al. SL, 1081; ; Hilt, G.; Smolka, K.I. S, 686; Tanaka, K.; Fu, G.C. OL, 4,933; Nair, V. et al. JOC, 67, 7533; Herndon, J.W. et al. OL, 4, 2121; Aumann, R. et al. CEJ, 8, 910.

R1

OR2

CH2C!2

R

43-98%

O

I.E.l-15 Yadav, J.S. et al. SL, 993; van der Eycken, E.; Kappe, C.O. et al. JOC, 67, 7904.

LiCIO4

Et20

a

R'

75-90% I.E.l-16 Nishiyama, Y.; Sonoda, N. et al. TL, 43, 4911; Fujita, M.; Okuyama, T. et al. CL, 908.

x
C!

,ai2.x<

THF, rt

29-48%

70

ORGANIC SYNTHESISm2003

I.E.l-17 Cho, C.-G. et al. JOC, 67, 290; Liao, C.-C. et al. OL, 4, 2477; Haider, N.; Stotelo, E. CPB, 50, 1479; Chung, W.-S. et al JOC, 67, 9267. Ph-Me of CH2C!2, 100*C . -

+

R1

R

Br

69-94% I.E.1-18 Szeimies, G. et al. CEJ, 8, 4506. h Br %

B

NaHMDS

CHBr2 +

THF,-15"C -* rt Ph

Ph 44%

I.E.1-19 Davies, H.M.L.; Hodges, L.M. JOC, 67, 5683. CO2Ph ~O2Me CO2Ph (~.~__/CO2Me N2 [ + ~ Rh2(s'TBSP)4~ / ~ [ ~ L ph

Ph-Me, rt

p/

68% ee = 82% I.E.1-20 Dimauro, E.F.; Kozlowski, M.C. JCS(P1), 439; Shibata, T. SL, 1681. M TMS

,

'\ /o

Ni(cod)~THF -

~

Me"" n2

TMS 4-92% conversion

I.E.1-21 Bodwell, G.J.; Li, J. OL, 4, 127.

N

Ph'NMe2,A ~

90%

CARBON-CARBON BOND FORMING REACTIONS

71

I.E.1-22 Fearnley, S.P.; Market, E. CC, 438. O .

.

.

.

.

O

.

O

Ph-CI2, 180"C

H 81%

~:~ = 4:1 I.E.1-23 De Clecq, P.J. et al. EJOC, 1051 and OL, 4, 1579; Taguchi, T. et al. OL, 4, 4619; Roush, W.R. et al. H, 58, 259; Sato, F. et al. TL, 43, 285; Suzuki, T.; Nakada, M. TL, 3263; Miyashita, M. et al. TL, 43, 1705; Maier, M.E. et al. JOC, 67, 2474; Clive, D.L.J. Fletcher, S.P. CC, 1940; see also: Takasu, K.; Mizutani, S.; Ihara, M. JOC, 67, 2881. Me2AIC!

~

%

CH2CI2,.250C ~ ~

' O]

86%

I.E.1-24 Padwa, A. et al. OL, 4, 4643.

N~

Ph-Me, 200 ~

Ac

Ac H II O 74%

I.E.1-25 Nemoto, H. et al. T, 58, 6097; Maurin, P.; Ibrahim-Ouali, M.; Santelli, M. EJOC, 151 N

N Me

Ph-CI2, reflux 75% H

72

ORGANIC SYNTHESIS--2003

I.E.1-26 Padwa, A. et al. JOC, 67, 3412.

SMe

1~ ,,SMe O Ph-Me, A 60-99%

I.E.1-27 Theodorakis, E.A. et al. OL, 4, 909.

Me

CO2H 1. Pd(OAc)4, CH2C!2, rt OMe

Me

2. Ph.H, 80~ 2h

OMe o

82% I.E.1-28 Wood, J.L. et al. OL, 4, 493.

~

O

CO2H BTIB ~ H MeCN

O

(other examples with intermolecular Diels-Adler) I.E.1-29 Mathey, F. et al. JOC, 67, 5422.

R3

/~__.._/ ~ X~

._ 3%

R2 ~

R2 ~-

R1

R "R 1

30-85%

~

I.E.1-30 Maier, M.E. et al. SL, 1097.

~ .O OH

OMEM

MEM~ OH~ .. . . . .

Ph-Me, reflux

,,OH )n

52-56%

CARBON-CARBON BOND FORMING REACTIONS

73

I.E.1-31 A. VoUe, J.-N.; Schlosser, M. EJOC, 1490; B. Yoshimatsu, M. et al. CPB, 50, 1520; C. Yuste, F.; Garcia Ruano, J.L. et al. T, 58, 2613; D. Fukuzawa, S. et al. OL, 4, 707

TE~O~2t2~ ~ ~ 2 E t C

F3~OEt A PhSe

Dienophile

/Ph B

H

0

~

Diels-Aider Dienes

OH

Se(OTf)3 Diels-Alder Catalyst

Asymmetric

I.E.1-32 Failer, T.W. et al. OM, 21, 1662; Rispens, T.; Engberts, J.B.F.N. JOC, 67, 7369. "Application of the Chiral Poisoning Strategy" Enentioselective Diels-Alder Catalysis with a Racemic Ru/BINAP-Monoxide Lewis Acid." I.E.1-33 Takeda, K. et al. OL, 4, 1031; Molander, G.A.; Jefferey, S.C. TL, 43, 359. ~TBDMS n/

+

I K

~'~

1.-80~ ~ rt TBSO~ 2. Davis' oxazolidine 3. Pb(OAc)4, Ph-H/MeOH 1

R 45-84 %

I.E.1-34 Ma, B.; Snyder, J.K. OM, 21, 4688. RR ' I V",~

1

CoI2,dppe, Zn, ZnI2

R2

IP,

~R2

CH2C!2,rt 59-99%

74

ORGANIC SYNTHESIS--2003

I.E.1-35 Mascarenas, J.L. et al. OL, 4, 3091, 3683; Ohmori, N. JCS(P1), 755; Tanino, K.; Miyashita, M. et al. OL, 4, 2217. O

~ +

~0 ~

CH2cI2T~,~C-~rt= ~ , ~ O ~H

OAc

91%

I.E.1-36 Wender, P.A. et al. JACS, 124, 2876. ~... OMe + R

CO, [Rh(CO)2CI]2 -~ H3O+,dioxane,60"C

R1 48-97%

I.E.1-37 Hong, B.-C. et al. OL, 4, 2249; Kundig, E.P. et al. S, 2053. e2

o

Ph-H,rt

)fx

O 65-87%

I.E.1-38 Pearson, W.H. et al. OL, 4, 3099. Bu3S~ _(,~._.~NH BuLi

n~'~OMe

MeO

28-32%

I.E.1-39 Tung, C.-H. et al. TL, 43, 19. FO2Me

CO2Me _-- ~

R

)---.R1 R

60-99%

CARBON-CARBON BOND FORMING REACTIONS

75

I.E.2. Other Thermal Reactions I.E.2-1 Tanaka, K.; Fu, G.C. et al. AG(E), 41, 1607. R2

Ph-OH, [Rh(dppe)12(BF4)2

= PhO2C~ R2

DCE, 80"C

R1

~ R R1 65-95%

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

Reactions

I.E.3-1 Bach, T. et al. JACS, 124, 7982; Bach, T.; Spiegel, A. EJOC, 645; Pete, J.-P.; Piva, O. et al. JOC, 67, 1061; Cominos, D.L. et al. OL, 4, 1611; see also: Booker-Milburn, K.L. et al., OL, 4, 1487. ~.,,H

N H

77-87% ee = 90-91%

I.E.3-2 Ishar, M.P.S. et al. JOC, 67, 2234. l'lv -" ~ aq MeOH

O

SiO2 o

H Ar 60-80%

Ar

I.E.3-3 Iwasawa, N. et al. OL, 4, 2569. TI

I

hv

W(CO)~, DABCO ,

H20/Ph-Me, rt EtO2C CO2Et

EtO2C

O Et 2

69-80%

76

ORGANIC SYNTHESIS--2003

I.E.3-4 Parsons, A.F. et al. TL, 43, 2535.

hv ClaC-~Br BrCCI3,nrMn(CO)s NaOH,BTAC,H20 = EtOzC CO2Et EtO2C CO2Et 99% 10:1 (similarlyfor tetrahydrofuransandpyrrolidines) ~'[~.~

I.E.3-5 Zhang, X.; Schultz, A.G. TL, 43, 3239.

PhO~

PhO2S

~Me 65%

I.E.3-6 Fleming, S.A. et al. JHC, 38, 1341

~'~~

iMe2

IW c.C6H12 ~

5 ~ iMe2 q

H

52% I.E.3-7 Piva, O. et al. S, 427.

CL.

Me2NCH2CH2OH CH2C!2,-40~ Et

Et

CI,. 62% de =83%

I.E.3-8 Butenschon, H. et al. EJOC, 2385.

O0

CO2Me [~CO2Me Ilv =- ~ , , MeO2C" Ph-H,rt, 5h ~O'CO2Me +

62%

CARBON-CARBON BOND FORMING REACTIONS

I.E.3-9 Rossi, R.A. et al. JOC, 67, 8500.

~ ~ f

77

~ t-'-Nuc

Iw, Nuc-H _ NH3 (L)

60-98% I.E.3-10 Park, B.S. et al. TL, 43, 4249. e

hv

Ph

.. (

MeOH

Ph

.~-~"OH 99%

I.E.3-11 Skalski, B. et al. TL, 43, 5127; see also: Quintero, L.; Clivio, P. et al. CC, 2550. "Photocycloaddtion of 5-Bromouraeil to Uracil in a Dinucleotide Model Compound." I.E.3-12 Fang, J.-M. et al. JOC, 67, 5208. "Synthesis of Polysubstituted Benzothiophenes and SulfurContaining Polycyclic Aromatic Compounds via Samarium Diiodide Promoted Three-Component Coupling Reactions of Thiophene-2-carboxylate." I,F, Argmatic Substitution~ Fgrmine a New Carbon-Carbon Bond I,F.1. Friedel-Craft~ Ty0f Aromatic Substitution Reactions I.F.I-1 Wang, T. et al. JOC, 67, 6226; Nagarajan, R.; Perumal, P.T. T, 58, 1229; Yadav, J.S. et al. TL, 43, 8133; Barrett, A.G.M. et al. SL, 1653; Aki, S. et al. BMCL, 12, 2317; Plazuk, D.; Zakrzewski, J. JOC, 67, 8672; Kaur, J.; Kozhevnikov, I.V. CC, 2508.

R ~ N

H

R-COCI,AICI3 CH2C!2, rt

H

35-94%

78

ORGANIC SYNTHESISm2003

I.F.1-2 Anderson, K.W.; Tepe, J.J. T, 58, 8475 and OL, 4, 459; Isobe, M. et al. S, 1658; Tsuboi, S. et al. SL, 899; Kraus, G.A. et al. TL, 43, 7077. R ~

+ C~"-~ R1

DCE, 0*C-* rt

NHR1 65-98%

I.F.1-3 Ge, C.-S.; Chen, Y.-J.; Wang, D. SL, 37; Sakai, N.; Hamajima, T.; Kanakahara, T. TL, 43, 4821. H + ~H ~HTs ~HTs

, TiCI4

R3 HOJ~~CO2 R* CH2CI2,rt R"

~ C O 2 R , Rb/~~R

3

R" 60-85% de -- 99 %

I.F.1-4 Pushechnikov, A.O. et al. SL, 1140; Wright, D.L. et al. OL, 4, 1997; Klumpp, D.A.: et al. JOC, 67, 5028; Shiina, I. et al. TL, 43, 6395; Cozzi, P.G.; Umani-R0nchi, A. et al. JOC, 67, 5386. O

R

R1

R2

NH2

I2 EtOH, rt-40~ 54-92%

I.F.I-5 Gibe, R; Kerr, M.A. JOC, 67, 6247. R~~~N

R2 N2C(CO2Me2)2,Rh2(OAc)4 R ~ C O 2 M e ~ 'CH2CI2,r t --- I / ~ N ~ - ' R 2 R1 R1 31-96%

I.F.1-6 Yamaguchi, M. et al. JACS, 124, 8528. x,~ GaCI3 X . r ~ / + CI- ~ - S i E t 3 ..... ----Ph-CI, 120"C \ OH OH

SiEt3 68.90%

CARBON-CARBON BOND FORMING REACTIONS

79

I.F.I-7 Jun, C.-H. et al. CEJ, 8, 485.

Me

+ ~"R

Rh(PPh3)3CI Ph.Me, 150"C

R

41-97% I.F.1-8 Chatani, N. et al. JOC, 67, 7557. ~ N

CO, CH2=CH2, Ru3(CO)I2 DMF, 160~

R

27-65% R

I.F.1-9 Ma, D. et al. TA, 13, 961; Banwell, M.G.; Smith, J.A. JCS(P1), 2613; Piras, P.P. et al. SL, 796; Ila, H.; Junjappa, H. et al. JOC, 67, 4916. , MeO2CHI~.,,~CO2M e M e ~ .," O2Me 1"

"2. AiCl3, CH2CI2 --'- R " - : ~ [ 92-93%

[~O

I.F.I-10 Branchaud, B.P.; Blanchette, H.S. TL, 43, 351; Casey, M. et al. SL, 1404; Nagumo, S.; Kawahara, N. et al. TL, 43, 2223; Ma. S.; Zhang, J. TL, 43, 3435. BF3.Et20 w

OH

CH2C12

"'SPh 63% ee = 75%

SPh

I . F . I - l l Allin, S.M. et al. JOC, 67, 9464 and TL, 43, 3661. TiCI4 CH2C12,.78~

M e - - O H

Me

%O

O 98% dr = 10"1

80

ORGANIC SYNTHESIS--2003

I . F . l - 1 2 Dufresne, C. et al. TA, 13, 1965.

i~

,Me

Ph

EtCO2H Ph.Me, reflux

"

Me

75% I.F.2. Couolin~ Reactions to Form an Aromatic CarbonAro~natic Carbon Bond

I.F.2-1 Stanforth, S.P. et al. JCS(P1), 581; Sotelo, E.; Ravina, E. SL, 223; Samat, A. et al. S, 213; Lukashev, N.V. et al. TL, 43, 7267; Zhang, J. et al. OL, 4, 4559.

R~BrK2CO3 ~__/N \

R~Br DME, reflux:

Arl-B(OH)~Pd(PPh3)4R(~ ~~ 'A~r K2CO:~DME,reflux~

Ar 57-96%

I

1

Ar 43-87%

I.F.2-2 Falck, J.R. et al. TL, 43, 8149; Jung, K.W. et al. TL, 43, 7899; see also: Zheng, X.; Zhang, Y. JCR(S), 562; Navarro, M. et al. JOC, 67, 1838; Takemoto, M. et al. TL, 43, 8499; Barhate, N.B.; Chen, C.-T. OL, 4, 2529; Uang, B.-J. et al. CC, 980; Kita, T. et al. TL, 43, 9241; Waldvogel, S.R. SL, 622; Tanaka, H. et al. SL, 637; Vlad, G.; Horvath, I.T. JOC, 67, 6550; Pomerantz, M.; Amarasekara, A.S.; Dias, H.V.R. JOC, 67, 6931.

R-B(OH)2

Ag20, CrCI2

= R.R 23-95%

I.F.2-3 Yamamoto, H. et al. JACS, 124, 5365. ~t

R

X = O, NH

brucine, MS R1 Ph-Me Pb(OAc)3

~ R 1 H2N,,.r R R

14-99% when X = NH

~ R H or

R1R 55-99% ee = 20.93% when X = O

1 R

CARBON-CARBON BOND FORMING REACTIONS

81

I.F.2-4 Cho, C.-G. et al. TL, 43, 9015, 5779; Michl, J. et al. JOC, 67, 443; Dietrich-Buchecker, C. et al. SL, 271; Bach, T.; Heuser, S. JOC, 67, 5789; Frey, J.; Bond, A.D.; Holmes, A.B. CC, 2424; HeUer, M.; Schubert, U.S. JOC, 67, 8269; Alvarez, M. et al. JCS(P1), 471; Fort, Y. et al. JOC, 67, 238; Bedford, R.B. et al. CC, 2608; Fu, G.C. et al. JACS, 124, 6343; Vaquero, J.J. et al. SL, 1904; Doucet, H.; Santelli, M. et al. TL, 43, 5625; Caminade, A.-M.; Majoral, J.-P. et al. OM, 21, 4680; Vedso, P. et al. JCS(P1), 428.

ri ~ / B B

r

+ Ar-SnBu3

Pd(PPh3)4,CuI Ph-Me, 100~

]~/Ar Br 51-80%

I.F.2-5 Queguiner, G. et al. SL, 1008; Mongin, F. et al. JOC, 67, 8991; Li, G.Y.; Marshall, W.J. OM, 4, 590; Fursmer, A.; Leitner, A. AG(E), 41, 609; Furstner, A. et al. JACS, 124, 13856; Belier, M. et al. AG(E), 41, 4056.

~MgCl

+ HetAr-X

Ni(acac)2, dppe THF

~HetAr

34-76% I . F . 2 - 6 0 s h i m a , K. et al. OL, 4, 3165 and SL, 1137.

I ~ Pd2(dba)3.CHCi~(2-furyl)3P GeAr + Arl"X ~ Ar'Arl L~3 TBAF,NMP,IO0*C 59-99% I.F.2-7 Denmark, S.E.; Pan, W. OL, 4, 4163; Denmark, S.E.; Sweis, R.F. OL, 4, 3771.

Bu

~ ao

1. (Me2SiH)2NH ~~ 2. [(Ph-H)RuCI2]2 _ BUk__R 3. R-Ph-I, TBAF, dioxane \ /OH 4. Pd(dba)2, TBAF,rt-45~ 59-72%

I.F.2-8 Kita, Y. et al. CEJ, 8, 5377.

Me%oMe R2 PhI(O2CCF3)2,HPA R2 R3'''x''~N',~ )n MeCN,'20to 0~ ~ R

Me%oMe

92-99%

)n

82

ORGANIC SYNTHESISm2003

I.F.2-9 Botella, L.; Najera, C. AG(E), 41, 179 and JOM, 663, 46; Najera, C. et al. JOC, 67, 5588; Herrmann, W.A. et al. AG(E), 41, 1363; Bedford, R.B. et al. AG(E), 41, 4120 and CC, 2610; Nolan, S.P. et al. OM, 21, 2866; Li, G.Y. JOC, 67, 3643; Carboni, B. et al. SL, 829; Chaumeil, H. et al. S, 757; Hebel, A.; Haas, R. JOC, 67, 9452; Gong, Y.; He, W. OL, 4, 3803; Kotha, S. et al. BMCL, 12, 105; Molander, G.A.; Biolatto, B. OL, 4, 1867; Molander, G.A.; Yun, C.-S. T, 58, 1465; Molander, G.A.; Rivero, M.R. OL, 4, 107; Molander, G.A.; Bernardi, C.R. JOC, 67, 8424; Tao, B.; Boykin, D.W. TL, 43, 4955 and S, 1043; Doucet, H.; Santelli, M. et al. SL, 1807; Zim, D.; Monteiro, A.L. TL, 43, 4009; Dinnell, K. et al. BMCL, 11, 1233; 1237; Verkade, J.G. et al. TL, 43, 8921; Hayashi, T. et al. JACS, 124, 9918; Buchwald, S.L. et al. JACS, 124, 1162; Richardson, M.L.; Stevens, M.F.G. JCR(S), 482; McNulty, J. et al. CC, 1986; Kumar, S. et al. JOC, 67, 8842; Hyeon, T. et al. JACS, 124, 7643; Janin, Y.L. et al. JCS(P1), 529; Colobert, F. et al. TA, 13, 659; Williams, J.A.G. et al. JCS(P2), 1669; Hirao, T. et al. JOC, 67, 2721; Shimada, S.; Tanaka, M. et al. JOM, 659, 117; Guillaumet, G. et al. SL, 447; Zhu, Q.; Yang, Z. et al. OL, 4, 3333; Fathi, R.; Yang, Z. et al. TL, 43, 4395; Sotelo, E. et al. SL, 2062; Oh, C.H. et al. TL, 43, 4645; Selles, P.; Lett, R. TL, 43, 4621; Desai, R.C. et al. TL, 43, 4569; Wallace, D.J.; Chen, C. TL, 43, 6987; Hnaby, V.J. et al. OL, 4, 4029; Kobayashi, Y.; William, A.D. OL, 4, 4241; Kerins, F.; O'Shea, D.F. JOC, 67, 4968;.

FC~~~/C!

+ PhB(OH)2

K2CO:~ TBAB, H20, reflux R1

27-99%

cr 4. Ji I.F.2-10 Pleixats, R.; Roglans, A. et al. S, 1903; van Leeuwen, P.W.N.M. et al. JACS, 124, 1586; Lemaire, M. et al. TL, 43, 1829; Gordon, R.S.; Holmes, A.B. CC, 640; Uozumi, Y.; Kimura, T. SL, 2045; Larhed, M. et al. S, 1611; Lathed, M. et al. JOC, 67, 6243; Cacchi, S. et al. SL, 439; Gallagher, T. et al. OL, 4, 3115; Hirama, M. et al. OL, 4, 1627; Belier, M. et al. CEJ, 8, 3901; Kawano, T.; Shinomaru, T.; Ueda, I. OL, 4, 2545; Anderson, J.C. et al. CC, 201'8; Chandrasekhar, V.; Athimoolam, A. OL, 4, 2113; Tietze, L.F. et al. CEJ, 8, 401; Tietze, L.F.; Krahnert, W.-R. CEJ, 8, 2116; Kohler, K. et al. CEJ, 8, 622; Andrus, M.B. et al. OL, 4, 2079; Jung, K.W. et al. JOC, 67, 7127; Gurjar, M.K.; Talukdar, A. S, 315; Tang, J. et al. JOM, 651, 146.

/CN

HetA/

+ Ar-I

Pd(OAc)2, KOAc, Bu4NBr DMF, 80~

-~

Ar~ /CN --HetA~f 24-89%

CARBON-CARBON BOND FORMING REACTIONS

83

I.F.2-11 Gallagher, T. et al. SL, 808; Gauthier, D.R., Jr. et al. OL, 4, 375; Feldman, K.S. et al. OL, 4, 3525; Lutzen, A.; Hapke, M. EJOC, 2292; Anderson, K. et al. S, 1509; Bach, T.; Heuser, S. SL, 2089; Anilkumar, R.; Burton, D.J. TL, 43, 6979; Ma, S.; Zhang, A. JOC, 67, 2287; Knochel, P. et al. OS, 79, 35. Ar

~F~~'-/

Br

1" LDA' THF' "78"C 2. ZnCI2, THF, -78~ -+ rt 3. Ar-I, Pd(PPh3)4

~

Br 34-53%

(also Suzuki, Heck couplings)

I.F.2-12 Harayama, T. et al. CPB, 50, 519. OTf ~NMh4ehh ipr2NEt,Pd(OAc)2,dppp _ PBu3, DMF, 30rain

-

e

O

O 92%

I.F.2-13 Buchwald, S.L. et al. JACS, 124, 1261; Spielvogel, D.J.; Buchwald, S.L. JACS, 124, 3500; Hennessy, E.J.; Buchwald, S.L. OL, 4, 269; Hartwig, J.F. et al. JACS, 124, 12557; Beare, N.A.; Hartwig, J.F. JOC, 67, 541; Culkin, D.A.; Hartwig, J.F. JACS, 124, 9330; Nolan, S.P. et al. OL, 4, 4053, Konopelski, J.P. et al. OL, 4, 4121; Mura, M. et al. TL, 43, 101; Liu, X.; Deng, M. CC, 622. Ph-~

N ~ M e Me

+ Ar.Br

Pd2(dba,3, tBuONa, Ph-Me

-- P h ~

~

N~,:If Me

~~--oa~

Pa~

40-88% ee = 42-94%

I.F.2-14 Buzhansky, L.; Feit, B.-A. JOC, 67, 7527; Pei, J. et al. JOC, 67, 4924; Barbakella, G. et al. JOC, 67, 8877; Janssen, R.A.J. et al. CEJ, 8, 2384; Liu, C.-Y.; Luh, T.-Y. OL, 4, 4305. ~S~/ 1. Hg(O2CCF3)2, Ph-H, 0~ H ~ H 2. PdCl2,TEA, Ph.H, 0~ n 70-92%

84

ORGANIC SYNTHESISm2003

I.F.2-15 Demir, A.S. et al. T, 58, 8055:

R~/-~/NHNH2.HCI + ~

Mn(OAc)3 R

~

~ 30-70%

I.F.2-16 Indolese, A.F.; Studer, M. et al. AG(E), 41, 3668; Kohler, K. et al. SL, 1118; Colacot, T.J. et al. OM, 21, 3301; Bedford, R.B. et al. OM, 21, 2599; Yudin, A.K. et al. OL, 4, 2597; Hayashi, T. et al. SL, 871; Shieh, W.-C. et al. SC, 32, 1059. "A New Generation of Air Stable, Highly Active Pd Complexes for C - - C and C - - N Coupling Reactions with Aryi Chlorides." I.F.2-17 Havranek, M.; Dvorak, D. JOC, 67, 2125.

1. LiAIH4,THF, 0*C ~OH 2. EtOAc -3. Ar.I, Pd cat., ZnCi2

R

R Ar)=,X_ - OH 27-78%

I.F.2-18 Gooben, L.J. et al. SL, 1721.

Ar-CO2H + RCH=CH2

(Boe)20, PdCI2,LiC!

Ar~

NMP, ~,.picoline,120~

a

45-88%

I.F,3. Other Aromatic Substitutions and Preoarations I.F.3-1 Zhu, X.; Ganesan, A. JOC, 67, 2706.

R__~N H

R1

R'Br'Zn(OTf)2"Pr2NEt, R - - ~ N Bu4NI, Ph.Me, rt

H 49-71%

I.F.3-2 Cheng, C.-H. et al. OL, 4, 807.

3

g ~

~

il R1 + Re

R3 SiBr(dppe),Zn MeCN,80~ 10h53-88%

CARBON-CARBON BOND FORMING REACTIONS

85

I.F.3-3 Moskalev, N.V.; Gribble, G.W. TL, 43, 197 to

t

O

1. TFA, Ph-H, 60~

OH +

NMe 2. BF3.Et20, rt

P=~h

e

Ph 85%

I.F.3-4 Miura, M. et al. JACS, 124, 12680; Li, C.-J. et al. SL, 1553; see also: Boumendjel, A. et al. JCR(S), 463. X- ~~

COCi

It [IrCi(cod)]~ptBu3 Ph-Me2

R X

R

R

R

35-91%

I.F.3-5 Deville, J.P.; Behar, V. OL, 4, 1403; Kim, J.N. et al. TL, 43, 6597; Ila, H.; Junjappa, H. et al. JOC, 67, 5398. Me ~ M e s C O 2 M e CO2Me ~"~ 1. NaCN, DMSO / ~ ' - , ~ C O 2 Me 2. Nan, TIPS-Ci, DMF'~" OTIPS OMe

OMe

68%

I.F.3-6 Takahashi, T. et al JACS, 124, 388, 576; Xi, Z.; Takahashi, T. et al. T, 58, 1107; see also: Murai, S. et al. JOC, 67, 1414; Furstner, A.; Mamane, V. JOC, 67, 6264. 1. CH212,ZnEt2 ZrCp2 . . . . . . . . 2. CO

R

R

40-55%

I.F.3-7 Kaufmann, D.E. et al. AG(E), 41, 3375; Ma, S.; Ni, B. JOC, 67, 8280; Bouyssi, D.; Gerusz, V.; Balme, G. EJOC, 2445; Sestelo, J.P.; Sarandeses, L.A. et al. CC, 2246. ~

~O

Ph

Pd(OAc)2, AsPh3,NaF HCO2H, OMSO

"

A

"

, ~NPh 46-63 %

86

ORGANIC SYNTHESISm2003

I.F.3-8 Miura, T.; Iwasawa, N. JACS, 124, 518; Ohe, K.; Uemura, S. et al. JACS, 124, 526. W(CO)s(THF) THF, rt I

I

83-93%

I.F.3-9 Frejd, T. et al. JOC, 67, 6376; Crich, D.; Sannigrahi, M. T, 58, 3319.

R'--ll~~~NH2tBuONO' CH2=CHCMecH2Br N R--~ 34-85%

I.F.3-10 Pal, M. et al. SL, 1976; Fu, X. et al. TL, 43, 6673. Ar-X +

~

\OH ~

PdCI2(PPh3)4,D80~ MF,

~

r A

~ 37-61%

I.F.3-11 Hallberg, A. et al. JOC, 67, 5854; Larock, R.C. et al. JOC, 67, 9276. /

1. Pd(OAc)2,dppp, base R__~[~OTf DMF, 120~ CHO + f O ~ , o H 2. AcOH,80~

~)

24-78% OH I.F.3-12 Alterman, M.; Hallberg, A. et al. JOC, 67, 6232. gW, imidazole,DMF,15-20min

R1R 2

59.94% I.F.3-13 Jonczyk, A.; Kowalkowska, A. S, 764; Lawrence, N.J. et al. JOC, 67,457; see also: Vogl, E.M.; Buchwald, S.L. JOC, 67, 106. ~

2

+ [....EWG

NaH

,. ~ E W G

N+Me3X" DMSOor DMF 62-83%

CARBON-CARBON BOND FORMING REACTIONS

87

I.F.3-14 Pletnev, A.A.; Larock, R.C. TL, 43, 2133. I~~nlCN Pd(OAc)2,PPh3,TEA =

R

H20/DMF,130"C

~

R

1

30-94%

R

I.F.3-15 Schmalz, H.-G. et al. SL, 1253.

r"~

(CO)3C

Sml2 r.,,~/ F + R.~O R1 tBuOH/HMPA/THF (CO)3C

(~i0H

10-74%

I.F.3-16 Danheiser, R.L. OL, 4, 2465. Ark.i / 1. TMS-CHN2, CH2Cl2/hex,rt R3S" " O 2. SiO2,rt, HCI, aq THF or K2CO3,MeOH

" ~ O Z

36-91%

I.F.3-17 Cottet, F.; Schlosser, M. EJOC, 327; Lopez, F.J. H, 56, 91. R---~ TMS-CF3,CuI, KF ,. R - - - ~ X

CF3

28-79%

I.F.3-18 Fort, Y. et al. SL, 628. Me.Me

Bu-Li/Me2N(CH2)2OLi, 0~ -78~hex, E+ " M e ~ E M e 65-98%

I.F.3-19 Liu, Y.; Gribble, G.W. TL, 43, 7135; Butz, R.H.-J.; Lindell, S.D. JOC, 67, 2699; see also: Kato, S. et al. TL, 43, 7315; Cai, D. et al. TL, 43, 4285; Sapountzis, I.; Knochel, P. AG(E), 41, 1610; Piazza, C.; Knochel, P. AG(E), 41, 3263; Yamamoto, Y. et al. SL, 561; Warnmark, K. et al. JOC, 67, 6008. Bv 1. tBu-Li,THF, .78oc ~ C H O 2. MeI, -78~ rt ~" ]/~~;/~'---Me 3. tBu-Li,THF, -78~ Me 4. DMF,-78~ -~ rt Me 88%

88

ORGANIC SYNTHESISm2003

I.F.3-20 Clayden, J. et al. EJOC, 3558 and SL, 290 and JACS, 124, 5266. MeO'"~"~

O /

1. R-Li, THF 2. E+

=

Me

R

""

O

12-75% I.F.3-21 Mongin, F. et al. T, 58, 6723; Mortier, J. et al. TL, 43, 8347; Overman, L.E. et al. AG(E), 41, 3884; Kraus, G.A.; Kim, J. JOC, 67, 2358; Madsen, U. et al. JOC, 67, 2375. Br-~ICO2H

LTMP,E+ _~ B r ~ C O 2 H THF, -50"C 58-80%

I.G.

Svnthesis

via

I.G.1. Synthesis

Oreanometallics

via OrganQboranr

I.G.1-2 Miyaura, N. et al. SL, 1733. [Rh(cod)CI]2, KOH EtOH, 60~ 91%

I.G.1-2 Gagnon, A.; Danishefsky, S.J. AG(E), 41, 1581. TBDM

TBDM 2. Pd(dppf)Cl2, AsPh3

I

0 60%

CARBON-CARBON BOND FORMING REACTIONS

89

I.G.1-3 Fu, G.C. et al. AG(E), 41, 1945; Netherton, M.R.; Fu, G.C. AG(E), 41, 3910; see also: He, R.; Deng, M.-Z. OL, 4, 2759; Gomez, A.M.; Lopez, J.C. et al. CC, 2024; Hara, S. et al. JCS(P1), 384; Hoshi, M.; Shirakawa, K. SL, 1101; Cheng, C.-H. et al. JOC, 67, 99; Ikegami, S. et al. OL, 4, 3371. R-Ci + RI.(9-BBN)

Pd2(dba)3, PCy3, CsOH.H20 . . . . -- R-R1 dioxane, 90"C 65-83%

I.G.1-4 Miyaura, N. et al. SL, 767.

R ~

[ R h+ c[/~/B(OiPr)2 l(c~ TMS

,- ~ R 1 H20/MeOH, 100*C TMS 43-94%

I.G.1-5 Murakami, M.; Igawa, H. CC, 390.

1

R,, H '

tRh(cod)Cl]2, P(OEt)3 _ + Ar-B(OH)2 NaHCO3,MeOH, reflux -

R

Ar

R

53-94%

I.G.1-6 Goodson, F.E. et al. JOC, 67, 5860; Lautens, M.; Mancuso, J. OL, 4, 2105; Bryce, M.R. et al. JOC, 67, 7541. ~ C Ar-X + Arl-B(OH)2 + [

Ar:

Pd(OAc)2,K2CO3 CO2Et Ar'~C~O2Et H20/THF O2Et O2Et 43-78%

I.G.1-7 Oh, C.H. et al. JOC, 67, 7155; Shirakawa, E. et al. CC, 2210. ~B r R'B(OH)2'Pd(PPh3)4' .. Cs2CO3-- ~ EtOH, 60~ R 33-90%

90

ORGANIC SYNTHESIS--2003

I.G.2.

Carbonvlations

Reactions

I.G.2-1 Magnus, P. et al. TL, 43, 947; Rios, R.; Moyano, A.; Pericas, M.A. TL, 43, 1023; Ishizaki, M.; Masamoto, M.; Hoshino, O. H, 57, 1409; Jiang, B.; Xu, M. OL, 4, 4077; Sturla, S.J.; Buchwald, S.L. JOC, 67, 3398 and OM, 21, 739; Areces, P. et al. JOC, 67, 3506; Chung, Y.K. et al. OL, 4, 3983; Hatzelt, A.; Laschat, S. CJC, 80, 1327. , co

TS~N~

(co)

.

BuSMe,DCE, 830C

Ts

Boc

~

:

O

~

NBoc

63-69%

I.G.2-2 Evans, P. et al. TL, 43, 7859. "Microwave Promoted Pausen-Khand Reactions." I.G.2-3 Gibson, S.E. et al. T, 58, 4937; see also: Perez-Castells, J. et al. TL, 43, 5763; Dahan, A.; Portnoy, M. CC, 2700; Derdau, V.; Laschat, S. JOM, 642, 131; see also: Moyano, A. et al. OL, 4, 1205. Co2(CO)7(PPh3) Stable Pauson-Khand Catalyst I.G.2-4 Chung, Y.K. et al. JACS, 124, 6838 and OL, 4, 4361. 1. Co nano particles, CO, THF, 1300C

/N

1~

2. [rl3-allyl)PdCI}z,dppe, BSA AcO

MeC-CCHzCH(COzMe)z, AcOK,"rt M e 0 2 C ~\ | .~x.. MeO2C/ v ' y 3. CO, 130~

O O

R 74-84 %

I.G.2-5 Brummond, K.M. et al. JOC, 67, 5156 and OL, 4, 1931 and TL, 43, 3735; Alcaide, B. et al. CEJ, 8, 1719; Mukai, C. et al. OL, 4, 1755.

~ I - I

Mo(CO)6

=

O

DMSO/Ph-Me, 95~ 80% E:Z = 8"1 ee = 95%

CARBON-CARBON BOND FORMING REACTIONS

91

I.G.2-6 Morimoto, T.; Kakiuchi, K. et al. JACS, 124, 3806; Shibata, T. et al. OL, 4, 1619. X

+ C6Fs-CHO

[Rh(cod)Cl]2, dppp Ph-Me2, 130"C

X~ ~. ~

O

R

R

71-97% I.G.2-7 Kang, S.-K. et al. AG(E), 41, 1584.

%0

CO, Ru3(CO)12. ~

O

48-82%

I.G.2-8 Groth, U. et al. SL, 2023; Krafft, M.E. et al. JOC, 67, 1233. +

Co2(CO)&CyNH2 Ph-Me, 100~C

R 46-72%

I.G.2-9 Pagenkopf, B.L. et al. TL, 43, 3739 and T, 58, 3813; Itami, K.; Mitsudo, K.; Yoshida, J. AG(E), 41, 3481. QR1 __ 2R~ ~ Re Co2(CO)8 O HeO/MeCN, reflux, 30min ReSi-~ 37-75% I.G.2-10 de Vries, J.G. et al. JOC, 67, 5022; Alper, H. et al. JOC, 67, 6224; Xiaozhong, L. et al. JOM, 664, 1; van Leeuwen, P.W.N.M. et al. CC, 3044. OH H 1~

H CO/H2. Rh(CO)2(acac) R ~ Ph-Me, 90~

71-87%

92

ORGANIC SYNTHESISm2003

I.G.2-11 Alper, H. et al. JOC, 67, 6623; BeUer, M. et al. JOM, 641, 30; Rodrigo, R. et al. JOC, 67, 6568; Takahashi, S. et al. CC, 2868; Lapidus, A.L. et al. S, 317; Takeuchi, R.; Akiyama, Y. JOM, 651, 137; Mori, H.; Souma, Y. et al. TL, 43, 7871; Ishii, Y. et al. JOC, 67, 5005. R//~" ~ I CO,, Pd-dendrimer, TEA, ~ R f / ~ CO2Me MeOH 42-99% I.G.2-12 Andrus, M.B. et al. TL, 43, 9137; Schmalz, H.-G. et al. SL, 1161; Campo, M.A.; Larock, R.C. JOC, 67, 5616; see also: Mori, M. et al. AG(E), 41, 1218. R//(~I

CO, Pd-deMdOiHer,T E A I ~ ~ C O 2 M e 42-99%

I.G.2-13 Kato, K.; Akita, H. et al. TL, 43, 4915; Ryu, I.; Komatsu, M. et al. JACS, 124, 3812; Fujiwara, S.; Kambe, N.; Sonada, N. et al. JOC, 67, 6275. CO, PdCI2(MeCN)2 , benzoquinone,MeOH

M

CO2Me

" 51-95%

I.G.2-14 Hanamoto, T. et al. BCJ, 75, 2497; Schnyder, A.; Indolese, A.F. JOC, 67, 594. R.._./~~.~X + FxffiSnBu3 CO, Pd(PPh3)4DMFD. R - - - - / ~

F

0-99% I.G.2-15 Leighton, J.L. et al. JACS, 124, 7890, 10672. e

~

S

~

RI~

~ R

1. CO, Rh(CO)z(acac),Ph-H _-- R Me 2. H202, NaHCO3,MeOH/THF ~

~ R

~

Me 65-67% ds = 2.57-13.3:1

CARBON-CARBON BOND FORMING REACTIONS

93

I . G . 2 - 1 6 Kim, J.N. et al. TL, 43, 1247. R . _ ~ ICHO

+ ~yNMe2 O

PBu3 R---~'~ THF, reflux--41-68%

IIr('NMe2 O

I.G.2-17 Onaka, M. et al. OL, 4, 1667.

(CH20) n, BF3-Et20, 4.~ MS CH2CI2, -5 to-10~

OH

59-72% I.G.3. O t h r

Synthesis

via O r g a n o m e t a l l i c s

I.G.3-1 Wu, H.; Ding, J. et al. JCR(S), 461; Shi, D. et al JCR(S), 452. /_...~C Ar

N

Sm, InCI3"4H20

CN

H20/THF, rt

. A r , , . . ~ CN ~ xX'-NH2 Ar"

/'" CN NC 74-90%

I.G.3-2 Jun, C.-H. et al. AG(E), 41, 2146; Duchene, A. et al. S, 543. R-CHO +

ah eeh ,

leh Oen

R 1 3-MePyr-2-NH 2, Ph-Me, 80~

,-

66-96 % I.G.3-3 Yamamoto, Y. et al. CEJ, 8, 4734; Xi, Z.; Takahashi, T. et ~1. JOM, 663, 13; Xi, Z. et al. CEJ, 8, 4292. R

TMS

ZrCp2 +

R

R

Z TMS

R

IDPOU

THF, 0~

TMS

--

Z R TMS 46-89%

94

ORGANIC SYNTHESIS--2003

I.G.3-4 Echavarren, A.M. et al. CEJ, 8, 3620 and JOC, 67, 5197; Widenhoefer, R.A. et al. OM, 21, 901; Liu, C.; Widenhoefer, R.A. et al. OM, 21, 5666; Kang, S.-K. et al. CC, 2634; Matsuda, I. et al. OM, 21, 3650; Takimoto, M.; Mori, M. JACS, 124, 10008; Evans, P.A. et al. JACS, 124, 8782; Cheng, C.-H. et al. JOC, 67, 7724; Yamazaki, S.; Yamabe, S. et al. JOC, 67, 2889. 1

1

nBu3R

Pd2(,dba)a.dba, PPh3,LiCI.

7_, ~ : ~ ~ " O A c

H20/DMF, 80*C

R+ 52-96%

I.G.3-5 Sato, F. et al. JOC, 67, 1024; Shibata, T. et al. JOC, 67, 7446. TMS TBSO~

TMS Ti(O'Pr). 'Pr.MgCI, -"- T B S ~ ~--- CO2Et

O

H "5 7 % (r

4:1

I.G.3-6 Huang, Q.; Larock, R.C. OL, 4, 2505; Murakami, M. et al. CL, 294; Yong, L.; Butenschon, H. CC, 2852; Mitsuda, T. et al. OM, 21, 4564. ~~~~X

Y

,ix

Pd(OAc)2, PPh3 DMF, 80C

y

R

R 60-88%

I.G.3-7 Tanaka, K.; Fu, G.C. JACS, 124, 10296; Pletnev, A.A.; Larock, R.C. JOC, 67, 9428; Jun, C.-H. et al. JOC, 67, 3945; Kang, S.K.; Yoon, S.-K. JCS(P1), 459; Chang, S. et al. JACS, 124, 750. OHq R

--

--

OMe

R

{Rh[(R)-Toi-BINAP]}BF4 CH2CI2,10~

R ~ ~,

~ R OMe 91-95% ee = 8 2 - 9 5 %

CARBON-CARBON BOND FORMING REACTIONS

95

I.G.3-8 Ikeda, S. et al. CC, 2422.

X~

1

]tl Ni(acac)2,AIMe3,Ph.OH, THF RS~,.~..~ R2 R R,tk?

.

R R1

R 21-95% ee = 4-58%

I.G.3-9 Molander, G.A.; St Jean, D.J., Jr. JOC, 67, 3861; Wang, J.; Li, C. JOC, 67, 1271.

IRI.,, RI~

O

SmI2,NiI2 tBuOH

~

O 23-99%

I.G.3-10 Bennaser, M.-L. et al. JOC, 67, 6268; Tsuji, Y. et al. JOC, 67, 5835.

~

S~Ph

~'N R

Bu3SnH,AIBN _ "Z Ph-H,reflux

Z R

25-82%

I.G.3-11 Cheng, C.-H. et al. JACS, 124, 9696; Shirakawa, E.; Hiyama, T. et al. CC, 1962; Yang, C.; Nolan, S.P. JOC, 67, 591; see also: Yamamoto, Y. et al. JOC, 67, 3445.

It I~ CoI2(PPh3)2,Zn, PPh3 : R1 + R2 H20/MeCN,80~

. R2 48-98%

I.G.3-12 Jung, K.W. et al. JOC, 67, 6582.

P h S O ~ I N-~ 1~21.....~ . j 9 R

Rh2(OAc) 4 PhSO~.... CH2C12,reflux,'12h"

O 64-97%

96

ORGANIC SYNTHESISm2003

I.G.3-13 Oshima, K. et al. OL, 4, 2257; Poli, G.; Giambastiani, G. JOC, 67, 9456. R ~ ~ . . I ~ '2 .......... CoCI2(dppb),TMS.Crefl H2MgCITHF, ux

= RI~

R2

66-94%

dr = 1-2:1 I.G.3-14 Barluenga, J. et al. CEJ, 8, 4149; Aumann, R. et al. OM, 21, 1637, 2736. . ~)R ~(CO)6 R~--~ "OMe R6-NC

RR ~ ~ R 4 R5

)Me ~NHR 6 i "

R R

THF " R

"/J'4 Rs 52-98%

I.G.3-15 DeShong, P. et al. JOC, 67, 327; Ozawa, F. et al. JACS, 124, 10968; Kann, N.C. et al. JOC, 67, 9460; Me Me Me ed(dba)3' ePh3' (Ph3SiF2)' 75~BR4N+~THF,

~

+Ph~ Ph

OBz

91% 10:1

I.G.3-16 Timbart, L.; Cintrat, J.-C. CEJ, 8, 1637; Bellina, F.; Rossi, R. S, 2729; see also: Takeda, T. et al. JOC, 67, 8450; Ghosh, I.; Jacobi, P.A. JOC, 67, 9304; Reginato, G. et al. TA, 13, 595. i

/Ts TMS-SnBu3 1~Bn Pd(PPh3)4 ~TM

Ts~

N--Bn R-X,Pd2(dba)3 SnBu3 AsPh3,CuCi TMS

Ts~

N-Bn R

28-80%

I.G.3-17 Beaudry, C.M.; Trauner, D. OL, 4, 2221. O2~_

+Me3Sn~

\-/ \--/

\

I1 i

MeO2C"

pd C I 2 ( M e C N ) ~ 2 _ N ~ ~ ~ DMF

- MeOzC"'~ 40%

CARBON-CARBON BOND FORMING REACTIONS

97

I.G.3-18 Takahashi, T. et al. JOC, 67, 7019, 7451; Yamamoto, Y. et al. JOC, 67, 5977; Marek, I. et al. JACS, 124, 10282. / _ ~ EWG1 ~~._~ EWG1 RI~R2Cp2 + R EWG T H F , -40"C R EWG 24-90% I.G.3-19 Lei, A.; Zhang, X. OL, 4, 2285; Jensen, A.E.; Knochel, P. JOC, 67, 79; Skerlj, R.T. et al. JOC, 67, 1407; Bauer, M.; Maier, M.E. OL, 4, 2205; see also" Yadav, J.S. et al. TL, 43, 5185. PdCI2 R-ZnX ~ R---R THF 20-99% I.G.3-20 Murakami, M. et al. JACS, 124, 13976.

[Ph(nbd)(dppp)PF6, . . . . . . BHT ~ Ph-Me2, 135~ 90min

~ 81%

I.G.3-21 Cai, M.-Z. et al. JCR(S), 376; Panek, J.S. et al. OL, 4, 2485.

PhSek R//~--Br~ + BrMg "--- "Ph

Pd(PPh3)4 THF,rt

PhSe R---'//

"'" Ph 61-91%

I.H. R e a r r a n e e m e n t s !.H.1. Ciaiscn, CQpe a n d

Similar Processes

I.H.I-1 Clive, D.L.J.; Ou, L. TL, 4, 4559.

.OMEM

TBDPSO

95%

98

ORGANIC SYNTHESIS--2003

I.H.1-2 Shiina, I.; Nagasue, H. TL, 43, 5837; Seki, K. et al. TL, 43, 265. ~OTES R1 OBn

,. . neat, 100~

ph~C102TES R R

62-99% I.H.1-3 Davies, S.G. et al. JCS(P1), 2141. Ph

1. BuLl, THF, -78"C Bn..N,.O 2. Zn, aq HCI, 80"C

~ e

H

NH Bn"

63% de = 90-97 %

I.H.1-4 Smith, S.C.; Bentley, P.D. TL, 43, 899; Wang, J. et al. JOC, 67, 5621. EtO2

K2CO3 CO2Et + ~HMe "] DMF, Ooc~ rt

Br

Me

CO2Et

cis:trans = 2.6"1 I.H.1-5 Troisi, L. et al. EJOC, 478, 3465. "Stereoselective a n d C o m p a r a t i v e [1,2]- a n d [2,3]Wittig R e a r r a n g e m e n t s of Allyl H e t e r o a r y l a l k y l E t h e r s . " I.H.1-6 Prabhakar, Si; Lobo, A.M. et al. CC, 746. R

R4

TBDMSO'N~R R1

3

R2 Ph-CI2, reflux

~TBDMS

R4

R

78-82% syn:anti = 1-99:1 I.H.1-7 Loh, T.-P. et al. OL, 4, 2389. TFA Ster R

CH2C12, rt

',

~...,~.R |Ster

71-82% dr = 49:1

CARBON-CARBON BOND FORMING REACTIONS

99

I.H.1-8 Mandal, S.K.; Sarkar, A. JCS(P1), 669; Seki, K. et al. TL, 43, 3633.

H ~" ,,r

R

L//

KH, 18-Cr-6

P

Et20, rt

R

77-78%

I.H.1-9 Barriault, L.; Denissova, I. OL, 4, 1371.

i"'O~ ~ R

R1

IzW Ph-Me, 220 ~C

-'-(R 2 ({H =

R1 60-98%

I . H . I - 1 0 Cooke, A. et al. TL, 43, 903.

H~~H

.....

+ OHC-CO2H S a e n H

Bn

Bn

CO2H

64%

I . H . I - l l Hatcher, M.A.; Posner, G.H. TL, 43, 5009; de la Pradilla, R.F. et al. OL, 4, 2373; Trauner, D. et al. SL, 411; Ley, S.V. et al. OL, 4, 3847; Davis, C.J.; Moody, C.J. SL, 1874.

TESO

ft

""'O

100"1400 C = TESO 82-96%

I.H.l-12 Miller, S.P.; Morken, J.P. OL, 4, 2743. [Rh(cod)CI]2, MeDuPhos MeSiCI2H, 50oc

HO2C~Me

~''Pr

70% dr -8:1

100

ORGANIC SYNTHESIS--2003

I . H . l - 1 3 Koch, G. et al. TL, 43, 4837; Mclntosh, M.C. et al. JOC, 67, 2042; Metzner, P. et al. CEJ, 8, 632; see also: Couty, F. et al. EJOC, 29. R

LHDMS, TiCI4, TMS.CI _

R~

THF,-78~

O

rt

H 40-99%

erythro:threo = 2-15:1

I . H . l - 1 4 Kazmaier, U. et al. CEJ, 8, 1850; Colombo, L. et al. T, 58, 9381. LHDMS, AI(Oipr)3, quinine = PGHr~ O.,.,,"x..~

THF, -78~

PGH

O

2Me

23-98% ds = 85-99 %

ee = 13-87 %

I.H.I-15

Hsung, R.P. et al. OL, 4, 1383.

~IN~ h Ph ,,,] ,,,,O Ph

Ill

O2N-Ph-SO3H ph " "]"'" "N Ph-Me, A Ph

oth~;: 1

/

OH

9

R' ' ' M ' ~

R9

50-90 % 1.5-20:1

I . H . 1 - 1 6 Kaden, S.; Hiersemann, M. SL, 1999. 2ipr i

H s,.

[Cu(S,S)-Ph-box](OTf)2 98% de = 78 % ee = 99 % I.H.2.

I.H.2-1

Other

Rearrangements v

Spencer, J.B. JOC, 67, 4627. PdCI2(MeCN)2 _ Ar ~ R

Ar"

R

CH2CI2,rt

85-96 %

O

1

CARBON-CARBON BOND FORMING REACTIONS

101

I . H . 2 - 2 Marson, C.M. et al. TL, 43, 6637; Tu, Y.Q. et al. TA, 13, 395. O

SnCi4

.'

CH2C12, -78"C 62% I . H . 2 - 3 Shinohara, T.; Suzuki, K. TL, 43, 6937; Suzuki, K. et al. CL, 281. Me

Ph

HO

1. MsCI, TEA, CH2CI~ 0*C 2. AIEt3, CH2CI~ -780C

M

~

9

e _:

~

Ph

85-93%

ee = 80-99% I . H . 2 - 4 Overman, L.E.; Wolfe, J.P. JOC, 67, 6421.

! ? g,a "

Tf20

(

'= "~

R2

CH2C12, -78"C 54-90% dr = 10-20:1

I . H . 2 - 5 Maier, M.E. et al. JOC, 67, 8692. OH

~

H :

H OH

R

H 2 S O4

_~

MeOH, 35~

~

H

Me H

35-66%

I . H . 2 - 6 Ila, H.; Junjappa, H. et al. JOC, 67, 9477.

Ar Ar

Ar X

SnCl4 ~"',,~"~N

R

MeNO2, 0~ ~ rt

~ X

R

57-69%

102

ORGANIC SYNTHESISm2003

I.H.2-7 Gimbert, Y.; Greene, A.E. et al. SL, 2086. r. :.-~ ..R3

R3. r, =~,

o)

B

-~"

o-/ R/~.~__ff,

(,

,)

'

'

BuLl

-

THF, -78~ ~

OH 41-85%

I.H.2-8 Cossy, J. et al. TL, 43, 823. PCC HO 27-95% I.H.2-9

OL,

S u z u k i , K. et al.

.~.~RI~

F

R-J~.~ [[ [ \R 2

"%

0-63%

4, 2 2 9 .

R3

R1

R2

Ph-Li

R3 A~ "OrI 70-01%

I.H.2-10 May, J.A.; Stoltz, B.M. JACS, 124, 12426.

p

h~~R3

~~.

Rh2(OAc)4_~ OH R DCE,80~

" R3 Ph R~ 63-87% dr = 6-20:1

R1

I.H.2-11 Bungard, C.J.; Morris, J.C. JOC, 67, 2361. )R

nH

~/1 ~]~ ' ~ X

R

Ph.Me,reflux ~"

H

Me X

76-84%

CARBON-CARBON BOND FORMING REACTIONS

103

I.H.2-12 Rao, P.N.; Cessac, J.W. ST, 67, 1065. /OAc

Ac

CH2C12 69-84%

I.H.2-13 Tu, Y.Q. et al. OL, 4, 363. ~

O

R~,."

R2 H

l~2 :.

ZnBr2 :_ CH2Ci2, rt

R'"

R1 Ts

83-90% I.H.2-14 Renaud, P. et al. AG(E), 41, 4321. X

~

Bu3SnH,~AIBN D. tBuOH, reflux

H 44-69%

I.H.2-15 Jung, M.E.; Piizzi, G. JOC, 67, 3911. PhMe2S"~~f M e

KF = Ph' ' ~ M e wet DMSO, rt, 18h 99%

I.H.2-16 Mataka, S. et al. BCJ, 75, 773. 48h

aq HBR

42-57% Ar - Ph, 4-MePh

dioxane, 35~

3h "

75% Ar = 2.MePh

~

I!

OXIDATIONS

II.A.

C-O

II.A.1.

Oxidations

A l c o h o l s - r Ketones.

Aldehvdes

II.A.I-1 Ansari, I.A.; Gree, R. OL, 4, 1507; Martin, S.E.; Suarez, D.F.

TL, 43, 4475.

R~OH

TEMPO,CuCI, 02 [bmim][PF6], 65"C

R-CHO 72-96%

(also with 2*alcohols) [similar oxidation with Fe(NO3)3,FeBr3, air] II.A.1-2 Shirini, F. et al. AJC, 54, 405 (2001); Lou, J.-D.; Xu, Z.-N. TL, 43, 6095, 8843. ~OH Mg(HSO4)2,wetS!O~ R ~ O R1 neat, 5-110min R1

5-95% [similar solvent free oxidation using CrO3] II.A.1-3 Degirmenbasi, N.; Ozgun, B. M, 133, 1417; Tajbakhsh, M.; Hosseinzadeh, R.; Niaki, M.Y. JCR(S), 508; see also: Alsters, L. et al. SL, 243. R~OH CH2CI2/AcOH R ~ O

Cr20~ 2

64-92%

II.A.1-4 Node, M. et al. TL, 43, 5177; Singh, V.K. et al. TL, 43, 8355; Khenkin, A.M.; Neumann, R. JOC, 67, 7075; Li, C. et al. SL, 2041. ~OH NCS,MeS(CH2)tlMe, TEA R~R10 R1 CH2Ci2,-60~-~ rt 89-99% (also odorless Swern) [similar oxidation with Ph3PX2,DMSO,TEA] 104

OXIDATIONS

105

II.A.1-5 Iwasa, S. et al. CL, 284; Chang, S. et al. SC, 32, 1279; Backvall, J.-E. et al. JOC, 67, 1657; Yu, W.-Y.; Che, C.-M. et al. JOC, 67, 7716; Park, J. et al. OM, 21, 5674; Chang, S. et al. OL, 4, 2369; Sheldon, R.A. et al. TA, 13, 879.

R~OH PhI(OAc)2,0*C-*rtD.R~O R1 ~ q , ~ N ~ sl

44-96%

O

II.A.1-6 More, J.D.; Finney, N.S. OL, 4, 3001; Warrin, L.; Viala, J. S, 326; Pozzi, G. et al. TL, 43, 6141; Kim, S.S.; Nehru, K. SL, 616. R ~ O H EtOAc'80*C-_ ~ R 1 0 ,o O

90-99%

OH

II.A.1-7 Muzart, J. et al. TL, 43, 6641; Shvo, Y.; Goldman-Lev, V. JOM, 650, 151; Sigman, MoS. et al. CC, 3034.

--CI2, u4N r neat, 120~

R1

R1

80-94%

[similar oxidation with Pd(OAc)2]

II.A.1-8 Khadilkar, B.M. et al. SC, 32, 2931; Lou, J.-D.; Xu, Z.-N. TL, 43, 6149. R O

Ro~~H 1

MnO2/SiO2 ~ O~.~R

DCE,reflux, 12h

1

80-94%

[similar oxidation using MnO2 without solvent] II.A.1-9 Maruoka, K. et al. OL, 4, 2669 and S, 279. OH tBu-CHO,Ph-Me, rt

~R1

f f ' ~ /SO2CsFz7

R1 80-94%

106

ORGANIC SYNTHESIS--2003

II.A.I-10 Vadakkan, J.J. et al. SC, 32, 2495; Kitagawa, H.; Mukaiyama, T. CPB, 50, 1276. Ar~..~OH MeO2CN-SO2N+Et3 A ~ / ~ O

Ar

CH2CI2, rt

O

Ar

52-67 %

I I . A . I - l l Moody, C.J.; Palmer, F.N. TL, 43, 139; Hu, S.; Dordick, J.S. JOC, 67, 314. R ~ O H tBuOOH,Rh2(OAc)2 R ~ O R1

.... CH2CI2,r t

-

R1 39-97%

II.A.l-12 Fujita, K.; Furukawa, S.; Yamaguchi, R. JOM, 649, 289. R ~ O H . CIrCpCI2)2,K2CO3 R ~ O R1

Me2CO, rt, 6h

R1 20-94%

II.A.I-13 Chang, H.S. et al. SC, 32, 31. -~OH O R1

NaOBr' i-, HCI'" = H20/...HzCI2

O~R 1 90-94%

II.A.I-14 Dolenc, D.; Harej, M. JOC, 67, 312. R /OH D PO Br '}, ~ R1 \R 2 C6HI~60~ -~ reflux

2 38-99%

II.A.l-15 Yamato, T.; Shinoda, N. JCR(S), 400. R ~ O H Nafion-Ce(IV)or Cr(III), NaBrO3 R ~ O R1

H20/MeCN, A

R1 70-99%

II.A.l-16 Uemura, S. et al. JOC, 67, 6718. H~ - - R1 .V~ ~. C~/ R

MeCN, 80~

R

R1 41-99%

OXIDATIONS

107

II.A.2. Alcohols.

Aldehvdes-,Acids.

Esters

II.A.2-1 Kaneda, K. et al. TL, 43, 7179. ~'OH Ru/Co(OH)2]CeO2 --- R'CO2H 64-99%

Ph-CF31600C

II.A.2-2 Yasuda, K.; Ley, S.V. JCS(P1), 1024. NaOCI, KBr, H20/MeCN R~ O H " R-CO2H *NMe3ClO2" *NM%n2PO," 76-99%

II.A.2-3 Giannis, A. et al. A G(E), 41, 4059. IBX, DMSO, rt R~OH 1-hydroxypyridine or N-hydroxysuccinimide

R-CO2H 40-95%

(also for oxidation of aldehydes) II.A.2-4 Patel, B.K. et al. TL, 43, 5123. R<

~

~

V205'H202 . MeOH, 0~ 80-96 %

II.A.2-5 Chavan, S.P. et al. SL, 267; see also: Huang, X. et al.

JCR (S), 514.

Ar-CHO

HzOz, TS-1 MeOH, reflux

--- Ar-COzMe 65-99%

TS-1 = titanium silicate

II.A.2-6 Smith, A.B., III; Kozbwski, M.C. et al. OL, 4, 4539. R-CHO + HO" v

~-O

SmI2 THF, -15~ -

O~

O' ' ' ~ / ' ~ ' O H 70-88%

108

ORGANIC SYNTHESIS--2003

II.B. C-H

Oxidations

II.B.1 C-H-* C- O I I . B . I - 1 Shaabani, A. et al. SC, 32, 675; see also: Cortes, D. et al. TL, 43, 757.

R~ NaBrO3,Bu4NHSO4 R ~ O Ph H20/MeCN ~ Ph

0-91% II.B.1-2 Shaabani, A.; Lee, D.G. et al. TL, 43, 5165.

~

X KMnO4'K10 = n

X 81-90%

II.B.1-3 Garcia-Valverde, M.; Pedrosa, R. et al. SL, 2092. R3R2N~ OH KOH,a i r R3R2N~O R~

R

R1

79-92% II.B.1-4 Lee, J.C. et al. TL, 43, 5661. ~tW R

R~

(/ ~'N-O X=/--

R1 R 45-90%

II.B.1-5 Lee, S.; Fuchs, P.L. JACS, 124, 13978. ~

CrO2(OAc)2,HslO6 .

.

.

.

.

AC20,40~ 20min : _ ~

Ac

h

\

69%

\

II.B.1-6 Yu, J.-Q.; Corey, E.J. OL, 4, 2727. "Diverse Pathways for the Palladium(II)-Mediated Oxidation of Olefins by tert-Butylhydroperoxide."

OXIDATIONS

109

II.B.1-7 E1-Qisairi, A.K.; Qaseer, H.A. JOM, 659, 50; Guicharo, G. et al. JOC, 67, 8440; Sulikowski, G.A. et al. T, 58, 4403.

~ R 1 0 2 ' CuCI2'cat" ( ~

OH

R

R1

R

85-94%

II.B.1-8 Christoffers, J.; Werner, T. SL, 119.

R~R1

X

02, CeCIa'7H20 _ iprOH 29-99%

II.B.1-9 Tanyeli, C. et al. T, 58, 9983; Nabana, T.; Togo, H. JOC, 67, 4362.

O~ RO

Mn(OAc)3 ~ O A c )n Ph-H q/x,,..~)n RO 56-73%

II.B.I-10 Andrus, M.B.; Zhou, Z. JACS, 124, 8806.

tBuO2C~

CuPF6,MeCN,-20~ NO2

r

,.

O

NO2

(

R R

3-61% ee- 15-99%

I . B . I - l l Li, Z. et al. TA, 13, 2141; Breslow, R. et al. JOC, 67, 5057. OH

~ R

0

sphingomonassp. ItXN200=

Q~O R

45-71% ee = 31-68%

110

ORGANIC SYNTHESIS--2003

II.B.2 C-tt~ C-Hal II.B.2-1 Stavber, S. et al. S, 2609. ~~+

F-N~~/N+-OH ieoH, reflux--- ~ ~ F (BF'4)2

40-98%

II.B.2-2 Kar, A.; Argade, N.P. S, 221. ~ ~ ~

Br2

=

Me CC!4,reflux O

O

CHBr2 94-96 %

II.B.2-3 Barluenga, J. et al. A G(E), 41, 2556; Sarandeses, L.A. et al.

JOC, 67, 4707.

~n

Phl(OAc)~I2 tBuOH, 40~

~n.I,, ' OAc 47-92%

II.C C-N Oxi0ations No Entries this year II.D, Amine Qxidation~ II.D-1 Gelalcha, G.; Schulze, B. JOC, 67, 8400. "Chemoselective Electrophilic Oxidation of Heteratoms by Hydroxy Sultams." II.E. Sulfur Oxidations II.E-1 Therisod, M. et al. TA, 13, 519; Boyd, D.R. et al. CC, 1914. "Enantioselective Synthesis of Sulfoxides Catalyzed by an Oxidase-Peroxidase Bienzymatic System."

OXIDATIONS

111

II.E-2 Scettri, A. et al. TA, 13, 1277. "New Procedures for the Enantioselective Oxidation of Sulfides under Stoichiometric and Catalytic Conditions." I.E-3 Kim, S.S. et al. S, 2484. R,, HsIO~,reC!3 _ R,.R~IO ~l MeCN,rt

64-99% II.E-4 Hajipour, A.R.; Mallakpour, S.E.; Adibi, H. JOC, 67, 8666. R,,R~1 PhCH2Ph3PHSOs IL.R 1~'I0 MeCN, reflux -

78-91% (also thiois oxidized to disulfides) I.E-5 Anson, M.S. et al. SL, 1055; Katsuki, T. et al. SL, 161; Skarzewski, J. et al. TA, 13, 2105. H2Oz, VO(acae)2, CH2CI2,0*C R,. O

Ar

- ~ o I

Ar 74-86 % ee = 89-97 %

H

~_./OH

I.E-6 Perrio, S. et al. OL, 4, 3619. Me t Bt~: ,q ...-~ 1 7 6 1. Me-Li NMe2 + e.~__.~N ~ ~'SH M SO2Ph 2. R-X

~ f" Me

NMe2

O 43-86 % dr = 4-5.67:1

I.E-7 Lakouraj, M.M.; Movassagh, B.; Ghodrati, K. SC, 32, 847; Najera, C. et al. TL, 43, 3459. R..~ .Caro's . . acid/SiO2 . . ,. R..~O2

R1

MeCN,40~

R1 81-99%

112

ORGANIC SYNTHESISm2003

I.E-8 Katsuki, T. et al. TL, 43, 3259. UHP, MeOH, 0*C R-'~

)n

1~,'-<:~ "

63-89% dr = 6-99:1 ee (major) = 39-99%

_ _ / = N 71 ~

II.F.

Oxidative

II.F.1

Additions

to C . C

)n

Multivle

Bonds

Evoxidations _

II.F.I-1 Che, C.-M. et al. CEJ, 8, 2495 and CC, 2906; see also" Chauhan, S.M.S. et al. CC, 2456. RulV(p~ Ar,~ R Ar/~,,-R ,. pyrazole, Ph.H, rt

25-88% ee = 10-88 %

I.F.1-2 Lattanzi, A. et al. TL, 43, 5629; Krasinski, A.; Jurczak, J. TA, 13, 2075; Wu, H.-L.; Uang, B.J. TA, 13, 2625; de la Pradilla, R.F. et al. JOC, 67, 8166; Wang, M. et al. CC, 118. ~r"-OH + ~ vie Ti(Oipr)4,L'DIPT _-- R ~ OH R1

R

MeOOH 4.AMS, CH2C12,-20~

R1 R 54-87% ee = 73-98%

II.F.1-3 Zheng, Z. et al. JCS(P1), 870; Li, C. et al. CC, 2696; Linde, C. et al. CEJ, 8, 2568. NaOCI, 4-PPNO, cat. ~ R or MCPBA, NMO, cat. 2

R

73-96%

cat. =

ee = 37-97%

OXIDAIIONS

113

II.F.1-4 Jia, M.; Thiel, W.R. CC, 2392. "Oxodiperoxo Molybdenum Modified Mesoporous MCM-41 Materials for the Catalytic Epoxidation of Cyclooctene." I.F.1-5 Hutchings, G.J. et al. JCS(P1), 2064, 1475. "Shape Selective Oxidation Using Titanium Silicates: Epoxidation of Dihydromyrcene and the Model Compounds 2-methylpent-2-ene and 3-methylpent-l-ene." II.F.1-6 Shi, Y. et al. JOC, 67, 2435 and JACS, 124, 8792; Page, P.C.B. et al. SL, 580; Armstrong, A. et al. JOC, 67, 8610; Denmark, S.E.; Matsuhashi, H. JOC, 67, 3479; Bartolini, O.; Fogagnolo, M. et al. JOC, 67, 5802. Oxone, K2CO3,DM.E/DMM,-10*C _-- t , . ~ ~/o,,.("~ O

R1 I

~'

O ~NR

47-93%

ee = 30-97%

II.F.1-7 Bonnet-Delpon, D. et al. EJOC, 3290; Burgess, K. JACS, 124, 11946; Saladino, R. et al. JOC, 67, 1323; Begue, J.-P. et al. TL, 43, 1001. R"~

H202"(NH2)2CO,CF3COCsF17 _-- R ~

(CF3)2CHOH

79-94%

II.F.1-8 Diaz, L.C.; Meira, P.R.R. TL, 43, 185; Harvey, R.G. et al.

JOC, 67, 6216. ?H

~

QTBS

Et .... MCPBA = :_. CH2C12,0~ Me Me

HO ~

OTBS E

t Me Me 96% ds - 19:1

II.F.1-9 Lygo, B.; To, D.C.M. CC, 2360. r ~ . A

aq NaOCI' Ph'Me' rt ~ R

Et

Ar

R

>90% conversion ee = 78-87 %

114

ORGANIC SYNTHESIS--2003

I.F.I-10 Adam, W. et al. JOC, 67, 259; Tomioka, K. et al. H, 58, 71; Arai, S.; Shioiri, T. et al. T, 58, 1623. (

~

Ph R-OOH, KOH, cinchona R

deriv.

H20/Vh-Me

84-99% ee = 30-98 %

I I . F . I - l l Lacour, J. et al. TL, 43, 8257. "Effect of the Medium on the Oxaziridinium-Catalyzed Enantioselective Epoxidation." II.F.2

Hvdroxvlations

II.F.I-1 Bonin, M.; Micouin, L. et al. JOC, 67, 3522; Chan, K.S. et al.

JOC, 67, 2769. ~N

,'R R

Catechol borane, (S,S)-BDPP H O ~ I ~ t [Rh(cod)Ci]2,'DME, -50~ ~

"R

N"R 49-90% ee = 60-84%

II.F.2-2 Fokin, V.V.; Sharpless, K.B. AG(E), 41, 472; Kim, Y.G. et al. TL, 43, 7209; see also: Song, C.E. et al. OL, 4, 4685; see also: Donohoe T.J. et al. JOC, 67, 7946; Cristea, I. et al. TA, 13, 915; Mehta, G.; Pallavi, K. CC, 2828.

~

O2N

CO2Me OsO4' NMO, H20/tBuOH ~'~

~ Me

NHTs

CO2Me O2N ~ " 75% ee = 70%

II.F.2-3 Hayashi, T. et al. JACS, 124, 1584. 1. HSiCl3, [PtCI2(C2H4)]2 2. HSiCI3, [VdCl(n-C3Hs)]2,1ig. A~ Ar .... -~ 3. H202, KF, KHCO3 lig. =

~.

OH

OH

ee = 94-98% F3

OXIDATIONS

115

II.F.2-4 Vidari, G. et al. TA, 13, 1245; Dominque, R.; Roy, R. TL, 43, 395; Bonini, C. et al. TL, 43, 3813; Choudary, B.M. et al. JACS, 124, 5341; Chapleur, Y. et al. JOC, 67, 7275; Walsh, P.J. et al. JACS, 124, 10272.

EtO2C,,,,

~

,,,

Eto2c~ = i~

AD-mix-~

H20/tBuOH, 0*C,

22h

A

f

TMS

TMS

II.F.2-5 Brown, R.C.D. et al. A G(E), 41, 3479.

R~~R

1 KMnOa,,cinch~ O

_

_r.

-

OH 91% ee = 88%

OH

~

CH2C!2' "600C

-

~OH

R1

OH O 19-52% ee = 65-80 %

I!.F.3 Other Oxidative Additions to C-C Multiole Bonds _

II.F.3-1 Demir, A.S. et al. TA, 13, 601; see also: Clennan, E.L. et al.

JOC, 67, 3975.

Me~-~ R*

tw, 10 2 CH2C12

~

0

R*

58-76%

I.F.3-2 Raghavan, S.; Nangia, A. et al. JOC, 67, 5838. ~) Me R O Me Br p h t ~ NBS H20/Ph'Me ~ P h ~ ~ R .

bH 75-90% anti:syn = 19:1

I.F.3-3 Ferraz, H.M.C.; Silva, L.F., Jr. S, 1033.

Th(NO3)3

e

AcOH, rt 63-71%

116

ORGANIC SYNTHESIS--2003

I.F.3-4 Khan, F.A. et al. JOC, 67, 3783. Meo~Mex

X

R NaIO4,RuCI3"3H~. ~=

I

R1

Meo~Me.x

H20/MeCN,0*C

R

H

R1 62-95%

II.F.3-5 Itoh, A. et al. SL, 522.

[IV,12,FSM-16

Ar'~

....

iPrOH, rt

12-87%

I.F.3-6 Donohoe, T.J. et al. JACS, 124, 12934.

R~O~O

K2OsO2(OH)4 ,BuOCI ~.~R~I ?

R1NH2

'

'

~--~

NaOH,PrOH

O

HO 51-63% II,G, PhenQl-Ouinone

Oxidations

II.G-1 Pettus, T.R.R. et al. OL, 4, 285. IBX DMF 20-99% II.H.

Dehvdro~enations

II.H-1 Srinivas, G.; Periasamy, M. TL, 43, 2785; Cossy, J.; Belotti, D. OL, 4, 2557; see also: Hayashi, M. et al. OL, 4, 3955. ~RR 1 NRR1 R R"

~

R2 ~R3

TiCI4, TEA ' CH2Ci2,0~

.

R R"

~

R2 ~R3

67-84%

OXIDATIONS

117

II.H-2 Li, X.-C.; Wang, Y.-L.; Wang, J.-Y. JCR(S), 540; Wang, Y.-L. et al. SC, 32, 3285. H NaNO2, NaHSO4.H20, SiO2 Ar.-N,N,.Ar , H Me2CO, rt - Ar"I~N"Ar

82-95%

II.H-3 Shibasaki, M. et al. TL, 43, 3621.

. .

"

Na2PdCi2,TBHP. H H20/AcOH

"

~O~p " . 54%

II.H-4 Nicolaou, K.C. et al. AG(E), 41, 993, 996, 1386 and JACS, 124, 2245.

R ~

R1

DMSO,rt

~

~ l . . OMe

R ~

R1

43-96%

o II.H-5 Dowden, J. et al. TL, 43, 6561.

lI.l Other

Me02%

Me02~

BzO OBz

BzO OBz 61%

OxidatiQns

II.l-1 Suda, K. et al. CC, 2570; Antoniotti, S.; Dunach, E. CC, 2566. R~IR1

Fe(Epp)OTf ._ ~~[~RIO

dioxane,reflux

O

85-95%

r

118

ORGANIC SYNTHESISm2003

II.I-2 Lee, J.C.; Ku, C.H. SL, 1679; Fell, J.D.; Heathcock, C.H. JOC, 67, 4742. ~ 1. HDNIB,MeCN,8 0 ' C M e O 2 ~ j ~ ~ CO2Me ~a 2. Oxone, Ts-OH, H20/MeOH, 65"C

80-92% II.I-3 Bjorsvik, H.-R. et al. TL, 43, 4985 and JOC, 67, 7493. M e O - - ~ - ~ O O2' tBuOK'tBuOH'80.C " M e ~ C O 2 H / Me ~ / MeO O 2 N ~ NOz MeO 78% II.I-4 Troast, D.M.; Porco, J.A., Jr. OL, 4, 991. M N.~H Me .,,Me HO2C""~" Pb(OAc)4,Cu(OAc)2 Mev~~~O pyrFFHF Me~~~~t~O

Me~

0

76% O

II.I-5 Fukuyama, T. et al. CL, 122. R2RIN~CN MCPB,,A, aq KOH ~ R2R1N~O R HzO/MeCN R 0-89% II.I-6 Sudhakar, S." Luh, T.-J. JOC, 67, 6860. # AIL~ ROH'PdCl2'n~176 Me2HS

SiHMe2

EtOH,rt

~ "AI ~ ' Me2S iMe2 OR OR 65-92%

III REDUCTIONS

III.A.

C=O

III.A.1

Reductions

Aldehvdes.

Ketones

-~

Alcohols

III.A.I-1 Zhao, G. et al. TA, 13, 2095; Procopioli, P.A. et al. JCS(P1), 2237; Costa, P.R.R.; Pinheiro, S. et al. OPP, 34,492; Kamal. A. et al. TA, 13, 815; Takabe, K. et al. JCS(P1), 707. R ~

SO2Ph

NaBH* TMS'Cl, THF, reflux ........ .. R H " . ~ SO2Ph ~~~p

96-99% ee = 56-97 % Ph

III.A.1-2 De Nino, A. et al. TL, 43, 7441; Luthman. K. et al JOC, 67, 9186. ~ ~qR2R3 LiBH4, CeCl3 ~H ~R2R 3 |"Q H NR2R3 R~ ' ' ~

R1

THF, -20 ~C

"" R1 + R~ 19-96 % s y n : a n t i = 1-13.3:1

R'" ~

R1

III.A.1-3 Hofmann, R.V. et al. JOC, 67, 1045; Ghosh, A.K. Lei, H.

JOC, 67, 8783.

LiAI(OtBu)2H PGHN R1 THF"5~ 71-76 % syn:anti = 4-18:1

LiA i(OtBu)3H PGHN

R 1 EtOH"78~

PGHN R1 81-88 % anti:syn - 19:1

I I I . A . 1 - 4 0 r d o n e z , M. et al. TA, 13, 559.

~

NBn 2

~ P(OMe)2

catechol borane THF, -20~

119

P(OMe)2 NBn2 69-89% dr - 9-49:1

120

ORGANIC SYNTHESIS--2003

III.A.1-5 Firouzabadi, H.; Iranpoor, N.; Alinezhad, H. SC, 32, 3575.

Zr(BH4)2Ci2(DABCO)

R-CHO . . . . . . . . . . . . iPrOH

= R-CH2OH 80-97%

III.A.1-6 Levacher, V. et al. CC, 2256. "Atropisomeric Quinolinium Salt Promoting the Access to Both Enantiomeric Forms of Methyl Mandelate: A Versatile NADH Mimic." III.A.1-7 Ponzo, V.L.; Kaufman, T.S. SL, 1128; Kanth, J.V.B.; Brown, H.C. T, 58, 1069; Hanessian, S. et al. CJC, 80, 885; Pelinski, L. et al. TA, 13, 1241; Basavaiah, D. et al. TA, 13, 1125; Dixon, R.A.; Jones, S. TA, 13, 1115.

R~~O

BH3.SMe2,Ph.Me/CsH17OH R , ~ / ~ p (\h........~ - ' O H -

Me

~

~ ~ h

\x

n

//'Me 96-99% ee = 25-98 %

III.A.1-8 Ramachandran, P. et al. JOC, 67, 5315.

9

" BX THF. -78~ 2

Ph

.o2

o. Ph 75-90%

ee = 27-99%

III.A.1-9 Cho, B.T. et al. TA, 13, 697; Delogu, G.; Patti, A. et al. TA, 13, 891; Schore, N.E. et al. JOC, 67, 8086; McMorris, T.C.; Staake, M.D. JOC, 67, 7902; Keuthe, J.T. et al. JOC, 67, 5993; Matos, K. et al. JOC, 67, 2970; Gomez, M.; Bonnet, M.C. et al. JOM, 659, 186. S-4-MePh

THF,rt _~ ~ / S . 4 - M e P h Ph_

91-98 %

ee = 73-99%

Me III.A.I-10 Nishiyama, Y.; Sonoda, N. et al. JOC, 67, 5696. R~O Bu3SnH,AIBN, TMS-SePh_. R ~ O T M S R1

Ph-H, 80~

R1 12-86%

REDUCTIONS

121

I I I . A . I - l l Yeung, C.; Chan, A.S.C. et al. JOC, 67, 7908; Bujoli, B. et al. JOC, 67, 8191; Lemaire, M. et al. TA, 13, 1141; Li, Y.; Izumi, T. JCR(S), 567; Bolm, C. et al. OL, 4, 2265; Ravasio, N. et al. TL, 43, 943; Balker, A. et al. CEJ, 8, 1430.

R--~

H2,tBuOK,iprOH . R - - Q Ml~_q" ~

O

Me

..,,OH

r2 Ha

MeO~

Me

xPh

90-99%

\ r~.,

ee = 93-99%

--2 OMe

(similar reduction with Ir catalyst)

III.A.I.12 Tao, B.; Fu, G.C. AG(E), 41, 3892; Dieguez, M. et al. TA, 13, 83; Lipshutz, B.H. et al. OL, 4, 4045. R~O

[Rh(cod)CI]2,MesPhSiH2, THF, rt_

"

Me

{, Me"~ Ph~P

R~OH

74-99% ee = 72-99%

Me

Me

III.A.I-13 Adolfsson, H. et al. CC, 2046; Wills, M. et al. JCS(P1), 416; Failer, J.W.; Lavoie, A.R. OM, 21, 2010,3493; Faller, J.W.; Crabtree, R.H. et al. OM, 21, 3596; Kim, G.-J. et al. TL, 43, 8059; Nyori, R. et al. JACS, 124, 6508; Ito, M. et al. JCS(P1), 2833; Genet, J.-P.; Marinetti, A. et al. CEJ, 8, 3327; Brunner, H. et al. TA, 13, 37. R~O Ar

[RuCl2(P-cymene)]2KOH, iPrOH Boe

:

q'r

-" HA1 OH

R~.,,,OH Ar 65-99% ee = 92-96 %

N

III.A.1-14 Nguyen, S.T. et al. AG(E), 41, 1020; Lin, C.-C. et al. OM, 21, 2066. ~o + M e y O H AlMe3, r t = ~Ph-Me, ./~ R.~..,,OH Ar

Me

Ii "T "1

~

on Oa

Ar 30-99% ee = 8-80%

122

ORGANIC SYNTHESISm2003

III.A.I-15 Kamiya, I.; Ogawa, A. TL, 43, 1701. R~O

Bu2SnH2,Pd(PPh3)4

R~OH

Ph-Me, rt, 3h

R1 54-95%

R1

III.A.l-16 Deng, J.-G. et al. JOC, 67, 5301; Ikariya, T. et al. JOC, 67, 1712; Wills, M. et al. SL, 263; Cossy, J. et al. OL, 4, 1263.

R~O R1

[RuCi2(cymene)]2, l i g . .dendritc. HCO2H, TEA

, R~,,OH.. R1 67-99%

ee = 45-99 %

III.A.l-17 Matsuda, T. et al. TA, 1 3, 971; Nakamura, K.; Yamanaka, R. TA, 13, 2529; Dehli, J.R.; Gotor, V. JOC, 67, 1716; Yadav, J.S. et al. JOC, 67, 3900; Mikolajczyk, M. et al. JOC, 67, 7872; Botes, A.L.; Frejd, T.; Gorwa-Grauslund, M.F. et al. JCS(P1), 1111; Buisson, D. et al. TA, 13, 579; Kim, M.-J.; Park, J. et al. JOC, 67, 9481.

R~O

R1

Geotrichum . . . . .candidum ..

NAD+,iprOH, MES buffer

~ R~..,,OH

R1 34-97% ee = 94-99%

III.A.l-18 Porta, O. et al. EJOC, 3326.

R~O Ar

.TiCI3,NH3 R ~ O H H20/MeOH Ar 58-99%

I I I . A . l - 1 9 Lebreton, J. et al. T, 58, 7381.

(+).DIP-Ci THF, .30~ 50.83%

ee = 89-96 %

III.A.1-20 Hekmatshoar, R. et al. M, 133, 195.

R~

Zn'aqNH4CiR ~~~_( . THF R OH 90-97%

REDUCTIONS

123

III.A.1-21 Yong, K.H.; Chong, J.M. OL, 4, 4139. CF~O ipr2Mg . CF~..,,OH Iv

BnH~~~.~ Vh ~

Ar 84-95%

R:S - 1.64:1-1:49

u .O

~

III.A.1-22 Keck, G.E.; Truong, A.P. OL, 4, 3131.

-o

MeOH/THF,0~

~ -

~

"OH

84-99% syn:anti = 4.26-9:1

III.A.1-23 Szendi, Z. et al. ST, 67, 31. ,,,.~n

"'" H

O

,

,,

n

H2NNH2,KOH ~~'-1"""

oJ' o

O H

87%

H

III.A.2 Acid~. Esters. Amides -~_Aldehvdes III.A.2-1 Fukuyama, T. et al. S, 1121; Nagashima, H. et al. JOC, 67, 4985. --NHR1 Et3SiH,Pd/C NHR1 R~..~.. SEt Me2CO,. .rt. . ~. RACHO O 84-96% III,A.3 Acid~. Ester~ A m i d e s - ,

Alcohols

III.A.3-1 Chen, M.H. et al. OPP, 34, 665 J~-~ CO2H BH3"THF' BF3"Et20 R / ~ O H 24-97%

124

ORGANIC SYNTHESISm2003

III.A.4 Acids. Esters. A n h v d r i d e s

-+ Other

III.A.4-1 Chang, N.-C. et al. TL, 43, 3233; Chang, N.-C.; Tai, H.-M. et al. JOC, 67, 5044; Xia, Q.; Ganem, B. TL, 67, 1597.

1. Nail, THF 2. LiAIH4,THF 3. BF3.Et20, CH2CI2,0~

Bn

Bn 80-90%

III.B. C - N

Multiole _

III.B.1. Imine

Bond

Reductions

Reductions

III.B.I-1 Samec, J.S.M.; Backvall, J.-E. CEJ, 8, 2955.

R ~ N R 1 [Ru2(CO)4(g-H)(C4Ph4OHOCC4Ph4)]R~NHR 1 R2

iprOH/Ph-H, 70*C

R2 93-98%

III.B.1-2 Naito, T. et al. TL, 43, 4369; see also: Wada, M. et al. CL, 274.

N.1 Ar

NHR'

CH2C12,rt

Ar 48-99%

I I I . B . I - 3 0 h s a w a , A. et al. TL, 43, 3105. R1

+ R2.NH2

Sc(OTt')3,5~kMS, Ph-l-I,,rt EtO2~___.~COzEt

~ R 1NHR2 62-82%

H

III.B.1-4 Allegretti, M. et al. T, 58, 5669.

R~O Rl

+ R2-NH2

NH4CO3,Pd/C H20/MeOH, rt

R ~ . NHR2 R1 0-80%

REDUCTIONS

125

III.B.1-5 Lu, Z.-H.; Senanayake, C.H. et al. TL, 43, 8617. "Novel Diacid Accelerated Borane Reducing Agent for Imines." III.B.2. Reduction

of Heterocvcles

III.B.2-1 Donohoe, T.J. et al. SL, 331; Donohoe, T.J.; House, D. JOC, 67, 5015. ,ff~

CO2iPr ..1.Na, NH3or Na, C!oH8 -

N,~_~co2ipr

2. R-X

..~

CO2ipr

H ] ~ ~ ~ co2ier 56-99%

III.C. Reduction of Sulfur Compounds III.C-1 Yoo, B.W. et al SC, 32, 63. 17,,,.r Cp2TiCI2,In THF, rt 0-93% III.C-2 Iranpoor, N.; Firouzabadi, H.; Shaterian, H.R. JOC, 67, 2826. R..R~O + ( ~

NBS,Br2CH2CI2, TABCOrtor

R"~R+ 1

I~

89-96% !II.D. N-O

Reduction

III.D-1 Sandhu, J.S. et al. TL, 43, 1877.

?

78-95% (pyridine N-oxidessimilarlyreduced)

R1

+ CH20

126

ORGANIC SYNTHESIS--2003

III.D-2 Chandrasekhar, S. et al. SL, 771; Selvam, P. et al. TL, 43, 8527; Yoo, B.W. et al. SC, 32, 2489; Rao, P.S. et al. SC, 32, 2849; Banik, B.K. et al. H, 56, 467; Smith, W.E.; Graham, D. et al. CC, 2514. R ~ N Sn, NH4CI,(Boc)2OorCICO2Et R ~ - ~ N 02 MeOH, (( ( 9 ~ HCO2R1 79-93% III.D-3 Balicki, R.; Maciejewski, G. SC, 32, 1681; see also" AlbanezeWalker, J. et al. TL, 43, 6747. R~~'~

HCO2NH4,Ra Ni MeOH

im

R----~

O

62-91%

III.D-4 Chandrasekhar, S. et al. SL, 349. "Efficient and Chemoselective Deoxygenation of Amine NOxides Using Polymethylhydrosiloxane." III.E. C-C Multivle Bond Reductions _

III.E.1. C=Q

Reductions

III.E.I-1 McEachern, E.J. et al. JOC, 67, 7890; Wai, C.M. et al. CC, 2388; Dyson, P.J. et al. JACS, 124, 9334. R

TFA, 60~

=

R 25-78%

III.E.1-2 Zhu, J. et al. JOC, 67, 3163. J ~ H2, Rh(PPh3)3CI J 02 R tBuOH/THF,rt 02

~ 12-98%

III.E.1-3 Fry, A.J. et al. T, 58, 4411. Ar~__ H3PO2,112 R/m\R 1 AcOn,reflux

R R1 0-99%

R

REDUCTIONS

12/

III.E.1-4 Pfaltz, A. et al. OL, 4, 4713; Buriak, J.M. et al. CC, 2518; Choi, M.C.K.; Chan, A.S.C. et al. TL, 43, 6803; Chi, Y.; Zhang, X. TL, 43, 4849; Zhang, X. et al. OL, 4, 4471; Weller, A.S. et al. OM, 21, 2856; see also: Belier, M. et al. TL, 43, 4977; Jia, G. et al. OM, 4, 1782; Weissensteiner, W.; Spindler, F.; Jalon, F.A. et al. OM, 21, 1766. e H2, CH2CI2, rt .:

R /'~~I~-~,~Ra

A

Ar~ R 87-99% conversiOnee = 0-97%

R x ~'K~,,,NRz

III.E.1-5 Zhang, X. et al. JACS, 124, 4952 and JOC, 67, 7618; Tang, W.; Zhang, X. OL, 4, 4159; Feringa, B.L. et al. JACS, 124, 14552; Lee, S.; Zhang, Y.J. OL, 4, 2429 and TA, 13, 1039; Lee, S. et al. AG(E), 41, 847; Chan, A.S.C. et al. TL, 43, 5541; Choi, M.C.K.; Chan, A.S.C. et al. TA, 13, 2519; Knochel, P. et al. AG(E), 41, 4708 and CEJ, 8, 843; Del Valle, J.R.; Goodman, M. AG(E), 41, 1600; Ohe, K.; Uemura, S. et al. TA, 13, 2155; Monsees, A.; Laschat, S. SL, 1011; Mezzetti, A. et al. JOC, 67, 5239; Pizzano, A. et al. OM, 21,4611; Boaz, N.W. et al. OL, 21, 2412; Jiang, Y. et al. TA, 13, 115; Hnaby, V.J. et al. T, 58, 7365 and S, 94

A/~~ AcHN

H2, [RuCl2(p-cymene)]2,EtOH, 50~ CO2R

[~.,~~

R OPPh2

A~_.~ AcHN

CO2R

ee = 80-99%

OPPh2

III.E.1-6 Paquette, L.A. et al. OL, 4, 937; Zhang, X. et al. OL, 4, 4495. OH H2, Nail

[Rh(NBD)(DIPHOS-4)]BF4 O~

'"

_

R ~ O ~

88% (80% conversion)

III.E.1-7 Ranu, B.C.; Samanta, S. TL, 43, 7405. R1 EWG1 NaBH4,InCl3 R1 /EWG1 R

EWG

MeCN, rt

-'- R EWG 57-96%

128

ORGANIC SYNTHESISm2003

III.E.1-8 Yue, T.-Y.; Nugent, W.A. JACS, 124, 13692.

~/"~O ..H2, Ir[(S,S)-BDPP)]MeOH/CH2CI2 ~ O H

H

92-99% ee= 67-95%

III.E.1-9 Bouzide, A. OL, 4, 1347; Venkateswaran, R.V. et al. JCR(S), 428.

H2,Pd/C,MgBr2 , R2 CH2CI2

R2 +

R2

71-98 % 2 8 - 8 8 : 1

III.E.I-10 Fan, Q-H. et al. JCR(S), 318.

'9 B ~

H2,[RuCl(BINAP)(cymene)]CliB ICO2H dendriticBINOL,H2,rt -'- ~ ~ _ . . CO2H Me 99% ee = 41-67%

I I I . E . I - l l Doris, E. et al. TL, 43, 2013.

R9

Cp2TiCI R2 MeOH/THF

~ R

1

aR2

56-89%

III.E.l-12 He, R.; Deng, M.-Z. T, 58, 7613.

R ~

NaBH4~CoCi2 CO2Me MeOH/IDMF

CO2Me 70-90%

III.E.l-13 Concellon, J.M.; Rodriquez-Solla, H. CEJ, 8, 4493.

R~ R CO2H SmI2'D20 _- D ~ . O2H 1 THF,rt R RI 61-85%

REDUCTIONS

129

III.E.I-14 Jurkauskas, V.; Buchwald, S.L. JACS, 124, 2892. ~

PMHS, CuCI, (S)-ToI-BINAP _

~

tBuOK, tBuOH/Ph-Me NR1

~R 1 89-95% dr = 9-24:1 ee = 91-94 %

III.E.I-15 Diequez, M. et al. JOC, 67, 3796. O2~ Me

R..

.=

~ H2, [Rh(cod)2]BF4, CH2CI2 CO2Me x.-CO2Me .: --_ R MeO2C " ~ X" 12.99 % conversion ee = 2-99% R1 RI R B

?

R1

III.E,2, C - C

; O ~

O

Rt

Rgductiolls

III.E.2-1 Trost, B.M. et al. JACS, 124, 7922; Faller, J.W.; D'Alliessi, D.G. OM, 21, 1743; Furstner, A.; Radkowski, K. CC, 2182. R.....~

R1

1. (EtO)3SiH, [CpRu(MeCN)3]PF6 CH2Ci2,0~ -~ rt . ~ 2. CuI, TBAF, THF

t~.~./R1 59-96%

III.E.2-2 Elsevier, C.J. et al. OM, 21, 1546. Ph

....

IVle

H2, THF, rt

R

Pd

R~

+ ph ~ M e

PI~ Me 28-87%

III.E.2-3 Parenty, A.; Campagne, J.-M. TL, 43, 1231. R

R1

LiAIH4,Cp2TiCI2 THF, reflux

~

/~

R1 54-75% Z:E = 1-18"1 R

130

III.F,

ORGANIC SYNTHESISm2003

Hetero

Bond

Reductions

I I I . F . 1. C-O-~ C - H III.F.I-1 Fleet, G.W.J. et al. TA, 13, 2667. 9 O MeCOEt,80*C -OTf

O 70%

III.F.1-2 Cain, G.A.; Holler, E.R. CC, 1168. R ~ O H TMS-CI,NaI R~ MeCN Ar Ar 1-99% III.F.1-3 Truesdale, L. et al. OS, 79, 93. ~ ~ O H OH

Ra Ni WtOH ~

Ph

OH

Ph 58% ee = 99%

III.F.1-4 Nutaitis, C.F. et al. OPP, 34, 332. ~ ~ NaBH4 ~~/.~ -'Arl TFA ~

l~-OH Ar

Arl

Ar 57-93%

III.F.1-5 Chandkasekhar, S. et al. JOC, 67, 9080. R~O PMHS,BPh3 R~R R1 CH2C!2,rt 1 65-90% III.F.1-6 Bolm, C. et al. S, 879. ~

Me

B~

~-~'~ Ph

CH2CI2'o~

Me Boc 50-71% "~Pho

REDUCTIONS

III.F.2.

131

C-Hal-+ C- H

III.F.2-1 Tokuda, M. et al. T, 58, 1491.

R~Br

I.tW,(EtO)zP(O)H,EtONa

Br

R~---~ Br 62-99%

E:Z = 1.38-199:1

III.F.2-2 Maleczka, R.E., Jr. TL, 43, 7087; Rahaim, R.J., Jr.; Maleczka, R.E., Jr. TL, 43, 8823.

PMHS, Pd(PPh3)4,Bn3N,DMSO/MeCN

R.X

or PMHS,PdCI2(PPh3)2,KF, THF

~

R-H 12-99%

III.F.2-3 Sajiki, H.; Hirota, K. et al. TL, 43, 7247; Rousseau, B. et al.

JOC, 67, 932.

R~~/~/CI

H2'Pd/C'TEA.

~

MeOH 99%

III.F.2-4 Fujita, K.; Owaki, M.; Yamaguchi, R. CC, 2964; Fort, Y. et al. OM, 21, 1554.

FG~ - - ~ / C I

CpRh(OAc)2"H2O, base

/~

FG ~

iprOH, reflux [similarly with Ni(0)]

III.F.2-5 Baba, A. et al. JACS, 124, 906.

R-Br

III.F.3. No Entries

C-S-~C- H _

NaBH4,InCl3 MeCN

R-H 83-95%

79-99%

132

ORGANIC SYNTHESISm2003

III.G.

Reductive

III.G.1.

Cleavages

Oxirancs

I I I . G . I - 1 Ahlberg, P. et al. JCS(P1), 1397. ( ..... ~ chiralLiamide, DBU _

~---

THF, -20"C

OH

57-96% ee = 16.96 %

III.G.1-2 Doris, E. et al. OL, 4, 1151; Concellon, J.M.; Bardales, E. OL, 4, 189; see also" Fuchs, P.L. et al. JACS, 124, 11093. Cp2TiCI THF

H

H 70%

III.G.1-3 Kim, Y.H. et al. JOC, 67, 9488.

~

R,~O~iSmX2 ~ ~ m O

~R1 71-93% 1-99:1

III.G.2,

N--O

Cleavages v

III.G.2-1 Pousset, C.; Larcheveque, M. TL, 43, 5257. R~NBoc

H2, Pd/C _--- R~..,,NHBo c

O~ P(OEt)2

EtOH

O~ P(OEt)2

64-77% III.G.2-2 Gowda, D.C. et al. TL, 43, 1329. Zn, HCO2H or CO2NH4 ~./. MeOH, rt x

X

INH2 t 2 80-95%

REDUCTIONS

133

III.G.2-3 Shipe, W.D.; Sorensen, E.J. OL, 4, 2063. PMP 1. SmI2, HMPA/THF, rt

PMP

2. Ph-SeX, rt 44%

III.G.3. Other Reductiv~ Cie~tvagfs III.G.3-1 Cho, C.-G. et al. TL, 43, 7463. Ag2CO3

iNBoc NH 2

DME, 80~

~-~NHBoc

=

70-95%

III.H. Reduction of Azides III.H-1 Mi, A. et al. SC, 32, 3279.

Zn, NI-I4C!

N3

R~

~ " NH2 87-98%

H20/EtOH

III.H-2 Wu, H. et al. SC, 32, 189. R-N 3

Sm, NiCI2.SH20

R-NH 2 75-90%

THF, 40~

III.H-3 Kamal, A. et al. TL, 43, 6861. R-N 3

FeCI 3, NaI MeCN, rt

R.NH 2 75-98%

III.H-4 Baskaran, S. et al. EJOC, 3740; Yoon, C.K. et al. TL, 43, 8735; see also" Reddy, P.G.; Baskaran, S. TL, 43, 1919; see also:, Chen, L.; Wiemer, D.F. TL, 43, 2705. R-N3

H2, Lindlar cat., (Boc)20 MeOH, rt

~

R-NHBoc 78-96 %

134

ORGANIC SYNTHESISm2003

I I I . H - 5 Kamal, A. et al.

TL, 43, 6629. aq HI

R-N3 ~

I I I . H - 6 Lindsley, C.W. et al. R-N3 +

lll.I. Other llI.I-1

rt

R.NH 2 80-98%

TL, 43, 4467. 1. THF, rt R-NH 2 ' C6F13 2. H20 , 60"C 80-92% 3. FluoroFlashTM SPE

Ph2

Reductions

Xi, F. et al.

TL, 43, 1395.

R-CN

1. PtO2, HCO2H, 1-120 9 2. H3O+

R-CHO 9-94%

I I I . I - 2 Khurana, J.M.; Kukreja, G. SC, 32, 1265. NaBH4, NiCI2 Ar-CN ~ Ar "/~NH2 + A ~ ~ " ' A r EtOH, rt, 5min 64-86 % H 3-11%

IV SYNTHESIS OF HETEROCYCLES

IV.A. Oxiranes. A~iridines and Thiiranes IV.A-I Metzner, P. et al. JOC, 67, 9083; Ishizaki, M.; Hoshino, O. H, 57, 1399; Arai, S.; Shioiri, T. et al. TL, 43, 833 and T, 58, 1407. NaOH, tBuOH/H20 Ar,,o R1 ~ --"

Ar-CHO + R

,,..~

R1 R

60-85% trans:cis = 2.2-50:1 ee (trans) = 37-90%

IV.A-2 Muller, M. et al. AG(E), 41, 634; Izawa, K.; Ikariya, T. et al. OL, 4, 4373. 1. HLADH, NAD+, EtOH CF__/ 2. DBu;H20/EtOHIrt ~ ~R 78%

ee = 9 9 %

IV.A-3 Aggarwal, V.K. et al. JACS, 124, 9964. NEt2 R-CHO,KOH Me Br" " EtOH, -50~

R'"~ NEt2 79-93% ee = 10-99%

IV.A-4 Curini, M. et al. EJOC, 1562.

~R1

+ N2CHCO2Et

Ln(OTf)3

="

R

1 ~

CO2Et

0-92 % % IV.A-6 Kowalski, G.; Pielichowski, J. SL, 2107. "A New Polyaniline-Based Catalyst for the Oxidation of Alkenes." 135

136

ORGANIC SYNTHESISm2003

I V . A - 5 Faber, K. et al. JOC, 67, 9115. ~~1~

El

bacterial ep~

hydr~

H

"

buffer

9

18-78% ee = 31-99 %

I V . A - 7 Siu, T.; Yudin, A.K. JACS, 124, 530. 'ONN

R2

\

H2 +

/

~

RI

R3

e', Et3NHOAc

"R4

MeCN, rt

O

PhtR~__~h" ~ ~

R 1 "17,4 42-93%

IV.A-8 Minakata, S.; Komatsu, M. et al. JOC, 67, 2101. ~,.

~O2R R2

Ph

r

R-SO2CI or R-COCi, CH2CI2, 0~

l~2?\..Ph r

N ,~R2 PI~ "R1 15-88% ee = 81-87%

or

R1

R1

37-70% ee = 24-90%

IV.A-9 Dias, H.V.R.; Lovely, C.J. et al. OM, 21, 1466; Scott, P. et al. JOC, 67, 3450; O'Brian, P. et al. TL, 43,723 and OL, 4, 1923.

Fs

R ~ R

1 [HB(3-CF3-5-R-pyrazole)3]CuC2H4) R ~ R

PhI=NTs, MeCN, rt

1

17-99 %

IV.A-10 Xu, J.; Jiao, P. JCS(P1), 1491; Yang, K.-S.; Chen, K. OL, 4, 1107. r +

2 NO2" NH2

"

r 15-99%

IV.A-11 Crousse, B.; Bonnet-Delpon, D. et al. CCC, 67, 1359; Aggarwal, V.K. et al. JOC, 67, 2335. CF

+ NzCHCOzEt N,, R

Yb(OTf)3 or BF3.Et20 CF3...~..~... . . . . . ~ . - - - - CO2Et "R" 64-90 %

SYNTHESIS OF HETEROCYCLES

137

IV.A-12 Uneyama, K. et al. TL, 43, 2069; Higashiyama, K. et al. H, 58, 85; Hou, X.-L. et al. JOC, 67, 8097.

,Ar

TMS"~'Ar

Me2S(O)=C.2 ,

~ R F

~R

DMSO

CHF2

32-92%%

IV.A-13 Chemla, F. et al. EJOC, 1385. 1. ZnBr2, THF C/

.rz. NBn

/

21-LAH'THF' "80~ ~

R

12-98%

I

IV.A-14 Yoshimura, T. et al. TL, 43, 5841.

R1

R2 7 2 ~ . . - N O 2

R~R3

CIS" v

~

MS

02

NO2

Ph3S-N . CH2CI2,-30~ 7-71%

IV.A-15 Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P.A. JOC, 67, 4972; R

~]

-'CO2R~ R202CNHONs,CaO CH2CI2,0~

.. ~ - ~ C O 2 R* _- K N.COR2 ~ R~ 78-92% de = 96-99 %

IV.A-16 Che, C.-M. et al. OL, 4, 4507; Dauban, P.; Dodd, R.H. et al. OL, 4, 2481; Guthikonda, K.; Du Bois, J. JACS, 124, 13672; Padwa, A.; Stengal, T. OL, 4, 2137. PhX(OAc)2,Rh2(OAc)4,A1203 _02

2

CH2CI2, 40~

02 74-97%

138

ORGANIC SYNTHESIS--2003

IV.A-17 Maycock, C.D. et al. TL, 43, 4329; Dalla, V. et al. T, 58, 8425; Somfai, P. et al. T, 58, 5979; Xu, J. TA, 13, 1129. ~ I R-NH2,Cs2CO3 phenanthroline

Ph-Me2,95~

~

N-R

87-96% IV.A-18 Inanaga, J. et al. TL, 43, 2735. MeO" H [

La(Oipr)3 ~

R ~ R

1

THF, rt

, R1 59-99%

IV.A-19 Brel, V.K. S, 1829. R__/ -'=\/-"CI NaN3 . R X~~O~r (EtO)zPxxO Me DMF/Ph-H,80~ (EtO)2 48-61% IV.A-20 Palacios, F. et al. JOC, 67, 7283. TSO..~ ~ Ph-H, 50~ ~.N R ~ , , ~ PPh2 = R.,,-<~..,,PPh2 ~ ~ 66-89% IV.A-21 Yadav, L.D.S.; Kapoor, R. S, 2344. R ~I R I X + (EtO)2PS2H t.tW,NaBH4.AI203 R1 81-94% trans:cis = 8-24:1 IV.A-22 Mirkhani, V. et al. SC, 32, 621. ,~ (NH4)s[CeWloO36]'20H20 NH4SCNor NH2CSNH2,MeCN,A A-~ 88-98% A B B-~ 81-98%

SYNTHESIS OF HETEROCYCLES

IV.B. Oxetanes.

139

Azetidines and Thietanes

IV.B-1 Xu, J.-H. et al. JCS(P1), 345. "Photoinduced [2+2] Reactions (The Paterno-Buchi Reaction) of 1-Aeetylisatin with Enol Ethers." IV.B-2 Couty, F. et al. TL, 43, 4633.

,9

Ci..~R 2 '~" ~) E LHMDS : R N" "P(O t)2 THF,-78-~ 0~ R1

R~, [/P(OEt)2 R*"~L-N" R1 30-75

IV.B-3 Yadav, L.D.S.; Kapoor, R. S, 1502. R1 IxW,Nuc Nuc.~~R1

O

IV.C.

S..~(OEt) 2 S

"

1~" 77-92%

Lactams

IV.C-1 Cesare, V. et al. S, 1716. ~ R 1NHR2 Nail, 15-Cr-5 Br CH2C12,rt

~N-R 2 R'hl 55-98%

IV.C-2 Lectka, T. et al. JACS, 124, 6626; Lassalttta, J.M.; Llera, J.M. et al. AG(E), 41, 831; Delpiccolo, C.M.L.; Mata, E.G. TA, 13, 905; Gonzalez, J. et al. JCS(P1), 571; Hodous, B.L.; Fu, G.C. JACS, 124, 1578; Gonzalez-Muniz, R. et al. JOC, 67, 3953 and H, 57, 501.

EtO2C,,]~Ts +Ci~OR

M•h,

Ph-Me,-78~

BzO""~x~

OMe

Tsx EtO2C"' "" R 36-65% dr = 7-99:1 ee = 95-99%

140

ORGANIC SYNTHESISm2003

IV.C-3 Domling, A. et al. TL, 43, 6897; Malachowski, W.P. et al. JOC, 67, 8962. H2

SH + RI"CHO

N=__C

......... = MeOH, -15*C-rt

1

\R 2

36-69% IV.C-4 Basak, A.; Mandal, S. TL, 43, 4241; Schunk, S.; Enders, D.

JOC, 67, 8034.

2

Rh2(OAc)4_ CO2Et CH2Ci2,rt

O ~'CO2Et 50%

O

IV.C-5 Coates, G.W. et al. AG(E), 41, 2781. Re \ CO, [Cp2Ti(THF)]2[Co(CO)4] .

R

.

~R1

.

.

.

.

DME

gU R

~R1

35-99% ,,

,

IV.C-6 Morken, J.P. et al. OL, 4, 2537. Rx CO2R2 Ry + r _[Ir(cod)C!]2,1P(OPh)3 R ~ / O Et2MeSiH, DCE, rt R Me 58-80%

trans:cis = 5-20:1 IV.C-7 Prabhakar, S. et al. JCS(P1), 513. R2 11 R

t

t/~

~10

1. PhI(O2CCF3)2,CIt2C!2,rt 9

HN,.NHCOR4 2. BF3.Et20 R

~

O

Rr"'y--NHcoR R

3-91%

4

SYNTHESISOF HETEROCYCLES

141

IV.C-8 Lo, M.M.-C.; Fu, G.C. JACS, 124, 4572; Basak, A. et al. TL, 43, 5499; Alcaide, B. et al. JOC, 67, 7004.

I2 % I + "o'N~gl

CuCI,MeNCyz,MeCN,0~ -~

~lte.~.~r

" "

R2\/Ro~_N "

~

sl 42-91%

~ ~ ~

ee = 67-93%

IV.C-9 Zhu, J. et al. JACS, 124, 2560.

R-CHO + R1-NH2+ ? CI~R 3 + C--~ k2 ~

RI~,.~ NH4CI Ph'Me,0~

/R3

R~\N~.

OH

32-70% R"~ IV.C-10 Zard, S.Z. et al. OL, 4, 2707; Benati, L.; Spagnolo, P.; Strazzari, S. et al. OL, 4, 3079; Kamimura, A. et al. TL, 43, 6911; Scanlon, E.M.; Walton, J.C. CC, 2086; Grande, M. et al. JOC, 67, 8243.

R ~

R~m ~r-R lauroylperoxide \g2 S~IS DCE,reflux

R S~OEt

OEt

30-77%

IV.C-11 Liu, R.-S. et al. OL, 4, 4151.

Cp(CO)3~V"~-~ Ts,, ~ " , 1. BF3"Et20,-40~ R,,.~',~.. X 2.12

.

.

.

.

.

S

~.~ -

T

....~\ .... i 1~ 54-63%

.

IV.C-12 Rigby, J.H.; Wang, Z. OL, 4, 4289.

(

CCI Ph + 3~N~ NCO PhN.../

Ph~ Ph.Me2,8O:C = (

O H 52-70%

NHPh

142

ORGANIC SYNTHESIS--2003

IV.C-13 Chatani, N. et al. JOC, 67, 7014. +

~ N

CO, Ru3(CO)12 -tBu --Ph-M e, 160"C

.tBu

O

27-75%

IV.C-14 Glorius, F. et al. CC, 2704. ~

~

Ph 'tBuONa' 1 0 0~'*~D CM ,oV E'/ .~~o

---- f f ~ O ~ _ ~ l ~ 95% ee = 30 %

IV.C-15 Weinreb, S.M. et al. S, 2057. 1 1. Ph2Se2or Ph2S2,(EtO)2PCI "~ DIEA, CH2CI2,-50"C~rt 2. tBuOK, THF, -30~

rt

OH Ts

Rl~~t~XPh H 52-64%

IV.C-16 Hsung, R.P. et al. OL, 4, 2417; see also: Guibe, F. et al. T, 58, 7275; Hoffmann, T.; Gmeiner, P. SL, 1014; Bach, T.; Lemarchand, A. SL, 1302. PhCH=Rh(PCy3)2CI2_---

+ 77% 9

IV.C-17 Zhang, T.Y.; Zhang, H. TL, 43, 193, 1363; Harayama, T. et al. H, 58, 159, 175; Grigg, R. et al. TL, 43, 2601; see also: Beccalli, E.M. et al. T, 58, 6673. R2 2

R1

LiHMDS, Pd2(dba)2,THF, 68~

40-90%

SYNTHESIS OF HETEROCYCLES

143

IV.C-18 Knight, J.G.; Tchabaneko, K. T, 58, 6659. R O

CO, Pd(PPh3)2CI2 _ EtOH, 60"C

H

9

-

""Bn H 29-51%

IV.C-19 Amat, M. et al. AG(E), 41, 335; Chang, M.-Y.; Chen, S.T.; Chang, N.-C. T, 58, 5075; Basavaiah, D. et al. T, 58, 3693; Shimizu, M. et al. OL, 4, 2755; Konno, H. et al. H, 57, 1793; Passacantilli, P.; Piancatelli, G. et al. TL, 43, 4653; Snow, R.J. et al. TL, 43, 7553. Ph"'['"~OH + E t O 2 ~

_ Q~N~',O e

Me Ph-Me, reflux

NH2

" ~ "Pr

" CO2PrEt

CO2Et 54% dr = 5.67:1

IV.C-20 Nagao, Y. et al. SL, 480. HMe0~ _ ~ N

-R-

RI.X, pd(PPh3)4, ~ M uxlefr ~K2CO3T

O

~ H

F

MeR1

, O 38-77%

IV.C-21 Bumell, D.J. et al. JCS(P1), 217. ~OTBDMS o

1.- M 2 "esSQ2ONH2, BF3"EC t 2H2CI2, 0 ' E0toc2 0 ' r t _ (~~[/,,~.~OTBDMS

~

H

60%

IV.C-22 Compernolle, F. et al. T, 58, 4225. MSA, r,

144

ORGANIC SYNTHESIS--2003

I V . C - 2 3 Molander, G.A.; Bibeau, C.T. TL, 43, 5385. O (

\

Ph-Me2, reflux R

R

33-83% I V . C - 2 4 Davenport, R.J. et al. T, 58, 5761.

.__~'[ ~ N 3

..... Bu3N Ph2CH2, 190-+ 210~ 1-54%

I V . C - 2 5 Oda, K. et al. H, 56, 69.

A~[~',.NH2+ ~ C O 2

H

H

hv Ph.H

Me

H

33-40% I V . C - 2 6 Wu, M.-J. et al. JOC, 67, 5907. R

NaOMe

lid

MeOH/DMSO, 60~ O 30-77 % I V . C - 2 7 Golden, J.E.; Aube, J. AG(E), 41, 4316. Bn

3

Bn(~..._

_H

OeAl ,2 O

CH2Ci2,reflux -

~o 45%

O

SYNTHESIS OF HETEROCYCLES

145

IV.C-28 Jabin, I. et al. TA, 13, 563. ]~(le §

45-61% de = 12-99% IV.C-29 Hayes, C.J. et al. TL, 43, 6011. O Pd(ptBu3)2, MeNCy2,

dioxane, 100*C 62% IV.C-30 Shea, K.J. OL, 4, 2637.

~

Ph

Bu4NIO4

CHC!3, 0~C O

Ph 85%

IV.C-31 Burke, S.D. et al. OL, 4, 2273; Jackson, R.F.W. et al. JOC, 67, 4882. "Synthesis and Structure of Preorganized, C3-Symmetric Trilactam Scaffolds with Conveniently Oriented (S)-Acetyl Thiomethyi Appendages." IV.D.

Lactones

IV.D-1 Kennedy, J.W.J.; Hall, D.G. JACS, 124, 898; Lee, A.S.-Y. et al. TL, 43, 8489. R~/----B(OR)2 R3-CHO ~ R ~ O R1 ~ ,CO2R3

R2~1 "% 26-89% dr = 15-20:1 [also with allyl bromides]

146

ORGANIC SYNTHESISm2003

IV.D-2 Barbas, C.F., III et al. OL, 4, 4519; ~,,CHO CO2Et 1. L-Proline, THF, rt + iff~ . .. R N-PMP 2. Et2AICN, THF/Ph-Me, -78"C-~ rt

N..-PMP H

42-62% ee = 97-98 % ,

,

,

,

I V . D - 3 Lin, G.-Q. et al. SL, 927. CHO Ni(PPh3)2CI2,Zn, (S)'BINAP Ph-Me, 90~

"

X

48-97% ee = 43-98 % I V . D - 4 Katsuki, T. et al. TL, 43, 4481. Ph--~O

UHP' Zr'salen -- V h ~ o ~ CH2Ci2, rt O 68% ee = 87%

IV.D-5 Zhang, X. et al. JACS, 124, 8198; Yamamoto, Y. et al. JOC, 67, 2653. Rt il

[.~'x R1AgSbF6, [Rh(cod)Cl]2, BINAP O/

DCE, rt

~ . . ' ~ / -90-99% ee = 99 %

[similar reaction with Pd(0)] I V . D - 6 Sato, F. et al. TL, 43, 4237. TM

1. Ti(Oipr)4, iprMgCI, Et20

r" "oco Et 2. Mg, MeO., (CO. OBn

Bnq

-O~ -R

O 44-59%

SYNTHESIS OF HETEROCYCLES

147

I V . D - 7 Yao, Z.-J. et al. T, 58, 8805.

e_~~

1. AD-mix-ct, tBuOH/HzO 2. H2SO4, THF M 02Et 3. TBAF, THF

M

O 65%

I V . D - 8 Ma, S.; Yu, Z.

Rk1 / R

AG(E), 41, 1775.

R2

/ " " + \CO2H

~ Off--R3

R3 I ~

PdCI2(MeCN)2

R2

MeCN, rt O 61-92%

I V . D - 9 Saicic, R.N. et al.

.o.2

__/ R l S S r ~ O T M S + R/

TL, 43, 5411.

/~

~ic,~4

R'--~

o.f~

CH2C12,-60~ .20~ ~

I V . D - 1 0 Nagumo, S.; Akita, H. et al.

tt

-O-

-O

44-83%

JOC, 67, 6618.

SiO2, Hex, rt =-

T S ~ c o 2 M e

R1

R ~ ~ O ~

or AcOH, 70~

O 74-99%

I V . D - 1 1 Evans, D.A. et al.

OH O

OL, 4, 3379.

H

R

O~o~A r

2. TsOItoH20

49-65% I V . D - 1 2 Zanoni, G.; Vidari, G. et al.

JOG, 67, 6064.

---OH

....

"~, ....

C o ~ 1NaOH

2. Cu(OAc)2, 02, Pd(OAc)2 MeOH/MeCN

-

,.

60%

+

O ~ -

OH

30%

148

ORGANIC SYNTHESISm2003

IV.D-13 Brun, P. et al. TL, 43, 5301; Taylor, D.K. et al. JOC, 67, 5307.

CO2Me

Mn(OAc)3 ,. ( y ~

MeO2~

Ar + CH2(CO2H)2 R-CO2H, reflux

""Ar

34-60% IV.D-14 Movassaghi, M.; Jacobsen, E.N. JACS, 124, 2456.

/~ R

~

+ TMS --" 'b~ /O

BF3"Et20. R ~

CHzCI2,0"C

O

65-96%

ee = 99% IV.D-15 Igglessi-Markopoulou, O. SL, 1736.

1~

H COY

AcO

..vt"t32R2

Y

aqHCl _-- R MeOH,rt

50-81%

IV.D-16 Cho, C.S.; Shim, S.C. et al. JCR(S), 550.

~~[~

,OR

CHO R-OH,CO, Pd(PPh3)2CI2,PPh3 ~ ~ O Br

THF, 80"C

O

46-86% IV.D-17 Tanabe, Y. et al. CC, 2542.

R~'~

R

~ + (~OM Re TC i I4B ,1u3N ~ O R OMe CH2C12,-78~ rt

IV.D-18 Huang, X.; Zhou, H. OL, 4, 4419.

~

R

CuX2

CO2Et H20/MeCN'85~ 70-83%

R1 R2

33-77%

SYNTHESIS OF HETEROCYCLES

149

IV.D-19 Wang, P.G. et al. OL, 4, 3875; Buszek, K.R. TL, 43, 181; see also: Louie, J. et al. JACS, 124, 15188. R2

RZ ,PhCn-RuO2tP.(CY

R3

52-97% IV.D-20 Kitamura, T. et al. CL, 380; Bose, D.S. et al. TL, 43, 9195.

R---~ OH

+

,tI

Pd(OAc)2 TFA, rt

18.97%

CO2Et

O

IV.D-21 Kaye, P.T.; Musa, M.A. S, 2701; Nair, V. et al. OL, 4, 2821; Yao, T.; Larock, R.C. TL, 43, 7401; see also: Negishi, E. et al. TL, 43, 5673.

R•

CO2Me

//~',,.? "

R1

,, . . . . .

,

,

HX _

AC20, AcOH

Bn

61-94% ,

,

,

,

IV.D-22 Bhide, B.H. et al. JHC, 39, 623. 3M R2 Me H2SO4 or AICI3 ~ R R

-2~_ R

/~

R

~

y ~

O

;Me "~Me

A

O

R

O

35-50% IV.D-23 Rayabarapu, D.K.; Cheng, C.-H. JACS, 124, 5630. R3 3 R 2 ~ I t Zn, Ni(dppe)Br2 ~ R

R~.~OH R

+ I MeCN' 80~ CO2Me

R R 44-81%

O

150

ORGANIC SYNTHESISm2003

IV.D-24 Furstoss, R. et al. TA, 13, 1953. recombinent E. coU _~ Bn

O

O 85% ee = 96%

i,|

i

IV.D-25 Trost, B.M.; Chisholm, J.D. OL, 4, 3743. 1. [RuCl2(p-cymene)]2 ~ O E t

O

OH 2. CSA, Ph-Me 64%

IV.D-26 Hiroi, K. et al. OL, 4, 2361. MeCOEt, rt-80"C

_--- ~ O

~

Oil ]

" Cl-~cr~'-'/~l

88-99%

IV.D-27 Shiina, I. etal. TL, 43, 7535; Selles, P.; Lett, R. TL, 43, 4627; Danishefsky, S.J. et'al. JOC, 67, 7730; Kume, M. et al. JOC, 67, 9146. f ~ ' V "NO2 D M A P R - ~ OH

CH2CI2, rt Me O

75-92%

IV.E. Furans and ThiQ_ohencs IV.E-1 Hashimoto, S. et al. OL, 4, 3887; Muthusamy, S. et al. BCJ, 75, 801; Wills, M. et al. JCS(P1), 965; Brown, R.C.D. et al. CC, 2042. ~oO 2Me "CO2Me Rh2(S-PTTL)4 ~ . , , , A r r Ph'Me' "780C 79-89% cis:trans = 99:1 ee = 91-99%

SYNTHESIS OF HETEROCYCLES

151

IV.E-2 Wardrop, D.J.; Zhang, W. TL, 43, 5389.

,

TMS-C(Li)N2 _ THF,-78-* 0~ 65%

IV.E-3 Nair, V. et al. TL, 43, 5349; Smitrovich, J.H.; Woerpel, K. S, 2778; Angle, S.R.; El-Said, N.A. JACS, 124, 3608. ( ~iiPr3 O+

~

~

SnCI4

O O

-" CH2C!2,-5*C-rt

R~

62-91% IV.E-4 Liao, Y.; Fathi, R.; Yang, Z. et al. OL, 4, 2607; Yang, Z.; Fahti, R. et al. JOC, 67, 2365. R1 O2 R2

~/'~"'~~/

CO, CsOAc,Pd(PPh3)2Ci2

5

R2.OH,45~

R

R1 R

50-90%

IV.E-5 McDonald, F.E.; White, B.H. OS, 79, 27. R ~ (TEA)Mo(CO)5,TEA R~ "OH Et20

R ~ 45-92%

IV.E-6 Eibracht, P. et al. OL, 4, 289. 1 H

CO, H2,,[Rh(cod)Cll2,P Ph3 CH2C12,120~

47-82%

152

ORGANIC SYNTHESIS--2003

IV.E.7 Arcadi, A.; Cacchi, S. et al. SL, 453 and OL, 2409.

R.._~~O//H' CuI,Pd(PPh3)2CI2,TEA _-- R - - - ~ or Pd2(dba)3, ptBu3 THF or D M F i

|

,

ii

,|

i

,,,

'R 45-84%

-

IV.E-8 Yamamoto, Y. et al. JACS, 124, 764; Wipf, P.; Soth, M.J. OL, 4, 1787.

//~CHO

.Pd(OAC)2MeOH ~ R~~.~OMe

R L

13.66%

,,

IV.E-9 Venkataraman, D. et al. OL, 4, 4727; Dai, W.-M.; Lai, K.W. TL, 43, 9377.

~ ~

+~

[Cu(phen)(PPh3)2lNO3 _ ~ R1 Cs2CO3,Ph-Me,U0*C

H

R

62-96% R

[similarreactionwithPd(PPh3)CI2] IV.E-10 Lee, E.; Han, H.O. TL, 43, 7295; Oshima, K. et al. SL, 337.

(~n Br EPHP,Et3B,air ~3"~. ,/CO2Et Cloll2f.."t~O ~ ' ~ CO2Et Et0H,rt -- CloH2t'"" 85-90% cis:trans= 15-20:1 ,,

,

,,,

,,

,

....

I V . E - I 1 Yue, W.S.; Li, J.J. OL, 4, 2201.

~ I o ~

(Me3Sn)2' = P hP-d(PPh3' Mrefluex2)CI2 , 57-92%

IV.E-12 Liu, R.-S. ct al. JOC, 67, 3930.

//~

R1

TpRuPPh3(MeCN)CI, TEA R DCE,80~ '

R1 45-91%

SYNTHESIS OF HETEROCYCLES

153

IV.E-13 Wu, M.-J. et al. AG(E), 41, 4077.

tBlk~-~~

NaOMeor K2CO3

I I ~ / ~"OTBDMS v

O

MeOH, reflux

50-94%

IV.E-14 Schrock, R.R.; Hoyveda, A.H. et al. OM, 21, 409; Salter, M.M.; Sardo-Inffiri, S. SL, 2068; Zhang, X. et al. AG(E), 41, 3457; Charrault, L.; Michelet, V.; Genet, J.-P. TL, 43, 4757; Yanada, R. et al. TL, 43, 4585. R

~" R y O

' M~176176

R ~ ~-~,,,.. C6D6,rt

R conversion = 83-99% ee = 86-98 %

R

IV.E-15 Krause, N. et al. S, 1759; Ma, S.; Gao, W. SL, 65; Ma, S.; Xie, H. JOC, 67, 6575. R4 ~1

OH

AuCI3or HCI(g)or Amb 15 CH2C!2

R,,..f-'-~..,~R3 65.99% ds = 1-15.7:1

IV.E-16 Tanaka, K.; Harada, N. JCS(P1), 713. R OH ~'~~OH

X

_ HX

~ R

AcOH,0*C 62-97%

IV.E-17 Mioskowski, C.; Falck, J.R. et al. OL, 4, 1387. O~-CC13/ ~i~,~? R CrCI2,THFMn/TMS'CI- ~ R 20-87%

154

ORGANIC SYNTHESIS--20O3

I V . E - 1 8 Roy, S.C. et al. JOC, 67, 3242. ,,,,.O,~., Ar 1 ,\ / 1. Cp2TiCI, THF, 60 Hi ,.~---~.,, H ~ . . . At~..../,,,.O~ 2. I2, THF, 60 C

A1 .

.

1. Cp2TiCI, THF, rt 2. H20 +

85-96 % ,

,.,,

60-95 %

.,

,.,,

IV.E- 19 Moeller, K.D. et al. JACS, 124, 10101.

M~

e __ Me Et4NOTs, MeOH, THF

MeO~A... R

)

n

51-96% trans:cis = 1-10:1 IV.E-20 Lattanzi, A.; Scettri, A. SL, 942; Antonioletti, R. et al. T, 58, 8825; Kim, H.R. et al. SL, 1691; Knight, D.W.; Staples, E.R. TL, 43, 6771; Rosini, G. et al. OL, 4, 4451; Takikawa, H. et al. TL, 43, 1713; Brown, R.C.D. et al. JOC, 67, 8079.

~

R1

VO(acac)2,TBHP .

.

.

TFA, CH2CI2, 40~ H

R1

~

OH

-" o 59-85%

IV.E-21 Parsons, A.F. et al. CC, 1350. R~ R

~~~_~

.

C~ .I.

CO2Et R2

Mn(OAc)3 [bmin][BF4],40~

,

R•O2Et R2

38-87%

IV.E-22 Duffy, M.G.; Grayson, D.H. JCS(P1), 1555; Karikomi, M. et al. TL, 43, 1495; Diez, D. et al. TA, 13, 639. ( y ~ 1. DCC, C u C ! _ ~ ' ~ H R 2. TFA R 64-90% IV.E-23 Nagumo, S.; Kawahara, N. et al. TL, 43, 5333.

SYNTHESIS OF HETEROCYCLES

155

Me Me

Me

Pr

Pr

TFA, 70"C 86%

IV.E-24 Gribble, G.W. et al. JOC, 67, 1001; Sha, C.-K. et al. JOC, 67, 831.

~__.~~O SO2Ph

I'SBuLi' R-CHO THF"78*C=2.

~

O

3. BF3.Et20,HQ, THF

SO2Ph 52-70%

IV.E-25 Langer, P. et al. CEJ, 8, 1443, 917. 9

~1

2~

+

TMSO

R2

R4 OTMS

TiCI4

=

R3

CH2C!2,-78~ -, rt

R4

30-70% IV.E-26 Kamimura, A. et al. T, 58, 2605. MeO2C,,,I~O~,,

Bu3SnH,AIBN: R -" Ph-Me, 80~ ~SePh

MeO2C~,. ~,,O~..,:R2 59-99%

IV.E-27 Shaabani, A. et al. JCR(S), 381; Nair, V. et al. TL, 43, 2293. R

CO2R1

~O2R 1

+ O

§ Ill CO2R!

Ph-H, reflux=

I "CO2R1 Z O 73-84%

156

ORGANIC SYNTHESIS--2003

IV.E-28 Jiang, Y.; Ma, D. TA, 13, 1033; Jiang, B. et al. TL, 43, 665; Rault, S. et al. S, 753; Calter, M.A.; Zhu, C. OL, 4, 205; Calter, M.A. et al. OL, 4, 209; Makosza, M.; Judka, M. CEJ, 8, 4234; Vales, L.; Rein, T. JOC, 67, 7226

Me.~ j.O ~

R1

~R~~~

DBU

O + ( ~ S+Me2Br"

sO =M

~

1

8-68%

0

o

IV.E-29 Yavari, I. et al. TL, 43, 4503.

3

O

PPh3 _-Ph CHzCi2,rt Mef XOf -~Ph 74%

Pi~

h

IV.E-30 Boger, D.L. et al. JACS, 124, 11292. O

o I

Et Ph-Me2or TIBF,160-180*C R

t ~e].i v

"R

0-79% IV.E-31 Chiacchio, U.; Romeo, G. et al. JOC, 67, 4380. "Intramolecular Cycloadditions of ct-Allyloxy CarbonylNitrones: Stereoselective Synthesis of 3-Amino.2(5H)Furanones."

3

IV.E-32 Mukherjee, C.; De, A. SL, 325; Cabiddu, S. et al. S, 875 and T, 58, 4529.

R2 RI.~~ R

NEt2 LDA S,-Me THF,-78~

R

65-78%

SYNTHESIS OF HETEROCYCLES

157

IV.E-33 Padwa, A. et al. JOC, 67, 1595; Kel'in, A.V.; Gevorgyan, V. JOC, 67, 95. M ~ N M e Me AcO

DMTSF,TEA ~ ~ ~ M e CH2C!2or MeCN,-40~ - Me

O

40-99%

.

IV.E-34 Hoomaert, G.J. et al. T, 58, 3655. .... C

R

KH

~

THF, rt, 20rain

S C R

80-88% .

.

.

.

.

.

.

.

.

.

.

.

.

.

IV.E-35 Aoyama, T. et al. H, 57, 1313.

DME,-78~ -~ reflux

-

SR

21-42% IV.E-36 Kirsch, G. et al. TL, 43, 257; Rodinovskaya, L.A. et al. T, 58, 4273; Cava, M.P. et al. JOC, 67, 2453. R/~ ~ / " ~

1

1. K2CO2,DMF O 21Ph-NCS :

10

R-A~R 1 1. BrCHzCO2Et 2. K2CO3,DMF HN"-\ s CO2 I P f i 19-65%

IV.E-37 Wong, K.-T.; Chen, R.-T. TL, 43, 3313. C8HITq rOCsH17 CsH17Q. 1. BuLi, Cp2ZrCI2,THF 2. $2C12 TMS TMS

CsH17

49%

IV.E-38 Dallemagne, P. et al. S, 1091. "Facile Diastereoselective Routes to Highly Functionalized Cyclopenta[c]thiophenes as Useful Scaffolds in Medicinal Chemistry."

158

ORGANIC SYNTHESIS--2003

iV.E-39 Yue, D.; Larock, R.C. JOC, 67, i905.

E E+

CH2Ci2, rt

SMe

25-99%

IV.E-40 Rao, U.N.; Biehl, E. JOC, 67, 3409.

2

R1

1/2

3

R3 +

I

R4 Me2CO,CHzCI2,reflux

S

OAc

~

R4

Rs

18-56 %

IV.F P v r r o l e s , Iltdoles.

R~

etc.

IV.F-1 Grigg, R. et al. T, 58, 2627; Blazey, C.M.; Heathcock, C.H.

JOC, 67, 298; Pedrosa, R. et al. OL, 4, 2513; Coldham, I. et al. JOC, 67, 6181; Raj, A.A.; Raghunathan, R.; SC, 32, 3295; Gu, Y.G. et al. TL, 43, 955; Ruana, J.L.G.; Tito, A.; Perominco, M.T. JOC, 67, 981; Nyerges, M. et al. S, 1823; Olsson, R. et al. OL, 4, 3147; Lovely, C.J. et al. TL, 43, 1171; see also: Li, R. et al. SC, 32,935; see also: Hanessian, S.; Bayrakdarian, M. TL, 43, 967; Iwasawa, N. et al. JACS, 124, 11592. R

R (~.._N~o

+

HN,.R1

+Ar-CHO

Ph-Me, 100~ 24h ' ~A r ~ \ N ~ ...., ~ R~

43-88% IV.F-2 Carreno, M.C. et al. AG(E), 41, 2753; Filippone, P. et al. JOC, 67, 8178; Barluenga, J.; Pedregal, C. et al. JOC, 67, 648; Campos, P.J.; Sampedro, D.; Rodriquez, M.A. OM, 21, 4076.

R R ~~

+ a

Ti(Oipr)2CI2 ~ R ~ , . ~ . ~ ,/,,....( /'%. R2 R2 MeCN' "40oc a ~---l~I-I\ H2N (fS'.-. To! al (fS.....To1 50-68%

SYNTHESIS OF HETEROCYCLES

159

IV.F-3 Balme, G. et al. TL, 43, 9311; Bunce, R.A. et al. JHC, 39, 1049; Quideau, S. JOC, 67, 3425; Scott, T.L.; Soderberg, B.C.G. TL, 43, 1621. Ar-"~ ~O2Me ~ MeO2C~,~CO2Me _ ~ ~ CO2Me Ar-I + I + "A~r 1 NaB, Vd(PPh3)2Cl2 DMSO/THF ~',Nc/'~Ar 1 NH i Me Me 50-81% IV.F-4 Mann, A. et al. CC, 958.

Ph s

~}n

Ph

BF3"Et20,-78~

4.

'

,

45-93% IV.F-5 Ciufolini, M.A. et al. TL, 43, 5193; Suarez, E. et al. TL, 43, 5113. Y H

~.~N~Y H( ~

PhI(OAc)2 _._

~'~ "Z

(CFa)2CHOH 60-97%

IV.F-6 Haskins, C.M.; Knight, D.W. CC, 2724; Schlummer, B.; Hartwig, J.F. OL, 4, 1471; Night, D.W. et al. JCS(P1), 622; Hashihayata, T. et al. CPB, 50, 423; see also" Komatsu, M. et al. OL, 4, 2097.

TfOH

R<>R

2Me CH2C!2,0~

Ts

R1 ~ "CO2Me Ts 91-97%

IV.F-7 S krydstrup, T. et al. JOC, 67, 2411.

".

"

EtO2C

O

Smi2 z

tBuOH/THF,20~

-~

~ HN

EtO2C (other examples given)

I/ 86%

160

ORGANIC SYNTHESISm2003

IV.F-8 Stahl, S.S. et al. AG(E), 41, 164; Hong, S.; Marks, T.J. JACS, 124, 7886; Fraga, C.A.M. et al. TL, 43, 1607; Bytschkov, I.; Doye, S. TL, 43, 3715; Kim, Y.K.; Livinghouse, T. AG(E), 41, 3845; Mitsudo, T. et al.

JACS, 124,186.

Ph-Me2,80"C

Ts

Ts

87%

IV.F-9 Takasu, K.; Ihara, M. et al. JOC, 67, 6001; Basak, A. et al. CL, 710; Besev, M.; Engman, L. OL, 4, 3023; Quirante, J.; Bonjoch, J. et al. JOC, 67, 2323; Johnston, J.N. et al. OL, 4, 4197; Grigg, R. et al. CC, 768; Yan g, S.; Denny, W.A. JOC, 67, 8958.

/~ TsN I

Bu3Sn,AIBN /~.,oCO2Me ~ / h , ,. + Ts /Ph Ph'H,reflux=- T S ~ p h H MeO2C 40-63% 0-20% MeO2C

V.F-10 Gaertzen, O.; Buchwald, S.L. JOC, 67, 465; Kozawa, Y.; Mori, M. TL, 43, 111. tBu02

,

R2

~

CO2Bu NMe2

51-99%

IV.F-11 Ma, S.; Gao, W. OL, 4, 2989; Ma, S.; Jiao, N. A G(E), 41, 4737; see also: Shibata, T. et al. H, 57, 2261.

R1

R2 >

~

R-X,Pd(PPh3)6K2CO3 _-DMF,70~

Ts

R2

Ts 68-84%

IV.F-12 Narasaka, K. et al. CL, 784; and see also:CL, 144. CuBr.Me2S, LiBr ~ B r dioxane, 80~

R

39-86%

R2

SYNTHESIS OF HETEROCYCLES

161

IV.F-13 Blechert, S. et al. T, 58, 7503; Mori, M. et al. OL, 4, 3855; s e e also: Pyne, S.G. et al. SL 731; Begtrup, M. et al. SL, 1889; Nishida, A. et al. AG(E), 41, 4732. ( ) n ~~ R/N""

j OTBS

OAc

PhCH=RuCI2(PCy3)2 ( = CH2C!2

~

(similarly oxacylesprepared))

IV.F-14 Murphy, P.J. et al. TL, 43, 299. O2Me

~

Ill

di0xane r

CO2Me

RI~C

c "."

-

86-94%

O2Me

R ~ . N ~ , , ,CO2Me

PG 13-96% cis:trans = 1-25:1

(furans similarly formed)

IV.F-15 Demir, A.S. et al. T, 58, 9793; Campos, P.J.; Rodriguez, M.A. et al. TL, 43, 8811. R

t

tBuOK

RO ~ L ~

tBuOH/DMso. 8O~ -~ R " ~ N ~ M e R2 83-95%

IV.F-16 Kang, S.-K. et al. TL, 43, 6693. RuHCI(CO)(PPh3)3 R ~ y Ph-Me,reflux

.N

y 56-75%

IV.F-17 Aurrecoechea, J.M. et al. T, 58, 6211, 6837; Hashimoto, K.; Shirahama, H. et al. H, 56, 105. CO Et RRIN~./C02Et

1..,NH, Btn. MS

"N" PG

2. SmI2, tBuOH, -78~ -* rt

PG 47-61% cis:trans = 0.89-1.63:1

162

ORGANIC SYNTHESIS--2003

IV.F.18 Karoyan, P.; Chassaing, G. TL, 43, 253; Chemla, F. et al. EJOC, 3536; see also: Ong, C.W. et al. H, 57, 1303.

j--CN

C 1. LDA,THF,-78"C ph~ h~ "~MeCO2Bn 2. -78"C-~ rt 0*C "'"CO2Bn 3. ZnBr2, CuCN,LiCI, Ts-CN, p "Me 68% IV.F-19 Jacobson, M.A.; Willard, P.G. JOC, 67, 32.

e ~ / ~ NHTS 1. BuLi,THF/Ph-H,60~ M 3. TBAF,THF

--

/ Me ~N" ~

H 41.71%

IV.F-20 Smith, N.D. et al. OL, 4, 3537; Airaksinen, A.J. et al. JOC, 67, 5019; see also: Bullington, J.L. et al. JOC, 67, 9439.

Aff/.~,./Arl/H tBuONa,Ts-MIC A~-~ Arl/H DMSO H 39-91% IV.F-21 Katritzky, A.R.; Steel, P.J. et al. JHC, 39, 759; see also: Pinho e Melo, T.M.V.D. et al. JOC, 67, 4045.

1. PCI5

R ~ ~ " Bt 2. tBuOK H

3. BnO2CCH=CHR1

H 76-90%

IV.F-22 McNeill, K.et al. OL, 4, 435; Ferreira, P.M.T. et al. TL, 43, 4491; see also: Pollini, G.P. et al. S, 331. 2

~~O ~ H2N~ O+ 9

Ts-OH,MS Ph-Me' 170oc~

H N.~ 47.98%

,,,,

IV.F-23 Palacios, F. et al. H, 58, 89; Langer, P.; Freifeld, I. CC, 2668.

SYNTHESIS OF HETEROCYCLES

RR~Br

163

~-,,~CO2R 2

o ;.~'~'~

TEA

~ ' - ~ CO2R2

~h'~e, ix~176

~'~r

41-57%

,

t

IV.F-24 Fukuyama, T. et al. H, 56, 313. Ac

_

Cbz

/NCbz AIBN,H3PO2, TEA PrOH, 90~

~ H ~ E t

CO2Me Et

40-50% IV.F-25 Wang, J. et al. SL, 1913; Nakamura, Y.; Ukita, T. OL, 4, 2317. /..-OH R

Rh2(OAc)4 ff--~ Ph-H, reflux, 10rain " A ~ H

A Ts ,~

..O R

64-94%

,,,

IV.F-26 de Meijere, A. et al. SL, 619; Narasaka, K. et al. BCJ, 75, 1451. Ac

Ac~ Ac

R

+

~ Pd(PPh~), R1

THF, 65~

"

R 31-82%

IV.F-27 Nicholas, K.M. et al. OL, 4, 699; Penoni, A.; Nicholas, K.M. CC, 484.

,F 1

+ NO

R

R1

-

-

~

R It

21-53%

164

ORGANIC SYNTHESISm2003

IV.F-28 Pirrung, M.C. et al. SL, 143; see also: Wang, T. et al. JOC, 67, 2345. Br 1. Ph.Li,-78"C . . . . _

~

NO2

2. R-X

3. CH2=CHMgBr, DME, .40"C

R

37.57% ,

,

,

,

,

IV.F-29 Senge, M.O. et al. OL, 4, 3807; Gupta, I.; Ravikanth, M. TL, 43, 9453; Shi, D.-F.; Wheelhouse, R.T. TL, 43, 9341. "A Practical Synthesis of Meso-Monosubstituted, 13Unsubstituted Porphyrins." IV.F-30 Jackson, R.F.W. et al. JCS(P1), 733; Bedford, R.B.; Cazin, C.S.J. CC, 2310; Traveras, A.G. et al. JMC, 45, 3854; Duncton, M.A.J. et al. TL, 43, 7581; Grigg, R. et al. CC, 964. ~ ~ R

NHB~ .Pd(dba)3, . . P(Ph'Me)3, . . . Cs2CO3,.. ~ N

-Br R

v

Ph.Me, 100*C

..,,R Boc 63-82%

.

.

.

.

.

.

.

.

.

.

.

.

.

J

.

.

.

.

.

J

,,,

IV.F-31 Zard, S.Z. et al. CC, 2214. R ~ O S ~ OEt

R1

~ AIBN + H CO2Et he;t}Ph-cl, reflux S02Et

R

~

CO2H H 36-67%

IV.F-32 Takahashi, S. et al. TL, 43, 6197; see also: Zhu, J. et al.

AG(E), 41, 4291.

Et2NH, Pd(OAc)2,dppp ,

ill"~--xl.--"~ / /

\~R

,

THF, 40"C

H

10-42% ,

-

_

IV.F-33 Wang, K.K. et al. JOC, 67, 7797, 5412.

Ph-Mez, 138'C

.X 58-69%

SYNTHESIS OF HETEROCYCLES

165

IV.F.34 Knochel, P. et al. TL, 43, 4875; Le Strat, F.; Maddaluno, J. OL, 4, 2791. R ~ ~ O A e

H

iprMgCl, THF-10*~ r t

Ts

69-95%

IV.F-35 Fan, X.; Zhan, Y. TL, 43, 1863; see also: Cheng, Y.; MethCohn, O. et al. S, 2426. AI~~

_ SmI2_ = A ~ - ' N ~ A 3

THF, rt

r

H 56-76%

IV.F-36 Sugiura, M. et al. TL, 43, 5295; see also: Imamoto, T. et al. TL, 43, 2885. ~ ~ 1

1. 03, AcOH,CHela, rt

R._..t~CHO

R i C o o~(OEt)2 2. aqNanCO3

~,~--RNI~::::O R

73-99% IV.F-37 Bunce, R.A. et al. OPP, 34, 483. 2Et R

_~

Fe

=

AcOH H

75-88% IV.F.38 Kamijo, S.; yamamoto, Y. A G(E), 41, 3230; Dai, W.-M. et al. TL, 43, 7699; Hiroya, K. et al. TL, 43, 1277; Yasuhara, A. et al. CPB, 50, 143, 235.

~'~

NCO+

CuCI _ ~ [~ OCO2R1 .Pd(PPh3)4, THF, 100~

N

R COzR1 62-81%

166

ORGANIC SYNTHESISm2003

IV.F-39 Barluenga, J. et al. CEJ, 8, 2034. ~

>

Br

1. BuLi, THF, -110 to -40~

....

2.E +

:

vM e

cf

R

R

38-75%

IV.F-40 Dang, Q.; Gomez-Galeno, J.E. JOC, 67, 8703.

X

+ H2

X

R

DMSO, 25 or 98~

R 57.96%

IV.F-41 Ogasawara, K. et al. TL, 43, 93. ....OH 1. Ms-Cl, ...... TEA,CH2C!2 ~ t B u O 2 ~ . . , , / O A c tBuO2

2. CsOAc, DMF, 70"C

Bn

IV.G. Pyri0ines.

Bn 75%

O uinolines,

etc.

IV.G-1 Varlamov, A.; Kouznetsov, V.; Zubkov, F. et al. S, 771. O H ~.,,M

1. Ph-H or Ph-Me, reflux & . M e . ~ e ph/'~N+"%C7H15 2. Zn, aq AcOH, 60-65"C Phv~J'"~'IV" ;"C7H15 1O" H 37% IV.G-2 Palacios, F. et al. JOC, 67, 2131, 1941; see also: Nicolaou, K.C. et al. A G(E), 41, 1941. R2 +

I[ R~OR

LiCIO4rt --- ~ /1("OR5 5 Et20, R" y XR4

CO2R3 (similarly for 1,3-oxazines)

CO2R3 30-70%

SYNTHESIS OF HETEROCYCLES

167

IV.G-3 Snaith, J.S. et al. OL, 4, 3727; Carbonnel, S.; Troin, Y. H, 57, 1807; Quiroga, J.; Nogueras, M. et al. JCS(P1), 555; Ruiz, M. et al. TA, 13, 795; Patel, I. et al. TL, 43, 4931; Sengupta, S.; Mondal, S. T, 58, 7983; Risitano, F. et al. S, 116; Dallemagne, P. et al. S, 1740; Marko, I.E. et al. TL, 43, 6591.

R

~ ~ R

cone,HCI CH2CI2, -78~ v

Ts

Ts

60-86% dr = 4-49:1 (trans productswith MeAICI2in refluxing CHCI3) IV.G.4 Ding, K. et al. OL, 4, 3309; Lau, J.F. et al. T, 58, 7339; Lesma, G. et al. TL, 43, 7155; Kuethe, J.T. et al. TL, 43, 29, 3871; Chou, S.-S.P.; Hung, C.-C. SC, 32, 3119; Bailey, P.D. et al. TL, 43, 1067, 1071; Avenoza, A.; Peregrina, J.M. et al. JOC, 67, 598; Barluenga, J. et al. TL, 43, 8159; see also: Hsung, R.P. et al. OL, 4, 2017.

+ R-CHO + Ar-NH2

TMS

"":O",

R Ar 67-99%

IV.G-5 Paulvannan, K. et al. TL, 43, 203; Peng, S. et al. JOC, 67, 22. CH2C12,rt O

O

CO2H

1

R

IV.G-6 Heller, B. et al. JOC, 67, 4414. I !11 + N

hv, [CpCo(cod)]

Ph-Me,rt 49-90%

R1

60-80%

168

ORGANIC SYNTHESISm2003

IV.G-7 Giorgi-Renault, S.; Husson, H.-P. et al. OL, 4, 3187; Henichart, J.-P. et al. JOC, 67, 3502; Swenson, R.E.; Sowin, T.J.; Zhang, H.G. JOC, 67, 9182; Chi, D.Y. et al. JOC, 67, 7884; Yoon, N.S. JHC, 39, 291; Fujita, K.; Yamamoto, K.; Yamaguchi, R. OL, 4, 2691; Bonacorso, H.G. et al.S, 1037. r O I~[~~RH+ '~'r CHO +~ O

E t 0 H , reflux ~ R" 45-94%

IV.G-8 Noack, M.; Gottlich, R. EJOC, 3171; Gottlich, R. et al. EJOC, 1848; Helaja, J.; Gottlich, R. CC, 720; Wang, P.G. et al. TL, 43, 2339; Pandey, G.; Kapur, M. OL, 4, 3883; Kimura, M.; Tamaru, Y. et al. AG(E), 41, 2784; Ackermann, L.; Bergman, R.G. OL, 4, 1475. R3 R2

,

,

Bu4NI

~

R1 CHCI3,5.0"C

CI

2

~N~R 1 R

63-99% IV.G-9 Koike, T.; Takeuchi, N. CPB, 50, 484. MeOzC~ ~,. ~, h./~q,,, j.~,. ICO2Me I(~ ~L_''" ~'" +CMe ~@R MIMe + Me R O~Me

eHh~ Me 36-69%

20-37%

~

IV.G-10 Trost, B./Vl.; Machacek, M.R. AG(E), 41, 4693. ,-NO2 ~SiR3 iR3 RuCy(MeCN)3]+PF6" MezCO,rt

~

Rl~)n NHNs

~

PPh~h2p~"

Ns

68-90% de 76-94% ee = 84-91%

SYNTHESIS OF HETEROCYCLES

169

IV.G-11 Mori, M. et al. OL, 4, 803; Hoveyda, A.H.; Schrock, R.R. et al. JACS, 124, 6991; Hu, X.E. et al. OL, 4, 4499; Carda, M.; Marco, J.A. et al. T, 58, 1185.

CH2=CH2,CH2Ci2,reflux _ I PhCH=Ru(PCy3)Ci2(Mes2Imid)-

Ts

~ Ts 85%

(also synthesis of pyrroles)

IV.G-12 Nishiwaki, N.; Ariga, M. et al. CC, 2170; Kelly, T.R.; Lebedev, R.L. JOC, 67, 2197.

02

I

Me +

IR 1 +

NH4OAc MeOH, reflux

H 0-88%

0-97%

IV.G-13 Chen, L.-C. et al. H, 57, 1; see also: Horiguchi, Y. et al. CPB, 50, 253.

2

~ 1 N~

~ S2Et PIFA Me DCE

HTs

1

Ts CO2Et 25-87%

IV.G-14 Marinelli, F. et al. S, 1912; Hughes, D.D.; Bagley, M.C. SL, 1332.

//•Ar

Me~NH2

Nu-H, K2CO3 EtOH or MeCN, 80~

Me

60-95% IV.G-15 Bagley, M.C. et al. JCS(P1), 1663 and TL, 43, 8331.

2

2 Bronsted or

NH;

Lewis acid " R3

R3 14-95%

r

170

ORGANIC SYNTHESISm2003

IV.G-16 Hsung, R.P. et al. JACS, 124, 10435; Ciufolini, M.A. et al. JOC, 67, 4304; Ghosh, C.K. et al. JCR(S), 311; Li, Z.M. et al. JCR(S), 454; Hibino, S. et al. H, 57, 2081.

~,rH +

~

EtOAc,150"C -

""Pr

N+R2

P "" Ph OPG

h OPG 61-67% dr = 15.7-24:1

IV.G-17 Montano, R.G.; Zhu, J. CC, 2448. EtO2~ COzEt ~ "~ "OMe OMe

SPh

2:TFA,-780C "

" Sl'h

Bn ~ . . . . O

OMe 92% OMe

IV.G-18 Yadav, J.S. et al. T, 58, 7891 and TL, 43, 3853; Zhang, J.; Li, C.-J.; JOC, 67, 3969; Chen, R.; Qian, C. SC, 32, 2543; Perumal, P.T. et al. SC, 32, 99; Sabitha, G. et al. S, 409; Beaton, G. et al. OL, 4, 4411; Henichart, J.-P. et al. SL, 2077.

+ NH2

MeCN, rt

=

70-90% endo:exo = 1.5.24:1 IV.G-19 Curran, D.P.; Du, W. OL, 4, 3215; Jiang, B.; Si, Y.-G. JOC, 67, 9449; Iqbal, J. et al. TL, 43, 6485. 2 R~ ~ ~ O 1 Ag2CO3, Pd(OAc)2 O + ~ NC Ph-Me, rt

SYNTHESISOFHETEROCYCLES

171

IV.G-20 Zhang, H.; Larock, R.C. OL, 4, 3035 and JOC, 67, 7048, 9318. ~...~CHO 1. tBu-NH2,100*C Br_.

1

~

2. Pd(OAc)),.PPh3,Na2COa- ~ R~MI~, ituu

R 2 ( ~ J ' ~ R~ R 88-95%

IV.G-21 Dechoux, L. et al. JOC, 67, 7573. MeO2~ H O~

R

THF

CI + , h , , " U OH

.,,~CO2Me 1. BH3.Me3S " O ~' ~ <:n ' R

,,CO2Me

2. H2, Pd/C = ~"N" ' : "' R

H 69-89%

Ph'" 44-61% de = 88-90% IV.G-22 Muller, T.J.J. et al. TL, 43, 6907. OH 1. Pd(PPh3)2CI2,CuI, TEA, reflux

+

2. reflux,

/-'No

r~A 31-70%

3. NH4CI,AcOH,reflux

r

IV.G-23 Takahashi, T. et al. JACS, 124, 5059; Itoh, K. et al. CC, 1102. 2

,F

+ R4-CN

R

1. Et2ZnCp2,THF , 2. R2C-CR3, NiCI2(PPh3)2

[similar intramolecular reaction]

R4 27.81%

IV.G-24 Zhang, W.; Curran, D.P. et al. JACS, 124, 10443; see also: Huang, X.; Liu, Z. JOC, 67, 6731; Wu, C.-Y.; Sun, C.-M. SL, 1709. "Solution-Phase Preparation of a 500-Compound Library of Individual Pure Mappicine Analogues by Fluorous Mixture Synthesis."

172

ORGANIC SYNTHESIS--2003

IV.G-25 Rykowski, A. et al. CPB, 50, 463; Neunhoeffer, H. et al. S, 2532. }n Ph-Br, reflux' - ph

Ph

~

}n

SO2R

SOzR

27-98%

IV.G-26 Chandrasekhar, S.; Jagannadh, B. et al. TL, 43, 1885; Katritzky, A.R. et al. JOC, 67, 8224.

OH Bn...~K~

AICI3

R1

CH2CI2,rt ~ B

~

65-90%

IV.G-27 Alajarin, M. et al. S, 2393.

1. PPh3, Ph-Me,rt ,'"~N3 ,~,r 2. Ph2C=C=O,Ph-Me,rt 3. Ph.Me, 130~ 4. Pd/C, Ph-Me2,reflux

Ph 20-50%

IV.G-28 Vedso, P. et al. OL, 4, 257; Pawlas, J.; Begtrup, M. OL, 4, 2687. R.Li ~

~CN

~-N/

R

82-98% IV.G-29 Gross, S.; Reissig, H.-U. SL, 2027; Fan, X.; Zhang, Y. TL, 43, 7001; Wang, X.; Zhang, Y. SC, 32, 3617. R2 .f~.,,~2

y_._~~L,O~__R 1 R

SmI2 HMPA/tBuOH/THF'rt. ~ . L ~ , .

__R1 R

19-63%

SYNTHESIS OF HETEROCYCLES

173

IV.G-30 Cossy, J.; Pardo, D. et al. EJOC, 3543.

..---OH 1. MsCI, DCE, 0*C-~r t C,....~.,~ "'''CI 2. TEA, reflux Bn

Bn

67% IV.G-31 Kim, J.N. et al. TL, 43, 6209. ~

COzR~1. PhI(OAc)~12, DCE, 60-70~

R'--:~ H~ Ts

2. K2CO3,DMF, 120-130'C

~

cO2R~

" R--:~~.~ ~ 58-80%

IV.G-32 Stevenson, P.J. et al. CC, 444; Osborne, D.; Stevenson, P.J. TL, 43, 5469. b/Heh + Ac~ b~Ph

Ph-NH2,Y(OTf)3._ ~ N H A c ....MeCN, rt

-

"..w" "N "Ph H 91%

IV.G-33 Bouman, R.W. et al. JCS(P1), 58.

O

Vh-' u, 150~ 45-73% IV.G-34 Huang, Q.; Larock, R.C. TL, 43, 3557; Dai, G.; Larock, R.C. JOC, 67, 7042; Larock, R.C. et al. JOC, 67, 3437.

~

Bu+ 1~. R

R1

CuC'2.PdBr2. NaHCO3 02. DMSO.70"C

R1

R

0-97%

174

ORGANIC SYNTHESISm2003

Cho, C.S.; Shim, S.C. et al. JOM, 650, 65.

IV.G-35

R__. ~

N02

SnCI2.2H20, . . Bu3N,Ru(PPh3)4CI2R - - - ~ E t H20/Ph-Me, 180"C

22-85%

Pr

!V,H Pyran~, P vrones and Sulfur Analogues

IV.H-1 Huang, Y.; Rawal, V.H. JACS, 124, 9662.

TBS(~

/R[~ 1.iBuOH +

"21AcCI, -78"C

NMez

33-82%

O

,,,

IV.H-2 Trost, B.M.; Rhee, Y.H. JACS, 124, 2528; Mascarenas, J.L. et al. JACS, 124, 4218; Cutchins, W.W.; McDonald, F.E. OL, 4, 749.

Me....t~O--

RuCp[P(Ph.4.F)3]2,NaHCO~~t~;.. ~ v ~

Me,,, ~ O ~ O 73% 11:1

,

J

.

IV.H-3

.

.

.

.

.

.

.

Maddaluno, J. et al. JOC, 67, 8054.

~HO

=

y~OR

Ph-Me, 50"C, 12 kbar y

CO2Et OR

40-69% exo:endo = 99:1 IV.H-4 Jacobsen, E.N. et al. A G(E), 41, 3059; Dahl. R.; Dujardin, G. et al. SL, 952; Baldwin, J.E. et al. OL, 4, 3009; Pettus, T.R.R. et al. JOC, 67, 6911. TBS

a

+ NMe2

1BuOH

2. AcCI,-78~ O

33-82%

SYNTHESIS OF HETEROCYCLES

175

IV.H-5 Minami, T. et al. JOC, 67, 7303. "The First Synthesis of Phosphonoacrolein. Application to Diels.AIder Reaction a s H e t e r o D i e n e . " IV.H-6 Donohoe, T.J. et al. OL, 4, 3059. 1.03, CH2C!2,-78"C,DMS CO2Ar 2. CSA, Ph-Me, A .

.

.

.

.

.

f~,~O

.

CO~Ar ~CO2 72-82%

IV.H-7 Portscheller, J.L.; Malinakova, H.C. OL, 4, 3679; Cox, R.J.; Williams, R.M. TL, 43, 2149; Kirschleger, B. et al. JCS(P1), 496; Finet, J.P.; Fedorov, A.Y. et al. TL, 43, 8245.

~

I

1. Pd2(dba)3,PPh3, 55~ 4"

"

E W G ~ R ~ 2. tBuOK,

THF/Ph-H, rt

EWG 64-95%

[also via Claisen rearrangement]

IV.H-8 Yao, C.-F. et al. H, 57, 1033; Sinou, D. et al. SC, 32, 3667; Hao, J.; Forsyth, C.J. TL, 43, 1.

NO2

OH

Ar /

neat, 40"C, l'Sh -

v

-O"

"Ar

75-99% IV.H-9 Takahashi, T. et al. JACS, 124, 1144.

R-"~

rCp2 + R

,~O2Et, O

CO2Et

BiCI3 =

R

CO2Et CO2Et 72-98% (pyridines and pyridazinesmade similarly)

IV.H-10 Snapper, M.L. et al. JACS, 124, 13390. ,R~~

PhCH=Ru(PCy3)2CI2,H2 R ~ CH2C!2,45-70~ 46-65%

176

ORGANIC SYNTHESIS--2003

IV.H-11 Ding, K. et al. OL, 4, 4349 and JACS, 124, 10 and CEJ, 8, 5033; Cousins, R.P.C.; Stoodley, R.J. et al. TL, 43, 489; Feng, X.; Jiang, Y. et al. JOC, 67, 2122, 2175; Maruoka, K. et al. SL, 931; Jung, M.E.; Pontillo, J. JOC, 67, 6848; Barrero, A.F. et al. JOC, 67, 5461; Organ, M.G.; Wang, J. JOC, 67, 7847. 1. Et2Zn, Ph.Me, 25"C

Me TMS~

+ R-CHO 2. TFA

C ~ Br OH

34-99% ee = 58-98% IV.H-12 Nishiyama, S. et al. TL, 43, 291.; Li, C.-S.; Lacasse, E. TL, 43, 3565.

MeO"~f~~

/ ~ OH Cell, PPh3 Me

HO-""-,,,~oHH 6

THF

H

OH 43%

IV.H-13 Evans, D.H. et al. OL, 4, 423. R1 R

R1

R

TEA +

CN

O

EtOH, rt, 12h r

H

64-84%

IV.H-14 Barluenga, J. et al. JACS, 124, 9056. S I'BuLi'THF'0~ O ~ ~ 2. (CO)sCr=C(OMe)CH=CHR 3. C3HsLi, THF,-78~ -~ rt H " ~ n "~ R1

4. H3PO4

5. THF, 90~

~ ~I ~R1 69-82% ee = >98%

)n

SYNTHESIS OF HETEROCYCLES

177

IV.H-15 Hidai, M.; Uemura, S. et al. JACS, 124, 7900.

,

,

1R~

Ru2(Cp)2(la2-SR)CI NH4BF, DCE, 60"C

27-97% ,,,

i

IV.H-16 Yadav, J.S. et al. JCS(P1), 165. .Iff~"~CHO R-t~J'~.OH

+

Me

( R1 CH(OMe)3,Yb(OTf)3 --OR2 CH2CI2,rt

OR2 75-92%

,

,

i

IV.H-17 Bernard, A.M.; Piras, P.P. et al. OL, 4, 2565. PhS~~

TsOH Ph-H, reflux R

67-90%

R

IV.H-18 Kawamura, Y. et al. S, 2490. R.._~~Ar OB z

1. HTIBor PSDIB 2. NaOH

R1

R---~. 56-99%

IV.H-19 Liu, J.; Wong, C.-H. AG(E), 41, 1404.

OH

2..eoyxyribose- .Phosphate H aldolase

22-65%

IV.H-20 Loh, T.-P. et al. S, 937. ~ In(OTf)3 ~ R-CHO + CHzC!2, rt

R R

75-91%

178

ORGANIC SYNTHESISm2003

IV.H-21 Perumal, P.T. et al. T, 58, 10301; Yadav, J.S. et al. TL, 43, 4527; see also: Nakata, T. et al. CL, 148.

OH

~

+

)n

InCI3 or PPh3.HCIO4 MeCN, rt

R

H 83-93%

R

t~:13= 2.3-6.7"1 IV.H-22 Gopalan, A.S. et al. T, 58, 3737; see also: Sosnovskikh, V.Y.; Usachev, B.I. S, 1007; Kaye, P.T. et al. JCR(S), 321; Kim, Y.-W.; Brueggemeier, R.W. TL, 43, 6113.

i ~ Ph

tBuO2.C ~

LHMDS

L O ~ R THF, -78~ 4h 57-99% IV.H-23 Kuhnert, S.M.; Maier, M.E. OL, 4, 643; Ferraz, H.M.C. et al. JOC, 67, 4022; see also: Hosomi, A. et al. JOC, 67, 6082; Mali, R.S. et al. JCS(P1), 371; see also: Ma, S.; Gao, W. JOC, 67, 6104. Bn

OMe O f f ~ O ~ . "~]

~)Bn N-PSP,CSA

~f ""OH

CH2C12 SePh 60%

L

,,

,

,

IV.H-24 Duan, S.; Moeller, K.D. JACS, 124, 9368. S

S e', Et4NOTs, pyr-Me2 Me

MeOH/THF, rt OMe

Me

OMe 52%

SYNTHESIS OF HETEROCYCLES

179

IV.H-25 Floreancig, P.E. et al. OL, 4, 2489.

OH .

OMe O ~ %

.

.

.

.

.

.

~

Me

e

Me rri

Me Ar

-.Ar

46%

IV.H-26 Keck, G.E. et al. OL, 4, 1189; Kjellgren, J.; Szabo, K.J. TL, 43, 1123; Suginome, M.; Ohmori, Y.; Ito, Y. CC, 1090; Leroy, B.; Marko, I.E. JOC, 67, 8744; Marko, I.E. et al. S, 958; Angle, S.R. et al. JOC, 67, 7699; Yu, C.-M. et al. AG(E), 41, 161; Loh, T.-P. et al. TL, 43, 7193; Dobbs, A.P.; Martinovic, S. TL, 43, 7055; Clarke, P.A.; Martin, W.H.C., IV OL, 4, 4527; Cho, Y.S. OL, 4, 2025.

IA'TS

R~OH

TMS-OTf

Et20

AAoL

R1

95-98% IV.H-27 Romero, D.L. JOC, 67, 3317.

..-OH

_ Ph,,,'(

H CH2CI2,40~

=

92%22:1

~/ IV.H-28 Torroba, T. et al. JOC, 67, 6439. EWG

~

Ph-CI, reflux EWG1

73-83%

EWG

180

ORGANIC SYNTHESIS--2003

IV.H-29 Lequeux, T. et al. TL, 43, 2033. Me

P(OEt)2

F F

50"C, 15h

1

I

= ~FP(OEt)

?

2

78-92%

IV.I. Other Heterocvcles with Orle Heteroatolp IV.I-1 Arsenyan, P. et al. TL, 43, 4817; Nishiyama, Y.; Sonoda, N. et al. JOC, 67, 1520; Lee, D. et al. JOC, 67, 6553; Pinto, B.M. et al. JACS, 124, 8245.

K,s~N +

R1

Ph-H,reflux "

15-80%

IV.I-2 Bendorf, H.D. et al. TL, 43, 7031.

,,~..~ ~,CHO A Ui 'Rh(PPh3)3CI : 'c:'~~:~

)

S 54-92%

n

IV.I-3 Wang, E.-C. et al. H, 57, 2021, 1997; Cossy, J. et al. TL, 43, 7263; oxepins: Fujiwara, K.; Murai, A. et al. SL, 1496; azepins: IbrakimOuali, M.; Santelli, M. et al. SL, 1987; Grela, K. et al. AG(E), 41, 4038; Gurjar, M.K.; Reddy, D.S. TL, 43, 295.

Rr~ R1 //

MeO~

\~ f

R

R.1

PhCH=Ru(PCy3)2CI2. M e ~ 32-36%

IV.l-4 Kroulik, J. et al. JCS(P2), 1909.

AI2Se3,HCI Ar'~O //"'Ar AcOH/Ph-Me,rt

Ph Ph -

A

45-72%

r

SYNTHESIS OF HETEROCYCLES

181

~

IV.I-5 Lautens, M. et al. JOC, 67, 3972; Grigg, R. et al. T, 58, 8613. 2Et CO2Et R__k~~~[ll I

(~'vi~ / Br Pd(OAc)2, M TFP, , Cs2CO3 + --eCN reflux '

R'--:~x,..../O 23-85%

IV.I-6 Dominguez, E. et al. JOC, 67, 7215. ~?-Ph OH

CuBr.DMS, Nail

R

R1 pyr,110-180~ R

R

R

1

1

74-87% (other Cu(I) salts and solvents were used)

IV.I-7 Wang, P.G. et al. TL, 43, 6525; Katritzky, A.R. et al. S, 601; Vargas, M.D. et al. T, 58, 6135; Fukuyama, T. et al. SL, 697; MortishireSmith. R.J. et al. JOC, 67, 9354; Nakata, T. et al. OL, 4, 675. RI"~~%OBnR

1.2.galatoseNH2OH.HcloXidase= R~..~ N~..,IOH 3. H2, Pd(OH)2

H 75-92%

IV.I-8 Yamamoto, Y. et al. JACS, 124, 3562. MgBr2"Et20 4A MS, CH2CI2 OAr

60-73%

182

ORGANIC SYNTHESIS--2003

IV.I-7 Wender, P.A. et al. JACS, 124, 15154.

[~'%NR +

~ O2Me

Ill

CO2Me

[Rh(CO)2CI]2 "Ph-Me,60~ 12h

N-R 61-91%

IV..l. Heterocycles with ~1 Bridgfbead Heteroatom IV.J-I Rejzek, M.; Stockman, R.A. TL, 43, 6505.

C EtO2

~

.

~

tl

1. NaBH4,iPrOH/H20 CO2Et 2. AcOH EtO2

66%

~CO2Et

IV.J-2 Cha, J.K. et al. TL, 43, 6657.

CITi(Oipr)~,c-CsHgMgCI THF

.

e IV.J-3

Bach, T. et al. CEJ, 8, 2464.

Ph

~

HN~N..../ O

hv

Ph-Me"

~

HO Me 61-65% 1-3:1

H:OH Ph

H

O

70% ee = 60%

IV.J-4 Esmaili, A.A.; Kheybari, H. JCR(S), 465.

~

N

C!

[IO2R CHO +

H

CO2R

PPh3 =~ CH2CI2,-10~ ~ rt

Ci

RO2C 85-99%

CO2R

SYNTHESIS OF HETEROCYCLES

183

IV.J-5 Vanecko, J.A.; West, F.G. OL, 4, 2813

/-~ \~'LMPS~ v-

'" '"

Cu(acac)2

-Vh-M"e,8O*C

I'~ " N2

58%

O

ee = 77%

IV.J-6 Renaud, P. et al. AG(E), 41, 3460.

R../I

~']

CO2E t + ?

)n

1. phSO2N3,(Bu3Sn)2,Ph-H, reflux 2. In, NH4Ci, EtOH, reflux O

Br

69-84%

IV.J-7 Laduron, F.; Viehe, H.G. T, 58, 3543; de March, P. et al. T, 58, 2667.

~__~CF3+ f CO2Me

CN SMe

DBU

= ~ ~ ' " ~ O2Me'"

CH2C12,-78~ 30min

-

~"CF3 MeS 57% 19:1

IV.J-8 Shen, Y. et al. S, 714; Weaver, G.W. et al. SL, 1547; Epperson, M.T.; Gin, D.Y. AG(E), 41, 1778; Merour, J.-Y. et al. S, 1879.

O~F(OR)2 Nail . + Ill THF Rf

EW

~ ~ p (OR)2 EWG

Rf 47-77%

IV.J-9 Ishizaki, M.; Kai, Y.; Hoshino, O. H, 57, 2279; Parsons, A.F. et al. SL, 1431; Cordham, I. et al. CEJ, 8, 195.

(~ CO2R [ SePh OAc

B u3SnH, AIBN

Ph-H, A O

69-84% 1.6-2:1

O

184

ORGANIC SYNTHESIS--2003

IV.K. Heterocvcles with TW9 or More Heteroatoms IV.K.I.a.

5-Membered

Heterocvcles

with

2 N's

IV.K.l.a-1 Helal, C.J.; Lucas, J.C. OL, 4, 4133; Hermitage, S.A. et al. TL, 43, 6997; Tepe, J.J. et al. OL, 4, 3533; Casey, M. et al. JOC, 67, 3919.

/CO2Et

N[~CO2Et R-NH2 + Me2N"

"' neat, 70~

R 31.85%

IV.K.I.a-2 Katritzly, A.R. et al. JOC, 67, 3109, 4951 and TA, 13, 933; Li, G. et al. JOC, 67, 4777; Paul, S. et al. S, 75.

.R1

R1

.R 1

Bt-H, CH20 f'~ Nuc" H20/Me0H, rt" R I ~ N ~ THF or Ph.Me NH2 Bt 85-96%

R--NH

R~/% 63-96%

Nuc

I V . K . l . a - 3 Gonda, J. et al. T, 58, 1611; Proenca, M.F. et al. JOC, 67, 5546; Seki, M. et al. S, 361.

~

N=c=~R

~/HB oc

A "

... ,R

HN~NBoc S 85-90%

I V . K . I . a - 4 Deniaud, D. et al. JCS(P1), 741.

~

-

~

-]'~ R~1

KOH EtOH' 78~

1

O

R 36-84%

I V . K . I . a - 5 Overman, L.T. et al. JOC, 67, 7880.

R o~

O2Me AcOH,700c

o

N--NH

EtO2C S

72-95%

SYNTHESIS OF HETEROCYCLES

185

IV.K.l.a-6 Laufer, S. et al. AG(E), 41, 2290. "Ones, Thiones, and N-Oxides" An Excercise in Imidazloe Chemistry." IV.K.l.a-7 Houghten, R.A. et al. JOC, 67, 3138. "Solid-Phase Synthesis of 1,5-Disubstituted 2-Aryliminoimi dazolidines." I V . K . I . a - 8 Haley, M.M. et al. JOC, 67, 6395.

Et2N" N " ' N ~

Ph-Ci 2,170"C

: Et2N--I~

+

14-89% 0-70% (78-98% using CuC! (83-99% at 200~ in DCE)

l V . K . l . a - 9 Diver, S.T. et al. JOC, 67, 1708; Seth, P.P. et al. TL, 43, 7303. ~ i ~ ~

Ph h

1. NHeOH _ ~[~N~. 2. R2C(OR3)3, H + -

a,,,..~ a 1

R2

R,.'~'I R1 86-98%

ee = 98-99%

I V . K . I . a . 1 0 Perez-Perez, M.-J. et al. JMC, 45, 3337 and SL, 155; Gilbert, A.M. et al. JMC, 45, 2342. H

1. NBS, MeCN, 0~ lh NH2

N

2. ~ ~ - R

Bn

Bn

58.74%

IV.K.l.a-ll

,... v

Nenajdenko, V.G. et al. S, 1379. R1

NH 2

F c. o. +RO ~

"OH

S.-~'-

,.

RI

.... H20

80-96%

186

ORGANIC SYNTHESISm2003

IV.K.I.a-12 Levai, A. et al. JHC, 39, 751; Molteni, G. et al. TA, 13, 1285; Svetlik, J.; Sallai, L. JHC, 39, 363; Pavlik, J.W. et al. JHC, 39, 1025; Sener, A. et al. JHC, 39, 869; Haddad, N.; Baron, J. TL, 43, 2171; Avery, M.A. et al. T, 58, 3639; Gonzalez-Nogal, A.M. et al. T, 58, 4975; Lange, M. et al. CPB, 50, 1109; Molteni, V. S, 1669; Flores, A.F.C. et al. TL, 43, 5005.

A

Ph NH2NH2 A AcOH

O

~

Ph

\~

I

N-'N",Ac

-'--

41-63% I V . K . I . a - 1 3 Kobayashi, S. et al. JACS, 124, 13678. Zr(OPr)4, CH2C!2,rt "'~,~/.~"--N- N-.PNB

R

I~IoH i~~ H

PNB

R

38-99% trans:cis = 8-99:1 ee = 72-97%

I V . K . l . a - 1 4 Roussel, C. et al. JCR(S), 449. ~ o EtO2~ N,. EtO2CCH=N2 +

0

EtOAc,rt

fi N

I~H~

_ O

70% IV.K.I.a-15 Grotjahn, D.B. et al. JOC, 67, 9200. "New Flexible Synthesis of Pyrazoles with Different, Functionalized Substituents at C3 and C5." I V . K . I . a - 1 6 Filippone, P. et al. S, 1546. /CO2 R1 CO2M2 Rf ~ ~ f / ~ N

1. NaOMe, THF TH + CH2(CO2Me)2 2. TFA, THF,~A = ~ N ' H ~ M e

41-44% (also formed from this type reaction are 1-arylpyrazolesand pyrroi-2-ones)

SYNTHESIS OF HETEROCYCLES

187

Yadav, J.S. et al. SL, 513.

IV.K.I.a-17

Ar-N3 + CH2=CHCO2R

RO2~

DABCO THF

.._

i-i CO2R 75-90%

IV.K.I.a-18 Yoon, Y.-J.; Lee, W.S. et al. JCS(P1), 207. N.R 1 1. Li.C=-CR2, THF, 0*C ~ N H R 2. H20

O

1

~~~~N

3. RNHNH2, EtOH

R2

R

6-96%

IV.K.l.a.19 Kim, T.; Kim, K.; Park, Y.J. EJOC, 493. T

-" ~ R Ar

AA

-

1 THF, 25~ lh r k.....~, R O

gl Ar 34-91%

IV.K.I.a-20 Servi, S.; Akgun, Z.R. SC, 32, 3399. Ph-CHO

NaHSO3 ~Ph

H NH2NHAr SO3Na DMF,A

. OTN H

73-85% I V . K . I . a - 2 1 Jet/ks, C.W. et al. T, 58, 6061. M

NaNO2

H2N "~ X

"g H20/AcOH"IOOdl16h ~

~

"~

"R

X 41-96%

IV.K.l.a-22 Cottineau, B.; Chenault, J. SL, 769. "An Efficient Synthesis of tetrasubstituted Pyrazoles."

188

ORGANIC SYNTHESISm2003

I V . K . l . a - 2 3 Bonin, M. et al. S, 1885. " A s y m m e t r i c Synthesis of Densely Functionalized

Pyrazolidines and 1,3-Diamines."

I V . K . l . a - 2 3 Katayama, H. et al. TL, 43, 3577.

~ R1

Pd(OAc)2,DPEphos

~

~

"

R1

,

R

~ /NH Ac

Cs2CO3, Ph-Me, 100-110~

! R

Ac 81-99%

IV.K.I,b 6 M c m b e r e d Heterocvcles with 2 N's IV.K.I.b-1 Sosnovskikh, V.Y. et al. JOC, 67, 6738; Young, D.W. et al. JCS(P1), 2459; Ueno, K. et al. H, 57, 723; Queguiner, G. et al. T, 58, 283; Alvarez-Ibarra, C.; Csaky, A.C.; de la Oliva, C.G. JOC, 67, 2789.

~~

F3

NHNH2

O2 NHeNH2.H20. R' " ~ "O" ~"O

2

EtOH,reflux

R

R

47-73%

I V . K . l . b - 2 Jin, T. et al. SC, 32, 1847; Zhang, Y. et al. JCR(S), 436; Dondoni, A. et al. JOC, 67, 6979; Kidwai, M. et al. JCS(P1), 1845; Lu, J.; Bai, Y. S, 466. TsOH RO2 Me

O + RI"CHO + H2

H

O tt 0-78%

I V . K . I . b - 3 Masaguer, C.F. et al. TL, 43, 3551. AcOa

+ -2

OMe

--

OMe

66%

SYNTHESIS OF HETEROCYCLES

189

IV.K.I.b-4 Mahajan, M.P. et al. JCS(P1), 774.

RLN R3 I

1 ~ C

TEA

CH2C12,rt

Ar

I

Ar 63-89%

IV.K.I.b-5 Fairfax, D.J. et al. S, 720; Bathini, Y. et al. TL, 43, 3295; Martins, M.A.P. et al. S, 2353; see also" Nenajdenko, V.G. et al. S, 133.

t.HCI

CO2Me

R~NH2

ICO2Me

MeG "OMe DMF,100~

39-90%

IV.K.I.b.6 Nematollahi, D.; Goodarzi, H. JOC, 67, 5036.

"Electroorganic Synthesis of New Benzofuro[2,3-d] pyrimidine Derivatives."

IV.K.I.b-7 Katritzky, A.R. et al. JOC, 67, 3115; Zaleska, B. et al. JOC, 67, 4526; Brower, J.O.; Lightner, D.A. JOC, 67, 2713.

~

CH20,Bt-H ~ Nuc" ~ "H20/NIeOH= -'-"---~" NH2 NH2 BtVK,,,.... ~.,,,, Bt Nucv N.,,...-N,x...-NRC 88% 81-95%

I V . K . l . b - 8 Itoh, T. et al. TL, 43, 9287.

+

H2

R2 1.FeCI3,MeOH CN 2. H2,Pd/C,50~ 55-80%

OH I V . K . I . b - 9 Palacios, F. et al. OL, 4, 2405.

PR2 R4r9

R~ ~ Ph-Me,reflux-

PR2 R32NH ~ P R 2 R1 R1 Ph-H,rt 42-98% OX

190

ORGANIC SYNTHESIS--2003

IV.K.I.b-10 Shinokubo, H.; Oshima, K. et al. JACS, 124, 9032; Su, W.; Yang, B. AJC, 55, 695; Martinez-Alvarez, R. et al. T, 58, 3755.

tr M eO..

B Br

R-MgX

R ~/'~

r "THF, -42*C--' rt

A

r 55-80%

I V . K . I . b - I 1 Cacchi, S. et al. OL, 4, 1355.

(

.,~

~

HN~I CF3

O~CF3

O

R-X, CO, Pd(PPh3)4,K2CO3 MeCN, 500C,24h

F3C" "N" 60-92%

IV.K.I.b-12 Young, D.W. et al. JCS(P1), 155, 613.

H21~~~~,~nO2tBu co2tBu

1. K2CO3,EtOH, reflux 2, HCI

.~ H ~ / ~

H

CO2H

NH2 H

54%

IV.K.I.b-13 Bartlett, P.A. et al. JOC, 67, 3985.

--zBr

O,,,11,O1. Sn(OTf)2,Me2CO, 40~

7x

O

Me

-'~

R

AI N, eh- e,,10~ II

NHCbz

NaIO4

~O2Et ~ R~N~CHO

H20/Me2CO,.25oc, 30minr C b z ~ . ~ CO2Et

--

O R 4-67%

I V . K . I . b - 1 4 Maison, W. et al. SL, 1795.

H

--/~.-x~ ie

OH 65-71%

SYNTHESIS OF HETEROCYCLES

191

IV.K.I.b.15 Nair, V. et al. OL, 4, 3575. Ts O2Me

~

~ N +

I[i + CO2Me

R DME,rt

,. Ts

COzMe CO2Me

43-93% dr = 5-10:1

IV.K.I.b-16 Yang, S.-C. et al. OM, 21, 2013; Pinho E Melo, T.M.V.D. et al. JOC, 67, 66; Aran, V.J. et al. JCS(P1), 790; Rasmussen, S.C. et al. JOC, 67, 9073; Antoniotti, S.; Dunach, E. TL, 43, 3971. H R~NH2 + C O H Pdcat.,Ti(O,Pr)4,4~MS~ ~ . R" ~ "NH2 OH Ph-H, reflux H 31-98% IV.K.l.b-17 Perillo, I.A. et al. S, 2687.

~

a

N~'~, n PPE or PPSE NO2 HN~R reflux O

~[~~,~~N ~q+ R O" 25-91%

!V.K.Ic. 7.Membered Heterocycles with 2 N's IV.K.I.c-1 Marcacchini, S. et al. S, 2756. A I=, ,~- C O 2 H CI~

"NO2

O /NH-c-C6Hll

1..R'CHO,C c'6H N lC ~'=~'-R/x.._ NH2CHRICO2R2 ~ 1 ~ 1 2 'Fe,Ac0H --- I ~ . ~ . . ~ R C! HN~o 49-71%

192

ORGANIC SYNTHESIS--2003

IV.K.I.c-2 Katritzky, A.R. et al. JOC, 67, 8237 and JCS(P1), 592. N"R

H

BuLi, ZnBr2 _-+ ( r~Rx ' THF

Bt

~'N.....NR 1 36-82%

~

I V . K . I . c - 3 Ho, T.-I. et al. H, 57, 1501. Me

tBuONa

/,~-NH r

Me

C02Me

DMF-

CO2Me

1~ Me

O

IV.K.I.c-4 Nishiwaki, N.; Ariga, M. et al. H, 57, 425.

R" "NH2

+OH/~~"'-NO2 ~MeOH'rt, 2h" NHtBu

r 79.99%

NO2

IV.K.2. Hftergcvcles with 2 O's or 2 S's IV.K.2-1 Karimi, B. et al. T, 58, 4513.

N SorN S )n +

CH2Cl2, rt, 5-10min

30-96% (interconversion also with 1,3-oxathiolanes) IV.K.2-2 Selegue, J.P. et al. H, 57, 2373. C![ ~ B r Na2S.9H20, Aliquat336. CIi ~ ~ ~ C l Ci

Br

Ph-H, reflux, 3h

C!~

v

54%

C!

SYNTHESIS OF HETEROCYCLES

193

IV.K.2-3 Decurtins, S. et al. JOC, 67, 3160; Bergman, J. et al. JCS(P1), 330; Pihlaja, K. et al. JOC, 67, 1910. "Facile Synthesis of Novel Functionalized Bis(ethylenedithio) tetrathiafulvalene ( B E D T - T T F ) ' Derivatives." IV.K.2-4 Jiang, B. et al. OL, 4, 2453; Nair, V. et al. T, 58, 4171; Bolm, C. et al. OL, 4 4631.

2~3C Rh2(OAc)2 A % o ~ C F 3 Ar-CHO + N OzMe 'CH2CI2,rt ~ ~_~ "CO2Me Ar 82-95% dr = 9-100:1 IV.K.2-5 Calo, V. et al. OL, 4, 2561.

CO2, R4N+I" R

molten TBAI or TBAB

/

R 10-91%

IV.K.2-6 Leger. S. et al. TL, 43, 1147.

EtO2

S Me

TiCI4 CH2Ci2, -78~ " =EtO2 65%

", Me

IV.K.2-7 Reynolds, J.R. et al. CC, 2498; Caros-Quintero, D.; Bauerle, P. CC, 2690. EtO2(~ EtO2(~ 1 a _ ~ R1 @ ~ ~ PPh3 or PBu3 R

EtO2C

OH

HO" "R

THF,reflux

R EtO2C 60.95%

194

ORGANIC SYNTHESISm2003

IV.K.3. Heterocycles with 1 iN and 1 0 IV.K.3-1 Yamada, T. et al. OL, 4, 2457; Karlsson, S.; Hogberg, H.-E. TA, 13, 923; Kanemasa, S. et al. TL, 43, 657; Kundig, E.P. et al. JACS, 124, 4968; Collon, S.; Kouklovsky, C.; Langlois, Y. EJOC, 3566; Grigg, R. et al. T, 58, 5827; Inomata, K. et al. SL, 302; Shimizu, T. et al. CPB, 50, 908; Aggarwal, V.K. et al. OL, 4, 1227; Termin, A.P. et al. TL, 43, 4407; Shindo, M. et al. OL, 4, 3119; Alcaide, B. et al. SL, 85; Zecchi, G. et al. T, 58, 4445.

Phi, +~O" 1 7 ~ I~A + r O H ~

1. cat., CH2C!2, 4 0 0 C ,,r ~ = Ph-2. NaBH, EtOH

_13

At -L'on

~/....~/j~~...._~ cat. =

18-99% endo:exo = 99:1 ee -- 83-91%

9

IV.K.3-2 Righi, P. et al. OL, 4, 965.

ph....,..,,,~n H..r ..,

+

X

.O" _-- Ph

X

O

OH OH O 20-48%

IV.K.3-3 Snider, B.B.; Che, Q. T, 58, 7821; Fukuyama, T. et al. SL, 1323.

NOeMn OAc'3,cu OAc 2

NO2. +

AcOH, 900C

48%

5%

IV.K.3-4 Fraga, C.A.M. et al. EJMC, 37, 163.

I~ I W.. x..Y

~

,n

+

n o .N

Me

2. H2SO4, 0~ ~h W. x~Y 20-65 %

SYNTHESIS OF HETEROCYCLES

195

IV.K.3-5 Joshi, N.N. et al. TL, 43, 5287; Katritzky, A.R. et al. TL, 43, 3449.

I~,~CO2R NH2CH2CO2Zn R1-CHO + O2NCH2CO:~ DMS0~rt - RO2C'~o~I~N~ o" 4r

66-88 %

IV.K.3-6 Passacantilli, P.; Piancatelli, G. et al. TL, 43, 4613.

OH

IO !

2. TsOH, CH2C!2,rt 70-81%

IV.K.3-7 Kurth, M.J. et al. JOC, 67, 876; Yamauchi, M. JHC, 39, 1013; Kai, H. et al. H, 57, 2299; Horiuchi, C.A. et al. TL, 43, 7035; Kamimura, A. et al. T, 58, 9613; Harrity, J.P.A. et al. SL, 2071; Taylor, R.E. et al. OL, 4, 2953.

EtO2C~.

R1

1. R-CH=NOH,NaOCI, CH2CI2 E t O 2 C ~ 2. Swern : ~~O

R1

/

R

64.76% IV.K.3-8 Reissig, H.U. et al. S, 1553; King, S.B. et al. JOC, 67, 6174; Gallos, J.K. et al. T, 58, 9351; Yan, T.-H. et al. TA, 13, 691.

\O~

1. tBuOMe,rt ~ 0 ~'' , 2. DBU, CH2CI2 51-82%

6S:6R = 3.76-19:1 IV.K.3-9 Magnus, P. et al. TL, 43, 7393.

Ph~~J'~ ~H 1. NCS, Ph.CI, rt . A -- P h ~ o o ~/~R 1 O~/', R1 2. SnCI4 50-79%

196

ORGANIC SYNTHESISm2003

IV.K.3-10 Xia, Q.; Ganem, B. S, 1969; Motoyama, Y. et al. OM, 21, 3408; Fossey, J.S.; Richards, C.J. OM, 21, 5259. L

R-CHO

1. tBu-N-C, Zn(OTf)2, TMS-C! = 2. CH(OMe)3,TsOH, CH2CI2

T

/

"

~

" ~ ~ , .bl 45.69%

IV.K.3-11 Polniaszek, R.P. et al. SC, 32, 2427. R.COCI +

MeGL ..OMe KHCO3 Me 7" --NH2

P205 MeSO3H, A

@ R 0-83%

IV.K.3-12 Hodgetts, K.J.; Kershaw, M.T. OL, 4, 2905. "Ethyl 2-Chlorooxazole-4.carboxylate: A Versatile Intermediate for the Synthesis of Substituted Oxazoles." IV.K.3-13 Costa,M. et al. JOC, 67, 4450; Shi, M.; Shen, Y.-M. JOC, 67, 16. R ~ R1 //~,~H

CO, O2, R.OH, Pd/C, KI

:

RO2

O~'~'R2

1

N

R2

38-73%

IV.K.3-14 Enders, D. et al. SL, 33. i / T B SI ~

1. RLLi,-100~ CICO~Me : o~O-'~.o.R 1 2. TBAF H 3. Li, NH3,-33~

N.. Me" ) r~ ~

27-78% de = 88-96 % ee = >96 %

IV.K.3-15 Overman, L.E.; Remarchuk, T.P. JACS, 124, 12. OAc ferrocenyi oxazoline Pd r

SO2Ar 88-98 %

ee = 89-93%

SYNTHESIS OF HETEROCYCLES

197

IV.K.3-16 Ariza, X.; Garcia, J. et al. OL, 4, 4511; Lu, X. et al. JOC, 67, 974. R

R 1. Ts-NCO, THF

_

R

2. Pd2(dba)3"CHCl3, P(OiPr)3

OH

Ts 70-93% dr = 1.4-19:1

IV.K.3-17 Tominaga, K.; Sasaki, Y. SL, 307; see also" Mizuno, T. et al. T, 58, 7805. H

R1

CO2, Bu2SnO

NHR

NMP,180"C

/

_

R1

R 53-94%

IV.K.3-18 Comins, D.L. et al. JOC, 67, 1972. Ph 9

I

Ph H

B u 3 S n H , A I B N o r Et3B

O

O 65-70%

IV.K.3-19 Westcott, S.A. et al. CJC, 80, 31.

[ ~ o H ~ N ~

Mn(OAc)3

[~~~'~t/,

I V . K . 3 - 2 0 Juhl, K.; Jorgensen, K.A. JACS, 124, 2420. C b z . N. .

1. cat., THF or CH2C!2 C 02Et 2. L-Selectride, -780C-~ rt

+

N"CBz

R

/CO2Et

-"

R

3. aq NaOH, 2h 4. TMS-CHN2, MeOH/Ph-Me

NHCbz

cat. = Pl~"("~ ~/'~Ph X~I~N....N-..Z p~

~.. O , ~

(OT02Ph

29-78% ee = 70-96%

198

ORGANIC SYNTHESIS--2003

IV.K.3-21 Morwick, T. et al. OL, 4, 2665; Palacios, F. et al. TA, 13, 2541; Dhar, T.G.M. et al. OL, 4, 2091.

cR1 R ~ ~ , ~ R1 C2C!6,PPh3 R~~"~ O CHO Pyr,MeCN 37-94%

IV.K.3-22 Hell, Z. et al. TL, 43, 3985; Rajaram, S.; Sigman, M.S. OL, 4, 3399.

r1

CO2H

ZeoliteE-4 Ph-Me2,130~

v-

30-90%

IV.K.3-23 Andrusziewicz, R.; Wyszogrodzka, M. SL, 2101.

o2.

HOe""]

CO2H

DPPA,TEA tBuOH,reflux-"- O

...CO2R H

H 70.80%

IV.K.3-24 Nicolaou, K.C. et al. JACS, 124, 2212, 2221, 2233.

( ~ X'~ R~

R~k~~7 NHRI~R3R4

(~.--X

DMP Ph-H,A

R__[~~R 2R1 ~O~R4R3 7-57%

IV.K.3-25 Conde-Frieboes, K. et al. JOC, 67, 8952.

"Diastereoselective Synthesis of 2-Aminoalkyl-3-sulfonyl1,3-oxazolidines on Solid Support."

IV.K.3-26 Luna, D. et al. JCS(P2), 227. "Study on Dry-Media Microwave Azalactone Synthesis on

Different Supported KF Catalysts: Influence of Textural and Acid-Base Properties of Supports."

IV.K.3-27 Kanger, T. et al. TA, 13, 857. "Asymmetric Synthesis of Novel C2-Symmetric Bimorpholines."

SYNTHESIS OF HETEROCYCLES

199

IV.K.3-28 Hofmann, R.V. et al. JOC, 67, 1102. EtO2CNH2 +

CO2Et Ph-Me,reflux

R

= O

CO2Et

H 30-80%

IV.K.3-29 Yadav, L.D.S. et al. TL, 43, 8551; Panunzio, M. et al. TA, 13, 2113. H2NCOH

Montmorillonite K-10,~tW ~ R

R 83-94%

IV.K.3-30 Selvakumar, N. et al. S, 2421. N 02

~

F

~

a q K O H_ N ~ DMSO 02

~ 69%

IV.K.3-31 Janza, B.; Studer, A. S, 2117. P h ~ NBS or NIS or PhSeBr or NaOC! _ O. CH2CI2or CHCI3or MeCN I~H SO2Ph

X SO2Ph 61-79%

IV.K.3-32 Willis, M.C.; Piccio, V.J.-D. SL, 1625. /

SCN"~CO2Et + R-CHO

Mg(CIO)4,TEA, bipyr THF, 0~

R

.....~O-~ ~ ~i~-"N" -CO2Et H 67-89% syn:anti = 1.5-3:1

200

ORGANIC SYNTHESISm2003

IV.K.3-33 Nicolaou, K.C. et al. AG(E), 41, 3866.

R2 R3 R2 R3 R ~ R 4 + Et3+N..s..N'CO2RS , -_ R ~ h " ~ R 4 . R..NH OH 02 THF, reflux R.,N,,s,,NCO2R~ 02 39-90% IV.K.3-34 Yavari, I. et al. T, 58, 6895.

IO2Me+ ! HH~]~

MeO2~ H PPh3 ~ ~ ~

CO2Me

70%

IV.K.4. Heterocvcles with 1 iN and 1 S IV.K.4-1 Enders, D.; Wallert, S. TL, 43, 5109.

HBr/AcOH R ~ ~ SO2CI CH2C12,rt ~ HN--SO2 NHCbz 29-78% ee = >96% IV.K.4-2 Shibata, N. et al. JCS(P1), 302.

.C,o

OH TMSU,NaI 2NHtBu MeCN,reflux

~N:I

H 02 92-99%

IV.K.4-3 Liu, B. et al. JOC, 67, 4595.

l[ R" ~'S

+

PBu3 Ph-Me, rt --

R

IV.K.4-4 Kim, K. et al. JOC, 67, 5375.

CO2Et 21-86 %

"Novel Synthesis of cis-Nickei(II) 3-Alkylimino-3-alkyi (or aryl) thio-l-arylpropenethiolates and Their Applications to the Preparation of 5.Aryl.3-(arylthio)isothiazoles."

SYNTHESIS OF HETEROCYCLES

201

IV.K.4-5 Bolm, C. et al. SL, 832.

~~[~~ Br

HI~s~O Pd2(dba)3'rac'BINAP + Ar/~Me tBuONa,Ph-Me, reflux Br

1~ 80-99%

IV.K.4-6 Tsolomitis, A. et al. JHC, 39, 149.

Argo

SOCI2 ~A Et20, rt R

R

53-78%

IV.K.4-7 Tale, R.H. OL, 4, 1641. K~/__ CAN,NaHCO3 r._(/~.. Ar-CN + R .... ---- A R H MeCN, rt, 0.5h 78-96% IV.K.4-8 Hahn, H.-G. et al. H, 57, 1697.

RI ~ S ~ O A c R1/~" Nj

K2CO3

2~~

H20/MeOH,30rain ~ R O

16-71%

IV.K.4-9 Sackus, A. et al. JCS(P1), 652; Okonya, J.F.; A1-Obeidi, F. TL, 43, 7051.

rtr~ CO2Et EtO2C~CO2Et Br Br

(NH2)2C=S_._H2N"'~ S/'~ CO2Et EtOH, rt 72%

IV.K.4-10 Tiecco, M. et al. TA, 13, 429.

"Asymmetric Synthesis of Thioamido Selenides: A Simple Synthetic Route to Enantiopure Thiazolines."

202

ORGANIC SYNTHESIS--2003

IV.K.4-11 Katritzky, A.R. et al. S, 1646; Hruby, V.J. et al. TL, 43, 6669; see also: Katti, S.B. et al. T, 58, 7619. F . ~ .CO2Et .._~CO2Et . . . . . . . . 1. Bt-H, CH20 ,NaOH,aqMeOH = ~ k t sR HS

NH28HCl 2. R-ZnX, THF, 0*C-~rt

47-55%

IV.K.4-12 Garcia-Valverde, M. et al. TL, 43, 8591. 1

S~

O CO2H

Rt H~~S~

R3"NH2' c'C6HllNC .. MeOH,reflux

c'C6HllN -]~ ~-R1RN2 .- O u -76-85%

IV.K.4-13 Katritzky, A.R. et al. JOC, 67, 8234; Bates, D.K.; Li, K.

JOC, 67, 8662.

R~~'.h.."(CH2)n Bt'-"N 1. BuLl, TMEDA, c-C6I-I12 R . L .R. 1L " SH + B t__./NR 2. ZnBr2 n = 0,1

20-65 %

I V . K . 4 . 1 4 Katti, S.B. et al. T, 58, 7619. R1-NH2 + R-CHO +

IV.K,5. HCterocycles with 1 0

CO2H

DCC R ' ~ THF -

Rx 80-95%

O

and 1 S

IV.K.5-1 Enders, D. et al. SL, 1727; see also: Metz, P. et al. SL, 2019. "A Practical Approach Towards the Asymmetric Synthesis of c~,~,-Substituted ~,-Sultones." IV.K.5-2 Eames, J.; Kuhnert, N.; Warren, S. JCS(P1), 2282. ~)H ~)I-I H(~.,,Me Et. ~ M ' ' ~ M e TsCI,TEA , 9 Et, .... O Me*"SH CH2CI2 M'~"- S,,'( 90%

SYNTHESIS OF HETEROCYCLES

203

IV.K.5-3 Dunach, E. et al. T, 58, 10455. R4

2

O

APSG'HC!

+

2 42-91%

IV.K.5-4 Porter, bd.J. et al. CC, 346; see also: Nair, V. et al. T, 58, 3235. Ar-~~

CUlIreflux .... " Ph-H,

+ Nz~E~ OgEt

Q,/-/--~? ~ ,TES AF "CO2Et 62-67% dr = 4-20:1

IV.K.6. Heterocvcles with 3 or more N's _

IV.K.6-1 Katritzky, A.R.; Singh, S.K. JOC, 67, 9077; Meldal, M. et al. JOC, 67, 3057; Fokin, V.V.; Sharpless, K.B. et al. AG(E), 41, 2596. 1

R'N3 + I |

/ RI

neat

~ R

62-84% IV.K.6-2 Yamamoto, Y. et al. TL, 43, 9707. R

TMS-N3 +

+ R

R1

Pd2(dba)3.CHCl3, dppp, IN, N EtOAc ~q" OCO2Me 15-66 %

IV.K.6-3 Guolin, Z.; Yongzhou, H. JCR(S), 560; Wang, Q. et al.

JCS(P 1), 991.

e~/N+ M

MsO"

NH2

Ar.CN,KOH EtOH,rt

M

~'~ N~._Ar ~ N--.N 35-50%

204

ORGANIC SYNTHESIS--2003

IV.K.6-4 Furber, M. et al. T, 58, 3185; Dehaen, W.; Bakulev, V.A. et

al. JCS(P1), 211. A R"+

,~R 1 "'

1. R2ph-NH2, NaNO2, aq HC!

"~~H~CO2H

2. Ac20, pyr

41-91%

IV.K.6-5 Svete, J. et al. TA, 13, 821; E1 Ashry, S.H. et al. JCR(S), 314.

••.._1.

HCI, MeOH, rt

~N/~

N.,NH2

R

H

_

2. Br2, AcONa, MeOHI rt -

NMe2

R

32-79% endo:exo = 5.25-32.3:1 de = 68-94%

IV.K.6-6 E1 Kaim, L. et al. TL, 43, 8925.

.R'CHNH2 1%. 2. NaNO 2 NHAr

:

Ar 52-65%

R1

IV.K.6-7 Koshima, H. et al. H, 57, 2145. l.tW, NHzOH'HCI Ar-CHO ...... -- Ar.CN NMP

ltW, N2H4"HCI N2H4"H20 HOCH2CH2OH

NH2 42-67 %

IV.K.6-8 Athey, P.S.; Kiefer, G.E. JOC, 67, 4081. "A New, Facile Synthesis of 1,4,7,10-Tetraazaeyelododeeane" Cyelen."

SYNTHESIS OF HETEROCYCLES

205

I V . K . 6 - 9 Bagley, M.C.; Singh, N. SL, 1718. " M i c r o w a v e - A s s i s t e d S y n t h e s i s of 5 - D e a z a - 5 , 8 dihydropterins."

IV.K.6-10 Suzuki, H. et al. JCS(P1), 696.

[~

'~

Nail NO2

H2N"

DMF, -10"C

~

+.O" II "r~" R H R1 48-63%

IV.K.6-11 Demko, Z.P.; Sharpless, K.B. AG(E), 41, 2113, 2110 and OL, 4, 2525; Sharpless K.B. et al. JACS, 124, 12210; Yamamoto, Y. et al. JOC, 67, 7413; May, B.C.H.; Abell, A.D. JCS(P1), 172. CN + RI"N3

' ~" neat, 120-130"C

RI/' ~ 83-99%

IV.K.6-12 Rao, A.R.R. et al. JCR(S), 490. +

H2N..NH pyr, reflux

H

O

X

IV.K.7. Heterocyclr

with 2 N's and 1 0

IV.K.7-1 Buscemi, S. et al. H, 57, 811. H

H

Ar _ O" N

O

Memo N~NI ~~..-

EtOH reflux, 10h

IV.K.7-2 E1-Rady, E.A. JHC, 39, 1109. NH2 1. NaNO2, HC!

~

OH

2. EWG-CH2CN, EtOH

Ar

HCi _~ EtOH reflux, 8h

r 75-90%

NeeN

. C 50-65%

o2 Ew~ NH2

206

ORGANIC SYNTHESISm2003

IV.K.8. Heterocvcles with 2 N's and 1 S

IV.K.8-1 Katritzky, A.R. et al. JOC, 67, 4960. Bt-'-~ ZnBr2 R...~\N~~ N

NH2

CH2C!2,rt, 48h

43-80%

IV.K.8-2 Zhang, A. et al. SC, 32, 3455.

R~~ SH + O~ B rR1 EtOH,reflux,3h R~~L~~1 NH2 60-85% IV.K.8-3 Nicolaou, K.C. et al. AG(E), 41, 3866.

R~R3

R502C'~" HO~~"q)n 2 +

RH~ ~lR

IV.L. Other

O~. N+Et3 THF,reflux "

R4 R3 RSo2c'~q~ )n O~.N~n'IR2

R v, 39-90%

Heterocvgl~s

IV.L-1 Adam, W. et al. JACS, 124, 8316. "Unusual Sulfur Chemistry in the Thermal Reaction of Sultene and Thiophene Endoperoxide Sulfur Donors with Cyclic AIkynes." IV.L-2 Bergman, J. et al. JOC, 67, 6220. "Sulfur-Rich Heterocycles from 2.Metalated Benzo[b]thiophene and Benzo[b]furan: Synthesis and Structure." IV.L-3 Takamiya, K.; Otsuba, T. et al. JOC, 67, 4218. "Synthetic Procedure for Various Selenium-Containing Electron Donors of the Bis(ethylenedithio)Tetrathiafulvalene (BEDT.TTF) Type."

SYNTHESIS OF HETEROCYCLES

207

IV.L-4 Mlosten, G.; Senning, A. et al. JOC, 67, 5690. "Highly Sulfurated Heterocyles via Dithiiranes and Trithietanes as Key Intermediates." IV.L-5 Gleiter, P. et al. JOC, 67, 4290. "Cyclic Tetraselenadiynes: Rigid Cycles with Long-Range van der Waal's Forces Between Chalcogen Centers." IV.L-6 Cava, M.P. et al. OL, 4, 2581. "Synthesis of the First 1,3-Ditelluride-Containing RadialeneType TTF Derivatives." IV.L-7 Auge, J.; Gil, R. TL, 43, 7919. R.CHO TMS-CI ~ 0 ~ 1 1 45-89% IV.L-8 Batey, R.A.; TL, 43, 7601. RR1NH + ~ N ~ ~

1"MeCN' MeI = N ~ S ~I~/N .. 2. NAN3,MeCN RR1 62.96%

IV.L-90rtiz, L. et al. T, 58, 2569.

1P~ /Ph IL~ ~.P.~ N3P(O)(OPh)2 1. BuLi,THF,-30~ ~ O P"~P(OPh)2 ePh2 THF, 250C,30min~" Ph2 ~) 2.'R~CN, THF,-85~ R"J~N"" H OPh 12-97%

IV.L-10 Beckert, R. et al. H, 57, 1257.

Ar

~C!

TEA

+ H2NNHR . . . . ~r- -,C! THF, rt, 60min Ar

~N~R H~"

Ar 38-55%

208

ORGANIC SYNTHESISm2003

IV.L-I1 Woerpel, K.A. et al. JACS, 124, 9370.

1. AgOTf,Ph-Me, -27"C tBu2"~ OMe SitBu2 '2. Znnr2, HCO2Me,-78-~22"C~61-92% 3-99:1

+

IV.L-12 Senanayake, C.H. et al. JACS, 124, 7880.

~ .

' SOCI2,base : ~ . ~ N... ..,,~ .45"C Y NHSO2R O2S O 95-98% endo:exo = 1:4-32.3:1 '",OH

IV.L-13 Ortiz, F.L. et al. JOC, 67, 3852. "Regio- and Diastereoselective Preparation of Tetrahydrobenzo[c]- 1-aza-2;~S-phospholes. '' IV.L-14 Lammertsma, K. et al. JOC, 67, 2485. "Synthesis, Structures, and Strain Energies of Dispirophosphiranes. Comparisons with Dispirocyclopropanes." IV.L-15 Ding, B.; Teng, Z.; Keese, R. JOC, 67, 8906. "Radical-Induced Formation of Some Siloles and Diazasiloles." IV.M.

Reviews

IV.M-1 Holten, D.; Bocian, D.F.; Lindsey, J.S. ACR, 35, 57. Review: "Probing Electronic Communication in Covalently Linked Multiporphyrin Arrays. A Guide to the Rational Design of Molecular Photonic Devices." IV.M-2 Torres, T. et al. CRV, 102, 835. Review" "Subphthalocyanines: Singular Nonpolar Aromatic Compounds--Synthesis, Reactivity, and Physical Properties." IV.M-3 Cacchi, S. et al. EJOC, 2671. Microreview" "The Aminopalladation/Reductive Elimination Domino Reaction in the Construction of Functionalized lndole Rings."

SYNTHESIS OF HETEROCYCLES

209

IV.M-4 Katritzky, A.R.; Belyakov, S.A. AA, 31, 35. Review: "Benzotriazole-Based Intermediates" Reagents for

Efficient Organic Synthesis."

IV.M-5 Fox, D.J.; House, D.; Warren, S. A G(E), 41, 2463. Review: "Mechanisms of Sulfanyl (RS) Migrations: Synthesis of Heterocycles." IV.M.6 Schneider, C. AG(E), 41: 4217. Highlights: "First De Novo Synthesis of the Bisindole Alkaloid Vinblastine." IV.M-7 De Kimpe, N. et al. CRV, 102, 29. Review" "The Chemistry of Azetidin-3-ones, Oxetan-3-ones, and Thietan-3.ones." IV.M-8 Marinetti, A.; Carmichael, D. CRV, 102, 201. Review: "Synthesis and Properties of Phosphetanes." IV.M-9 Scott, J.D.; Williams, R.M. CRV, 102, 1669. Review: "Chemistry and Biology of the Tetrahydroisoquinoline Antitumor Antibiotics." IV.M-10 Knolker, H.-J.; Reddy, K.R. CRV, 102, 4303. Review" "Isolation and Synthesis of Biologically Active Carbazole Alkaloids." IV.M-11 Sweeney, J.B. CRV, 102, 247. Review" "Aziridines" Epoxides' Ugly Cousins?" IV.M-12 Gryko, D.T. EJOC, 1735. Microreview" "Recent Advances in the Synthesis of Corr'oles and Core.Modified Corroles." IV.M-13 Gros, P.; Fort, Y. EJOC, 3375. Microreview" "n-BuLi/Lithium Aminoalkoxide Aggregates" New and Promising Lithiating Agents for Pyridine Derivatives." IV.M-14 Honda, T.; Saito, N. H, 56, 633. Review: "Recent Progress in the Chemistry of Polyacylated Anthocyanins as Flower Color Pigments."

210

ORGANIC SYNTHESIS--2003

IV.M-15 Cacchi, S. et al. H, 56, 613. Review" "Palladium Catalysis in the Construction of the Benzo[b]furan and Furan Rings from Alkynes and Organic Halides o r Triflates." IV.M-16 Liu, Z.; Takeuchi, Y. H, 56, 693. Review" "Benzosultams: Synthesis and Applications." IV.M- 17 Abrahim, W.-R.; Spassov, G. H, 56, 711. Review" "Biotransformations of Alkaloids: A Challenge." IV.M-18 Sliwa, W. H, 57, 169. Review: "Calixpyrroles and Related Compounds." IV.M-19 Abele, E.; Lukevics, E. H, 57, 361. Review" "Recent Advances in the Synthesis and Transformations of Heterocycles Mediated by Fluoride Ion Activated Organosilicon Compounds." IV.M-20 Sung, P.-J. et al. H, 57, 535. Review" "Survey of Briarane-Type Diterpenoids of Marine Origin." IV.M-21 Robinson, B. H, 57, 1327. Review: "Synthesis of (.)-Physostigmine, with Particular Emphasis upon the Clarification of Two Enigmatic Early Synthetic Approaches." IV.M-22 Csende, F.; Stajer, G. H, 57, 1353. Review" "Methods for Preparation of ~,-and 6-Oxo Acids as Useful Synthons for Heterocycles." IV.M-23 Ha, H.-J.; Lee, W.K. H, 57, 1525. Review" "Synthetic Applications of Lewis Acid-Induced NMethyleneamine Equivalents." IV.M-24 Wojciechowski, K. H, 57, 1717. Review: "l,2.Dihydro-2,1-benzisothiazole 2,2-Dioxides (Benzosultams) in Organic Synthesis." IV.M-25 Thiemann, T. Dongal, K.G. JCR(S), 303. Review" "Thiophene S-Oxides."

SYNTHESIS OF HETEROCYCLES

211

IV.M-26 Sung, P.-J.; Chen, M.-C. H, 57, 1705. Review: "The Heterocyclic Natural Products of Gorgonian Corals of Genus Briareum Exclusive of BriaraneType Diterpenoids." IV.M.27 Majumdar, K.C.; Basu, P.K. H, 57, 2413. Review" "Formation of Five. and Six-Membered Heterocyclic Rings by Radical Cyclization." IV.M-28 Cacchi, S. et al. H, 58, 667. Review: "Nitrogen-Containing Heterocycles via PalladiumCatalyzed Reactions of Alkynes with Organic Halides or Triflates." IV.M-29 Lavilla, R. JCS(P1), 1141. Review: "Recent Developments in the Chemistry of Dihydropyridines." IV.M-30 Collins, I. JCS(P1), 1921. Review" "Rapid Analogue Syntheses of Heteroaromatic Compounds." IV.M-31 Elliot, M.C. JCS(P1), 2301. Review" "Saturated Oxygen Heterocycles." IV.M-32 Sweeney, J.B. et al. JCS(P1), 2324. Review" "Recent Developments in the Synthesis of Furan2(5H)-ones." IV.M-33 Osborn, H.M.I. et al. JCS(P1), 2419. Review- "1,3-Dipolar Cycloaddition Reactions of Carbohydrate Derived Nitrones and Oximes." IV.M-34 Levai, A. JHC, 39, 1. Review" "Synthesis of 2-Pyrazolines by the Reactions of ~,13Unsaturated Aldehydes, Ketones, and Esters with Diazoalkanes, Nitrile Imines, and Hydrazines." IV.M-35 Sannicolo, F. et al. JHC, 39, 471. Lecture: "Free Design of Chiral Diphosphine Chelating Ligands for Stereoselective Homogeneous Catalysis by Assembling Five-Membered Aromatic Heterocycles."

212

ORGANIC SYNTHESIS--2003

IV.M-36 Bowman, W.R. et al. JCS(P1), 2747. Review" "Synthesis of Heterocycles by Radical Cyclization." IV.M-37 Lobo, A.M.; Prabhakar, S. JHC, 39, 429. Lecture: "Recent Deelopments in the Synthesis of Biologically Active Indole Alkaloids." IV.M-38 Svete, J. JHC, 39, 437. Lecture: "Synthesis of Heteraryl Substituted a-Amino Acid Derivatives, Polyoi, and Related Compounds." IV.M-39 Stanetty, P. JHC, 39, 487. Lecture: "Synthesis of Annelated 1,2,3.Thiadiazole Derivatives." IV.M-40 Haider, N. JHC, 39, 511. Lecture: "Pyridazine-Fused Carbazoles: Synthesis, Reactivity, and Antitumor Activity." IV.M-41 Dal Piaz, V. et al. JHC, 39, 523. Lecture: "4-Amino-5-vinyl-3(2H)-pyridazinones and Related Compounds" Synthesis and Evaluation of Antinociceptive Activity." IV.M-42 Lemiere, G.L.F. et al. JHC, 39, 535. Lecture" "Palladium-Catalyzed Reactions on Chloropyridazines." IV.M-43 Cignarella, G.; Barlocco, D. JHC, 39, 545. Lecture: "Versatility of the Pyridazine System: Chemistry and Biology." IV.M-44 Kurasawa, Y.; Kim, H.S. JHC, 39, 551. Lecture: "Synthesis and Biological Activies of Quinoline Analogues: Pyridazino[3,4-b]quinoxalin-4-ones." IV.M-45 Puentes, C.O.; Kouznetsov, V. JHC, 39, 595. Review" "Recent Advancements in the Homoallylamine Chemistry." IV.M-46 Olivo, H.F.; Hemenway, H.S. OPP, 34, 1. Review" "Recent Syntheses of Epibatidine."

SYNTHESIS OF HETEROCYCLES

213

IV.M-47 Krakowiak, K.E. et al. JHC, 39, 1239. Review: "One-Step Syntheses of Macroeyclie Compounds: A ShOrt Review." IV.M-48 Tominaga, Y. et al. JHC, 39, 571. Lecture" "Synthesis of Methylthiomaleimides for the Preparation of Pyridazines and Related Compounds." IV.M-49 Jedlinski, Z. JHC, 39, 1249. Review" "Nucleophilic Substitution and Electron Transfer in the Ring Opening Reactions of 13-Lactones: A Short Review." IV.M-50 Mealy, M.J.; Bailey, W.F. JOM, 646, 59. Review" "Synthesis of Heterocycles by Cyclization of Unsaturated Organolithiums: A Review." IV.M-51 Palacios, F. et al. OPP, 34, 219. Review: "Preparation, Properties and Synthetic Applications of 2H-Azirines." IV.M-52 Dinsmore, C.J.; Beshore, D.C. OPP, 34, 367. Review: "Syntheses and Transformations of Piperazinone Rings." IV.M-53 Cheng, W.-C.; Kurth, M.J. OPP, 34, 585. Review" "The Zincke Reaction." IV.M-54 Krapcho, A.P., conference editor, PAC, 74, 1317-1368. Plenary "Presented at the 3rd Florida Conference on Lectures: Heterocyclic Chemistry (FloHet.III), University of Florida, Gainesville, Florida, 6-8 March 2002. IV.M-55 Trofim0v, B.A. et al. RCR, 71, 563. Review" "Synthesis of C-Vinylpyrroles." IV.M-56 Chupakhin, O.N.; Beresnev, D.G. RCR, 71, 707. Review" "Nucleophilic Attack on the Unsubstituted Carbon Atom of Azines and Nitroarenes as an Efficient Methodology for Constructing Heterocyclie Systems."

214

ORGANIC SYNTHESIS--2003

IV.M-57 Kaberdin, R.V.; Potkin, V.I. RCR, 71, 673. Review: "Isothiazoles (1,2-Thiazoles): Synthesis, Properties and Applications." IV.M-58 Voitekhovich, S.V. et al. RCR, 71,721. Review" "1,3- and 1,4-Substituted Tetrazolium Salts." IV.M-59 Voskressensky, L.G. et al. S, 155. Review" "Hydrogenated Pyrrolopyridines. Synthesis and Reactivity." IV.M-60 Reddy, P.S.N. et al. S, 1311. Review" "Synthesis of N,N'-Linked Bisazaheterocycles." IV.M-61 Alcaide, B.; Almendros, P. SL, 381. Account: "Selective Bond Cleavage of the 13-Lactam Nucleus: Application in Stereoeontrolled Synthesis." IV.M-62 Padwa, A. et al. SL, 851. Account" "Linked Pummerer-Mannich Ion Cyclizations for Heterocyclic Chemistry.' IV.M-63 Kanemasa, S. SL, 1371. Account" "Metal-Assisted Stereocontrol of 1,3.Dipolar Cycloaddition Reactions." IV.M-64 Tsoungas, P.G. T, 58, 915, 1149. Report: "l,2-Oxazines and Their N-Oxides in Synthesis." IV.M-65 Dinsmore, C.J.; Beshore, D.C. T, 58, 3297. Report" "Recent Advances in the Synthesis of Dik eto pipe r azin es." IV.M-66 Hamama, W.S.; Zoorob, H.H. T, 58, 6143. Report: "Chemistry of Bicyclic Pyridines Containing a Ring-Junction Nitrogen." IV.M-67 Howell, A.R., editor, T, 58, 6979-7194. Symposia-"Strained Heterocycles as Intermediates in Organic in-Print: Synthesis."

V PROTECTING

GROUPS

y,A. Aldehxde and Ketone Protecting Groups V.A-1 Curini, M. et al. TL, 43, 2709; Karimi, B. et al. SC, 32, 669; Ramalingam, T. et al. SL, 604; Roy, S.C.; Banerjee, B. SL, 1677. 0-91% Zr(M ePO3)I.2(O3PC61"~O3H)Q8 _._~OAc Ac20, rt R-CHO Zr(M ePO3)l.2(O3PC6II~SO 3H)~8 OAc dioxane, 50~ 0-95% [similarly with WCia; LiBF3 or CAN as catalysts] V.A-2 Yadav, J.S. et al. SC, 32, 715; Kamal, A.; Chouhan, G. TL, 43, 1347 and SL, 474. R~...O

R2-SH,InCl3

Rz

R.. ~S R 2

CH2Ciz,rt

70-90% [similarly with Sc(OTf)3 or NBS catalysts]

V.A-3

Ranu, B.C. et al. SL, 727; Muthusamy, S. et al. T, 58, 7897. OR 2 +

H

)n

,

DCE :

[similarly using In(OTf)3 as catalyst]

V.A-4 Khan, A.T. et al. JCS(P1), 1026; Yadav, J.S. et al. TL, 43, 4679. R ~

H202, VgOs, NH4Br ~ R ~ O H20/CH2CI2, 0-5~

Rz

68-95% [similarly with CeCiy7H20/NaI] 215

216

ORGANIC SYNTHESIS--2003

V.A-5 Khan, A.T. et al. TL, 43, 2843; Maiti, G.; Roy, S.C. SC, 32, 2269; Sato, T. et al. SL, 1535; Khan, A.T. et al. SL, 463; Kamal, A. et al. TL, 43, 6947. 45-85% HOCH2CH~H, TBATB ~O R1

CH2CI2,0-50C

-

-~ CetTMATB or TBATB CH2CI2, 0-5~ 60-97%

V.A-6 Firouzabad, H.; Iranpoor, N.; Shaterian, H.R. BCJ, 75, 2195; Patel, B.K. et al. JOC, 67, 5842; Mohan, R.S. et al. JOC, 67, 5202; Banik, B.K. et al. SL, 319; Karimi, B.; Golshani, B. S, 784. R~O CH(OEt)3,TABCO _ OMe R1

. . . .

EtOH, 40~

~- %

OMe

60-92% [similar acetal formation using Bu4NBr3, Bi(OTf)3 or I2 catalysts] V.A-7 Yoon, C.M. et al. TL, 43, 2699; Mohan, R.S. et al. JOC, 67, 1027; Procopio, A. et al. JOC, 67, 9093. 0-99% CH(OMe)3, B10HI4 R~O MeOH _ OMe R1

~

B10H14

~ R 1OMe

H20/THF 0-99% [deprotection also reported with Bi(OTf)3 or Ce(OTf)3] V.A-8 Wakharkar, R.D. et al. TL, 43, 6031; Liu, J.; Wong, C.-H. TL, 43, 4037; Firouzabadi, H. et al. JOC, 67, 2572. -MeOH' reflux

R1

70-95% [similarly with SelectfluorTM or Si03/CI] V.A-9 Roschangar, F. et al. T, 58, 1657. "Use of L i t h i u m N , O - D i m e t h y l h y d r o x y l a m i d e as an Efficient In Situ, Protecting Agent for Aromatic Aldehydes."

PROTECTING GROUPS

217

V.A- 10 Wu, Y. et al. TL, 43, 6443.

M~CO2Me 86% recovery

M~~"~CO2Me

("1

a2o ,Mso

Me

M~OM

e

e e

70%

V.A-11 Khazaei, A.; Vaghei, R.G. TL, 43, 3073; de Lijser, H.J.P. et al. OL, 4, 2325; Banik, B.M. et al. SC, 32, 1917; Firouzabadi, H. et al. BCJ, 75, 1761; Hajipour, A.R.; Mallakpour, S.E.; Khoee, S. SC, 32, 9; Hosseinzadeh, R.; Tajbakhsh, M.; Niaki, M.Y. TL, 43, 9413; Ganguly, N.C. et al. SC, 32, 1; Salehi, P.; Khodaei, M.M.; Goodarzi, M. SC, 32, 1259; Shirini, F. et al. SC, 32, 315; Feng, J.-C. et al. SC, 32, 959; Chandrasekhar, S.; Gopalaiah, K. TL, 43, 4023. R~NOH CCI4, :40"C R ~ O R1

~

soych

R1 84-96%

[similar oxime deprotectionreportedusing chloranii/hv;SiO2/BiNO3,

Zn, WCI6or MoCI6; 1-benzyl-4-aza-l-azoniabicyclo[2.2.2]octane

dichromate; 2,6-dicarboxypyridiniumchlorochromate;pyridinium fluorochromate; PCC; HIO3/wetSiO2 or HCO2H/SiO2,hv]

V.A-12 Hosseinzadeh, R.; Sharifi, A. et al. M, 133, 1413; Hosseinzadeh, R. et al. ZN(B), 57,961. R~NNMe2 l.tW,SnCl2,PdCI2 ~ O R1

H20

R1

78-98% [similarlywith MontmorilloniteK-10/I.tW] V.A-13 Lence, E.; Castedo, U; Gonzalez, C. TL, 43, 7917.

~

R1

OH

vN'OH

+

a

pM~

'CH2'C1'2' 0~ 70-99% OMe

218

ORGANIC SYNTHESIS--2003

V.A-14 Das, N.B. et al. SC, 32, 3647; Srinivas, K.V.N.S.; Das, B. JCR(S), 556; Heravi, M.M. et al. M, 133, 107. R ~ N - R 2 SnCl2"2H20/SiO2" R1

R~O

THF

R1

semicarbazones 64-92% 2,4-DNPs 78-90 % phenylhydrazones 76-90% oximes 70-86% [semicarbazone and imine deprotection reported using

CAN with AI203 or SiO2]

V,B, Amino Acid! PrQtecting Grou0s V.B-1 Takahata, H. et al. OL, 4, 585. AA-NH3Ci

AA-NHBoc 76-98%

V.B-2 Kunishima, M. et al. CL, 66. TEA R ~ C O 2 H +MeO~l ~ O C O 2 B n H20 or aq MeOH NH2 N~N OMe

R ~ CO2H NHCbz 67-95%

V.B-3 Rao, T.S. et al. TL, 43, 7793. R

H2N-R-CO2H

.O

O

88-99%

O

CF3 o o

V.B-4

Fields, S.C. et al. OL, 4, 1249. 50-98% CO2H 9-BBN-H,MeOH

[~

NH2

.,,

aq HCI (62-89%) H2NCH2CH2NH2 (0-94%)

PROTECTING GROUPS

219

V.B-5 Zanatta, N. et al. S, 2409. R~CO2R1 + R 3 ~ C X 3 R" O

NH2

aq NaOH

% "CO2R1

CH2Ci2,rt

H~CX3 i,~

||

R~ O 54-91%

V.B-6 Prakash, G.K.S.; Olah, G.A. et al. CC, 2882.

o o

'~AA~oc ~e~O~H~'nH ~ "78~

AAH 91-93%

V.B-7 Waldmann, H. et al. JOG, 67, 6902.

A&

A

O

N.._jPh H

mushr~176176 A% -

buffer, H20/MeCN, rt

A

..OH

O 13-94%

V.C. Amine Proteqting Groups V.C-1 Routier, S. et al. TL, 43,589; Yadav, J.S. et al. SL, 468. R.. R~IBOc

Bu4NF R . . ~ R H THF, reflux 0-95%

[similarly using CeCIy7H20.Nai] V.C-2 Avery, M.A. et al. SL, 883. N~ RH O~CCi3

In, aq NH4C! H20/EtOH,reflux

V.C-3 Moody, C.J. et al. TL, 43, 135.

R-NH2 66-98%

220

ORGANIC SYNTHESISm2003

67-73% Nail, CICHzCH2SO2Ph X - - ~ R

DMF tBuOK, DMF

H

91-99%

SOzPh

V.C-4 Iqbal, M.A. et al. TL, 43, 8063.

R~

4-99% Ph3COH, PTSA

N..R1 H ~ TFA, H20/CH2CI2 40.50%

Tr

V.C-5 Deaton-Rewolinski, M.V. et al. TL, 43, 399. N R

Bn

R

tBuOK, 02 nl~ar rt -

R

H 85-94% (other heterocycles debenzylated)

R

V.C-6 Tsujimoto, T.; Murai, A. SL, 1283.

RA

Cbz 1. Et2AICI,CH2C!2,-78~ ~I 2. PhSMe, 0~ 90-99%

V.C-7 Hibino, S. et al. H, 58, 325.

~ ~ / N

CF3SO3H,HC(OMe)3

'/t'k,,.,~~l~ "R1 MeOH/MeNO2,100~ IVlOM

~'lN

H 45-94%

"R1

PROTECTING GROUPS

V.C-8

221

Hu, L. et al. TL, 43, 4589. H2, Pd/C or PtO2 aq AcOH

R-NH 2 80-97%

V.D. Carboxvl Protecting Grouo~ V.D-1 Paul, S.; Schmidt, R.R. SL, 1107; Yadav, J.S. et al. SL, 826. NaH R-CO2tBu - R-CO2H DMF, rt or 70-800C 60-87% [tbutyl ester deprotection also reperted using Montmorillonite KSF]

V.D-2 Yadav, J.S. et al. SL, 137; Kitamura, M. et al. JOC, 67, 4975. R ~ O ~ ~/ NHBoc

CeCI3-7H20,N a I . MeCN, reflux

R~OH NHBoc 85-93% [allyl ester deprotection reported also with [CpRu(PPh3)(MeCH)2]PF6]

V.D-3 Burger, K. et al. M, 133, 41. HO2C.."~CO2H OH

(CF3)2C=O

HO2

O O~CF3 F3C

V.D-4 Wagner, M.; Kunz, It. ZN(B), 57, 928. "The (2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) Ester---A Carboxy Protecting Group Cleavable Under Neutral Conditions." V.D-5 Hattori, T.; Mayano, S. et al. JCS(P1), 377. "7-Mesityl-2,2-dimethylindan-l-ol" A Novel Alcohol Which Serves as Both a Chiral Auxiliary and a Protective Group for Carboxyl Functions."

222

ORGANIC SYNTHESIS--2003

V.D-6 Blanc, A.; Bochet, C.G. JOC, 67, 5567. "Wavelength-Controlled Orthogonai Photolysis of Protecting Groups." y . E . Hydroxvl

Protecting

Groups

V.E-1 Mineo, T. TL, 43, 7975; Oriyama, T. et al. BCJ, 75,367; Karimi, B.; Maleki, J. TL, 43, 5353; Namboodiri, VV.; Varma, R.S. CC, 342 and TL, 43, 1143; Reddy, B.M.; Sreekanth, P.M. SL, 32, 3561; Autino, J.C. et al. TL, 43, 7589; Kazemi, F.; Kiasat, A.R.; Ebrahimi, S. SC, 32, 2483; Mohammadpoor-Baltork, I. et al. SC, 32, 1633. 33-87% .

.

.

.

In(OTf)3' CH2CI2'0~ In(OTf)3, H20/MeOH, rt

R-OH + 4l-

.

.

.

.

O ~ R

.

60-95% [similar tetrahydropyranylation using Sc(OTf)3; LiOTf; imidazolium AICI4"; AICIa'6H20; SO42"/ZRO2;LiBF4/MeCNor a solid acid catalyst. Depyranylation using LiB4qVIeOHor Bi(III)species] V.E-2 Nagano, H.; Katsuki, T. CL, 782. 79-99% de = 40-98%

V.E-3 Schneider, D.F.; Viljoen, M.S. SC, 32, 721. BrCHzCOBr (f,~,...jOH Ph(Y/'''/OMe ~ Ph (other examples given)

80%

V.E-4 Danishefsky, S.J. et al. TL, 43, 7027. "Reducing Oligosaccharides via Glycal Assembly: On the Remarkable Stability of Anomeric Hydroxyl Groups to Global Deprotection with Sodium in Liquid Ammonia."

PROTECTING GROUPS

223

V.E-5 Lin, W.; Lawrence, D.S. JOC, 67, 2723. "A Strategy for the Construction of C a g e d Diols U s i n g a Photolabile Protecting Group." V.E-6 Giacomelli, G. et al. JOC, 67, 5152. CI,,~I~CI LiF RA O H + ~N DMF/CH2CI2,rt CI

R...'~o..CHO 67-99%

(selective for 1~alcohols)

V.E-7 Depreux, P. et al. TL, 43, 6533. ~ ~ HCI,Et20 ,,

,

~

R

70-99%

OH

V.E-8 Hashimoto, M. et al. SC, 32, 3347. /S~ 93% IN3 I/O. ,, DMAP,CH2C!2 O AZMB

B

A .Ill

AZMBO _SAc

OH .SAc

AcO/---~/O. ,~ ' ~ . " ~ i

OH

"'O" \

PPh3, NaH2PO4 aqTHF, 70*C 78%

AcO I

AZMBO

""0" \

V.E-9 Hajipour, A.R.; Mallakpour, S.E. et al. T, 58, 143; Hajipour, A.R. et al. OPP, 34, 169. ~OTMS LBnP+Ph3(CIO4"),AIC13 R ~ O R1

MeCN (similarly with THP ethers)

R1 20-99%

V.E-10 Jin, T.-S. et al. JCR(S), 456. HMDS, 12MoO3oH3PO4 = RO-TMS R-OH CH2C!2,rt 68-96%

224

ORGANIC SYNTHESIS--2003

V.E-11 Stanescu, M.A.; Varma, R.S. TL, 43, 7307; Namboodiri, V.V.; Varma, R.S. TL, 43, 4593. H%IPh Nafion-H R O y Ph R-OH + Ph MeCN,80C Ph 35-92% [similarly with Fe(NO3)3"9H20] V.E-12 Chakraborti, A.K. et al. JOC, 67, 1776. Ar.OMe or Ph~S2, Na Ar-OH Ar-OCOR or NMP, 90~ or reflux 50-99% Ar.OTs V.E-13 Vatele, J.-M. T, 58, 5689 and SL, 507; Iyengar, D.S. et al. SC, 32, 133. 12, 3~, MS, CH2Ci2 (0-92%) R O ~ /

or DDQ, H20/CH2CI2 (33-94%)

R-OH

Nail, BrCH2CH=CMe2, DMF 46.97% [similarly with DDQ or LiCI/NaBH4] V.E-14 Schlaf, M. et al. JACS, 124, 10508. "Regioselective Silylation of Sugars Through Palladium Nanoparticle-Catalyzed Silane Alcoholysis." V.E-15 Theodorakis, E.A. et al. JOC, 67, 7887; see also: Heldmann, D.K. et al. SL, 1919. "Synthesis of 2'-O-Methoxy ethylquanosine Using a Novel Silicon-Based Protecting Group." V.E.16 Ito, Y. et al. TL, 43, 3273. "Desilylation Under High Pressure." V.E-17 Rotulo-Sims, D.; Prunet, J. OL, 4, 4701; Wu, Y. et al. OL, 4, 2141. Pd/C R-OTES --- R-OH MeOH 49-99% (TBDMS and aromatic TES ethers are uneffected) [TES ether cleavage also reported with o-iodoxybenzoie acid]

PROTECTING GROUPS

225

V.E-18 Yin, D. et al. TL, 43, 8727. NaIO4 RO.SiR1R2R 3

R-OH 82-94%

V.E-19 Parilli, M. et al. SL, 1645; Swamy, N.R.; Venkateswarlu, Y. TL, 43, 7549. H?fOTr I

HObM e

'H2oC/MA~co~68*C" H 67%

[similarly with BiCI3]

V.E-20 Chen, M.-Y.; Lu, K.-C.; Lee, A.S.-Y.; Lin, C.-C. TL, 43, 2777. T TBDMSO--~ B D M S ~

R2

OR1

hv, CBr4 __ T B D MHS H O ~ o ....MeOH, rt

R2

RO~'~OR1 71-95"/o

V.E-21 Ankala, S.V.; Fenteany, G. TL, 43, 4729. TBSOt~'- //

'OTBS MeCN,reflux TBSO-~,~__6/ 'OH 85-97%

V.E-22 Yoon, C.M. et al. JCS(P1), 1223; Procopio, A. et al. TL, 43, 5945; Crouch, R.D. et al. TL, 43, 7151. decaborane R-OTBS " Iv, ' e utl ~'''' " R-OH 90-98% [similarly with Ce(OTf)4 or ZnBr~ H20] V.E-23 Chen, M.-Y.; Lee, A.S.-Y. JOC, 67, 1384. R(~

O/.,.../TMS

CBr4 -"- R-OH MeOH or iprOH 43-95%

226

ORGANIC SYNTHESIS--2003

V.F. Other Protectin~ Grouns V.F-1 Coleman, M.P.; Boyd, M.K. JOC, 67, 7641. "S-Pixyl Analogues as Photocleavable Protecting Groups for Nucleosides." V.F-2 Beaucage, S.L. et al. JOC, 67, 6430. "The 3-(N.tert-Butylcarboxamido).l-propyl Group as an Attractive Phosphate/Thiophosphate Protecting Group for Solid-Phase Oligodeoxyribnucleotide Synthesis." V.F-3 Vedejs, E.; Little, J. JACS, 124, 748. "Aziridinomitosenes by Anionic Cyclization" Deuterium as a Removable Blocking Group." V.F-4 Couturier, M. et al. JOC, 67, 4833. "5,5-Dimethyl-l,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups." V.F-5 Goeldner, M. et al. TL, 43, 8947.

Br_~~ ,,

OH

R-SH EtOH,buffer pH 7 (70%) R

hv, (60-71%)

OH

Vl USEFUL SYNTHETIC PREPARATIONS

YI.A, Functional Grou0 Pre0arations VI.A,I,, Acetals and Ketals see also: IV.K.2 VI.A.I-I Wittmann, V.; Lennartz, D. EJOC, 1363. AC~Q R-OH, CuCI2 AC~Q .

A,

.

.

.

.

.

.

.

.

.

-OH

.-

CHCI3, rt

AcLr'-

"NHAc 36-92%

(R can be a sugar)

VI.A.1-2 Crotti, P. et al. OL, 4, 3695.

MsO"" "(

~2.R'-0H.Ph-H ....

Ott

VI.A.1-3 Lin, C.C. et al. TL, 43, 7721. B z~)r,,,OBz n~OP(OBn)2 R-OH, TfOH B CH2CI2 BnO

H O4"'-,~ ' 76-92%

BnO-.x--"~

BnOoR

64-95%

VI.A.1-4 Handerson, S.; Schlaf, M. OL, 4, 407. BnO"'- BnO

-.,.-..iph..ny.-1,10-phenanthroline 70% ot:~3=9:1%

VI.A.1-5 Kaneko, S. et al. TL, 43, 6705.

"A No'vel Approach to the Stereoselective Semi-Synthesis of GM.237354 by Employing a Highly 13-Selective Glycosylation." 227

228

ORGANIC SYNTHESIS--2003

VI.A.I-6 Mukaiyama, T. et al. BCJ, 75,291; see also: Lam, S.N.; Gervay-Hague, J. OL, 41, 2039; Yamago, S.; Yoshida, J. et al. JOC, 67, 8584.

Bn~q B~nO ~

B B ~ ~ o ~0'~'X .TfOH'.S'&MS= BTF/tBRCN B

F HO~t~ +

82-99% ' ~ ' X

VI.A.1-7 Iadonisi, A. et al. SL, 269.

Q~

.

.

R2-OH,12,Et3SiH .

.

(/'--09)R2

.

R NR1 CH2CI2/MeCN,0~ -~ rt MeO2CO I CX3

RO,'x_~ MeO2CO 69-85%

VI.A.1-8 Balasubramanian, K.K. et al. TL, 43, 6795; Yadav, J.S. et al. TL, 43, 7009; Swamy, N.R.; Venkateswarlu, Y. S, 598. AC~A ~ Ac

HW,R-OH,MontmorilloniteK-10 Ph-CI

AA~-~- ~/O

[similarlywithCeCI3-7H20or BiCI3]

R

52-85% ~:13= 20.100:1

VI.A.1-9 Holson, E.B.; Roush, W.R. OL, 4, 3719, 3723.

~PMB

NIS CH2C!2, .9o0c;

HOr

OBn

~OPMB H~PMB BnO--"/ i 63% dr =8:1

VI.A.I-10 Aloui, M.; Fairbanks, A.J. CC, 1406. SPh BnO

NISac BBn~ ~ MeOH

o,BnO Me ~

USEFUL SYNTHETIC PREPARATIONS

229

Suarez, E. et al. JOC, 67, 7439.

VI.A.I-ll

O ~ R I H hv, PhI(OAc)2, I2 CH2C12

~ R X 66-88%

V I . A . I - 1 2 Fraser-Reid, B. et al. TL, 43, 6953. " Y t t e r b i u m ( I I I ) Trifluoromethanesulfonate for Specific Activation of n-Pentenyl Orthoesters in the Presence of AcidSensitive F u n c t i o n a l i t i e s . " V I . A . I - 1 3 Bach, T.; Lobel, J. S, 2521. H2CO, dioxane

T .OBF2 ~Bu

VLA.2.

Acids

and

55-97%

Anhvdrides

see also: I.G.2, II.A.2, V.D, VI.A.9 VI.A.2-1 Kim, Y.G. et al. T, 58, 9925. CHO R- v

1. CBr4, PPh3, CH2C!2,0~ 2. pyrrolidine, H20, rt 3. aq H CI, dioxane, reflux

CO2H R"

v

40-93%

VI.A.2-2 Lakouraj, M.M.; Movassagh, B.; Bahrami, K. M, 133, 1193; Borham, B. et al. JACS, 124, 3824. O---OOH Af."~,.~ NO2 . = Ar-CO2H dioxane, rt 0-95 % [similar result with 1,2.diphenylethylene, oxone and OsO4]

VI.A.2-3 Six, Y. JCS(P1), 1159. + R

1. Ti(O~Pr)4,.70 to-30~ MgC! . . . . 2.

R

19-87%

230

ORGANIC SYNTHESISm2003

VI.A.2-4 Niwayama, S. et al. TA, 13, 953.

I ~

CO2R

,,esteraseor iipase

,

C~C OzR O2H 49-99% ee = 14-99%

O2R

VI.A.2-5 DeSantis, G. et al. JACS, 124, 9024.

nitrilase _ X H f~ H r ~ A CN - A CO2H A ee = 95-99%

H

nitrilase H

CN-

A

-

r ~

H CO2H

ee -- 91-99 %

VI.A.2-6 Badham, N.F. et al. JOC, 67, 5440.

CN

LiBr

__

H20/DMF/MeCN, 91~

CO2H 49-75%

VI.A,3< Alcqhqls and Related Species. see also: I.A.7.a, II.B.1, III.A VI.A.3-1 Wolker, D.; Haufe, G. JOC, 67, 3015, 3022; Demir, A.S.; Sesenoglu, O. TA, 13, 667; Nakamura, K.; Takenaka, K. TA, 13, 415; Lo, L.-C. et al. JOC, 67, 282; Femandez-Lafuente, R.; Guisan, J.M. et al. TA, 13, 1337; Gotor, V. et al. JOC, 67, 1266 and TA, 13, 1091; Brenna, E. et al. TA, 13, 899. ( F ( F

~OAc

Lipase ~

~""OH + Ac )n O, v 29-47% 23-50% ee = 5-91% ee = 3-95% [various other lipase-catalyzed alcohol resolutions reported] VI.A.3-2 Matsumoto, K. et al. TL, 43, 6933.

PPL R buffer

H 13-33% ee = 46-88%

R

+ ~

R

30-61% ee = 10-99%

USEFUL SYNTHETIC PREPARATIONS

231

VI.A.3-3 Liese, A. et al. TA, 13, 1068. "Enzymatic Synthesis of All Stereoisomers of 1Phenylpropane- 1,2-diol." VI.A.3-4 Matsumoto, T. et al. SL, 122.

~ R Ac~.

Pseudomonascepacia l i p a s e OAc or Candidaantartica lipase Ac

~ R OH 67-86% ee = 96-99%

VI.A.3-5 Curran, D.P. et al. OL, 4, 2585. v

-O "

QH

1. CandidaantarticumB ,,page 2. Fiuorous separation 45% ee = 89%

HQH

48% ee = 95%

VI.A.3-6 Barluenga, J. et al. OL, 4, 2817; Cossy, J. et al. TL, 43, 7083; Ready, J.M.; Jacobsen, E.N. AG(E), 41, 1374. ~n

O

R'OH' Cu(BF4)2"nH20 CH2CI2, rt

{ ~ n .,,,OR OH

90-95% [other epoxide ring openings reported with different nucleophilesand catalysts] VI.A.3-7 Ahn, C.; DeShong, P. JOC, 67, 1754; DeShong, P. et al. JOC, 67, 1751. "An Approach to the Stereoselective Synthesis of syn and anti-l,3-Diol Derivatives: Retention of Configuration in the Mitsunobu Reaction." VI.A.3-8 Joshi, N.N. et al. TA, 13, 851. "Synthesis and Resolution of 2,2-Dimethyl-l,3-diphenyi-l,3propanediol. A New C2-Symmetric and Conformationally Rigid Acyclic Diol."

232

ORGANIC SYNTHESISm2003

VI.A.3-9 Cadot, C.; Dalko, P.I.; Cossy, J. JOC, 67, 7193. "Free Radical Hydroxylation Reactions of Alkyiboronates." VI.A.3-10 Dussau, P.H. et al. OL, 4, 4591.

. ~ R

H202,Yb(OTf)3or TMS-OTf Et20, 0*C-' rt .

.

.

.

r- OH

.

37-60%

VI.A.3-11 Andersson, P.G. et al. JOC, 67, 1567 and OL, 4, 3777; see also: Pietrusiewicz, K.M. et al. TA, 13, 1017.

.oa

LDA,DBU,THF,0~ O

. . . . .

~-

~ ' ~ VI.A.4. A!dehvdes

and

80-95% ee = 91-99%

Ketones

see also: I.A.1, I.A.7.b, II.A.1, V.A VI.A.4-1 Kantlehner, W. et al. ZN(B), 57, 1295. "Formyl-aalen [Tris(diformylamino)methane]---A New Formylating Reagent for Activated Aromatic Compounds." VI.A.4-2 Cheng, C.-H. et al. JOC, 67, 1682.

R _ _ ~ I I + R-CHO .... Ni[Ph3P(CH2)nPPh3]2Br2' ' THF' Zn _- R . _ ~ R 33-87% VI.A.4-30chiai, M. et al. JOC, 67, 4407.

AR% Nu-H,TEA R ~ N u IPh(BF4) MeOH 33-98% VI.A.4-4 Ballini, R. et al. TL, 43, 5233.

R~NO2 DBU R ~ O R1 MeCN,60~ R1 54-80%

1

USEFUL SYNTHETIC PREPARATIONS

233

VI.A.4-5 Goujon, J.-Y.; Shipman, M. TL, 43, 9573. RH~NHR

"R2"COCI'Mg(OEt)2 = R ~ ~ ' ~ N H R

NHR 1

NHR 1 46-95%

V I . A . 4 - 6 0 s h i m a , K. et al. CC, 114. 1. R.Li ~/SiMe2Ph 2. RI-X

R1

~

3. HBF4"Et20 \SiMe2Ph 4. TBAF, KHCO3, aq H202

68-73%

VI.A.4-7 Shi, Y. et al. JOC, 67, 2831. OBz [(R)-BINOL]2.Ti(O/Pr)4,TsOH

~

O

~

Et2 or CH2C!2,0"C

~.,/O ~

OBz 78% ee = 93%

VI.A.4-8 Nishizawa, M. et al. CL, 12; Yusubov, M.S. et al. T, 58, 1607. Hg(OTf)2.(TMU)2 _ Me,~O R ~ ~ H20~4eCN/CH2CI2'rt'i2hR 54-99% [1,2-diketone formation reported similarly from diarylalkynes and PdCI~/DMSO] VI.A.4-9 Li, L.-S.; Wu, Y.-L. TL, 43, 2427. KMnO,NaHCO3 M e O 2 C ~ O ~ B r " H20/MeOH = R 0-90% VI.A.4-10 Wakatsuki, Y. et al. TL, 43, 7531. H -~- _ RuCpCI(PMe3)2 ~ C H O R

H20/PrOH, 100~

75-96%

234

ORGANIC SYNTHESISm2003

VI.A.5. Amides and Related Soecies _

VI.A.5-1 Garrett, C.E.; Jiang, X. et al. TL, 43, 4161; Basel, Y.; Hassner, A. TL, 43, 2529; Zhang, X. et al. JOC, 67, 9471; Makara, G.M. et al. TL, 43, 7221; Peng, Y.; Song, G. OPP, 34, 95. R-CO2H + HzN-R1 NMM,.MeCN,rt ~ ~L~NHR 1 MeO~l ~ O M e

R

r~N 30-96% Cl [amide formation from carboxylic acids also reported using Boc.ODHBT; HOBT, EDC; HOBT/PS-carbodiimideor NH4HCO3/HCONH2/IxW] VI.A.5-2 Liskamp, R.M.J. et al. TL, 43, 9203. H2N.../CO2H : R/

1. R1R2SiCI2,pyr ~ H 2 N ~ N H R 1 2. R1.NH2 -" R~

51-98%

VI.A.5-3 Amedjkouh, M.; Ahlberg, P. TA, 13, 2229. X ~ O

RR1NH O MeCNor EtOH, rt

X~ ~NRR1

,

, Cl3(~"

H O 45-95%

VI.A.5-4 Feroci, M.; Inesi, A. et al. JOC, 67, 1719; Yamada, S. et al.

TL, 43, 43, 647. 647. TL,

(~~]N

a

;'Ph

1"e', TEAP, MeCN ~ J ~ / 2. (RCO)20 R ;'Ph ,

~

86-96%

[N-acylation of amides reported also with MgBr2.Et20as catalyst] VI.A.5-5 Sharghi, H.; Hosseini, M. S, 1057; Giacomelli, G. et al. JOC, 67, 6272. O ~ R 1 NH2OH'HCi'ZnO l , ~ ~NHR R

neat, 140-170~

R 60-95%

[Beckmann rearrangement reported also with a trichiorotriazine]

USEFUL SYNTHETIC PREPARATIONS

235

VI.A.5-6 Nazih, A.; Heissler, D. S, 203. 1. Rt-COX, Nal, MeOH, rt R-NHBoe 2. K2CO3or tPr2NEt, 0*Co rt

~

NHR

R1 61-99%

VI.A.5-7 Hodous, B.L.; Fu, G.C. JACS, 124, 10006. X,~

+ ~Q--"--,? H

At

.

Ph-Me,rt

C ~ N

-v

,

X-..~~r ~

~~... -

R Ar 80-96% ee = 81-98%

VI.A.5-8 Curini, M.; Epifano, F. et al. TL, 43, 4895. Yb(OTf)3, 800C R-NHz + (MeO)2C=O = R-NHCO~e 61-96% VI.A.5-9 Jessop, P.G. et al. JOC, 67, 9070. Pd CI2(MeCN)2,PPh3 R2NH + CO2 CCI4/MeCN

Q-.....NR2

"1" NR2

14-99% VI.A.5-10 Davies, S.G.; Dixon, D.J. JCS(P1), 1869; Parrish, D.A.; Mathias, L.J. JOC, 67, 1820; Kim, T.H.; Yang, G.-Y. TL, 43, 9553; Yoon, Y.-J. et al. S, 733.

RIReNH neat, rt

R1R2

R

"Me Me

l~e 92-98% [trans.amidations reported also with a thiazoline amide or a dichloropyridinazone amide] VI.A.5-11 Goodman, S.N.; Jacobsen, E.N. AG(E), 41, 4703. R~

+ TMS-Nk/---~/O CO' [C~ ~ ~ EtOAc, rt or 50C 56-85%

236

ORGANIC SYNTHESISI2003

VI.A.5-12 Taguchi, T. et al. JOC, 67, 8682.

[PdCi(C3Hs)h R~

(S)-Tol-BINAP Bu

+

(CH2=CHCH20)2C=O

~

THF, rt

N,,- - , , , ~

~..tB

u

U

90-96% ee = 32-44% VI.A.5.13 Shaabani, A.; Teimouri, M.B. JCR(S), 433.

HO2%

C-N-R

O H20,

CH2C!2 or MeCN

~

Z" ~"

83-88%

VI.A.5-14

NHR

0

Su, W. et al. JCR(S), 542. SmI2,, B~ Bt-CH2C! + R-N=C=O THF, 0-15*C~ 65-86

NHR

%

VI.A.5-15 Shen, W.; Kunzer, A. OL, 4, 1315; Kim, Y.G. et al. T, 58, 9925.

Br'R~IBr

R1R2NH

H20/DMF, 80-100~

~ NRIR2

0-95%

VI.A.5-16 Jorgensen, K.A. et al. JACS, 124, 6254 and AG(E), 41, 1790; List, B. JACS, 124, 5656; see also" Yadav, J.S. et al. CL, 318. +

1

EtO2C" N II

N...CO2Et

L-proline

. . . .

rt

.

N..~ H

~1 CO2Et 67-92% ee = 79-99% [aromatic amidation reported with diethyl azodicarboxylate/Sc(OTf)3]

USEFUL SYNTHETIC PREPARATIONS

237

VI.A.5-17 Shibata, N. et al. JCS(P1), 197. PGHN'~CO2 H +

NH2 MeOH/Me2CO---PGH.,e,,.,,,~.~NHR 1 "

+ RLR

+

II O

C-N.R 1

42-51%

VI.A.5-18 Nicolaou, K.C. et al. AG(E), 41, 834. H~ R"--l~t~

/x

RR

NHCO2R1

OH 1. Et3NSO2N'CO2R1, THF, reflux R . _ ~ 2. aq HCI, dioxane, rt 70-82% .

.

.

.

.

.

.

~-

OH

VI.A.5-19 Nozaki, K.; Hiyama, T. et al. OL, 4, 2849; Cunico, R.F.; Maity, B.C. OL, 4, 4357. POCi3, Pd2(dba)3 (~..NMe2 R.I + Me2CHO -- "1" R

66-92% % [similarly with TMS-CONMe2] VI.A.5-20 Kang, J. et al. TL, 43, 9509. A r~.

R ~

chirai Pd cat.

CH2Ci2

A

O

R,.'~. ~ 43-91% ee (R) = 67-95% ee (S) = 40.90 %

VI.A.5-21 Buchwald, S.L. et al. JACS, 124, 7421; Crawford, K.R.; Padwa, A. TL, 43, 7365; Kang, S.-K. et al. SL, 427; see also" Manley, P.J.; Bilodeau, M.T. OL, 4, 3127. Ar.X +

CuI, Cs2CO~ K2CO3,K3PO4 i R1 ..... : HN..R MeHNCH2CH2~IHMe,Ph-Me AC..-N'-R 51-99%

238

ORGANIC SYNTHESIS--2003

VI.A.6.

Amines

VI.A.6-1 Jung, K.W. et al. JOC, 67, 674; Krein, D.M.; Lowary, T.L. JOC, 67, 4965; Grehn, L.; Ragnarsson, U. JOC, 67, 6557; Lattuada, L.; Uberti, F. OPP, 34, 643. R1-NH2 + R.Br

CsOH.H20, 4A MS

RI-NHR + R1NR2 75-93% 0-13% [secondary amines prepared also from 2-aminopyridine, Boc20 followed by NaH/R-X then TFA; by 2 consequtive N-alkylations or from alkyl halides/NH2CN/OH- then H2SO4] DMF, rt

>

VI.A.6-2 Knochel, P. et al. CC, 2546. Ph

Ac Ph

~HR R.NHK, [Pd(C3Hs)CI]2, THF,.rt,. p h . 1 ~ . ~ , . . Ph Ph2

Ph2P5

71-96 % ee = 82-97%

~

[also allylic alkylations] VI.A.6-3 Kanno, H.; Taylor, R.J.K. TL, 43, 7337; Kitamura, M. et al. JOC, 67, 8685; Belier, M. et al. OL, 4, 2055; Merla, B.; Risch, N. S, 1365; Verardo, G. et al. CJC, 80, 779. MnO2, PS-BH3CN = R.CHzNHR1 R-CHzOH + NH2-R1 CH2CI2,MS 57-93%

[reductive aminations reported also with aldehydes or ketones and ammonia, ammonium formate, ammonium acetate or amino esters with Rh catalysts, NaCNBH3 or NaBH4] VI.A.6-4 Pelletier, J.C. et al. OL, 4, 4611. R.NHz,MeOH ~BH4

R , , ~ ' - R1 H 34-81%

VI.A.6-5 Srirangam, J.K. et al. JOC, 67, 1699. EW%ff"~ Ar(BOH)2, Cu(OAc)2, pyr EW%6"--~ ~N ~ H

CH2C12, rt,'air

~

~N ~ Ar 31-99%

USEFUL SYNTHETIC PREPARATIONS

239

VI.A.6-6 Prakash, G.K.S.; Petasis, N.A.; Olah, G.A. et al. JOC, 67, 3718. ~IRtR 2

HF2~ICHO

RIR2NH.R-B(OH)2 HF2C~..t,, .

OH

.

.

.

~

'

EtOH, rt

..

R

()H 30-90% ee = 86-99%

VI.A.6-7 Nishiwaki, K.; Ogawa, T.; Matsuo, K. A G(E), 41, 484. R

f

BuLi, E +

THF

••NvR R 41-96%

VI.A.6.8 Hartwig, J.F. et al. AG(E), 41, 4746 and JOC, 67, 5553, 6479; Buchwald, S.L. et al. OL, 4, 581, 2885 and JACS, 124, 11684; Job, G.E.; Buchwald, S.L. OL, 4, 3703; Alterman, M. et al. S, 1597; Sharifi, A.; Hosseinzadeh, R.; Mirzaei, M. M, 133, 329; Wu, Y.-J. et al. TL, 43, 9291; Maes, B.U.W. et al. SL, 1995; Basu, B. et al. TL, 43, 7967; Hibert, M. et al. SL, 1123; Yin, J. et al. OL, 4, 3481; McManus, H.A.; Guiry, P.J. JOC, 67, 8566; Nolan, S.P. et al. OL, 4, 2229; Fort, Y. et al. JOC, 67, 3029; Andrus, M.B. et al. JOC, 67, 8284; Boykin, D.W. et al. TL, 43, 4221. k ~ --x tBuONa' THF' rt' 15min k ~ / + HNR1R2 ,n,r - -NR1R2 ['Bth(1.Ad)P]P ~

,,rd(P(1-Ad)'Bt h

Br

68-99%

VI.A.6-9 Heutling, A.; Doye, S. JOC, 67, 1961; Siebeneicher, H.; Doye,

S. EJOC, 1213.

R2-NH2 + R ~

R~ .1. CP2TiMe2, Ph-Me, lll~ RL-'r~""" . . . . . . 2. NaBH3CN,ZnCI2,MeOH, rt R R1 78-97%

VI.A.6-10 Srivastava, R.S. et al. TL, 43, 9505. Ph.NHOH + ~ R [Cu(MeCN)4]PF6 p hH 1 ~ dioxane, 80-100~ 15-75%

R

240

ORGANIC SYNTHESIS--2003

VI.A.6-11 Fort, Y. et al. T, 58, 6913 and JCS(P2), 1844; Chaudhari, R.V. et al. TL, 43, 7143.

H~"~N C~

Ni(0,, Nail, rAmONa ~'f~ I'THF, bipyr, styrene, 650C ~ ~

H 2. R1ph.Ci,Ni(0),NaH, tAmON: THF, bipyr, styrene, 65 C

~ / ~ ..-1 I~ ~J"-'tr 66-73% [3 ~ amines formed also from anilines/Ar.I/Cul/tBuOKby double arylation] VI.A.6-12 Barluenga, J. et al. CC, 2362; Willis, M.C.; Brace, G.N. TL, 43, 9085; see also: Jiang, B. et al. T, 58, 261,265. ~R2 HNRaR4,Pd(dba)2 or Pd(OAc)2 ~ R 2 R

Br

tBuONa, B1NAP, Ph-Me, 90~

NR3R4 45-90%

R

VI.A.6-13 Jorgensen, K.A. et al. CC, 1240; Enders, D.; Wallert, S. SL, 304. Af-NH +

Ni(CIO4)2"6H20 : A r ~ R ~ ~ chiral bisoxazoline R" v 6-93% ee - 0-96% [similarly with chiral hydrazines and vinyl sulfonates]

O

VI.A.6-14 Sapountzis, I.; Knochel, P. JACS, 124, 9390.

H

~".w. --MgC! ~ FC~ II + I! O 2 ~

NaBH4,FeCI 2

.L--FG1 THF,-20~-' rt

Cr._~~'i ~ _ _ -- F

FG1

63-86%

VI.A.6-15 Yadav, J.S. et al. SL, 53 and S, 1061; Hou, X.-L. et al. JOC, 67, 5295; Lautens, M. et al. OL, 4, 3465. LiCIO4 _- ~ . NHTs ~NTs + H2N-Ar MeCN,rt ~"'NHAr 83-95% [different catalysts used for similar transformations]

USEFUL SYNTHETIC PREPARATIONS

241

VI.A.6-16 Moskalev, N.; Makosza, M. CC, 1248.

H 1. KF/AI203 or KOH, D M S O ~ I ~ . _ . 7 . , . R .... = 2. Me-I

Z~~INO20~.._ +

R

15-63% OMe VI.A.6-17 Matteson, D.S.; Kim, G.Y. OL, 4, 2153. R-N3 + Re'I-'B"3 K+ 1. SiCI4, Ph-Me, A _ R,. 2H O 70-85% VI.A.6-18 Nicholas, K.M. et al. TL, 43, 931. Ar-NO2 +

R CO, [(CsMes)Fe(CO)212 dioxane,120oc At"

42-83%

VI.A.6-19 Yamamoto, Y. et al. H, 58, 347. Pd(PPh3)4, Ph-CO2H Ar , Me + HNRR1 dioxane

R

g

77-98% VI.A.6-20 Ollevier, T.; Lavie-Compin, G, JOC, 67, 7891; Olofsson, B.; Somfai, P. JOC, 67, 8574.

~

BiCi3, rt

O + H2N-Ar

~ n . , , OH

c-hex

NHAr

56-85% VI.A.6-21 Shimizu, M. et al. BCJ, 75, 1819; Erdik, E.; Daskapan, T.

TL, 43, 6237.

~ O2Et

Oc2Et O2Et

"~CO2Et

R-MgBr THF, -78~ OMe

f'~ y

KOH, air H20/EtOH

OMe [similarly with iminosulfonates]

OMe 29-93 %

242

ORGANIC SYNTHESISm2003

VI.A.7. Amino Acid Derivatives VI.A.7.1 Taylor, R.J.K. et al. JOC, 67, 1802; O'Donnell, M.J. et al.

JACS, 124, 9348.

"Enantiomerically Pure ~.Amino Acid Synthesis via Hydroboration-Suzuki Cross-Coupling."

VI.A.7-2 Wang, M.-X.; Lin, S.J. JOC, 67, 6542. "Practical and Convenient Synthesis of Enantiopure a-Amino Acids and Amides." VI.A.7-3 Markidis, T.; Kokotos, G. JOC, 67, 1685. "Synthesis of Enantiopure co-Functionalized Cls a.Amino Carboxylates." VI.A.7-4 Barbas, C.F., III et al. JACS, 124, 1842, 1866; Jorgensen, K.A. et al. JOC, 67, 4352. PMR,, + R

R1

(L)-Proline CO2Et

~

.-

CO2Et

R ~1 47.86% dr = >19:1

ee = > 9 5 %

[similarly with Ar-H, iminoesters and (R)-ToI-BINAP-CuPF6]

VI.A.7-5 Dal Pozzo, A. et al. JOC, 67, 6372. "Amino Acid Bromides: Their N-Protection and Use in the Synthesis of Peptides with Extremely Difficult Sequences." VI.A.7.6 Hayes, C.J. et al. JOC, 67, 7613. "Enantioselective Synthesis of the Excitatory Amino Acid (lS, 3R)-l-Aminocyclopentane-l,3-dicarboxylic Acid." VI.A.7-7 Imperiali, B. et al. CC, 1912. "Enantioselective Synthesis and Application of the Highly Fluorescent and Environment-Sensitive Amino Acid 6-(2Dimethylaminonaphthoyl)alanine (DANA)." VI.A.7-8 Hughes, A.B. et al. OL, 4, 3767. " A Novel Synthesis of N-Methyl Asparagine, Arginine, Histidine, and Tryptophan."

USEFUL SYNTHETIC PREPARATIONS

243

VI.A.7-9 Porzi, G.; Sanoli, S. et al. TA, 13, 1181. "Stereoselective Synthesis of Bis(a-amino Acid) Derivatives Isomeric with Cysteine." VI.A.7-10 Boto, A.; Hernandez, R. et al. TL, 43, 8269 [from serines]; Badet, B. et al. JOC, 67, 5408 [cx.alkylamino]; Venkatraman, S. et al. JOC, 67, 2686 [4.BocCyclohexyl]. "Glycines" VI.A.7-11 Ranu, B.C. et al. T, 58, 2529; Davis, F.A. et al. JOC 67, 7802. R~O InCI3 ~ b ~ H R 2 + R2-NH2 + KCN -"R1 THF R1 47.93% VI.A.7-12 Walsh, P.J. et al. JACS, 124, 12225. ~ / Ph

1. KH, CI3CCN,0~ ~ r t CI3C~~H 03, NaOH CI3C~~HR R "2. Ph-Me, reflux

-Ph ~'''~/A" R MeOH 64-96% ee = 89-99%

HO2C " 57-92%

VI.A.7-13 Lu, T.-J. et al. JOC, 67, 2309. R-X, base

..........

aq HCI

~

........

THF

R.~/CO2 H ~

NH2 94-96%

74-96% de = >98 %

ee = 94-98 %

VI.A.7-14 Davies, H.M.L.; Venkataramani, C. AG(E), 41, 2197; Perez, P.J. et al. CC, 2998.

Bn. e +N Ar Boc

1. L SO2Ar .i 4 -~

2. TFA

Bn., ~

~02Me 55-67% ee = 87-96% [diazoesters used also for cx.aminoacid synthesis] CO2Me

H

Ar

244

ORGANIC SYNTHESIS--2003

VI.A.7-15 Park, H.; Jew, S. et al. AG(E), 41, 3036. "Highly Enantioselective and Practical Cinchona-Derived Phase-Transfer Catalysts for the Synthesis of a - A m i n o Acids." VI.A.7-16 Hamada, Y. et al. JOC, 67, 9210. "Diastereoselective Synthesis of All Stereoisomers of 13methoxytyrosine, a Component of Papuamides." VI.A.7-17 Scobie, M. et al. TL, 43, 5965, 5969; Portlock, D.E. et al.

TL, 43, 6845.

HNRIR2, OHCCOzH

CH2C!2,rt 5-82%

(2* amines only) [hydrazides used similarly] VI.A.7-18 Nubbemeyer, U. et al. T, 58, 1317 [enentioselective 3-aryi]; Kurth, M.J. et al. JOC, 67, 5673 [spirooxazolino]; Yao, Z.-J. et al. JOC, 67, 1038 [2S,3R-3-hydroxy-3.methyl]; Taylor, C.M. et al. JOC, 67, 4466 [3,4-dihydroxy]; Stevens, C.V. et al. JOC, 67, 6509 [2,4-methanol; Qiu, X.; Qing, F. JOC, 67, 7162 IN-Boo cis.4.di, and trifluoromethyl]; Hale, K.J.; Lazarides, L. CC, 1832 [L-proline A83586C mimetic]. "Prolines" VI.A.7-19 Chemla, F. et al. SL, 919; see also: Reissig, H.-U. et al. SL, 863.

J

BnN\

/R

\CO2Me

1. LDA ,2. ZnCI2

Bn ~ R

3. E+

E

CO2Me

56-82%

VI.A.7-20 Jorgensen, K.A. et al. AG(E), 41, 4236.

AI,,,,,~N,,,~CO2Me + R O 2 ~

R TEA,THF, rt ~ R A O ~ c o 2 M e 'll,u ,,Z. _~u

a

12-95% ee = 5-94%

USEFUL SYNTHETIC PREPARATIONS

245

VI.A.7-21 Maison, W.; Adiwidjaja, G. TL, 43, 5957 [stereoselective disubstituted]; Burke, T.R., Jr. et al. JOC, 67, 1448 [constrained phenylalanine analog]; Kadouri-Puchot, C. et al. JOC, 67, 2424 [trans-6alkyl]. "Pipecolic Acids" VI.A.7-22 Tang, T.P.; Ellman, J.A. JOC, 67, 7819 [from enolates and t.butanesulfinyi imines]; Wyatt, P.B. et al. TL, 43, 6991 [homologated histidine]; Uneyama, K. et al. JOC, 67, 2692 [S-tBu-13-CF3 isocysteine]; Chakraborty, T.K.; Ghosh, A. SL, 2039 [via Hoffmann rearrangement]; Fustero, S. et al. JOC, 67, 4667 [via ester a-condensation with imidoyl chlorides]. "13-Amino Acids" VI.A.7.23 Davies, S.G. et al. TA, 13, 1555 and JCS(P1), 1858.

p h : e N . . Bn + R ~ C O 2 Li

(-)-camphorsulfonyl- p h ~ : ~ B n tBu ~ ~. R~CO2tBu THF,-780C-~ rt _ OH 70-91% de = 88-96 %

VI.A.7-24 Raines, R.T. et al. JOC, 67, 4993.

Ac

O

PPh2

R

Bn

HzO/THFI rt, 12h H Ac

O R 90-99%

H Bn

VI.A.7-25 Ikunaka, M. et al. TA, 13, 1201 [2S,3S-Boc AHPBA and (R). Boc DMTA building blocks]; Martin, S.F. et al. JOC, 67, 4062 [cyclopropane derived]; Pelliciari, R. et al. JOC, 67, 5497 [spiro[2.2]pentane scaffold]; Tamamura, H.; Fujii, N. et al. JCS(P1), 577 [hydroxyethylamine dipeptide isosteres]. "Peptidomimetics" VI.A.7-26 Guama, A. et al. JOC, 67, 7483 [6-endo-BT(t) L containing peptides]; Hruby, V.J. et al. JOC, 67, 6353 [7.Bn and 8-eh azabicycio[4.3.0]nonane amino acid esters]; Liskamp, R.M.J. et al. OL, 4, 2173 [cyclic c~2[3-tripeptides]. "Peptide Turn Mimetics"

246

ORGANIC SYNTHESIS--2003

VI.A.7-27 Herranz, R. et al. JOC, 67, 3866 [2-oxopiperazine-based]; Pyne, S.G. et al. JOC, 67, 227 [cyclopentenyl glutamic analogs]. "Conformationally Constrained Peptide Analogs" VI,A.8.

Azides

VI.A.8-1 Klump, S.P.; Schecter, H. TL, 43, 8421; see also: Wong, C.-H. et al. JACS, 124, 10773. 1. BuLi R-NH2 . . . . R-N3 2. (Et2N)3P+-N3Br" 41-88% VI.A.8-2 Tale, R.H.; Patil, K.M. TL, 43, 9715; Deshmukh, A.R.A.S. et al. TL, 43, 1345. NAN3,Na2SO4,MeCN, rt ~ - [ N3 Ph-CO2H ~. Ph

~

_=

~_

66-96%

B(on)2

F [similarlywith triphosgeneas catalyst] VI.A.8-3 Guerin, D.J.; Miller, S.J. JACS, 124, 2134.

:base,caol,st-

R chiraipeptide

R 65-95% ee = 63-92%

VI.A.8-4 Baruah, M.; Bols, M. SL, 1111. IN3 ~ R ~ O MeCN, reflux 41-78%

}n

VI.A.8-5 Goksu, S.; Secen, H.; Sutbeyaz, Y. S, 2373. ~n

O

.

HN3, PPh3, DEAD .

.

.

.

.

~n

N3

N3 50-85%

USEFUL SYNTHETIC PREPARATIONS

247

VI.A.8-6 Yadav, J.S. et al. S, 2383; Sabitha, G. et al. OL, 4, 343. NTs NAN3, . . . LiCIO4 . . ~ . . NHTs MeCN, reflux ~'~'~N3 85-90% [similarly with CeCly7H20 as catalyst] YI.A.9.

Carbohydrates

VI.A.9-1 Barbas, C.F., III et al. TL, 43, 9591. R-CHO + yHO (L)-prol!ne R,..~.,O~OH Me"

DMF, 40C-~rt

Me""y

"Me OH

24-53% ~:13 = 1:2.2.5

VI.A.9.2 Nelson, A. et al. JCS(P1), 1444. "Towards Complete Stereochemical Control: Complementary Methods for the Synthesis of Six Diastereoisomeric Monosaccharide Mimetics." VI.A.9-3 Boulineau, F.P.; Wei, A. OL, 4, 2281 [from 4deoxypentenosides]; Lin, C.-H. et al. T, 58, 253 [L.gulose and L-xylose]; Akagi, M. et al. CPB, 50, 866 [L-ribose]. "Synthesis of L-Sugars" VI.A.9-4 Wong, C.-H. JOC, 67, 4559. "Synthesis of a-Galactosyl Ceramide, a Potent lmmunostimulatory Agent." VI.A.9-5 Dubreuil, D. et al. TL, 43, 237, 241. Bn~)~-OBn Bn~ V..OBn DBU, imidazole ~ B n[O / ~~]B. .n- NS.. O2~ BnO II [ DCE, rt, 1.5h

NO2

O 70%

248

ORGANIC SYNTHESIS--2003

VI.A.9-6 Hauser, F.M.; Hu, X. OL, 4, 977. New Route to C-Aryl Glycosides."

"A

VI.A.9-7 Rye, C.S.; Withers, S.G. JOC, 67, 4505. "Synthesis and Evaluation of Potential Inhibitors of Chondroitin AC Lyase from Flavobacterium heparinum." VI.A.9-8 Knapp, S.; Myers, D.S. JOC, 67, 2995. Synthesis of a.GalNAc Thioconjugates from an a . G a l N A c Mercaptan." VI.A.9-9 Meijer, A.; Ellervik, U. JOC, 67, 7407 [sialylation promoters]; Yao, Z.-J. et al. JOC, 67, 6758 [analog precursor]; Wu, S.-H. et al. JOC, 67, 1376; Lin, C.-C. et al. JOC, 67, 7565; [dimer derivatives]; Koreeda, M. et al. JOC, 67, 5654; Hanessian, S. et al. JOC, 67, 3346; Gege, C.; Geyer, A.; Schmidt, R.R. CEJ, 8, 2454 [sialyi Lewis x mimetics]. "Carbohydrates Related to Sialic Acids" VI.A.9-10 Oscarson, S.; Sehgelmeble, F.W. JOC, 67, 8457 [inulin and levan]; de Lederkremer, R.M. et al. JOC, 67, 4430 [ct.D-Galp-(1-~a)-[5-DGalf-(l~3)-D.Man]; Crich, D.; Li, H. JOC, 67, 4640 [Salmonella type E core].

"T risa cc h ari des"

VI.A.9-11 Lowary, T.L. et al. JOC, 67, 892 [13-arabinofuranosyl hexasaccharides]; Houseknecht, J.B.; Lowary, T.L. JOC, 67, 4150 [oligofuranosides]; Robina, I. et al. T, 58, 521 [related to plant defense]; Seeberger, P.H. et al. EJOC, 826 [branched high mannose]; Belot, F. et al. TL, 43, 7743 [sulfated MECA-79 epitopes]. "Oligosaccharides" VI.A.10.

Esters (see also: I.A.2, I.A.3, I.G.2, II.A.2)

VI.A.10.1 Zhang, N.; Vozzolo, J. JOC, 67, 1703.

f.~ R

EWG-A

MeOH

DMF/DMA, reflux

r~ OMe 4-955

EWG-A

USEFUL SYNTHETIC PREPARATIONS

249

VI.A.10-2 Kaimal, T.N.B. et al. TL, 43, 879; Appendino, G. et al. OL, 4, 3839; Wagner, A.; Mioskowski, C. et al. TL, 43, 7597; Kobayashi, S. et al. CC, 94. R-CO2H + R1-OH ,

12, reflux

---- R-CO2R 1 0-98%

[similar esterification using DIAD/TPP; Me2N+C(CI)SPh CI', DIEA, or TfOH with thiol nucleophiles]

VI.A.10-3 Singh, V.K. et al. T, 58, 1369; Habibi, M.H. et al. M, 133, 323; Clarke, P.A. et al. JOC, 67, 5226 and TL, 43, 4761. R~OH

Ac20, Cu(OTf~

R1

= R~OAc

with or without AcOH

R1 70-99%

[KsCoW12046"3H20 also used as catalyst; YbCI3 or CeCI3 used for monoacylation of diols]

VI.A.10.4 Nolan, S.P. et al. OL, 4, 3583; Waymouth, R.M.; Hedrick, J.L. et al. OL, 4, 3587; Das, B. et al. SC, 32, 249. R-CO2R1 R2-OH,4A MS, THF, r t . ~r~S..R

R-CO2R2 95-99%

,o

[transesterificaion reported also with SiO2-supported BF3/EtOAc]

VI.A.10-5 Tanaka, A. et al. SC, 32, 3319; Ram, R.N.; Meher, N.K. T, 58, 2997. R-OH + BrPh3 P+"

Br Br/

ZnBr 2 DMF

~

R-OCHO 71-99%

[similarly with CI3CCHO/K2CO3]

VI.A.10-6 Pamies, O.; Backvall, J.-E. JOC, 67, 9006, 1261.

R:L

X

4-CIPh-OAc. 0" H" Ph

Ru~

X

eh

ee = 85-97%

, ,phP

PhH'R I

P

:

oc ~o c'o co

39-99%

250

ORGANIC SYNTHESIS--2003

VI.A.10-7 Panza, L. et al. TA, 13, 867; Ma, S. et al. CEJ, 8, 5012; Kielbasinski, P. et al. TA, 13, 735; Kirihara, M. et al. TA, 13, 2283; Hedenstrom, E. et al. TA, 13, 835.

C13 ~

CDH27

OH Candidaantartica

C

lipase

c-C6H12,40'C -

YOAc

C13H27

",,OAc

OH

§

38% 57% de = 100% de = 100% [lipase.catalyzed esterification/resolution reported with various substrates]

VI.A.10-8 Gotor, V. et al. JOC, 67, 4978; Kita, Y. et al. JOC, 67, 411; Ned, C.; Williams, J.M.J. TA, 13, 2197. OH OH MeO2C--~OH "~'OH

CAL'Aor.CAL-B M e O 2 C ~ .

-~

~ / ' ~ 1 o !i

"OHo g 37-97% [diol desymmetrizationreported under similar conditions] VI.A.10-9 Takahashi, T. et al. CC, 1018; Mohammadpoor-Baltork, I.; Khosropour, A.R. M, 133, 189; Kagan, H.B. et al. TL, 43, 5715. MCIs/6 R-OR1 + R2.COCi ~ R2.CO2R1 75-99% [similarly with TMS ethers and Bi0II) salts or Sc(OTf)3] VI.A.10-10 Otera, J. et al. AG(E), 41, 4117; see also: Theil, F. et al. JOC, 67, 1781. "Fluorous Biphasic Esterification Directed Towards Ultimate Atom Efficiency." VI.A.10-11 Taylor, R.J.K. et al. SL, 1293. MnO2, NaCN R.CH2OH MeOH/THF, rt or reflux (also amides with R1-NH2)

R-CO2Me 53-80%

USEFUL SYNTHETIC PREPARATIONS

251

VI.A.10-12 Takahashi, T. et al. T, 58, 7327; Mudryk, B. et al. TL, 43, 6317. MoCls, . h_..~0 Ph-COCl + )n DCE,80*C P " O"{J) n CI 52-96%

[similarly with trioxane/ZrCh] VI.A.10-13 Ramig, K. et al. TL, 43, 7731. K ~ C F 3 ,.!'Na.Oie , i e C N . ~ C O 2 M e

R1

2. aq HCI

RI

23-59% VI.A.10-14 Lee, J.C. et al. CC, 956.

R~ R

TI(OTf)3 1 R2CONMe2 .

.

.

.

.

.

.

.

.

.

.

R ~ ( ~ R2 R1 O 90-99%

VI.A.10-15 Tang, L.; Deng, L. JACS, 124, 2871.

D"QD)"QN (CO2"' R1-OH, Et20 O

OH 61-85%

ee = 60.96%

VI.A.10-16 Shieh, W.-C. et al. TL, 43, 5607 and JOC, 67, 2188; Linclau, B. et al. OL, 4, 2961. I.tW (MeO)2C=O, DBU R-CO2H ...... = R-CO2Me MeCN, 160~ 95-99% [similarly with o-alkylisoureas] VI.A.10-17 Glatzhofer, D.T. et al. OL, 4, 2349. NHAr NaNO2

~R

Acz~), AcOH, 0~ ~ rt

~

OAr R

72-94%

252

ORGANIC SYNTHESISm2003

V I . A . 1 1,. E t h e r s VI.A.11-1

Shah, S.T.A.; Voelter, W. et al. TL, 43, 8603. CsF, celite _ R-OH + X - R 1 MeCN R-OR1 54-91%

VI.A.11-2

Jha, S.C.; Joshi, N.N.

"

O~_~O[ H + B~m B R

JOC, 67, 3897.

"S

NaH DMF/THF

~O

H

R 38-90%

V I . A . 1 1 . 3 Kobayashi, S. et al. CL, 10; E1 Gaied, M.M. et al. 366; Sharma, G.V.M. et al. TA, 13, 687. DBSA R.OH + HO.R 1~ R-OR l H20, 24h 77-91%

JCR(S),

(also for thioethersand dithioacetals) [similar ether formation catalyzed by PTSA, FeCI3, or Yb(OTf)3] VI.A.11-4

Ishii, Y. et al. R-OH +

JACS, 124, 1590.

Ac(I'~

V I . A . 1 1 - 5 Zhang, W. et al.

JOC, 67, 3494. R --

Me

[Ir (cod) C l] 2,Na 2CO3 ' = RO~ 63-95%

TL, 43, 6575; see also" Yamamoto, Y. et al.

Pd(PPh3)4, H + + HO-R 1 . . . . = dioxane, 100 ~

-R ~.J"O

..R 1

30-89%

(also couplings with carboxylic acids) Y I . A . 1 1 - 6 Buchwald, S.L. et al. OL, 4, 973; Song, J. et al. OL, 4, 1623; see also" Nicolaou, K.C.; Boddy, C.N.C. JACS, 124, 10451. . ~

R--

I

+ HO-R1

CuI, C s 2 C O 3

R---~

1,10-phenanthrone, 110~

OR ! 70-97%

USEFUL SYNTHETIC PREPARATIONS

VI.A.11-7

K i m , H.; Lee, C.

JACS, 124, 7882.

~

OL,

253

4,

4369; Evans, D.A.; Leahy, D . K .

~c Et2Zn, Pd(OAc)2,THF, rt R1 + R2-OH , ~ R~

Q--"

54-99%

IHBN

[similarly with carbonate leaving groups, R-OLi, CuX, P(OMe)3,Rh(PPh3)CI] VI.A.11-8 Jiang, X. et al. TL, 43, 9225; Bajwa, J.S. et al. TL, 43, 6709; Hosomi, A. et al. SL, 313; see also: Wada, M. et al. CL, 248. R ~ O + R3~[,.OR2 BiBr3~CI(R1)2SiH. ~R10'..R 2 R1

R3 82-92%

VI,A,12.

Halides

VI.A.12-1 Heasley, V.L. et al. JOC, 67, 2183. "Addition of Bromine Chloride and Iodine Monochloride to Carbonyl-Conjugated, Acetylenic Ketones: Synthesis and Mechanisms." VI.A.12-2 Yang, D. et al. JOC, 67, 7429. O R ~ . R1

R2 +

~O

Mg(CIO4)2 N-X MeCNor EtOAc, rt

~ ~ R

2

X R1 65-99%

VI.A.12-3 Nakajima, M. et al. TL, 43, 8827; Sharghi, H.; Eskandari, M.M. S, 1519; Righi, G. et al. TL, 43, 5867. OH SiCI4, ipr2NEt ph/~'..~ Ci chiral bipyr di-N-oxide Ph Ph 95% ee = 90% [similar epoxide opening with X2, cat. PhNHNH2 or N-Boc aziridine cleavage with LiX, Arab 15]

254

ORGANIC SYNTHESIS--2003

VI.A.12-4 Singh, R.P.; Shreeve, J.M. CC, 1196. Selectfluor TM R-NH2 ' ' --- R-NF2 or R.NHF DMF or DMA 65-80 % 63-85% VI.A.12-5 Shreeve, J.M. et al. JOC, 67, 6415, 1918, 1588. "Synthesis of Fluorinated a-Keto Ethers, Benzil, 6,6'Dialkoxy-2,2'-bipyridines, Polyfluoroethers, and 2-Methyi2-polyflu oroalkanyloxy-methyl-l,3.propane diols" VI.A.12-6 Prakash, G.K.S.; Olah, G.A. et al. JACS, 124, 7728. "Stable Dialkyl Ether/Poly(hydrogen Fluoride) Complexes: Dimethyi Ether/Poly(hydrogen Fluoride), A New, Convenient and Effective Fluorinating Agent." VI.A.12-7 Sodeoka, M. et al. JACS, 124, 14530; Kim, D.Y.; Park, E.J. OL, 4, 545. RI~ O NFSI, EtOH ,. R I ~ O RI ~co2tBB

[~'~A~

~.~

IArA~~ r [ ~ ] ~

yd Ar/'~r~i , Ar/"~A r~ , ~

R 17 cO2tBu

x. [

49-96 ee = 83-94%

[a different catalyst used similarly]

VI.A.12-8 Hara, S. et al. BCJ, 75, 1597. IF5, TEA.3HF F,N/F RS''x" R1 . . . . . - R~R 1 7-83% (monofluorination also achieved) VI.A.12-9 Peppe, C. et al. SC, 32, 3711. R~R

1

CuCI2,LiC! ,CR~RIC! DMF ~ CI 65-94%

VI.A.12-10 Gladysz, J.A. et al. JOC, 67, 6863. "Synthesis and Reactivities of Disubstituted and Trisubstituted Fluorous Pyridines with High Fluorous Phase Affinities."

USEFUL SYNTHETIC PREPARATIONS

255

VI.A.12-11 Rozen, S. et al. JOC, 67, 8430. " F r o m Alkyi Halides to Alkyltrifluoromethyls Using B r o m i n e Trifluoride." VI.A.12-12 Kim, D.W.; Song, C.E.; Chi, D.Y. JACS, 124, 10278. KF, [bmin][BF4] R.OMs ~ R-F MeCN, 100"C 40-95% VI.A.12-13 Flosser, D.A.; Olofson, R.A. TL, 43, 4275; see also: Mikami, K. et al. JOM, 662, 77. 1. (C!3CO)2C=O,KF, 18-Cr-6, MeCN R-OH ~ R-F 2. (BuzN)2C-N*BuzF" 62-89% VI.A.12-14 Baba, A. et al. JACS, 124, 13690. R~O In(OH)3 + HSiMe2C! ~ = R1 CHCI3

R•CI R1 0-99%

VI.A.12-15 Giacomelli, G. et al. OL, 4, 553; Hiegel, G.A.; Rubino, M.

SC, 32, 2691.

CIv~Cl

R,.~OH R1

+

. %.c,

N~N

DMF/CH2CI2,rt

R1

C! 70-98% [similarly with a trichlorotriazinetrione] VI.A.12-16 Hajipour, A.R.; Ruoho, A.E. OPP, 34, 647; Hajipour, A.R. et al. JOC, 67, 8622; Starber, S. et al. S, 1513 and SL, 598; Syvret, R.G. et al. JOC, 67, 4487; Colobert, F. et al. TL, 43, 5047; Tilve, R.D. et a l. TL, 43, 9457. j=amnmm.

!

Ar-H + Lf"~q+--Bn ~ Ar-I \"-~ / ICI2" neat 50-99% [similar aromatic iodination with SelectfluorrM/I2; NIS/TFA or I2, SiO2-Fe(NO3)3.9H20] V I . A . 1 2 - 1 7 Muathen, H.A. S, 169. " P y r i d i n i u m Dichlorobromate: A New, Stable B r o m i n a t i n g Agent for Aromatic C o m p o u n d s . "

256

ORGANIC SYNTHESISm2003

VI.A.12-17 Zard, S. et al. SL, 811. R"

OR1

COzEt +

S

cumyl peroxide Ph-CI, reflux

Br

~

R.F

30-87%

VI.A.12-18 Yadav, J.S.; Mishra, R.K. TL, 43, 5419; Firouzabad, H.; Iranpoor, N.; Hazarkhani, H. TL, 43, 7139. R-OPMB

CBr4, PPh3

----

CH2CI2, 0-30"C

R-Br 45-94 %

[iodination from TMS, TBDMS or THP ethers with SiO2-Cl, NaI]

VI.A.12-20 Klapars, A.; Buchwald, S.L. JACS, 124, 14844. Ar.Br

Nal, Cul, dioxane, ll0*C ....... = Ar-I ~ . NtlMe 93-99 % V

'e Nil Me

VI,A.13. Nitriles and lmines VI.A.13-1 Boruah, M.; Konwar, D. JOC, 67, 7138; Iranpoor, N.; Firouzabadi, H.; Aghapour, G. SC, 32, 2535; Hekmatshoar, R. et al. M, 133, 111; Bose, D.S.; Goud, P.R.; SC, 32, 3621; Yamamoto, H. et al. AG(E), 41, 2983; Talukdar, A. SC, 32, 3503; Sharghi, H.; Sarvari, M.H. T, 58, 10323; Das, B. et al. SL, 625. R-CH=NOH

A1CI3.6H20 , KI

---- R-C-N H20/MeCN, 8 0 " C 60-96 %

[similarly with PPh3/NCS; phthalie anhydride; triphosgene; [(HO)ReO3] or [(TMS-SiO)ReO3]; PhCH=Ru(PCy3)2CI2 or "one-pot" from aldehydes with NH2OH.HCI and AI203/MeSO2CI or

Hy.Zeolite/l.tW]

VI.A.13-2 Kim, S.; Song, H,-J. SL, 2110. R-X + Ts-CN +

~...~SOeMe

.... hv, rt . azo.bis(cyciohexanecarbonitrile

VI.A.13-3 Smaliy, R.V. et al. S, 2416. Het.H

OCN-P(O)CI2 ..... DCE, rt

Het-CN 20-95%

R-C--N 53-95 %

USEFUL SYNTHETIC PREPARATIONS

257

VI.A.13-4 Chen, F.-E. et al. S, 1804; Taylor, R.J.K. et al. SL, 1291. NH4HCO3, (Bu4N)2S2Os, Cu(HCO2)2 R-CH2OH , ~ R-C--N Ni(HCO2)2, aq KOH, ~PrOH 85-92% [similarly with NH3/IPA/MgSO4/MnO2] VI.A.13-5 Kikugawa, Y. et al. SC, 32, 3871; Yonezawa, N. et al. SC, 32, 2519. R-"%N-'O~

ZrCI4 ,.. ~ R-C-N "CN MeNO2 or Ph.H 68-86% [similarly with NiCi2/Zn]

V I . A . 1 3 - 6 0 u t u r q u i n , F. et al. T, 58, 3275. R k ' ' ' ' x ~ N"NR2 + Ph.XC! LDA _--- R~.T.,,CN XPh 0-75% V I . A . 1 3 - 7 Sato, N. TL, 43, 6403. (~DMG tBuLi + Ph-OCN ...... THF or EhO,-70-, 0~

V I . A . 1 3 - 8 Fukumoto, Y. et al. OM, 21, 3845. TpRuCI(PPh3)2 R1 ~ + HzNNR2 . . . . . . . . dioxane, reflux

~

DMG

CN 47-98%

Rr~"-CN 17-88%

VI.A.13-9 Weibel, N.; Charbonniere, L.J.; Ziessel, R.F. JOC, 67, 7876. x

r Br

R1-NH2,K2CO3 =

N''RI

MeCN, reflux 69-98%

258

ORGANIC SYNTHESIS--2003

VI.A.14, O t h e r

N-Containing

V I . A . 1 4 . 1 Roy, S. et al.

Functional Grgups

OL, 4, 3055.

HNO3, AIBN

R-CO2H

-

MeCN, 50~

V I . A . 1 4 - 2 Kawada, A. et al.

R-No2 30-80%

CPB, 50, 1060.

~ ~ LiNO3' Sc(OTf)3~ Ac20" ~ MeCN, rt

+ N~ NO2

02

32-85% 1:3-4

VI.A.14-3 Ishii, Y. et al.

JOC, 67, 5663 and CC, 1352. NO2 or HNO3

R.H

N-OH

- R-NO2 12-73%

o V I . A . 1 4 - 4 Melguizo, M. et al.

SL, 255. iAmONO ,

X

y

DMSO,rt

NO X

Y 32-86 %

VI.A.14-5 Zolfigol, M.A.; Bamoniri, A.

SL, 1002.

R1RNH

SL, 1621; Zolfigol, M.A. et al.

NaN,O2, wet SiO2, CH2C!2, rt ~OSO3H

~ R1RN.NO 60-99%

[similarly with trichioroisocyanuric acid]

VI.A.14-6 Gowda, S.; Gowda, D.C. S, 460; Suzuki, H. et al. 8254. HCO2NH, Pb R-Ar-NO2 ~ R-Ar-N=N-Ar-R MeOH, reflux 88-94% [azo oxides formed from nitroarenes and Bi metal]

JOC, 67,

USEFUL SYNTHETIC PREPARATIONS

259

VI.A.14-7 Momiyama, N.; Yamamoto, H. OL, 4, 3579 and AG(E), 41, 2986. R-NO + R

R3

THF

R

R

42-98% [a.O-substituted hydroxylaminessimilarly from Ph-NO, TMS ethers and Et3Si-OTf] VI.A.14-8 Sibi, M.P. et al. OL, 4, 3343. RL~~)O

R1-NHOR2, Sm(OTf)3 RLN..OR2 THF, rt ~1 50-98%

VI.A.14-9 Gielen, H. et al. TL, 43, 419. R.CO2R1 1. MeAICI(NH2) --r ~rI~SH.HC 1 2. MeOH NH2 43-87% VI.A.14-10 Shi, Y. et al. TL, 43, 57; Cunha, S. et al. TL, 43, 49; Manimala, J.C.; Azslyn, E.V. TL, 43, 565; Wu, Y.-Q. et al. JOC, 67, 7553. Q~....NH2 1. NaH, DMF" R

2. R1.NCS

H

(~N~S R HN,,R1

R2-NH2,EDCI_ ( ~ ~ N H R DMAP,TEA

[guanidines formed also by treatment of thioureas with EDCi or and R-NH2 or from bisimidazole imines and amines]

R NHR1 30-80% Bi(NO3)3.5H 2

VI.A.14-11 Ballini, R.; Maggi, R. et al. TL, 67, 8445. MCM-41.TBD R t t ~ I NHR R.NH2 + CS2 S 57.91% VI.A.14-12 McGuiness, M.; Schecter, H. TL, 43, 8425. 1. BuLl R2C=N-NH2 -- RzC=N2 2. (Et2N)3P+-N3Br" 46-90%

2

260

ORGANIC SYNTHESISm2003

VI.A.14-13 Heydari, A. et al. CL, 368.

TMS-CN, LPDE R-CHO + Me2N-NH2 rt, 30min

H

NC~N"NMe2 R

92-96% VI.A.14-14 Yamamoto, Y. et al. AG(E), 41, 1780. H

R-CHO + Me2N-NH2

TMS-CN, LPDE NC~N,.NMe2 ' -'rt, 30min R

92-96%

YI,B. Additions to /~,lkenes arid Alkynes VI.B-1 Morrill, T.C. et al. JOC, 67, 2481. "Transition Metal-Promoted Hydroboration of Alkenes: A

Unique Reversal of Regioselectivity."

VI.B-2 Miura, M. et al. JOM, 648, 297.

[RhCl(cod)]2 ~ p R + Ph4BNa + (RCO)20 ........ -~ dppp 27-126% (based on Ph4BNa)

R~O Ph 0-86%

VI.B-3 Tiecco, M. et al. CEJ, 8, 1118.

~,SMe OMe

..~.H4)2S208 , ~SeOSo3HSMe RCH=CHR

R

2

Ar*Se/ R 58-79% dr = 2.57.99:1 (also selenocyclizations, selenylation.deselenylation) OMe

VI.B-4 Huang, X.; Xie, M. OL, 4, 1331.

R~Ts

+ Ph-SeMgBr + R1-CHO ' THF/CH2CI2, -20oc PhSd Ts 73-89% Z:E 24-99:1 PhMgBr

lSe

R

USEFUL SYNTHETIC PREPARATIONS

261

VI.B-5 Tsuji, Y. et al. JOM, 660, 173.

Bu3SnCN, Pt(PPh3)2CI2 Bu3S~..~CO2R COzR ................. = -'THF, rt RO2C CN 73-92%

ROzC ~

VI.B-6 Zhao, H.; Cai, M. S, 1347. R

~

TMS

1. iBuMgBr, Cp2TiCI2,Et20, r t 2. Ar-SeBr, THF,-10--* 30"C

r

I~__/TMS \SeAr 68-86 %

,

J

VI.B-7 Marcotullio, M.C. et al. TL, 43, 1201.

P~__/R 2 KI, NAN3,Ox0ne,wet A1203 R1

rt

.I~

/R 2

R1 N3 64-92%

V I.B-8 Gagosz, F.; Zard, S.Z. OL, 4, 4345.

R,.

S~

OEt

lauroyl peroxide, CSA, DCE E t O ~ ~ /~N~ ~.s g.,..,-'x',,,~N-,.Z~ ~'~r~Z ) 61-88%

VI.B-9 Ait-Mahand, S.; Dolbier, W.R., Jr. OL, 4, 3013. R2 SFsC1,Et3B F ~ 2 ~R 1 ~ / \ CI R h e x , - 3 0 * C ~ rt R R1 79-98% VI.B.10 Campos, P.J.; Garcia, B.; Rodriguez, M.A. TL, 43, 6111.

R--'''---R 1 .CuO.HBF, ....... 12, Et3SiH = R~ R 1 CH2CI2, -30"C I 43-80%

VI.B-11 Hartwig, J.F. et al. JACS, 124, 3669; Doye, S. et al. SL, 799; Odom, A.L. et al. OL, 4, 2853.

"Hydroamination of 1,3-Dienes and Alkynes"

262

ORGANIC SYNTHESIS--2003

VI,C. B o r o n Comoounds VI.C-1 Ishiyama, T.; Miyawa, N.; Hartwig, J.F. et al. JACS, 124, 390; Ishiyama, T.; Miyaura, N. et al. TL, 43, 5649. Ar-H +

~(~

/O-...___ dB'-~O~ __

Ir(I) .... R

/O~ =- A r--B~o~ ___ 58-95%

R

VI.C-2 Wong, K.-T. et al JOC, 67, 1041; Li, W.; Nelson, D.P. et al. JOC, 67, 5394; Cai, W.; Ripin, D.H.B. SL, 273. iPrMgBr [Ar-MgX] 1. B(OMe)3,THF,-78"C I(~ Ar-X ~ .... ~ ArTHF,-40~ 2. HOCH2(~H2OH,Ph-Me 62-96% [Ar-Li/B(O/Pr)3 then HC! for boronic acid preparation. 3-Bromopyridineconverted to the corresponding diethylborane with EtMgCI, Et2BOMe] VI.C-3 Suginome, M.; Ito, Y. et al. OM, 21, 1537. / PhMe2Si---

+

.... Ni(acac), PCy3 . DIBAH, Ph-Me, 900C

~a

~,, B,,O

15-89% VI.C-4 Yamamoto, Y.; Akiba, K. et al. CEJ, 8, 2976. M ~ e 2

e2 BX2CI THF, -78~ 16-84%

VI.C-5 Podesta, J.C.; Rossi, R.A. et al. OM, 21, 4886. "Synthesis of Benzene- and Pyridinediboronic Acids via Organotin Compounds."

USEFUL SYNTHETIC PREPARATIONS

VI.D. Nucleosides,

Nucleotides.

263

etc.

VI.D-1 Hegedus, L.S. et al. JOC, 67, 4076, 7649.

Bn~~

B-H,Pd2(dba)3.CHCl3,TBAF,DMF Bnt~O~~ 9.44

13:r = 32.3:1 VI.D-2 Haraguchi, K. et al. JOC, 67, 5919.

S ~ tBu2

PhSeC!or NIS,silylatedpyrimidine MeCN tBu2

~. ~_ 62-88%

VI.D-3 Wnuk, S.W.; Robins, M.J. et al. JOC, 67, 1816. "Stereodefined Synthesis of O3'-Labeled Uracil Nucleosides." VI.D-4 Gillet, L.C.J.; Scharer, O.D. OL, 4, 4205. "Preparation of C8-Amine and Acetylamine Adducts of 2'Deoxyguanosine Suitably Protected for DNA Synthesis." VI.D-5 Chattopadhyay, A.; Salaskar, A. JCS(P1), 785. "A Facile and Simple Entry into Isodideoxynucleosides." VI.D-6 Csuk, R.; Kern, A. ZN(B), 57, 1169; Ortuno, R.M. et al. JOC, 67, 4520. "Cyclopropanoid Nucleoside Analogues" VI.D-7 Schneller, S.W. et al. T, 58, 9889; Mauquez, V.E. et al. JOC, 67, 5938 [bicyclo[3.1.0]hexanederived]; Kitade, Y. et al. T, 58, 1271 [noraristeromycin derivatives];Garcia-Mera, X. et al. S, 1084 [indan derived]; Hrebabecky, H. et al. CCC, 1681. "Carbocyclic Nucleosides" VI.D-8 Fisera, L. et al. SL, 1113. "New Chiral Nitrones in the Synthesis of Modified Nucleosides."

264

ORGANIC SYNTHESIS--2003

VI.D-9 Popsavin, M. et al. T, 58, 569 [pyrazole and tetrazole-related]; Veronese, A.C. et al. T, 58, 1005 [pyrazole]; Benhida, R. et al. JOC, 67, 3724 [heterocyclic], Fuentes, J. et al. JOC, 67, 2577 [isothiocyanato and thioureylene di-]; Sun, J.-S.; Benhide, R. et al. OL, 4, 4209 [6-thiazolyl-5. )benzimidazole]. "C-Nucleosides" VI.D-10 Robins, M.J. et al. JOC, 67, 6788. "Nucleic Acid Related Compounds. Nonaqueous Diazotization of Aminopurine Nucleosides." VI.D-11 Tahmassebi, D.C.; Kool, E.T. et al. JOC, 67, 5869. "A Highly Effective Nonpolar Isostere of Deoxyguanosine" Synthesis, Structure, Stacking, and Base Pairing." VI.D-12 Groziak, M.P.; Thomas, D.W. JOC, 67, 2152 [transglycosidically tethered]; Raap, J. et al. JOC, 67, 1480 [pyrimidine bases]; Kraszewski, A. et al. JCS(P1), 31 [aryl phosphate and phosphorothiolates]; Li, P.; Shaw, B.R. CC, 2890 and OL, 4, 2009 [cyclic boranophosphorothioate]; Zhao, Y.F. et al. CC, 2414 [hydrogen phosphonate d4T and AZT derivatives]; Wiemer, D.F. et al. JOC, 67, 9331 [5'-phosphonate derivatives of cytidine and cytosine arabinosides]. "Nucleotides" VI.D-13 Nielsen, P. et al. S, 797. "A Ring-Closing Metathesis Strategy Towards Conformationally Restricted Di. and Trinucleotides." VI.D-14 Huang, Z.; Benner, S.A. JOC, 67, 3996 [with bridging S groups]; Grinstaff, M.W. et al. OL, 4, 4571 In-stacked phenothiazinelabeled]. "Oligodeoxynucleotides" VI.D-15 Wendeborn, S. et al. TL, 43, 5461 [amide-modified]; Manoharan, M. et al. TL, 43, 7613 [1~ amine guanidylation of]; Griesang, N.; Richert, C. TL, 43, 8755 [ethynylfluorobenzene nucleobase surrogates]; Grandas, A.; Farras, J. et al. OL, 4, 1827 [novel preparation]. "Oiigonucleotides" VI.D-16 Miller, G.P.; Kool, E.T. OL, 4, 3599. "A Simple Method for Electrophilic Functionalization of DNA,"

USEFUL SYNTHETIC PREPARATIONS

265

VI.D-17 Koch, T. et al. S, 802. "Preparation of LNA Phosphoramidites." VI.E Phosvhorus. Selenium and Tellurium Comvounds VI.E-1 Deprele, S.; Montchamp, J.-L. JOM, 643-644, 154.

,?

A.O-]:L..H + H

,

,?

RxSi(OR1)4.x ------4.. R O'-'~-.H H 85-99%

VI.E-2 Mantyla, A. et al. TL, 43, 3793. (RO)21LOH +

Bu4NHSO4,NaHCO3 CISO20,.,./Ci . . . . . . . . . . HzO/CHzCI2, 0*C~ rt

(RO)2R~,,,CI 36-90%

VI.E-3 Fischer, B. et al. JOC, 67, 711. "Diethyl Chlorophosphite: A Versatile Reagent." VI.E-4 Chan, A,.S.C. et al. TL, 43, 2789; Newman, P.D. et al. CC, 2558. "New Chiral Phosphine Ligands" VI.E-5 Han, L.-B.; Tanaka, M. et al. JACS, 124, 3842; Deprele, S.; Montchamp, J.-L. JACS, 124, 9386. R ....

Pd(PPhMe2)2Me2, Ph2PO2H : menthyl-(~P.,,,,1 R + menthyl'O--~P"Hph Ph'Me'70~ Ph [r 60-96 %

VI.E-6 Bunlaksananusorn, T.; Knochel, P. TL, 43, 5817. tBuOK Ph2PH + ~ ' R . . . . . . . Ph2 P ' ' ' ' ~ DMSO, rt-40~ 63-90% VI.E-7 Rossi, R.A. et al. JOM, 664, 223. 1. Na, NH3 2. R3SnCi Ph3P . . . . . . . . . : 3. Ar-I, Pd(PPh3)2CI2 4. H202

Ph2R,,Ar 69-97%

266

ORGANIC SYNTHESIS--2003

VI.E-8 Baldwin, L.C.; Fink, M.J. JOM, 646, 230; Turro, N.J. et al.

JOM, 646, 239.

"Arbuzov Type Rearrangements"

VI.E-9 Chan, K.S. et al. TL, 43, 3537; Stadler, A.; Kappe, C.O. OL, 4, 3541. R/X~._

X

P Ph3, Pd(OAc)2 j ~ ~ . . _ . . . . . --PPh2 neat, 115"C 0-44% [similarly with Ph2PH]

VI.E-10 Mikolajczyk, M. et al. TA, 13, 2571; Doye, S. et al. EJOC, 457. I~H3 ToI,,-S'-N~-~',.Ar +

(Et2N)2R.Li

=.

~

Ar ~

O P(OH) 2

. NH2 53-95% ee = 76-98%

[similarly with imines, HP(O)(OR)2, Me2AICi]

VI.E.11 Xu, X.-H.; Liu, W.-G. JCR(S), 444; Nishiyama, Y.; Sonoda, N. et al. JOC, 67, 8696. Arl.ZnCI

S e __ ~ Arl.SeZnCl ......... Ar2I + X" ~ Arl.SeAr THF, 0oc HMPA/THF, 60~ 67.75% [similarly with (PhSe)2, R-X, La, I2]

VI.E-12 Koketsu, M.; Ishihara, H. et al. JCS(P1), 737 and JOC, 67, 486; Koketsu, M.; Fukuta, Y.; Ishihara, H. JOC, 67, 1008. "Reactions of Acyl Chloride, [Me2+N=CCI2]Ci" or R-NCO with LiAIHSeH" VI.E-13 Wirth, T. et al. CEJ, 8, 1125. "New and Efficient Chiral Selenium Electrophiles." VI.E-14 Comasseto, J.V. et al. T, 58, 1051. (EtO)2P.,. R~ . ~ R

1

~[BuTeLi] _

BuT r RA~,.';~ R1 65-85%

USEFUL SYNTHETIC PREPARATIONS

267

VI.E-15 Capparelli, M.V. et al. JOM, 654, 91. X2

BrMg

ArTe-TeAr -------- [Ar-TeX] . . . .

!--MgBr

ArTe ---- TeAr 42-97%

VI.E-16 Magnier, E.; Wakselman, C. CCC, 67, 1262. "A Mild and Practical Preparation of Trifluoromethaneselenenyl Chloride." VI.E-17 Marino, J.P.; Nguyen, H.N. JOC, 67, 6291. "Electrotelluration" A New Approach to Tri- and Tetrasubstituted Alkenes." VI.F Silicon

Comoourl~ls _

VI.F-1 Johannsen, M. et al. JACS, 124, 4558; Pedersen, H.L.; Johannsen, M. JOC, 67, 7982; Han, J.W.; Hayashi, T. TA, 13, 325; Sherrington, D.C. etal. JCS(P1), 1523; Osakada, K. et al. JOC, 67, 6889; Wagner, A.; Mioskowski, C. et al. OL, 4, 2117; Geuorgyan, V. et al. JOC, 67, 1936; Yoshida, J. et al. JOC, 67, 2645; Ozawa, F. et al. JOM, 645, 192; Boudjouk, P. et al. JOM, 645, 1. A~". ~ v, R r

HSiCI3, [CIPd(C3Hs)]2,rt _ ............. ~ O P~,iMe

~

O'/~~'ph'|Me

A

R

74-95% ee = 86-98%

[hydrosilylations reported with other silanes, substrates and catalysts]

VI.F-2 Murata, M.; Masuda, Y. et al. OL, 4, 1843. RI~~" ~ [Rh(coO)(MeCN)2]BF4 ~ Si(OEt)3 X + HSi(OEt)3 . . . . TEA, DMF, 80~ R/\~/ 70-90% VI.F-3 Woerpel, K.A. et al. JACS, 124, 6524. .OP. ..OP~;i(tBu) 2 ipI""'"~ tBu2SiCI2,Li ~ ip~"",,. 46-54% ds = 11.5-24:1

268

ORGANIC SYNTHESISw2003

VI.F-4 WrackmVI.F-3 Le Bideau, F. et al. CC, 1408. R1-OH, KOH, 18-Cr-6 R

=

CH2C!2 or neat, rt

R 50-94%

VI.F-5 Hodgson, D.M. et al. TL, 43, 7895. R~

.LTMP'TMS'CI ........ -- R/, ~ TMS THF, 0*C 0-75%

VI.F-6 Wrackmeyer, B. et al. CCC, 67, 822.

R3

R3

~S S BR3 R ~ ~ B R 2 R ~ R 3 ----90-99% VI.F-7 Tokitoh, N. et al. OM, 21, 4024; Nishimura, K. et al. OM, 21, 3667. "Transient 9-Silaanthracene Derivatives" yI.G.

Sulfur

Cgmpounds

VI.G-1 Voelter, W. et al. TL, 43, 8281. R-SH + R1-X

--CsF/ce!ite " MeCN

:

R.SR 1 49-90%

VI.G-2 Lakouraj, M.M. et al. SC, 32, 1237; Zhang, S. et al. JCR(S), 582. (RS)2 + RI'X

Zn, AICI3 .~ nwl"2"~fD~'~'Vu

R'SR1 0-99%

VI.G-3 Mitsuda, T. et al. JACS, 124, 12960. R1-SH, CpRuCl(cod) R ..... "--"

\

OCO2Me

N-Me-piperidine

100~ 30rain

~

S

R

1 20-83%

USEFUL SYNTHETIC PREPARATIONS

269

VI.G-4 Node, M. et al. TL, 43, 8569. "Synthetic Equivalents of Benzenethioi and Benzylmercaptan Having Faint Smell: Odor Reducing Effect of Trialkylsilyl Group." VI.G-5 Martin, M.T. et al. TL, 43, 2145. 1. Zn, AcOH, H20 SO2CI . . . . . . 2. Me2SiCl2 3. Ar-CH2OH, EtOAc

34-87%

VI.G-6 Ranu, B.C. et al. SL, 987. ~ ' ~ )n

I'tw' R'SH' InCl3' siO2

R

SR 53-82%

VI.G-7 Deng, L. et al. AG(E), 41, 338; Nishiyama, K.; Tomioka, K. JOC, 67,431; Kamimura, A. et al. TL, 43, 6189. ::~O

R-SH +

(DHQD)2pyr R ~ O Ph.Me, rt ~ Et

h

o,,, (DHQD)2Pyr =

~NI.,

'j

~

Et" [ - , f j

80-98 % ee = 2 1 - 7 7 %

o,,. Ph

~N ~

[other catalysts and substrates used similarly] VI.G-8 Kwong, F.Y.; Buchwald, S.L. OL, 4, 3517; Venkataraman, D. et al. OL, 4, 2803; McWilliams, J.C. et al. OS, 79, 43. R.,,/~-~

X + HS.R1

C uI, K2CO3

HOCHzCH2OH, iPrOH, 80~

-~ R / ~ ~ ~ . _ SR1

71-95% [other catalysts and a triflate leaving group used for aryl sulfide preparation] VI.G-9 Wang, L. et al. TL, 43, 8141. Sm RS-SO3Na H20 , 90~

RS-SR 83-92%

270

ORGANIC SYNTHESISm2003

VI.G-10 Karami, B. et al. S, 2513; Karimi, B.; Zareyee, D. SL, 346 [HMDS, DMSO]; Sanz, R.; Arnaiz, F.J. et al. S, 856 [DMSO, MoO2CI2(DMSO)2]; Zeynizadeh, B. JCR(S), 564 [iodine]; Hajipour, A.B.; Ruoha, A.E. JCR(S), 547 [Me4N.CrO3.HCI]. TMS-CI or NC-CI, DMSO R-SH

-

:

CH2C!2, rt

RS-SR

75-98 %

[various other reagents used for disulfide formation] VI.G-11 Crich, D.; Neelamkavil, S. OL, 4, 4175. " F l u o r o u s Dimethyl Sulfide" A Convenient, Odorless, Recyclable Borane C a r r i e r . " V I . G - 1 2 Srogi, J.; Liebeskind, L.S. et al. OL, 4, 4309. N~ R-B(OH)2 + RiS O

THF, 45.50"C . .......... ~ R.SR 1 COzMe 51-83% ~

"OCu

VI.G-13 Yadav, J.S. et al. SL, 784; Smyth, T.P. et al. JCR(S), 326. Sc(OTf)3 _ Ar~ s~O Ar-H + SOC12 "'~"u ,~..z CL-rt .z, / Ar 70-95% V I . G - 1 4 Naso, F. et al. JOC, 67, 7289. "A S t r a i g h t f o w a r d Enantioselective Route to Dialkyl Suifoxides Based upon Two C a r b o n - f o r - C a r b o n Substitution Reactions on the Sulfinyl G r o u p . " VI.G-15 Baskin, J.M.; Wang, Z. OL, 4, 4423; Cacchi, S. et al. OL, 4. 4719. (CuOTf)2.Ph-H Ar-I + R-SO2" . . . . . . . . . . . . ~ Ar-SO2R MeHNCH2CH2NHMe, DMSO, ll0~ 27-96% [similarly with Pd2(dba)3, xantphos] VI.G-16 Benaglia, M. et al. JOC, 67, 7911. R1N=NR1 R-CS2CPh3 .... EtOAc or Ph.Me, reflux

R.CS2R1 50.85%

USEFUL SYNTHETIC PREPARATIONS

271

VI.G-17 Bouchez, L.; Vogel, P. S, 225; Huang, X.; Vogel, P. S, 232. TM~

1. SO2, TBDMS-OTf, CH2C!2,-90-~ -10*C~ , . / , 2. TBAF, RI-x

SO2R1 60-70%

VI.G-18 Baskin, J.M.; Wang, Z. TL, 43, 8479; Chan, W.Y.; Berthelette, C. TL, 43, 4537. 1. MeO2C(CH2)2SO2Na R-X --- R-SO2NH2 2. base 3. NH2OSO3H

41-85%

[suifonamide formation reported also from sulfinate, bistrichloromethylazodicarboxylatethen Zn] VI.G-19 Malacria, M. et al. OL, 4, 4093; see also: Malacria, M. et al. SL, 116. M~

R~qH2 . O H oPh-I=O, ~Me , ~ CN, rt

"

M~ P ? N H 60-95%

VI.G-20 Gais, H.-J.; Bohme, A. JOC, 67, 1153. )n (~__NHR yd2(dba)3.CHCl3,CH2C!2,rt

C? VI.G-21 Bargon, R.M. et al. JOC, 67, 7037. S8, Mo(O)(S2CNEt2)2 R-NC Me2CO, 56~

91-96% ee = 92-99%

R-NCS 61-93%

VI.G-22 Hashimoto, S. et al. TL, 43, 9561. ) n + PhI=NNs R

R

chiral diRh cat.

NHNs ~

)n R

R

52-88% ee = 70-84%

272

ORGANIC SYNTHESIS--2003

VI.G-23 Renard, P.-Y.; Mioskowski, C. et al. CEJ, 8, 2910; Iranpoor, N.; Firouzabadi, H.; Shaterian, H.R. TL, 43, 3439. TMS-NCS, Bu4NF R-Br ..... = R-SCN THF 77-98% [thiocyanates f o r m e d also from

R-SH and PPh3(SCN)2]

VI.G-24 Caddick, S. et al. OL, 4, 2549. 02 1. R1-X, Bu3SnH, AIBN, Ph-Me, reflux 02 . . . . . . . . . . . , RHN.S..~..-~ R1 C6FS ' . x ~ f 2. RNH2, DBU, THF, 65~ 30-99% VI.G-25 Kim, J.N. et al. SL, 173.

EWG

DABCO, H20/THF, rt 2. TsNH~ 50-700C

1.

EWG

__ w

42-79% VI.G-26 van Boom, J.H. et al. TL, 43, 6451. R

~ "''N'Ns

O=~:' ~ ,'.i

RNHNs,Pd(dba).CHCl3, PPh3TEA, THF HO'"'~

,NBn Ns"

VI.H., Tin

,.NBn Ns' 36-85%

Comr~ounOs _

VI.H-1 Shen, Y.; Wang, G. OL, 4, ;2083. F3~SO2Ph Bu3SnH,AIBN = F 3 ~ S n B u 3

R

F

Ph.Me, 85~

R

F

77-98% Z:E = 100"1 VI.H-2 Chopa, A.B. et al. OM, 21, 1425.

Arc(P(OEt)2

Me3SnNa NH3(L) ~

Ar-SnMe3 20-98%

USEFUL SYNTHETIC PREPARATIONS

273

VI.H-3 Tanner, D. et al. JOC, 67, 7309; Nielsen, T.E.; Tanner, D. JOC, 67, 7309. " ~ _R1 l'(Bu3Sn)(PhS)CuLi'THF"78~ R ~ = R

2. NH4OH.NH4CI

Rl

SnBu3

41-95%

VI.H-4 Gasfaldi, S.; Stien, D. TL, 43, 4309; Clive, D.L.J.; Wang, J.

JOC, 67, 1192.

"New Tin Reagents Easily Removable from Reaction Mixtures"

VI.H-5 Braune, S.; Kazmaier, U. JOM, 641, 26; Podesta, J.C. et al. JOM, 650, 173; Alami, M. et al. AG(E), 41, 1578. "Regioselective and Stereoselective Hydrostannations"

VI.H-6 Cheng, C.-H. et al. CC, 2552. Pd~dba)3.dba TMS-SnR3 + :~:. . \R 1 Ph-Me,rt

T ~ R3S

R1 80-91% E:Z = 99:1

VI.H-7 Uhlig, F. et al. JOM, 646, 271. "Reaction Pathways Towards 1,1,2,2-Tetratbutyl distannanes."

VII REVIEWS

Vll./k T e c h n i q u e s VII.A-1 Haswell, S.J. et al. T, 58, 4735. Report"

"Micro Reactors: Principles and Applications in Organic Synthesis."

VII.A-2 Bose, A.K. et al. S, 1578. "Microwave-Induced Organic Reaction Enhancement Special (MORE) Chemistry for Less Pollution" Applications Topic: for Process Development." VII.A-3 Heydari, A. T, 58, 6777. Review" "Organic Synthesis in an Uneonvential Solvent 5.0 M Lithium Perehlorate/Diethyl Ether." VII.A-4 Kobayashi, S.; M~abe, K. A CR, 35, 209. Review"

"Development of Novel Lewis Acid Catalysts for Selective Organic Reactions in Aqueous Media."

VII.A-5 Zhao, H.; Malhotra, S.V. AA, 35, 75. Review"

"Applications of Ionic Liquids in Organic Synthesis."

VII.A-6 Gladysz, J.A.; Curran, D.P. eds. T, 58, 3827-4131. Symposia "Fluorous Chemistry." in-Print" VII.A-7 Bannwarth, W.; Haag, R. et al. AG(E), 41, 3964. Review"

"Modern Separation Techniques for the Efficient Workup in Organic Synthesis." 274

REVIEWS

275

VII.A-8 Gladysz, J.A., guest ed. CRV, 102, 3215-3892. Reviews- "Recoverable Catalysts and Reagents." VII.A-9 Rajender, R.S. T, 58, 1235. Report: "Clay and Clay-Supported Reagents in Organic Synthesis." VII.A- 10 Budnikova, Y.H. RCR, 71, 111. Review:

"Metal Complex Catalysis in Organic E le ct r osyn th esi s."

VII.A-11 Duggan, P.J.; Tyndall, E.M. JCS(P1), 1325. Review:

"Boron Acids as Protective Agents and Catalysts in Synthesis."

VII.A-12 Coates, G.W. et al. AG(E), 41, 2237. Review:

"Catalysts for the Living Insertion Polymerization of Alkenes: Access to New Polyolefin Architectures Using Ziegler-Natta Chemistry."

VII.A-13 Saljoughian, M. S, 1781. Review"

"Synthetic Tritium Labeling: Reagents and Methodologies."

VII.A.14 Dehli, J.R.; Gotor, V. CSR, 31, 365. Review" "Parallel Kinetic Resolution of Racemic Mixtures" A New Strategy for the Preparation of Enantiopure Compounds." VII.A-15 Zimmerman, H.; Nesterov, E.E. A CR, 35, 77. Review"

"Development of Experimental and Theoretical Crystal Lattice Organic Photochemistry: The Quantitative Cavity. Mechanistic and Exploratory Organic Photochemistry."

VII.A-16 Bochet, C.G. JCS, 125. Review"

"Photolabile Protecting Groups and Linkers."

276

ORGANIC SYNTHESISm2003

VII.A-17 Monti, S.; Sortino, S. CSR, 31, 287. Review:

"Photoprocesses of Photosensitizing Drugs Within Cyclodextrin Cavities."

VII.A-18 Tucker, J.H.R., Collinson, S.R. CSR, 31, 147. Review:

"Recent Developments in the Redox-Switched Binding of Organic Compounds."

VII.A-19 Hansch, C. et al. CRV, 102, 783. Review"

"Chem-Bioinformatics" Comparative QSAR at the Interface Between Chemistry and Biology."

VII.A-20 Jerschow, A. et al. AG(E), 41, 3097. Review"

"Solid-State NMR Spectroscopic Methods in Chemistry."

VII.A-21 Ardisson, J.; Pancrazi, A. et al. SL, 1. Account" "13C NMR Analysis as a Useful Tool for Structural Assignment of Vinyl- and Dienyitin Derivatives." VII.B Asymmetric Synthesis and Molgs

Recognition

VII.B-1 Beck, G. SL, 837. Account" "Synthesis of Chiral Drug Substances." VII.B-2 Noyori, R. AG(E), 41, 2008. Review"

"Asymmetric Catalysis" Science and Opportunities."

VII.B.3 Sharpless, K.B. AG(E), 41, 2024. Review:

"Searching for New Reactivity."

VII.B-4 Todd, M.H. CSR, 31, 211. Review"

"Asymmetric Autocatalysis: Product Recruitment for the increase in the Chiral Environment."

REVIEWS

277

VII.B-5 Jones, S. JCS(P1), 1.

Review"

"Stoichiometric Asymmetric Processes."

VII.B-6 Lectka, T. et al. CEJ, 8, 4114. Concept: "Sequential Column Asymmetric Catalysis." VII.B-7 Reetz, M.T. AG(E), 41, 1335.

Highlight" "New Methods for the High-Throughput Screening of Enantioselective Catalysts and Biocatalysts." VII.B-8 Manabe, K.; Kobayashi, S. CEJ, 8, 4094. Concept: "Catalytic Asymmetric Carbon--Carbon BondForming Reactions in Aqueous Media." VII.B-9 Shibasaki, M. et al. CC, 1989. Review"

"Recent Progress in Asymmetric Two-Center Catalysis."

VII.B-10 Woodward, S. T, 58, 1017. Report:

"HSAB Matching and Mismatching in Selective Catalysis and Synthesis."

VII.B-11 Gibson, S.E.; Ibrahim, H. CC, 2464. Review"

"Asymmetric Catalysis Using Planar Chiral Arene Chromium Complexes."

VII.B-12 Mikami, K. et al. AG(E), 41, 3555. Review:

"Asymmetric Catalysis by Lanthanide Complexes."

VII.B-13 Molt, O.; Schrader, T. S, 2633. Review:

"Asymmetric Synthesis with Chiral Cyclic Phosphorus Auxiliaries."

VII.B-14 Ishikawa, T.; Isobe, T. CEJ, 8, 552. Concept: "Modified Guanidines as Chiral Auxiliaries."

278

ORGANIC SYNTHESIS--2003

VII.B-15 Ansell, J.; Wills, M. CSR, 31, 259.

Review:

"Enantioselective Catalysis Using PhosphorousDonor Ligands Containing Two or Three P--N or P--O Bonds."

VII.B-16 Fletcher, N.C. JCS(P1), 1831. Review" "Chiral 2,2'-Bipyridines" Ligands for Asymmetric Induction." VII.B-17 Chelucci, G.; Thummel, R.P. CRV, 102, 3129.

Review-

"Chiral 2,2'-Bipyridines, 1,10-Phenanthrolines, and 2,2"6',2"-Terpyridines: Syntheses and Applications in Asymmetric Homogeneous Catalysis."

VII.B-18 Trost, B.M. CPB, 50, 1. Review" "Pd Asymmetric Allylic Alkylation (AAA). A Powerful Synthetic Tool." VII.B-19 Alexakis, A.; Benhaim, C. EJOC, 3221. Microreview: "Enantioselective Copper-Catalyzed Conjugate Addition." VII.B-20 Knowles, W.S. AG(E), 41, 1999. Review" "Asymmetric Hydrogenations." VII.B-21 Pavlov, V.A. RCR, 71, 33. Review:

"Mechanisms of Asymmetric Induction in Catalytic Hydrogenation, Hydrosilylation and Cross-Coupling on Metal Complexes."

VII.B-22 GooBen, L.J. AG(E), 41, 3775. Highlight" "Asymmetric Hydrovinylation: New Perspectives Through Use of Modular Ligand Systems." VII.B-23 Griesbeck, A.G.; Meierhenrich, U.J. AG(E), 41, 3147. Review"

"Asymmetric Photochemistry and Photochirogenesis."

REVIEWS

279

VII.B-24 Cho, B.T. AA, 35, 3. Review"

"Boron-Based Reducing Agents for the Asymmetric Reduction of Functionalized Ketones and Ketimines."

VII.B-25 Jarosz, S.; Mach, M. EJOC, 769. Microreview: "Regio- and Stereoselective Transformations of Sucrose at the Terminal Positions." VII.B-26 Huang, H.-C. et al. OPP, 34, 271. Review"

"New Developments in the Use of Enantiomerically Enriched Sulfoxides in Stereoselective Synthesis."

VII.B-27 Fensterbank, L.; Malacria, M. et al. EJOC, 3507. Microreview: "The Chemistry of C2-Symmetric Bis(Sulfoxides): A New Approach in Asymmetric Synthesis." VII.B-28 Hoffmann-Roder, A.; Krause, N. A G(E), 41, 2933. Review:

"Enantioselective Synthesis of and with Allenes."

VII.B-29 Ellman, J.A. et al. ACR, 35, 984. Review:

"N-tert-Butanesulfinyl Imines- Versatile

Intermediates for the Asymmetric Synthesis of Amines."

VII.B-30 Micouin, L. et al. OPP, 34, 457. Review"

"Recent Proress in the Asymmetric Synthesis of c~Substituted Propargylamines."

VII.B-31 Liu, M.; Sibi, M.P. T, 58, 7991. Report"

"Recent Advances in the Stereoselective Synthesis of 13-Amino Acids."

VII.B-32 Jarvo, E.R.; Miller, S.J. T, 58, 2481. Report"

"Amino Acids and Peptides as Asymmetric O rganocatalysts."

280

ORGANIC SYNTHESIS--2003

VII.B-33 Lauret, C.; Roberts, S.M. AA, 35, 47. Review: "Asymmetric Epoxidation of a,13-Unsaturated Ketones Catalyzed by Poly(amino Acids)." VII.B-34 List, B. T, 58, 5573. Report:

"Proline-Catalyzed Asymmetric Reactions."

VII.B-35 Bringmann, G. et al. JOM, 661, 31. Account: "The Lactone Concept--A Novel Approach to the Metal.Assisted Atroposelective Construction of Axially Chiral Biaryl Systems." VII.B-36 Bringmann, G. et al. JOM, 661, 49. Account" "The Directed Synthesis of Axially Chiral Ligands, Reagents, Catalysts, and Natural Products Through the 'Lactone Methodology'." VII.B-37 Schneider, C. AG(E), 41, 745. Highlight: "Catalytic Enantioselective Syntheses of 13Lactones---Versatile Synthetic Building Blocks in Organic Chemistry." VII.B-38 O'Brian, P., ed. T, 58, 4567-4733. Symposia "Recent Developments in Chirai Lithium Amide in-Print" Base Chemistry." VII.B-39 Eames, J. EJOC, 383. Microreview" "Recnt Developments in Enantioselective Deprotonation Mediated by Sub-Stoichiometric Quantities of Chiral Bases." VII.B-40 Andersson, P.G. et al. CSR, 31, 223. Review"

"Asymmetric Base-Mediated Epoxide Isomerization."

VII.B-41 Periasamy, M. AA, 35, 89. Review"

"Novel Methods of Resolving Racemic Diols and Amino Acids."

REVIEWS

281

VII.B.42 Kilburn, J.D. et al. JCS(P1), 841. Review:

"Synthetic Receptors for Carboxylie Acids and Carboxylates."

VII.B-43 Wulff, G. CRV, 102, 1. Review-

"Enzyme-Like Catalysis by Molecularly Imprinted Polymers."

VII.B-44 Toda, F. AJC, 54, 573 (2001). Review:

"Crystalline Inclusion Complexes as Media of Molecular Recognitions and Selective Reactions."

VII.B-45 Grave, C.; Schluter, A.D. EJOC, 3075. Review"

"Shape-Resistant, Nano-Sized Macromolecules."

VII.B-46 Gohlke, H.; Klebe, G. AG(E), 41, 2645. Review"

"Approaches to the Description and Prediction of the Binding Affinity of Small-Molecule Ligands to Macromolecular Receptors."

VII.B-47 Gerasko, O.A. et al. R CR, 71, 741. Review:

"Supramolecular Chemistry of Cucurbiturils."

VII.B-48 Seidel, S.R.; Stang, P.J. A CR, 35, 972. Review:

"High-Symmetry Coordination Cages via SelfAssembly."

VII.B-49 Bourgeois, J.-P.; Fujita, M. AJC, 55,619. Review"

V!I.C

"Chemical Transformations Within Isolated Nanospaces."

Reactions

VII.C-1 Palomo, C. et al. CEJ, 8, 36. Concept: "The Aldoi Addition Reaction: An Old Transformation at Constant Rebirth."

282

ORGANIC SYNTHESISm2003

VII.C-2 Alcaide, B.; Almendros, P. EJOC, 1595. Microreview: "The Direct Catalytic Asymmetric Aldo, Reaction." VII.C-3 Beller, M. et al. SL, 1579. Account" "Advances and Adventures in Amination Reactions of Olefins and Alkynes." VII.C-4 Mangion, D.; Arnold, D.R. ACR, 35, 297.

Review"

"Photochemical Nucleophile-Olefin Combination, Aromatic Substitution Reaction. Its Synthetic Development and Mechanistic Exploration."

VII.C-5 Hilt, G. AG(E), 41, 3586. Highlight: "Direct Electrochemical Aziridation of Alkenes under Metal.Free Conditions." VII.C-6 Pellissier, H.; Santelli, M. OPP, 34, 609. Review:

"The Birch Reduction of Steroids."

VII.C-7 Kakiuchi, F.; Murai, S. A CR, 35, 826. Review:

"Catalytic C---H/Olefin Coupling."

VII.C-8 McIntosh, M.C. et al. T, 58, 2905. Report:

"New Aspects of the Ireland and Related Claisen Rearrangements."

VII.C-9 Kuniyasu, H.; Kurosawa, H. CEJ, 8, 2660. Concept: "Transition-Metal-Catalyzed Carbon-Heteroatom Three.Component Cross-Coupling Reactions: A New Concept for the Carbothiolation of Alkynes." VII.C-10 Denmark, S.E.; Sweis, R.F. ACR, 35, 835. Review"

"Design and Implementation of New, Silicon-Based, Cross-Coupling Reactions: Importance of SiliconOxygen Bonds."

REVIEWS

283

VII.C-11 Hiersemann, M.; Abraham, L. EJOC, 1461. Microreview: "Catalysis of the Ciaisen Rearrangement of Aliphatie Allyl Vinyl Ethers." VII.C-12 Tamao, K.; Hiyama, T.; Negishi, E., guest eds. JOM, 653, 1291. Special Issue"

"30 Years of the Cross.Coupling Reaction."

VII.C.13 Denmark, S.E.; Sweis, R.F. CPB, 50, 1531. Review:

"Cross-Coupling Reactions of Organosilicon Compounds: New Concepts and Recent Advances."

VII.C-14 Marchand, A.P.; Coxon, J.M. ACR, 35, 271.

Review:

"On the Origins of Diastereofacial Selectivity of [4+2] Cycioadditions in Cage-Annulated and Polycarboxylic Diene/Dienophile Systems."

VII.C-15 Widenhoefer, R.A. ACR, 35, 905.

Review"

"Synthetic and Mechanistic Studies of the Cycloisomerization and Cyclization/Hydrosilylation of Functionalization Dienes Catalyzed by Cationic Palladium(II) Complexes."

VII.C-16 Corey, E.J. AG(E), 41, 1651. Review-

"Catalytic Enantioselective Diels-Alder Reactions" Methods, Mechanistic Fundamentals, Pathways, and Applications."

VII.C- 17 Donohoe, T.J. SL, 1223. Account" "Development of the Directed Dihydroxylation Reaction." VII.C-18 Blakemore, P.R. JCS(P1), 2563. Review:

"The Modified Julia Olefination: Alkene Synthesis via the Condensation of Metallated Heteroarylalkylsulfones with Carbonyl Compounds."

284

ORGANIC SYNTHESIS--2003

VII.C-19 Nicolaou, K.C. et al. AG(E), 41, 1669. Review"

"The Diels-Alder Reaction in Total Synthesis."

VII.C-20 Gerrard, J.A. AJC, 55, 299. Review"

"New Aspects of an AGEing Chemistry---Recent Developments Concerning the Maillard Reaction."

VII.C-21 Martin, S.F. ACR, 35, 895. Review"

"Evolution of the Vinyiogous Mannich Reaction as a Key Construction for Alkaloid Synthesis."

VII.C-22 Enders, D. et al. EJOC, 1877. Microreview" "Asymmetric Michael Additions to Nitroalkenes." VII.C-23 Teoba!d, B.J. T, 58, 4133. Review"

"The Nicholas Reaction" The Use of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations in Synthesis."

VII.C-24 Andrus, M.B.; Lashley, J.C. T, 58, 845. Report:

"Copper Catalyzed Allylic Oxidation with Peresters."

VII.C-25 Hartung, J.; Grob, M. JOM, 661, 67. Account: "Transition Metal.Catalyzed Oxidations of Bishomoallylic Alcohols." VII.C-26 Adam, W. et al. JOM, 661, 3. Account" "Catalytic Oxidations by Peroxy, Peroxo, and Oxo Metal Complexes" An Interdisciplinary Account with a Personal View." VII.C-27 Bonini, C.; Righi, G. T, 58, 4981. Report:

"A Critical Outlook and Comparison of Enantioselective Oxidation Methodologies of Olefins."

REVIEWS

285

VII, C-28 Mihovilovic, M.D. et al. EJOC, 3711. Mieroreview: "Monooxygenase-Mediated Baeyer-Villiger Oxidations." VII.C-29 Ager, D.J. et al. CSR, 31, 195. Review"

"New Developments in the Peterson Oiefination Reaction."

VII.C-30 Pizzo, F. et al. OPP, 34, 109, Review"

"Selected Methods for the Reduction of the Azido Group."

VII.C-31 Silva, L.F., Jr. T, 58, 9137. Report:

"Construction of Cyclopentyl Units by Ring Contraction Reactions."

VII.C-32 Bodkin, J.A.; McLeod, M.D. JCS(P1), 2733. Review:

"The Sharpless Asymmetric Aminohydroxylation."

VII.C-33 Leber, P.A.; Baldwin, J.E. ACR, 35, 279. Review:

"Thermal [1,3] Carbon Sigmatropic Rearrnagemetns of Vinylcyelobutanes."

VII.C-34 Kotha, S. et al. T, 58, 9633. Report" "Recent Applications of the Suzuki-Miyaura CrossCoupling Reaction in Organic Synthesis." VII.C-35 Nakamura, E.; Yamago, S. ACR, 35, 867. Review"

"Thermal Reactions of Dipolar Trimethylenemethane Species."

VII.C-36 Rein, T.; Pedersen, T.M. S, 579. Review"

"Asymmetric Wittig Type Reactions."

VII.C-37 Kirmse, W. EJOC, 2193. Microreview: "100 Years of the Wolff Rearrangement."

286

ORGANIC SYNTHESIS--2003

VII.D Reactive Intermediates VII.D.1 Fleming, F.F.; Shook, B.C. T, 58, 1. Report:

"Nitrile Anion Cyclizations."

VII.D.2 Cristau, H.J.; Taillefer, M.; Rahier, N. JOM, 646, 94. Account" "Lithium Phosphonium Azayidiides RaP=NLi. Applications in Organic Synthesis and Coordination Chemistry." VII.D-3 Langer, P. S, 441. Review:

"Cyclization Reactions of 1,3-Bis-Silyl Enoi Ethers and Related Masked Dianions."

VII.D-4 Yoshida, J.; Suga, S. CEJ, 8, 2650. Concept: "Basic Comcepts of 'Cation Pool' and 'Cation Flow' Methods and Their Applications in Conventional and Combinatorial Organic Synthesis." VII.D-5 Garcia, H.; Roth, H.D. CRV, 102, 3947. Review: "Generation and Reactions of Organic Radical Cations in Zeolites." VII.D-6 Fokin, A.A.; Schreiner, P.R. CRV, 102, 1551. Review:

"Selective Alkane Transformations via Radicals and Radical Cations: Insights into the Activation Step from Experiment and Theory."

VII.D-7 Ishibashi, H. et al. S, 695. Review:

"5-Endo-Trig Radical Cyclizations."

VII.D-8 Studer, A.; Amrein, S. S, 835. Review:

"Tin Hydride Substitutes in Reductive Radical Chain Reactions."

VII.D-9 Wille, U. CEJ, 8, 340. Concept: "Inorganic Radicals in Organic Synthesis."

REVIEWS

287

VII.D-10 Clark, A.J. CSR, 31, 1. Review: "Atom Transfer Radical Cyclization Reactions Mediated by Copper Complexes." VII.D-11 Gilbert, B.C.; Parsons, A.F. JCS(P2), 367. Review" "The Use of Free Radical Initiators Bearing MetalMetal, Metal-Hydrogen, and Non-Metal-Hydrogen Bonds in Synthesis." VII.D-12 Hartung, J. et al. S, 1469. Review:

"Selectivity in the Chemistry of Oxygen-Centered Radicals--The Formation of Carbon-Oxygen Bonds."

VII.D-13 Lasammertsma, K.; Vlaar, M.J.M. EJOC, 1127. Microreview: "Carbene-Like Chemistry of Phosphinidene Complexes--Reactions, Applications, and Mechanistic Insights." VII.D-14 Herrmann, W.A. AG(E), 41, 1291. Review"

"N-Heterocyclic Carbenes" A New Concept in Organometallic Catalysis."

VII.D.15 Mehta, G.; Muthusamy, S. T, 58, 9477. Report"

"Tandem Cyclization-Cycloaddition Reactions of Rhodium Generated Carbenoids from cx-Diazo Carbonyl Compounds."

VII.D-16 Marek, I. T, 58, 9463. Review:

"Sp30rganozinc Carbenoid Homologation in Organic Synthesis."

VII.D-17 Van De Water, R.W.; Pettus, T.R.R. T, 58, 5367. Report:

"o-Quinine Methides: Intermediates Underdeveloped and Underutilized in Organic Synthesis."

288

ORGANIC SYNTHESIS--2003

VII.E. Or~anometallics and metalloids v

VII.E-1 Luh, T.-Y., Conference Chair PAC, 74, 1-186. Lectures: "Presented at the 11 th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS-11)." VII.E-2 Severin, K. CEJ, 8, 1514.

Concept" "Asymmetric Halegeno-Bridged Complexes" New Reagents in Organometallic Synthesis and Catalysis." VII.E-3 Paley, R.S. CRV, 102, 1493. Review:

"Enantiomerically Pure Planar Chiral Organometailic Complexes via Facially Selective ~-Complexation."

VII.E-4 Marek, I. et al. S, 2473. Review:

"New Preparation of sp 2 0 r g a n o m e t a l l i c Derivatives."

VII.E-5 Tor, Y. SL, 1043. Account: "Coordination Compounds as Synthetic Building Blocks." VII.E-6 Lappert, M.F. et al. CRV, 102, 3031. Review:

"The Chemistry of 13-Diketiminatometal Complexes."

VII.E-7 Alvaro, G.; Savoia, D. SL, 651.

Account" "Addition of Organometallic Reagents to Imines Bearing Stereogenic N-Substituents. Stereochemical Models Explaining the 1,3-Asymmetric Induction." VII.E-8 Mugesh, G.; Singh, H.B. A CR, 35, 226. Review" "Heteroatom-Directed Aromatic Lithiation" A Versatile Route to the Synthesis of Organochalcogen (Se, Te) Compounds."

REVIEWS

289

VII.E-9 Kukushkin, V.Y.; Pombeiro, A.J.L. CRV, 102, 1771. Review:

"Additions to Metal-Activated Organonitriles."

VII.E- 10 Familoni, O.B. SL, 1181. Account: "Metalated Sulfonamides and Their Synthetic Applications." VII.E-11 Lemaire, M. et al. CRV, 102, 1359. Review-

"AryI-Aryl Bond Formation One Century After the Discovery of the UIImann Reaction."

VII.E-12 Hodgson, D.M.; Gras, E. S, 1625. Review"

"Recent Developments in the Chemistry of Lithiated Epoxides."

VII.E-13 Vaultier, M., guest ed. JOM, 657, 1-278. Special Issue"

"Euroboron II: 2nd European Symposium on Boron Chemistry."

VII.E.14 Ramachandran, P.V. AA, 35, 23. Review-

"Pinane-Based Versatile 'Allyl'boranes."

VII.E.15 Kanth, J.V.B. AA, 35, 57. Review-

"Borane-Amine Complexes for Hydroboration."

VII.E-16 Knochel, P. et al. S, 565. Synthetic "Preparation and Reactions of Functionalized Procedure" Arylmagnesium Reagents." VII.E-17 Weidenbruck, M. JOM, 646, 39. Account: "Some Recent Advances in the Chemistry of Silicon and its Homologues in Low Coordination States." VII.E- 18 Fryatt, R.; Christie, S.D.R. JCS(P1), 447. Review"

"Applications of Stoichimetric Transition Metal Complexes in Organic Synthesis."

290

ORGANIC SYNTHESISm2003

VII.E-19 Fagnov, K.; Lautens, M. A G(E), 41, 27.

Review:

"Halide Effects in Transition Metal Catalysis."

VII.E-20 Li,C.-J. A CR, 35, 533.

Review:

"Quasi.Native Catalysis: Developing C--C Bond Formations Catalyzed by Late Transition Metals in Air and Water."

VII.E-21 Jun, C.-H. et al. CEJ, 8, 2422. Concept: "Chelation-Assisted Carbon-Hydrogen and CarbonCarbon Bond Activation by Transition Metal Catalyzed Metal Catalysts VII.E-22 Aubert, C.; Buisine, O.; Malacria, M. CRV, 102, 813. Review"

"The Behavior of 1,n-Enynes in the Presence of Transition Metals."

VII.E-23 Bates, R.W.; Satcharoen, V. CSR, 31, 12. Review"

"Nucleophilic Transition Metal Based Cyclization of Allenes."

VII.E-24 de Azevedo, C.G.; Vollhardt, K.P.C. SL, 1019. Account: "Oligocyclopentadienyl Transition Metal Complexes." VII.E-25 Backvall, J.-E. JOM, 652, 105. Mini-Review: "Transition Metal Hydrides as Active Intermediates in Hydrogen Transfer Reactions." VII.E-26 Cossy, J. et al. SL, 1595. Account: "Chiral Titanium Complexes. Synthesis of Optically Active Unsaturated Alcohols, Diois, Polypropionates and Their Use in the Synthesis of Biologically Active Compounds." VII.E-27 Wipf, P.; Kendall, C. CEJ, 8, 1778. Concept: "New Applications of Alkenyl Zirconocene."

REVIEWS

291

VII.E-28 Hartley, R.C.; McKiernan, G.J. JCS(P1), 2763. Review"

"Titanium Reagents for the Alkylidenation of Carboxylic Acid and Carbonic Acid Derivatives."

VII.E.29 Knizhnikov, V.A.; Maier, N.A. RCR, 71, 295. Review"

"Titanocene Derivatives Containing TitaniumCarbon c-Bonds."

VII.E-30 Chin, C.S. et al. ACR, 35, 218.

Review:

"Carbon-Carbon Bond Formation Involving Reactions of Alkynes with Group 9 Metals (Ir, Rh, Co)" Preparation of Conjugated Olefins."

VII.E-31 Takeuchi, R. SL, 1954. Account: "Iridium Complex-Catalyzed Highly Selective Organic Synthesis." VII.E-32 Chandrasekaran, S. et al. SL, 1762. Account" "Chemistry of Tetrathiomolybdate" Applications in Organic Synthesis." VII.E-33 Pfeffer, M. et al. CRV, 102, 1731. Review:

"Ru-, Rh-, and Pal-Catalyzed C---C Bond Formation Involving C---H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects."

VII.E-34 Littke, A.F.; Fu, G.C. AG(E), 41, 4177. Review"

"Palladium-Catalyzed Coupling Reactions of Aryl Chlorides."

/

VII.E-35 Shirakawa, E.; Hiyama, T. BCJ, 75, 1435. Account" "Transition Metal-Catalyzed Carbostannylation of Alkynes and Dienes." VII.E-36 Sadekov, I.D. RCR, 71, 99. Review:

"Synthesis and Reactions of Organic Compounds Containing Bonds of Te to Group 14 Elements."

292

ORGANIC SYNTHESIS--2003

VII.E-37 Toyota, M.; Ihara, M. SL, 1211.

Account" "Development of Palladium-Catalyzed Cycloalkenylation and Its Application to Natural Product Synthesis." VII.E-38 LLoyd-Jones, G.C. et al. AG(E), 41, 953. Highlight" "Palladium.Catalyzed a-Arylation of Esters" Ideal New Methodology for Discovery Chemistry." - -

,

,

,

VII.E-39 Mendez, M.; Eschavarren, A.M. EJOC, 15. Review"

"New Strategies for the Synthesis of Carboeycles Based on Transition Metal Catalyzed Cyclization Reactions of Organostannanes and Organosilanes."

VII.E-40 Kagan, H.B., guest ed. CRV, 102, 18052476. Review"

"Frontiers in Lanthanide Chemistry."

VII.E-41 Lappert, M.F.; Evans, W.J.; Mingos, D.M.P., eds. JOM, 647, 2-249. Special Issue"

"Advances in the Organometallic Chemistry of the Group 3 and Lanthanoid Elements."

VII.E-42 Banik, B.K. EJOC, 2431. Microreview: "Samarium Metal in Organic Synthesis." VII.E-43 Agarwal, S.; Greiner, A. JCS(P1), 2033. Review:

"Diiodosamarium Based Polymerisations."

VII.E-44 Mohan, R.S. et al. T, 58, 8373. Report"

"Applications of Bismuth(llI) Compounds in Organic Synthesis."

VII.E-45 Le Roux, C.; Dubac, J. SL, 181. Account" "Bismuth(III) Chloride and Triflate" Novel Catalysts for Acylation and Sulfonylation Reactions. Survey and Mechanistic Aspects."

REVIEWS

293

VII.F. Halogen Comvounds and Halo~enation (see also: VI.A.10.) VII.F-1 Yus, M. et al. CRV, 102, 4009. Review"

"Metal-Mediated Reductive Hydrodehalogenation of Organic Halides."

VII.F-2 Gree, R. et al. ACR, 35, 175. Review"

"The Propargylic Route as a Short and Versatile Entry to Optically Active Monofluorinated Compounds."

VII.F-3 van Steenis, J.H.; van der Gen, A. JCS(P1), 2117. Review"

"Synthesis of Terminal Monofluoro Olefins."

VII.F-4 Singh, R.P.; Shreeve, J.M. S, 2561. Review"

"Recent Advances in Nucleophilic Fluoration Reactions of Organic Compounds Using Deoxofluo and DAST."

VII.F-5 Braun, T.; Perutz, R.N. CC, 2749. Review"

"Routes to Fluorinated Organic Derivatives by Nickel Mediated C---F Activation of Heteroaromatics,"

VII.F-6 Grushin, V.V. CEJ, 8, 1006. Concept" "Palladium Fluoride Complexes: One More Step Toward Metal-Mediated C - - F Bond Formation." VII.F-7 Gouverneur, V.; Greedy, B. CEJ, 8, 766. Concept" "Synthetic Applications of Electrophilic FI u o r o desil yla t i o n." VII.F-9 Zhdankin, V.V.; Stang, P.J. CRV, 102, 2523. Review"

"Recent Developments in the Chemistry of Polyvalent Iodine Compounds."

294

ORGANIC SYNTHESIS--2003

VII.F-8 Togo, H.; Sakuratani, K. SL, 1966. Account" "Polymer-Supported Hypervalent Iodine Reagents."

VII.G Natural Products VII.G-1 Jikai, L. H, 57, 157. Review:

"Biologically Active Substances from Mushrooms in Yunnan, China."

VII.G-2 Ueda, M.; Takada, N.; Yamamura, S. BCJ, 75, 2337. Account: "Bioorganic Studies on Nyctinasty of the Plant Controlled by a Biological Clock." VII.G-3 Sener, B., conference ed. PAC, 74, 511-584. Lectures: "3 ra IUPAC International Conference on Biodiversity (ICOB-3)." VII.G-4 Erhardt, P.W. PAC, 74, 703. Special Topic"

"Medicinal Chemistry in the New Mellenium. A Glance Into the Future."

VII.G-5 Wasserman, H.H.; Martin, S.F., eds. T, 58, 6223. Symposia "Beyond Natural Product Synthesis." in-Print" VII.G-6 Mehta, G.; Singh, V. CSR, 31, 324. Review"

"Hybrid Systems Through Natural Product Leads: An Approach Towards New Molecular Entities."

VII.G-7 Ernst, H. PAC, 74, 2213. Lecture:

"Recent Advances in Industrial Carotenoid Synthesis."

VII.G-8 Yamamura, S.; Nishiyama, S. SL, 533. Account" "Anodic Oxidation of Phenol Towards the Synthesis of Bioactive Natural Products."

REVIEWS

295

VII.G-9 Bertram, J.S., Symposium ed. PAC, 74, 1369-1477. Lectures: "13 th International Symposium on Carotinoids." VII.G-10 Thirsk, C.; Whiting, A. JCS(P1), 999. Review"

"Polyene Natural Products."

VII.G-11 Krohn, K. EJOC, 1351. Microreview" "Biomimetic Synthesis of Deca- and Dodecaketide-Derived Quinone Antibiotics." VII.G. 12 Ferraz, H.M. et al. S, 2155. Review:

"Syntheses of Mintlactone and lsomintlactone."

VII.G.13 Sickle, E.S. et al. JCS(P1), 1735. Review"

"The Emergence of the Cyclopentenone Prostaglandins as Important Biologically Active Compounds."

VII.G-14 Vyvyan, J.R. T, 58, 1631. Report:

"Allelochemicals as Leads for New Herbacides and Agrochemicals."

VII.G-15 Meunier, B. et al. ACR, 35, 167. Review:

"From Mechanistic Studies on Artemisinin Derivatives to New Modular Antimalarial Drugs."

VII.G-16 Spivey, A.C. et al. CSR, 31, 43. Review:

"Celastraceae Sesquiterpenoids" Biological Activity and Synthesis."

VII.G-17 Tius, M.A. T, 58, 4343. Report:

"Synthesis of the Crytophycins."

VII.G-18 Brenna, E. et al. EJOC, 967. Microreview: "Optically Active Ionones and Derivatives: Preparation and Olfactory Properties."

296

ORGANIC SYNTHESIS--2003

VII.G-19 Ritter, T.; Carreira, E.M. AG(E), 41, 2489. Highlight: "The Diazonamides" The Plot Thickens." VII.G-20 Pellissier, H. OPP, 34, 431. Review-

"Synthesis of L-Iduronyl Synthons."

VII.G-21 Kalesse, M.; Christmann, M. S, 981. Review:

"The Chemistry and Biology of the Leptomycin Family."

VII.G-22 Williams, R.M. CPB, 50, 711.

Review:

"Total Synthesis and Biosynthesis of the Paraherquamides: An Intriguing Story of the Biological Diels.Alder Construction."

VII.G-23 Bates, R.W.; Sa-Ei, K. T, 58, 5957. Report:

"Synthesis of the Sedum and Related Alkaloids."

VtI.G-24 Kinston, D.G.I. CC, 867. Feature "Taxol, a Molecule for All Seasons." Article: VII.G-25 Armstrong, A.; Blench, T.J. T, 58, 9321. Report"

"Recent Synthetic Studies on the Zaragozic Acids ( S qu al est at ins )."

VII.G-26 Miyaoka, H.; Yamada, Y. BCJ, 75, 203. Account" "Total Synthesis of Bioactive Marine Terpenoids." VII.G-27 Hirama, M.; Rainier, J.D. T, 58, 1779-2040. Symposia "Synthesis of Marine Natural Products Containing in-Print: Polycyclic Ethers." VII.G-28 Yeung, K.-S.; Paterson, I. AG(E), 41, 4632. Review"

"Actin.Binding Marine Macrolides: Total Synthesis and Biological Importance."

REVIEWS

297

VII.G-29 Kinder, F.R., Jr. OPP, 34, 559. Review"

"Synthetic Approaches Toward the Bengamide Family of Antitumor Marine Natural Products."

VII.G-30 Angyal, S.J., guest ed. AJC, 55, 1-178. S pecial Edition"

"Carbohydrates."

VII.G-31 Wrodnigg, T.M. M, 133, 393. Review:

"From Lianas to Glycobiology Tools" Twenty-five Years of 2,5-Dideoxy-2,5-imino-D-mannitol."

VII.G-32 Petrus, L. et al. M, 133, 383. Review:

"Conversions of Nitroalkyl to Carbonyl Groups in Carbohydrates."

VII.G-33 Nicotra, F. et al. M, 133, 369. Review:

"Carbohydrate.Based Scaffolds for the Generation of Sortiments of Bioactive Compounds."

VII.G-34 Kvaerno, L.; Wengel, J. CC, 1419. Feature Article:

"Antisense Molecules and Furanose Conformations---Is It Really that Simple?"

VII.G-35 Love, K.R.; Seeberger, P.H. AG(E), 41, 3583. Highlight: "Carbohydrate Arrays as Tools for Glycomimics." VII.G-36 Singh, G. et al. SL, 16. Account: "Glycosylation Based on Giycosyl Phosphates as Glycosal Donors." VII.G-37 Fernandez, J.M. et al. CEJ, 8, 1982. Review"

"Multivalent Cyclooligosaccharides" Versatile Carbohydrate Clusters with Dual Role as Molecular Receptors and Lectin Ligands."

298

ORGANIC SYNTHESIS--2003

VII.G-38 Seeberger, P.H. et al. EJOC, 595. Microreview: "Oligosaceharide Synthesis in Solution and on Solid Support with Giycosyl Phosphates." VII.G-39 Streicher, H. M, 133, 1263. Review"

"Approaches to Carbocyclic Sialidase Inhibitors."

VII.G-40 Jensen, K.J. JCS(P1), 2215. Review"

"O-Glycosylation under Neutral or Basic Conditions."

VII.G-41 Dwek, R.A.; Butters, T.D., guest eds. CRV, 102, 283-601. Reviews" "Glycobiology." VII.G-42 Ito, Y.; Manabe, S. CEJ, 8, 3076. Concept: "TAG-Reporter and Resin Capture-Release Strategy in Oligosaccharide Synthesis." VII.G-43 Dyason, J.C.; von Itzstein, M. AJC, 54, 663 (2001). Review" "Anti-Influenza Virus Drug Design- Sialidase Inhibitors." VII.G-44 Kusano, G. et al. H, 57, 1359. Review"

"Polyhydoxylated Alkaloids with Lipophilic Moieties as Glycosidase Inhibitors from Higher Plants."

VII.G-45 La Ferta, B. M, 13J, 351 Review"

"Lipases as Useful Tools for the Stereo- and Regioselective Protection and Deprotection of Carbohydrates."

VII.G-46 Sewald, N. AG(E), 41, 4661. Highlight: "Efficient Racematization-Free Peptide Coupling of N-Alkyl Amino Acids by Using Amino Acid Chlorides Generated In Situ---Total Syntheses of the Cyclopeptides Cyclosporin 0 and Omphabtin A."

REVIEWS

299

VII.G-47 Park, K.-H.; Kurth, M.J. T, 58, 8629. Report:

"Cyclic Amino Acid Derivatives."

VII.G-48 Najera, C. SL, 1389. Account" "From a-Amino Acids to Peptides: All You Need for the Journey." VII.G-49 Yoder, N.C.; Kumar, K. CSR, 31, 335. Review"

"Fluorinated Amino Acids in Protein Design and Engneering."

VII.G-50 Muller, M. et al. CEJ, 8, 5288. Concept" "Thiamin.Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C--C Bond Formation." VII.G-51 Adam, W.; Schreier, P. et al. JOM, 661, 17. Account- "Biocatalytic Synthesis of Optically Active Oxyfunctionalized Building Blocks with Enzymes, Chemoenzymes and Microorganisms." VII.G-52 Hedstrom, L., guest ed. CRV, 102, 4429-4912. Review"

"Proteases."

VII.G-53 Savage, P.B. EJOC, 759. Microreview" "Design, Synthesis and Characterization of Cationic Peptide and Steroid Antibiotics." VII.G-54 Chambert, S.; Decout, J.-L. OPP, 34, 27. Review"

"Recent Developments in the Synthesis, Chemical Modifications and Biological Applications of Sulfur Modified Nucleosides, Nucleotides and Oligonucleotides."

VII.G-55 Lamberth, C. OPP, 34, 149. Review.

"Nuc!eosides with a Carbon Bridge Between Sugar and Nucleobase" The Chemistry of l'Homonucleosides and Reversed Nucleosides."

300

ORGANIC SYNTHESISm2003

VII.G-56 Pathak, T. CRV, 102, 1623. Review"

"Azidonucleosides: Synthesis, Reactions, and Biological Properties."

VII.G-57 Zatsepin, T.S. et al. RCR, 71, 513. Review:

"Synthesis of 2'-O-Alkylnucleosides."

VII.G-58 Lagoja, I.M.; Herdewijn, P. S, 301. Review:

"Chemical Synthesis of 13C and 16N Labeled Nucleosides."

VII.G.59 Ichikawa, E.; Kato, K. S, 1. Review"

"Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-Branched Sugars."

VII.G-60 Reese, C.B. T, 58, 8893. Perspective: "The Chemical Synthesis of Oiigo- and Poly. Nucleotides" A Personal Commentary." VII.G-61 Christopherson, R.I. et al. ACR, 35, 961. Review"

"Inhibitors of de novo Nucleotide Biosynthesis as Drugs."

VII.G-62 Kumar, N.A. EJOC, 2021. Microreview" "Structural Reorganization of Peptide Nucleic Acids: Chiral Cationic Analogues with Five. of SixMembered Ring Structures." VII.G-63 Zubin, E.M. et al. RCR, 71, 239. Review:

"Modern Methods for the Synthesis of PeptideOligonucleotide Conjugates."

VII.G-64 Antsypovitch, S.I. RCR, 71, 71. Review:

"Peptide Nucleic Acids: Structure, Properties, Applications, Strategies and Practice of Chemical Synthesis."

REVIEWS

301

VII.G-65 Kool, E.T. A CR, 35, 936. Review"

"Replacing the Nucleobases in DNA with Designer Molecules."

VII.G-66 Wolkenberg, S.E.; Boger, D.L. CRV, 102, 2477. Review"

u

"Mechanisms of in situ Activation for DNATargeting Antitumor Agents."

Others

VII.H-1 Gavezzotti, A. SL, 201. Account: "The Chemistry of Intermolecular Bonding: Organic Crystals, their Structures and Transformations." VII.H-2 Rowan, J. et al. A G(E), 41, 899. Review"

"Dynamic Covalent Chemistry."

VII.H-3 Jenner, G. T, 58, 5183. Report:

"Comparative Activation Modes in Organic Synthesis. The Specific Role of High Pressure."

VII.H-4 Nicolaou, K.C.; Baran, P.S. AG(E), 41, 2679, Review: "The CP Molecule Labyrinth: A Paradigm of How Endeavors in Total Synthesis Lead to Discoveries and Inventions in Organic Synthesis." VII.H-5 Gottschalk, K.-E.; Kessler, H. AG(E), 41, 3767. Review:

"The Structures of Integrins and Integrin-Ligand Complexes: Implications for Drug Design and Signal Transduction."

VII.H-6 Neslon, M.B.; Diederich, F. SL, 544. Account" "Modules for Acetylenic Scaffolding." VII.H-7 Tykwinski, R.R.; Zhao, Y. SL, 1939. Account" "Cross-Conjugated Oligo(enynes)."

302

ORGANIC SYNTHESISm2003

VII.H-8 Meanwell, N.A. et al. T, 58, 3111. Report" "The Mono-Funetionalization of Symmetrical Polyamines." VII.H-9 Freeman, S.; Alder, J.F. EJMC, 37, 527. Review"

"Arylethylamine Psychotropic Recreational Drugs" A Chemical Perspective."

VII.H-10 Kennedy, R.D.; Lloyd, D.; McNab, H. JCS(P1), 1601. Review:

"Annulenes,

1980-2000."

VII.H-11 Lambert, J.B., guest ed. ACR, 35, 583-684. Special Edition"

"Archaeological Chemistry."

VII.H-12 Mahajan, M.P. et al. T, 58, 379. Report:

"Recent Advances in Synthetic Applications of Azadienes."

VII.H-13 Rulev, A.Y. RCR, 71, 195. Review:

"Captodative Aminoallanes."

VII.H-14 Bouwman, E. et al. JOM, 650, 1. Review" "Homogeneously Catalyzed Isomerisation of Ailylic Alcohols to Carbonyl Compounds." VII.H-15 Liao, C.-C.; Peddinti, R.K. ACR, 35, 856. Review:

"Masked o-Benzoquinones in Organic Synthesis."

VII.H-16 Osman, F.H.; E1-Samahy, F.A. CRV, 102, 629. Review:

"Reactions of a-Diketones and o-Quinones with Phosphorous Compounds."

VII.H-17 King, A.S.H.; Twyman, L.J. JCS(PI), 2209. Review"

"Heterogeneous and Solid Supported Dendrimer Catalysts."

REVIEWS

303

VII.H.18 Grinstaff, M.W. CEJ, 8, 2838. Concept" "Biodendrimers: New Polymeric Biomaterials for Tissue Engineering." VII.H-19 Marmsater, F.D.; West, F.G. CEJ, 8, 4346. Concept" "New Efficient Iterative Approaches to Polycyclie Ethers." VII.H-20 Horvath, I.T., guest ed. ACR, 35, 685-816. Reviews-"Green Chemistry." VII.H-21 Yamamoto, H. ed. T, 58, 8153. Symposia "Molecular Design of Lewis and Bronsted Acid in Print: Catalysts--The Key to Environmentally Benign Reagents." VII.H-22 Sels, B.F. et al. SL, 367. Account" "Peroxide Reactions with Anion-Exchanged Layered Double Hydroxide Catalysts." VII.H-23 Blass, B.E. T, 58, 9301. Report:

"KF/AI203 Mediated Organic Synthesis."

VII.H-24 Richter-Addo, G.B.; Legzdins, P.; Burstyn, J., guest eds. CR V, 102, 857-1270. Reviews" "Nitric Oxide Chemistry." VII.H-25 Adams, J.P. JCS(P1), 2586. Review:

"Nitro and Related Groups."

VII.H-26 Morales-Rojas, H.; Moss, R.A. CRV, 102, 2497. Review"

"Phosphorolytic Reactivity of o-lodosylcarboxylates and Related Nucleophiles."

VII.H-27 Arason, K.; Bergmeier, S.C. OPP, 34, 337. Review"

"Synthesis of Succinic Acids and Derivatives."

304

ORGANIC SYNTHESIS--2003

VII.H-28 Agami, C.; Couty, F. T, 58, 2701. Report" 9

_

-

,

.

"The Reactivity of the N-Boo-Protecting Group: An Unprecedented Feature." .

.

.

.

.

.

.

-

_

VII.H-29 Steudel, R. CRV, 102, 3905. Review:

"The Chemistry of Organic Polysulfanes R-Sn-R (n>2)." _

_

VII.H-30 Chemla, F. JCS(P1), 275. Review:

"ct-Oxy Sulfones and Sulfoximines: Versatile Intermediates."

VII.H-31 Decout, J.-L. et al. S, 2319. Review"

"The 2-(Trimethylsilyl)ethyi Sulfur Group in Synthesis."

VII.H-32 Yamasaki, K.; Tanaka, O., eds. PAC, 74, 1101-1316. Special Topic"

"The Science of Sweeteners."

VII.H-33 Kimball, D.B.; Haley, M.M. AG(E), 41, 3338. Review:

"Triazines: A Versatile Tool in Organic Synthesis."

VIii SELECTED TOPICAL AREAS

VIII.A Fullerene

Chemistry

VIII.A.1 Diels-Aider-Type

Cycloadditions

VIII.A.I-10rfanopoulos, M. et al. JOC, 67, 3284. "Stereochemistry of the [2+2] Cycloadditions of trans, transand cis, trans.2,4.hexadiene to C60." VIII.A.2 Other

Cvcloadditions

VIII.A.2-1 Sawamura, M.; Nakamura, E. et al. JOM, 652, 31. "Regioselective Penta-Addition of 1-Alkenyl Copper Reagent to [60]Fullerene. Synthesis of Penta-Alkenyl FCp Ligand." VIII.A.2-2 Nair, V. et al. S, 1655. "Reaction of Allenamides with [60]Fullerene: Formation of Novel Cyciobutanone Annulated Fullerene Derivatives." VIII.A.2-3 Xu, J.-H. et al. SC, 32, 1647. "Synthesis of a New Spiropyran Based on [60]Fullerene Unit." VIII.A.2-4 Nair, V. et al. T, 58, 3009. "Dipolar Cycloaddition of Carbonyl Ylids with [60]Fulerene: Formation of Novel Heterocyclic Fused Fullerene Derivatives." VIII.A.2-5 Li, Y. et al. S C, 32, 2507. "Synthesis of New C60-Based Dyads Containing Carbazole and Benzothiazole Moieties." VIII.A.2-6 Dondoni, A.; Marra, A. TL, 43, 1649. "Synthesis of [60]Fulleropyrrolidine Glycoconjugates Using 1,3-Dipolar Cycloaddition with C-Glycosyl Azomethine Yiides." 305

306

ORGANIC SYNTHESISm2003

VIII.A.2-7 Tome, A.C. et al. TL, 43, 1689. "Synthesis of Novel [60]Fullerene-Flavonoid Dyads." VIII.A.3. Photochemical

Reactions

VIII.A.3-10uchi, A.; Ito, O. et al. JACS, 124, 13364. "Large Substituent Effect on the Photochemical Rearrangement of 1,6-(N-Aryl)aza-[60]fulleroids to 1,2-(N-Arylaziridino)[ 60 ] full e ren es." VIII.A.3-2 Murata, S. et al. OL, 4, 1217. "A Novel Photorearrangement of a Cyclohexadiene Derivative of C60. " VIII.A.3-30rfanopoulos, M. et al. OL, 4, 945. "Synthesis and Self.Photooxygenation of Alkenyl.Linked [60]Fullerene Derivatives. A Regioselective Ene Reaction." VIII.A.3-4 Nishimura, J. et al. JOC, 67, 1247. "Photochemical Synthesis, Conformational Analysis, and Transformation of [60]Fullerene-o-Quinodimethane Adducts Bearing a Hydroxy Group." VIII.A.4 Other Fullerene Chemistry VIII.A.4-1 Chiang, L.Y. et al. CC, 1854. "Synthesis of C60-Diphenylaminofullerene Dyad with Large 2 PA Cross Sections and Efficient Intramolecular Two-Photon Energy Transfer." VIII.A.4-2 Guldi, D.M.; Martin, N.; Saricirtci, N.S. et al. JOC, 67, 1141. "Molecular Engineering of C60-Based Conjugated Oligomer Assemblies." VIII.A.4-3 Komatsu, K. et al. OL, 4, 2541. "Synthesis, X.Ray Structure, and Properties of the Singly Bonded C60 Dimer Having the Diethoxyphosphorylmethyl Groups Utilizing the Chemistry of C602".''

SELECTED TOPICAL AREAS

307

VIII.A.4-4 Martin, N. et al. JOC, 67, 3529. "Synthesis is l,l'-BinaphthyI-Based Enantiopure C6o Dimers." VIII.A.4-5 Qian, W.; Rubin, Y. JOC, 67, 7683. "Convergent Regioselective Synthesis of Tetrakisfullero[ds from C60." VIII.A.4-6 Meier, M.S. et al. JOC, 67, 5946. "Alkylation of Dihydrofullerenes." VIII.A.4-7 Gan, L. et al. JOC, 67, 883. "Acylation of 2,5-Dimethoxycarbonyl[60]fulleropyrrolidine and Synthesis of Its Multifullerene Derivatives." VIII.A.4-8 Hirsch, A. et al. CEJ, 8, 2261. "A Highly Regioselective Approach to Multiple Adducts of C~0 Governed by Strain Minimization of Macrocyclie Malonate Addends." VIII.A.4-9 Mirakyan, A.L.; Wilson, L.J. JCS(P2), 1173. "Functionalization of C~0 with Diphosphonate Groups" A Route to Bone-Vectored Fullerenes." VIII.A.4-10 Keller, P.A.; Pyne, S.G. et al. JOC, 67, 8316. "Synthesis and Characterization of Mono- and BisMethano[60]fullerenyl Amino Acid Derivatives and Their Reductive Ring-Opening Retro-Bingel Reactions." VIII.A.4-11 Taylor, R. et al. JCS(P2), 41. "Reaction of C60Fls with Diethyl Bromomalonate: Diversion of the Bingel Reaction and Formation of the First 18re Annulenic Fullerene." VIII.A.4-12 Taylor, R. et al. JCS(P2), 47. "Products from the Reaction of C60Fls with Sarcosine and Aldehydes" The Prato Reaction." VIII.A.4-13 Hauke, F.; Hirsch, A. CC, 1316. "Regioselective Formation of Highly Functionalized Heterofullerenes: Pentamalonates of RCs9N Involving an Octhedral Addition Pattern."

308

ORGANIC SYNTHESISm2003

VIII.A.4-14 Taylor, R. et al. JCS(P2), 1251. "Methylation of [70]Fullerene.' ,,

,

,

VIII.A.4-15 Prato, M. et al. JACS, 124, 760. "Organic Fuctionalization of Carbon Nanotubules." VIII.A.4-16 Langa, F.; Nierengarten, J.-F. et al. TL, 43, 7507. "Synthesis of Dumbbell-Shaped bis-(Pyrazolino[60]fullerene). oligophenylenevinylene Derivatives." --.

,,

,

i

VIII.A.4-17 Tome, A.C. et al. TL, 43 4617. "Synthesis of [60]Fullirene.Quercetin Dyads." ,..

i

VIII.A.4-18 Vasapollo, G. et al. TL, 43, 4969. "Synthesis of Novel Nitroso-Fulleropyrrolidines." VIII.A.4-19 Gan, L. et al. JACS, 124, 13384. "Fullerenes as a tert.Butylperoxy Radical Trap, Metal Catalyzed Reaction of tert-Butyl Hydroperoxide with Fullerenes, and Formation of the First Fullerene Mixed Peroxides C60(O)(OOtBu)4 and CT0(OOtBu)10 .'' .

i

,

.

,

.,,,

,

,,

,

,

.,.

VIII.A.4-20 Saigo, K. et al. CL, 728. "Regio- and Stereoselective Synthesis of a trans-4[60]Fullerenobisacetic Acid Derivative by a Tether-Directed Biscyciopropanation: A Dyad Component Applicable for the Synthesis of Regio- and Stereo.Regular [60]Fullerene PearlNecklace Polyamides." VIII.A.4-21 Avent, A.G.; Taylor, R. CC, 2726. "Fluorine Takes a Hike: Remarkable Room-Temterature Rearrangement of the C1 Isomer of C60F36 into the C3 Isomer via a 1,3-Fluorine Shift." VIII.A.4-22 Yashima, E. et al. AG(E), 41, 3602. "A Helical Array of Pendant Fullerenes on an Optically Active Polyphenylacetylene." VIII.A.4-23 Nierengarten, J.-F.; Rio, Y. TL, 43, 4321 "Water Soluble Supramolecular Cyclotriveratrylene[60]Fullerene Complexes with Potential for Biological Applications."

SELECTED TOPICAL AREAS

309

VIII.A.4-24 Kay, K.-Y. et al. TL, 43, 5053. "Dendritic Fullerenes (C6o) with Photoresponsive Azobenzene Groups." ,

|

,,,

i

ill

,

,

VIII.A.4-25 Mehta, G.; Sarma, P.V.V.S. TL, 43, 6557. "A Rapid, Two Step Construction of Novel C48H24 and C54H24 Polycyclic Aromatic Hydrocarbons Represented on the C6o-Fullerene Surface via a Threefold Intramolecular Heck Coupling Reaction." ,,,,,,,

i

,,,,

,,, , ,

VIII.A.4-26 Shinohara, H. et al. JACS, 124, 178. "Novel Synthesis and Characterization of Five Isomers of (C7o)2 Fullerene Dimers." .

.

.

.

.

,,,

,

VIII.A.4-27 Taylor, R. et al. JCS(P2), 251. "Isolation and Characterisation of C60F4, C60F6, C60F8, C60FTCF3 and C60F20, the Smallest Oxohomofullerene: The Mechanism of Fluorine Addition to Fullerenes." ,

,,

VIII.A.4-28 Taylor, R. et al. JCS(P2), 53. "Isolation and Characterisation of Symmetrical C60Me6, C~0MesC! and C60MesO2OH, Together with Unsymmetrical C6oMesO3H, C60MesOOH, C6oMe4PhO2OH, and C60Me]2: Fragmentation of Methylfullerenols to Css." ,

,

,

,

,,

,

VIII.A.4-29 Wilson, S.R. et al. JACS, 124, 1977. "Preparation and Photophysical Studies of a Fluorous PhaseSoluble Fullerene Derivative." VIII.A.4.30 Sho11, D.S. et al. JACS, 124, 1858. "Can Chiral Single Walled Carbon Nanotubes Be Used as Enantiospecific Adsorbents?" VIII.A.4-31 Mehta, G.; Sarma, P.V.V.S. TL, 43, 9343. "Rapid Acquisition of a Sixty-Carbon Fullerene Precursor. A New Synthetic Approach to C60." VIII.A.4-32 Taylor, R. et al. CC, 2370. "C60F36: There is a Third Isomer and It Has C1 Symmetry." ,

,

,

,,,

VIII.A.4-33 Scorrano, G. et al. CEJ, 8, 1015. "[60]Fullerene as a Substituent."

310

ORGANIC SYNTHESIS--2003

VIII.A.4-34 Toniolo, C. et al. CEJ, 8, 1544.

"A Helical Peptide Receptor for [60]Fullerene."

VIII.A.4-35 Armaroli, N.; Nierengarten, J.-F. et al. CEJ, 8, 2314. "Photophysical Properties of the Re I and Ru II Complexes of a New Cn0-Substituted Bipyridine Ligand." VIII.A.4-36 Tajima, Y.; Takeuchi, K. JOC, 67, 1696. "Discovery of C~i003 Isomer Having C3~ Symmetry." VIII.B. Taxol and Related Taxane Chemistry VIII.B-1 Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. TL, 43, 8587. "Synthesis of the CD Ring System of Paclitaxel by AtomTransfer Radical Annulation Reaction." VIII.B-2 Martinez, A.G.; Cerero, S. de la M. et al. TA, 13, 17. "A New Enantiospecific Synthetic Procedure to the TaxoidIntermediate 10-Methylenecamphor, and 10Methylenefenchone." VIII.B-3 Banwell, M.G. et al. AJC, 54, 691 (2001). "Model Studies Directed Towards the Synthesis of Oxetane DRing of Paclitaxel" Assessment of the Oxyanion-Assisted Retro-Diels-Alder Reaction as a Means for Generating Oxete." VIII.B-4 Mukaiyama, T. et a. CL, 92. "A Synthesis of AB-Ring Model System of Taxane Framework by Way of Intramolecular Knoevenagel Cyclization." VIII.B-5 Aubert, C.; Malacria, M. et al. OL, 4, 1027. "New Efficient Construction of the ABC Core of the Taxoids via a Sequence of Consecutive Cobalt(D.Mediated [2+2+2] and [4+2] Cyclizations." VIII.B-6 Appendino, G. et al. EJOC, 277. "Synthesis and Evaluation of 14.Nor.A-secotaxoids." VIII.B-7 Vrudhula, V.M. et al. BMCL, 12, 3591. "Reductively Activated Disulfide Prodrugs of Paclitaxel."

SELECTED TOPICAL AREAS

311

VIII.B-8 Monti, H. et al. TL, 43, 2757. "A Stereocontrolled Approach Towards Highly Oxygenated Taxane C and CD-Ring Precursors." VIII.B.9 Mehta, G.; Nandakumar, J. TL, 43, 699. "Novel Tandem Ring.Opening/Ring-Closing Metathesis Reactions of Functionalized Cyclohexenoids Derived from (-)ct-Pinene." VIII.B-19 Srikishna, A. et al. SL, 1907. "An Enantiospecific Approach to 8,9-seco-C-Aromatic Taxanes." VIII.B-11 Soga, T. et al. CPB, 50, 1398. "A New Method for Synthesis of 7-Deoxytaxane Analogues by Hydrogenation of A6,7-Taxane Derivatives." VIII.B-12 Shen, Y.-C. et al. CPB, 50, 781. "New Taxane Diterpenoids from the Roots of Taiwanese Taxus

mairei."

VIII.B.13 Yuan, Y.-J. et al. BMCL, 12, 3301. "Synthesis and Evaluation of Water.Soluble Paclitaxoi Prodrugs." ,

,,,

,

VIII.B-14 Soga, T. et al. BMCL, 12, 1083, 2815. "New Highly Active Taxoids from 913-Dihydrobaccatin-9,10acetals." VIII.B-15 Fang, W.-S. et al. BMCL, 12, 1543. "Synthesis and Cytotoxicity of 2a.Amidodocetaxel Analogues." VIII.B.16 Gimbert, Y.; Greene, A.E. et al. JOC, 67, 9468. "Synthesis of C-3' Methyl Taxotere (Docetaxel)." VIII.B-17 Ojima, I. et al. BMCL, 12, 349. "Design, Synthesis and Biological Activity of Novel C2-C3' N-Linked Maeroeyelie Taxoids." ,

i

,i,,

,

,

VIII.B-18 Yin, D. et al. TL, 43, 9425. "Synthetic Study of 1,7,9-Trideoxypaelitaxel via Sinenxan A."

312

ORGANIC SYNTHESISm2003

VIII.B-19 Williams, R.M. et al. JOC, 67, 4901. "Studies on Taxoi Biosynthesis. Preparation of Taxa4(20),11(12)-dien-5a-acetoxy.1013.ol by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew." y l I I . C Dendrimers, Calixeranes and Other Unnatural Products yIII.C.I

Dendrimers

y I I I . C . l . a Dendrimer

Svnthesis

VIII.C.I.a-1 Percer, V. et al. CEJ, 8, 1106, 2011. "Eploring and Expanding the Three-Dimensional Structural Diversity of Supramolecular Dendrimers." VIII.C.I.a.2 Cardona, C.M.; Gawley, R.E. JOC, 67, 1411. "An Improved Synthesis of a Trifurcated Newkome-Type Monomer and Orthogonally Protected Two-Generation Dendrimers." VIII.C.I.a-3 Bo, Z.; Schluter, A.D. JOC, 67, 5327. "Synthesis of Low-Generation, Aryl/Alkyl-Type, Nonpolar Dendrons Carrying Protected Hydroxyalkyl Groups in the Periphery." . , .

VIII.C.I.a-4 Vargas-Berenguel, A. et al. CEJ, 8, 812. "Dendritic Galagosides Based on a 13-Cyclodextrin Core." VIII.C.I.a-5 De Schryuer, F.C. et al. JACS, 124, 9918. "Photo-Induced Electron Transfer in a Rigid First Generation Triphenylamine Core Dendrimer Substituted with a Peryleneimide Acceptor." VIII.C.I.a-6 Nithyanandhan, J.; Jayaraman, N, JOC, 67, 6282; see also" Krishna, T.R.; Jayaraman, N. JCS(P1), 756. "Synthesis of Poly(alkyi Aryl Ether) Dendrimers." .,

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VIII.C.I.a-7 Frechet, J.M.F. et al. CC, 2954; see also" Tully, D.C.; Frechet, J.M.J. CC, 1229; Grayson, S.M.; Frechet, J.M.J. OL, 4, 3171; Gillies, E.R.; Frechet, J.M.J. JACS, 124, 14137 "Self-Assembled Oligonucleotide-Polyester Dendrimers."

SELECTED TOPICAL AREAS

313

V I I I . C . I . a . 8 Stoddart, J.F. et al. CEJ, 8, 3001 and see also: CJC, 80, 983 and OL, 4, 679, 3565 "Large Oligosaccharide.Based Glycodendrimers." VIII.C.I.a-9 Newkome, G.R. et al. JOC, 67, 3957. "Improved Synthesis of an Ethereal Tetramine Core for Dendrimer Construction." .

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....

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VIII.C.l.a-10 Vogtle, F. et al. CEJ, 8, 4434. "Dendronized Molecular Knots: Selective Synthesis of Various Generations, Enantiomer Separation, Circular Dichroism." |

VIII.C. 1.a. 11 Piers, W.E. et al. OM, 21, 4300. "Synthesis and Characterization of (Perfluoroaryl) BoraneFunctionalized Carbosilane Dendrimers and Their Use as Lewis Acid Catalysts for the Hydrosilation of Acetophenone." .,

VIII.C.I.a-12 Backinowsky, L.V. et al. CEJ, 8, 4412. "An Efficient Approach Towards the Convergent Synthesis of ' F u l l y - C a r b o h y d r a t e ' Mannodendrimers." i

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VIII.C.I.a-13 Peng, Z. et al. JOC, 67, 7781 and TL, 43, 7903. "Synthesis of Conjugated Dendrimers with Nonlinear Optical Activity." -

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VIII.C.I.a-14 Royo, M.; Pons, M.; Albericio, F.; Giralt, E. et al. JACS, 124, 8876. "Peptide Dendrimers Based on Polyproline Helices." .

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VIII.C.I.a-15 Dehaen, W. et al. JOC, 67, 1004. "New Acceerated Strategy for the Synthesis of Poly(ethr Ketone) Dendrimers." VIII.C.I.a-16 Caminade, A.-M.; Majoral, J.-P. et al. JOM, 643-644, 112. "Synthesis of Dendrimeers with Phosphine End Groups at Each Generation." VIII.C.l.a-17 Smith, D.K. et al. JACS, 124, 856. "Ferrocene Encapsulated Within Synthetic Dendrimers: A Deeper Understanding of Dendritic Effects on Redox Potential."

314

ORGANIC SYNTHESISm2003

VIII.C.l.a-18 Sha, Y. ct al. TL, 43, 9417 "A Divergent Synthesis of New Aliphatic Poly(ester-Amine) Dendrimers Bearing Peripheral Hydroxyl or Acrylate Groups." VIII.C.l.a-19 Zaitsu, K. ct al. TL, 43, 8185. "Synthesis of Poly(3,4,5-trihydroxybenzoate Ester) Dendrimers and Their Chemiluminescence."

VIII.C.I.a-20 Thayumanavan, S. et al. OL, 4, 3751 and TL, 43, 7217. "Functional Group Diversity in Dendrimers." VIII.C.I.a-21 Bansal, S.S. et al. TL, 43, 6723. "Synthesis of a Dendron and Dendrimer Consisting of MALDI Matrix Like Branching Units." VIII.C.l.a-22 Ghosh, S.; Banthia, A.K. TL, 43, 6457. "Towards Fluorescence Sensing Polyamidoamine (PAMAM) Dendritic Architextures." VIII.C.1.a-23 Imai, M.; Arai, T. TL, 43, 5265. "Synthesis and Photochemical Properties of Polyphenylene Dendrimers with Photoreaetive Stilbene Core." VIII.C.1.a-24 Kokotos, G. et al. S, 1359. "Synthesis of Chiral n,n+l-Diamino Acids and Their Applications to the Construction of Dendrimers." VIII.C.l.a-25 Kevwitch, R.M.; McGrath, D.V. S, 1171. "Synthesis of Photolabile Dendrimer Cores." VIII.C.l.a-26 Sun, C.; Wirsching, P.; Janda, K.D. BMCL, 12, 2213. "Syntheses of Dendritic Containing Chlorambucil Residues for the Preparation of Antibody-Multidrug Immunoconjugates." VIII.C.l.a-27 Pieters, R.J. et al. BMCL, 12, 1567. "Synthesis and Biological Activity of Polygalloyl-Dendrimers as Stable Tannic Acid Mimics." ,

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VIII.C.l.a-28 Cao, X. et al. SC, 32, 3149. "A New Convergent Approach to Dendritic Macromolecules."

SELECTED TOPICAL AREAS

315

VIII.C.l.a-29 Lemcoff, M.G.; Fuchs, B. OL, 4, 731. "Toward Novel Polyacetals by Transacetalization Techniques: Dendrimeric Diacetals." VIII.C.I.a-30 Takaguchi, Y. et al. BCJ, 75, 1347. "Synthesis and Characterization of a Poly(amide Amine) Dendrimer Disulfide Having Hydroxy Groups as the Terminals." VIII.C.I.a-31 Brana, M.F. et al. EJMC, 37, 541. "Synthesis and Antitumour Activity of New Dendritic Polyamines(Imide-DNA-lntercalator) Conjugates" Potent Lck Inhibitors." VIII.C.l.a-32 Armarol, N,; Nierengarten, J.-F. et al. TL, 43, 65. "Functionalization of [60]Fullerene with New Light-Collecting Oligophenylenevinylene-Terminated Dendritic Wedges." VIII.C.l.a.33 Sengupta, S. et al. TL, 43, 1117. "Synthesis of Dendritic Stilbenoid Compounds: Heck Reactions for the Periphery and the Core.' V I I I . C . l . a . 3 4 Hu, Q.S. et al. TL, 43, 927. "Optically Active Dendronized Polymers as a New Type of Macromolecular Chiral Catalyst for Asymmetric Catalysis." VIII.C.l.a-35 Salamonczyk, G.M. et al. TL, 43, 1747. "Dendrimers Bearing Three Types of Branching Functions." VIII.C.l.a-36 Soai, K. et al. EJOC, 3115. "Asymmetric Synthesis of N-(Diphenylphosphimyl)amines Promoted by Chiral Carbosilane Dendritic Ligands in the Enantioselective Addition of Dialkylzinc Compounds ot N(Diphenylphosphinyl)imines." VIII.C.l.a-37 Bradley, M. et al. TL, 43, 2475. "Rapid Synthesis of High-Loading Resins Using Triple Branched Protected Monomer for Dendrimer Synthesis."

316

V I I I . C . I . b Dendrimgr

ORGANIC SYNTHESIS--2003

Catalysts

VIII.C.I.b-1 Deng. J.-G. et al. CC, 1488. "Dendritic Catalysts for Asymmetric Transfer Hydrogenation." i

VlII.C.l.b-2 van Koten, G. et al. CEJ, 8, 45. "New Mono- and Tricyclopalladated Dendritic Systems with Encapsulated Catalytic Sites." VIII.C.I.b-3 Che, C.-M. et al. CEJ, 8, 1554. "Dendritic Ruthenium Porphyrins: A New Class of Highly Selective Catalysts for Allene Epoxidation and Cyclop ropanation." V I I I . C . I . c Hctero-Containin~ and Miscellaneous Dendrimers VIII.C.I.c-1 Rico-Lattes, I.; Majoral, J.-P. et al. CC, 1864. "Phosphorous-Containing Dendrimers Baring Galactosyiceramide Analogs: Self-Assembly Properties." VIII.C.I.c-2 Takahashi, S. et al. CC, 2576. "Platinum-Acetylide Dendrimers Possessing a Porphryn Core." VIII.C.I.c-3 Lin, W. et al. OL, 4, 2149. "Chiral Hybrid Metal-Organic Dendrimers." VIII.C.I.c-4 Credi, A.; Raymo, F.M. et al. CEJ, 8, 673. "Ferrocene-Containing Carbohydrate Dendrimers." VIII.C.I.c.5 Humphrey, M.G. et al. OM, 21, 2353. "A Rapid Convergent Approach to Organometallic Dendrimers: Sterically Controlled Dendron Synthesis." VIII.C.I.c-6 Advincula, R.C. et al. OL, 21, 2067. "A First Synthesis of Thiophene Dendrimers."

SELECTED TOPICAL AREAS

317

YIII.C.2 Cali:geranes y I I I . C . 2 . a Calixarene

Receptors

VIII.C.2.a- 1 Lukes, I. et al. JCS(P2), 1370. "Synthesis, Characterisation and Extraction Behaviour of Calix[4]arene-Based Phosphonic Acids." VIII.C.2.a-2 Arimura, T. et al. JCR(S), 333. "Synthesis and Binding Properties of Calix[4]arene Dual Porphyrin Conjugate: Tweezers for DABCO." VIII.C.2.a-3 Chowdhury, S.; Georghiou, P.E. JOC, 67, 6808. "Synthesis and Properties as a New Member of the Calixnaphthalene Family." VIII.C.2.a-4 Kohnke, F.H. et al. CEJ, 8, 3148. "Calix[6]pyrrole and Hybrid Calix[n]furan[m]pyrroles (n+m = 6)" Syntheses and Host-Guest Chemistry." VIII.C.2.a-5 Wang, J.; Gutsche, C.D. JOC, 67, 4423. "Tricalixarenes and Pentacalixarenes: Synthesis and Complexation Studies." ,

VIII.C.2.a-6 Ashram, M. JCS(P2), 1662. "Synthesis of Calix[4]crowns Containing Soft Donor Atoms and a Study of Their Metal-Cation Binding Properties" Highly Selective Receptors for Cu2+.'' VIII.C.2.a-7 Ito, K. et al. JOC, 67, 7519. "Synthesis of Chiral Homoazacalix[4]arenes Incorporating Amino Acid Residues" Molecular Recognition for Racemic Quaternary Ammonium Ions." VIII.C.2.a-8 Yilmaz, M. et al. OPP, 34, 417. "Synthesis and Extraction Studies of a Novel TetraCalix[4]arene." VIII.C.2.a-9 Hioki, H. et al. TL, 43, 7949. "Synthesis of Fluorescence-Labeled Peptidocalix[4]arene Library and Its Peptide Sensing Ability."

318

ORGANIC SYNTHESIS--2003

VIII.C.2.a-10 Molard, Y.; Parrot-Lopez, H. TL, 43, 6355. "Molecular Scaffolds for Di.Metallic Complexation" The Synthesis, Characterisation and Complexation Properties of T et rak is- T erp yri din yl- C alix [ 4 ] a re n e." ,,

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VIII.C.2.a-11 Wu, C.-T. et al. TL, 43, 6249. "New Type Chiral Calix[4](aza)crowns: Synthesis and Chiral Recognition." ,,,,

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VIII.C.2.a-12 Cheng, J.-P. et al. TL, 43, 5665. "Design, Synthesis and Enantiomeric Recognition of Dicyclodipeptide-Bearing Calix[4]arenes" A Promising Family for Chiral Gas Sensor Coatings." ,,

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VIII.C.2.a.13 Tuntulani, T. et al. T, 58, 10277. "Synthesis of tripodal Aza Crown Ether Calix[4]arenes and Their Supramolecular Chemistry with Transition-Alkali Metal Ions and Anions." ,,1

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VIII.C.2.a-14 Hwang, G.T.; Kim, B.H. T, 58, 9019. "Synthesis and Binding Studies of Multiple Calix[4]arenes." .

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VIII.C.2.a-15 Zeng, X.; Zhang, Z.-Z. et al. TL, 43, 131 and JCS(P2), 796. "The First Synthesis of a Calix[4](diseleno)crown Ether as a Sensor for Ion-Selective Electrodes." VlII.C.2.a-16 Talanov, V.S.; Bartsch, R.A. et al. JCS(P2), 209. "Novel Caesium-Selective, 1,3-Alternate Calix[4]areneBis(crown-6-ethers) with Proton-lonizable Groups for Enhanced Extraction Efficiency." VIII.C.2.a-17 Engrand, P.; Regnouf-de-Vains, J.-B. TL, 43, 8863. "A Bifunctional Calixarene Designed for Immobilisation on a Natwal Polymer and for Metal Complexation." ,

VIII.C.2.a-18 Beer, P.D. et al. JACS, 124, 1341. "Calix[4]tubes" A New Class of Potassium.Selective lonophore." .

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VIII.C.2.a-19 Speranza, M. et al. JACS, 124, 7658. "Enantioselective Guest Exchange in a Chiral Resorcin[4]arene Cavity."

SELECTED TOPICAL AREAS

319

VIII.C.2.a-20 Valeur, B. et al. JCS(P2), 1429. "Synthesis and Binding Properties of Calix[4]biscrown-Based Fluorescent Molecular Sensors for Caesium or Potassium Ions." VIII.C.2.a-21 Raston, C.L. et al. JCS(P2), 1801. "Synthesis and trans.p.Carotenoid Inclusion Properties of a New'Class of Water Soluble Calixarenes." VIII.C.2.a-22 Bartsch, R.A. et al. JCS(P2), 1869. "New Mono-Ionizable Li+-Selective Calix[4]arenes." VIII.C.2.a-23 Dondoni, A.; Banks, H.D. et al. JOC, 67, 4722. "Glycoside-Clustering Round Calixarenes Toward the Development of Multivalent Carbohydrate Ligands." V I I I . C . 2 , b Svnthesis of Calixirane VIII.C.2.b-1 Dumazet-Bonnamour, I. et al. TL, 43, 3785. "Synthesis of Novel Chromogenic Bi- and Tri-Functionalized Calix[4]arenenes." VIII.C.2.b-2 Psychogios, N.; Regnouf-de-Vains, J.-B. TL, 43, 77, 7691. "A New Water-Soluble Calix[4]arene Podand Incorporating pSulfonate Groups and 2,2'-Bipyridine Chelating Units." i

VIII.C.2.b-3 Deligoz, H.; Ercan, N. T, 58, 2881. "The Synthesis of Some New Derivatives of Calix[4]arene Containing Azo Groups." VIII.C.2.b.4 Black, S.StC. et al. T, 58, 5125. "Acid-Catalyzed Reactions of Activated Benzofuranylmethanols: Formation of Calixbenzofurans." .

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VIII.C.2.b.5 Kovalev, V. eta;. T, 58, 5153. "First Synthesis of Adamantylated Thiacalix[4]arenes." Vlll.C.2.b-6 Bohmer, V.; Wurthner, F. et al. OL, 4, 2901. "Calix[4]arene-Functionalized Naphthalene and Perylene Imide Dyes."

320

ORGANIC SYNTHESIS--2003

VIII.C.2.b-7 Kalchenko, V.I. et al. JCS(P1), 1405. "Symmetrical and Inherently Chiral Water.Solubale Calix[4]arenes Bearing Dihydroxyphosphoryl Groups." ,,

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VIII.C.2.b-8 Kim, S.J.; Kim, B.H. TL, 43, 6367. "Design and Synthesis of Calix[4]arene-Nucleoside Hybrids." VIII.C.2.b-9 Raston, C.L. et al. JCS(P1), 354. "Unsymmetrical o-Bridged Calixarenes Derived from tBucalix[4]arene and p-Benzylcalix[4]arene." ,

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VIII.C.2.b-10 Colby, D.A.; Lash, T.D. JOC, 67, 1031. "Calix[4]azulene." V I I I . C . 2 . b - l l Cragg, P.J. et al. JOC, 67, 3124. "Acid.Catalyzed Formation of Hexaomooxcalix[3]arenes." VIII.C.2.b-12 Varadarajan, R. et al. TL, 43, 7073. "One Step Facile Synthesis of Bromo Calix[n]arenes." VIII.C.2.b-13 Chen, Q.; Ma, J. et al. SC, 32, 1041, 1051. "A Facile Highly Efficient Synthesis of Fully N-Confused Calix[5]pyrrole." VIII.C.2.b.14 Pappalardo, S.; Williams, D.J. et al. JOC, 67, 7569. "Calix[4]- and Calix[5]arene-Based Multicavity Macrocycles." VIII.C.2.b-15 Ito, K. et al. SC, 32, 53. "Facile Formation of Calix[4,5,6, and 9]arene Analogs Having the intra- and extra-Hydroxyl Groups." VIII.C.2.b-16 Kohnke, F.H.; Williams, D.J. et al. OL, 4, 2695. "The Elusive 13-Unsubstituted Calix[5]pyrrole Finally Captured." VIII.C.2.b.17 Bohmer, V. et al. S, 1898. "Extended Calix[8]arenes by Sonagashira Cross-Coupling with Ethynylarenes." VIII.C.2.b.18 Parisi, M.F. et al. TL, 43, 7663. "Guest-Induced Capsular Assembly of Calix[5]arenes."

SELECTED TOPICAL AREAS

321

VIII.C.2.b-19 Hosseini, M.W. et al. TL, 43, 8975. "Molecular Baskets Based on Tetramecaptotetrathiacalix[4]arene and Tetrathiacalix[4]arene." VIII.C.2.b-20 Lu, G.-Y. et al. OPP, 34, 542. "Synthesis of Calix[4]arene Diazacrown Containing mXylylene Phenol Subunit." VIII.C.2.b-21 Miyazaki, Y.; Kanbara, T.; Yamamoto, T. TL, 43, 7945. "Preparation of New Type of Azacalixarene, Azacalix[n](2,6)pyridine." VIII.C.2.b-22 Lee, C.-H. et al. TL, 43, 9493. "Bithiophene-Containing Super-Expanded Calixpyrrole Analogues." VIII.C.2.b-23 Sessler, J.L. et al. CEJ, 8, 1134. "Missing-Link Macrocycles" Hybrid Heterocalixarene Analogues Formed from Several Different Building Blocks." VIII.C.2.b-24 Glass, T.E. et al. JOC, 67, 904. "Synthesis of 3,5- and 3,6-Linked Calix[n]naphthalenes." ......

VIII.C.2.b~25 Pulpoka, B.; Vicens, J. et al. JHC, 38, 1383. "Novel Calix[4]cryptands: 'Mappemonde-ll' and 'Mill H'." VIII.C.2.c Synthesis on Calixiranes VIII.C.2.c-1 Narumi, F.; Miyano, et al. TL, 43, 621. "Proximal O, O'.Capped Calix[4]arenes with a Disiloxane Bridge as Highly Efficient Synthetic Intermediates for 1,2Dialkylation at the Lower Rim." VIII.C.2.c-2 Nayak, S.K. et al. T, 58, 5287. "Ultrasound Mediated Selective Monoalkylation of 4.tertButylcalix[6]arene at the Lower Rim." VIII.C.2.c-3 Ito, K. et al. CPB, 50, 432. "Facile Formation of Chiral Calixarene Analogs Incorporating Cystine Peptide into the Macrocyclic Ring."

322

ORGANIC SYNTHESIS--2003

VIII.C.2.c-4 Varadarajan, R. et al. TL, 43, 2495. "A One-Step, One-Pot Synthesis of p-Acyi Calix[n]arenes." ,.,,,

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VIII.C.2.c-5 Chawla, H.M. et al. T, 58, 5591. "Synthesis of Selectively Formulated Calixarene Ethers." ...,~

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VIII.C.2.c-6 Ned, P. et al. OL, 4, 1531 and TL, 43, 8875, 9521. "Regioselective O-Substitution of p-tert-Butylcalix[7]arene." ,, .

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VIII.C.2.c-7 Huang, Z.T. et al. T, 58, 3729. "Macrocyclic, Linear and Starlike Assemblies of Calix[4]arenes Covalently Bridged by Methylenes at the Upper Rims: Simple Routes to Novel Receptors with Defined Polycavaties." . .

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VIII.C.2.c-8 Fukazawa, Y. et al. TL, 43, 8191. "Synthesis and Binding Behavior of a Zn(lI)pporphyrin Having a Calix[5]arene Cap." .

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VIII.C.2.c-9 Llotak, P. et al. TL, 43, 9621. "Alkylation of Thiacalix[4]arenes." .

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VIII.C.2.c-10 Verboom, W.; Reinhoudt, D.N. et al. TL, 43, 9675. "Cation Control on the Synthesis of p-t-Butylthiacalix[4](bis)crown Ethers." VIII.C.2.c.11 Biali, S.E. et al. JOC, 67, 6136. "Functionalization of the Methyl Groups of p-tertButhylcalix[4]arene" S--C, N--C, and C - - C Bond Formation." 9

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VIII.C.2.c-12 Tsubaki, K.; Fuji, K. et al. JOC, 67, 8151. "Modification of the Upper Rim of Homooxacalix[3]arenes and Complexation Between a Nitrohomooxacalix[3]arene Derivatives and n.Hexylamine." .....

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VIII.C.2.c-13 Kim, J.S. JOC, 67, 1372, 3165, 6514. "Chromogenic Azo-Coupled Calix[4]arenes."

SELECTED TOPICAL AREAS

323

VIII.C.2.d Calixirane Isolation,

Conformation.

etc,

VIII.C-1 Mathieu, A.; Asfari, Z.; Vicens, J. TL, 43, 1225. " W a t e r Soluble para.Sulfonated 1,2;3,4.Calix[4]arene. Biscrowns in the Cone Configuration." ,,,

VIII.C.2 Lattman, M. et al. OM, 21, 4442. "Isolation of All Four Conformations of p-tert. Butylcalix[5]arene Using Bridging Silyl Groups." i

VIII.C-3 de Mendoza, J. et al. EJOC, 640. "A Calix[4]arene Dimer Linked Through Amino Acid Hydrogen Bond Interactions." VIII.C.3

Rotaxanes

VIII.C.3-1 Smith, B.O. et al. JOC, 67, 1436. "Templated Conversion of a Crown Ether-Containing Macrobicycle into [2]Rotaxanes." .

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VIII.C.3-2 Takata, T. et al. T, 58, 6609. "Synthesis of [2]Rotaxanes by Tritylative Endcapping of in situ Formed Pseudorotaxanes Having Thiol or Hydroxyl Functionality on the Axle Termini." VIII.C.3-3 Stoddart, J.F. JOC, 67, 9175; and see also: OL, 4, 3561 and CCC, 67, 1719. "An Acid.Base Switchable [2]Rotaxane." .

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VIII.C.3-4 Schalley, C.A. et al. CC, 2628. "Novel Template Effect for the Preparation of [2]Rotaxanes with Functionalized Centre Pieces." VIII.C.3-5 Sauvage, J.-P. et al. CEJ, 8, 1456. "Chemically Induced Contraction and Stretching of a Linear Rotaxane Dimer." u

Nakamura, E. et al. OL, 4, 1287. "Synthesis of Disubstituted Cucubit[6]uril and Its Rotaxane Derivative."

324

ORGANIC SYNTHESISm2003

VIII.C.3-7 Tokunaga, Y. et al. CL, 810. "A High-Yielding and Convenient Synthesis of Rotaxane Based on an Ester Forming Capping Methodology." VIII.C.3.8 Asakawa, M.; Shimizu, T. et al. CL, 174. "Preparation of Porphyrin-Stoppered Rotaxane Aiming at Immobilization on Substrate." VIII.C.3-9 Haley, M.M. et al. S, 1256. "Synthesis and Characterization of Annulene-Fused Pseu dorotaxanes." VIII.C.3-10 Hiratani, K. et al. TL, 43, 5747. "A New Synthetic Method for Rotaxanes via Tandem Ciaisen Rearrangement, Diesterification, and Aminolysis." VIII.C.3-11 Stoddart, J.-F.; Williams, D.J. et al. CEJ, 8, 5170. "Post-Assembly Processing of [2]Rotaxanes." VIII.C.3-12 Takata, T. et al. CC, 2720. "Highly Efficient Synthesis of [3]- and [5]-Rotaxanes Consisting of Crown Ether and a seC.3-Ammonium Salt." VIII.C.3-13 Kim, K. et al. CC, 1042. "A Kinetically Controlled Molecular Switch Based on Bistable [2]Rotaxane." VIII.C.3-14 Puddephatt, R.J. et al. CC, 1310. "An Organometallic Polyrotaxane and a New Type of Polyrotaxane Architecture."

u

$uoramolecu!es _

VIII.C.4.1 Laine, P. et al. CEJ, 8, 3162. "Triarylpyridinium-Functionalized Terpyridyl Ligand for Photosensitized Supramolecular Architectures." VIII.C.4-2 Lehn, J.-M. et al. CEJ, 8, 3448. "Helical Self.Organization and Hierarchical Self-Assembly of an Oligoheterocyclic Pyridine-Pyridazine Strand into Extended Supramolecular Fibers."

SELECTED TOPICAL AREAS

325

VIII.C.4-2 Benvegnu, T. et al. CEJ, 8, 585. "Supramolecular Self-Assembling Properties of MembraneSpanning Archaeal Tetraether Glycolipid Analogues." ....

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VIII.C.4-4 Lehn, J.-M. et al. CEJ, 8, 1227. "Supramolecular Polymers Generated from Heterocomplimentary Monomers." .

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VIII.C.4-5 Zaworotko, M.J. et al. JACS, 124, 9990. "Supramolecular Isomerism in Coordination Compounds" Nanoscale Molecular Hexagons and Chains." ...

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VIII.C.4-6 Kim, K. et al. CEJ, 8, 498. "Transition Metal Ion Directed Supramolecular Assembly of One- and Two-Dimensional Polyrotaxanes Incorporating Cucurbituril." VIII.C.4-7 Benshafrut, R. et al. JOC, 67, 4040. "Synthesis and Characterization of a New Tetradendate Ligand for Cu(ll) Metal Ions." VIII.C.4-8 Tykwinski, R.R. et al. JOC, 67, 1133. "Functionalized Macrocyclic Ligands for Use in Supramolecular Chemistry." .

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VIII.C.4-9 Sekiya, R.; Nishikiori, S. CEJ, 8, 4803. "Design and Structural Extension of a Supramolecular Inclusion-Compound Host Made by the Formation of Dimers of lsonicotinic Acid and Thiocyanato Coordination Bridges." ,

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.,

VIII.C.4-10 Mar'sura, A. et al. CEJ, 8, 2438. "New Scaffolds for Supramolecular Chemistry: Upper Rim Fully Tethered 5.Methyleneureido-5'-methyl-2,2'-bipyridyl Cyclodextrins." ,,|

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VIII.C.4-11 Wang, G.; Hamilton, A.D. CEJ, 8, 1954. "Synthesis and Self-Assembling Properties of Polymerizable Organogelators." VIII.C.4-12 Jaskolski, M.; Desiraju, G.T. et al. CC, 1830. "Supramolecular Synthons Based on N--H---N and C--H---O Hydrogen Bonds. Crystal Engineering of a Helical Structure with 5,5-Diethylbarbituric Acid."

326

ORGANIC SYNTHESIS--2003

VIII.C.4-13 Hannon, M.J. et al. CEJ, 8, 4957. "Helical (Isotactic) and Syndiotactic Silver(I) MetalloSupramolecular Coordination Polymers Assembled from a Readily Prepared Bis-Pyridylimine Ligand Containing a 1,5Naphthalene Spacer." VIII.C.4-14 Rybak-Akimova, E.V. et al. CC, 3014. "Stable Supramolecular Dimer of Self-Complimentary Benzo18-crown-6 with a Pendant Protonated Amino Arm." ,

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VIII.C.4-15 Turro, N.J. CC, 2279. "From Molecular Chemistry to Supramolecular Chemistry to Superdupermolecular Chemistry Cotrolling Covalent Bond Formation Through Non-Covalent and Magnetic Interactions." VIII.C.4-16 Moghimi, A. et al. JCR(S), 477. "Synthesis, NMR Characterization, X-Ray Crystal Structure and Solution Studies of Ni(II) Complexes of a Pyridine Containing Self-Assembling System." ,

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VIII.C.4-17 Hamachi, I. et al. JACS, 124, 10954. "First Thermally Responsive Supramolecular Polymer Based on Giycosylated Amino Acid." . . . . . . . . . .

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VIII.C.4-18 Hirao, T. et al. JACS, 124, 9356. "Self-Assembly of Dipeptidyl Ureas" A New Class of Hydrogen-Bonded Molecular Duplexes." ,,

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VIII.C.4-19 Timmerman, P.; Reinhoudt, D.N. et al. JACS, 124, 7638; and see also: CEJ, 8, 2288, 2302. "Molecular 'Chaperones' Guide the Spontaneous Formation of a 15-Component Hydrogen-Bonded Assembly." VIII.C.4-20 Schuster, D.I.; Guldi, D.M. et al. CC, 2538. "Formation and Photophysics of a Stable Concave.Convex Supramolecular Complex of C60 and a Substituted s-Triazine Derivative." VIII.C.4-21 Custelcean, R.; Vlassa, M.; Jackson, J.E. CEJ, 8, 302. "Supramoleeular Synthesis Through Dihydrogen Bonds: SelfAssembly of Controlled Architectures from NaBH4.Poly(2hydroxyethyl)cyelen Building Blocks."

SELECTED TOPICAL AREAS

327

VIII.C.4-22 Alajarin, M.; Steed, J.W. et al. JOC, 67, 7091. "Dimerie Self-Assembling Capsules Derived from the Highly Flexible Tribenzylamine Skeleton." VIII.C.4-23 Zhao, D.; Moore, J.S. JOC, 67, 3548. "Synthesis and Self-Assembly of an Imine-Containing mPhenylene Ethylene Maeroeyele." _,

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VIII.C.4-24 Sherman, J.C. et al. JACS, 124, 16. "Synthesis and Characterization of a Disulfide-Linked CsSymmetric [5]Carceplex." ,

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VIII.C.4-25 Kawano, T.; Ueda, I. et al. TL, 43, 6697. "Synthesis of Oligo(2-ethynylpyridines)" Novel Building Blocks for Supramolecular Systems." ,

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VIII.C.4-26 Pollino, J.M.; Weck, M. S, 1277. "Supramolecular Side-Chain Functionalized Polymers: Synthesis and Self-Assembly Behavior of Polynorbornenes Bearing Pd n ScS Pincer Complexes." . . . . _ .

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VIII.C.4-27 Jaskolski, M.; Desiraju, G.R. et al. OL, 4, 921. "An Organic Ladder Formed with Three-Connected Molecular and Supramolecular Synthons." VI!I.C.5

Cvcloohanes _

VIII.C.5-1 Xu, J.; Lai, Y.-H. OL, 4, 3211. "Synthesis Complexation, and Supramolecular Assembly of 21,30-Dithia- 17,25-dimethyl-l,4,7,10,13pen taoxa [ 13.3.3 ] (1,2,6) cyclop ha ne." VIII.C.5-2 Yamato, T. et al. CJC, 80, 510. "Medium Size Cyclophanes. Synthesis and Conformational Studies of 9-Substituted [3.3]Metacyclophane-2,11-diones and Conversion to the Corresponding [3.3]Metacyclophanes." VIII.C.5-3 Shinmyozu, T. et al. JACS, 124, 10136. "An Alternative Synthesis Route of [35](1,2,3,4,5)Cyciophane, and Structural Properties of Multibridged [3N]Cyclophanes and Their Charge-Transfer Complexes in the Solid State."

328

ORGANIC SYNTHESISm2003

VIII.C.5-4 Bartholomew, G.P.; Bazan, G.C. S, 1245. "Strategies for the Synthesis of Through-Space Chromophore Dimers Based on [2+2] Paracyclophane." VIII.C.5-5 Nishimura, J. et al. TL, 43, 5821. "Behavior of [2.n]Metacyclophane-Fused Cyclobutane Rings in Brominati0n." VIII.C.5-6 Alcalde, E. et al. CEJ, 8, 474. "Novel Bis-Betaines and Betaines Within [14]metaHeterophane Frameworks." ,

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VIII.C.5-7 Furstner, A. et al. CEJ, 8, 1856. "Total Synthesis of the Turrianes and Evaluation of Their DNA-Cleaving Properties." .

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VIII.C.5-8 Pigge, F.C. et al. JOC, 67, 4547. "An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Synthesis." VIII.C.5-9 Lin, C.-H.; Tour, J. JOC, 67, 7761. "Hydrogen-Bond-Assisted ~.Stacking of Shape-Persistent Cyclophanes." f

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VIII.C.5-10 Hopfl, H. et al. CEJ, 8, 612. "Facile Preparation of [4.4]Metacyclophane- and [5.5]Paracyclophane-Type Macrocycles from Arylboronic Acids and Salicylidene Amino Aryl Alcohols." ,,~ . . . . . . . . . . . .

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VIII.C.5-11 Kwochka, W.R. et al. JOC, 67, 5333. "Synthesis of IN]- and [N.N] Cyclophanes Using SuzukiMiyaura Coupling." VIII.C.5-12 Pandey, P.S. et al. JCS(P1), 918. "Synthesis of Cholic Acid-Based Molecular Receptors: Headto-Head Cholaphanes." VIII.C.5-13 Braddock, D.C. et al. JOC, 67, 8679. "Improved Synthesis of (+)-4,12.Dihydroxy [2.2]Paracyclophane and Its Enantiomeric Resolution by Enzymatic Methods" Planar Chiral (R)- and (S)-Phanol."

SELECTED TOPICAL AREAS

329

VIII.C.5-14 Park, K.K. et al. JCS(P1), 310. "Synthesis of Novel Cyclophanes Containing Both Benzo[1,2-

b'5,4-b']-difuran and Naphthalene Rings."

VIII.C.5-15 Gibson, S.E. et al. CC, 1938. "Synthesis and Structural Analysis of Dehydrophenyl Alanine Cyclophanes." VIII.C.5-16 Fyles, T.M. et al. JOC, 67, 1548. "Synthesis and Membrane Activity of a Bis(metacyclophane)bolaamphiphile. VIII.C.6 Other VIII.C.6-1 Harano, K. et al. JCS(P2), 1611. "Non-Hydroxylic Clathrate Hosts of [4+2]~ Cycloadducts of Phencyclone and N.Arylmaleimides: Recognition of Aromatic Guests , .

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VIII.C.6-2 Bencini, A.; Bianchi, A.; Giorgi, C. et al. JOC, 67, 9107. "Synthesis of New Tren-Based Tris-Macrocycles. Anion Cluster Assembling Inside the Cavity Generated by a BowlShaped Receptor." VIII.C.6-3 Shizuma, M.; Sawada, M. et al. JOC, 67, 4795. "New Artificial Host Compounds Containing Galaetose Eno Groups for Binding Chiral Organic Amine Guests." VIII.C.6-4 Meier, H. S, 1213. "Areno-Condensed Annulenes---Extended Discotie Mesogens." VIII.C.6-5 Isaacs, L. et al. JACS, 124, 8297. "Diastereoselective Formation of Glycouril Dimers" Isomerization Mechanism and Implications for Cueurbit[N]urii Synthesis." VIII.C.6-6 Threadgill, M.D. et al. CC, 2876. "Formation of a Remarkably Robust 2:1 Complex Between 13Cyelodextrin and a Phenyl-Substituted Ieosahedral Carborane."

330

ORGANIC SYNTHESISm2003

VIII.C.6-7 Marsella, M.J. et al. S, 1133. "Expanding Tetra[2,3-thienylene].Based Molecular Muscles to Larger [4n]Annulenes." VIII.C.6-8 Hellberg, J. et al. S, 1195. "Regiospecifically Aikylated Oligothiophenes via Structurally Defined Building Blocks." VIII.C.6-9 Pinto, M.R.; Schanze, K.S. S, 1293. "Conjugated Polyelectrolytes" Synthesis and Applications." VIII.C.6-10 Yu, J.; Yang, R. SC, 32, 3113. "Synthesis and Characterization of New Polyoxa-aza Cryptands." ,

VIII.C.6-11 Sherman, T. et al. CEJ, 8, 3717. "Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands." VIII.C.6-12 Isaacs, L. et al. JOC, 67, 5817. "Methylene-Bridged Glyocaril Dimers: Synthetic Methods." VIII.C.6-13 Feiters, M.C. et al. JOC, 67, 5901. "Synthesis and Self-Inclusion of Bipyridine-Spaced Cyclodextrin Dimers." ,

VIII.C.6-14 Fukase, K. et al. JOC, 67, 8182. "Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation." VIII.C.6.15 Darcy, R. et al. CC, 2864. "Cationic 13-Cyclodextrin Bilayer Vesicles." ylII.C,7

Reviews

VIII.C.7-1 Tyman, L. et al. CSR, 31, 69. Review" "Catalysis Inside Dendrimers." VIII.C.7-2 Mueller, A.; O'Brien, D.F. CRV, 102, 727. Review" "Supramolecular Materials via Polymerization of Mesophases of Hydrated Amphiphiles."

SELECTED TOPICAL AREAS

331

VIII.C.7-3 Sliwa, W. et al. H, 57, 2179. Review" "Cavitands and Related Container Molecules." _ L

VIII.C.7-4 Rudkevich, D.M. BCJ, 75, 393. Account" "Nanoscale Molecular Containers." VIII.C.7-5 Raehm, L.; Hamilton, D.G.; Sanders, J.K.M. SL, 1743. Account" "From Kinetic to Thermodynamic Assembly of Catenanes: Error Checking Supramolecular Protection and Oligocatenanes." _

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VIII.C.7-6 Rotello, V.M., guest ed. T, 58, 621-843. Symposia "Recognition-Mediated Self-Assembly of Organic in-Print: Systems." VIII.C.7-7 Tsuji, T. et al. BCJ, 75, 415. Account" "Preparation and Kinetic Stabilization of Highly strained Paracyclophanes." .

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VIII.C.7-8 Mikami, K. et al. SL, 1561. Account" "Tropos or Atropos? That is the Question!" VIII.C.7.9 Kim, K. CSR, 31, 96. Review: "Mechanically Interlocked Molecules Incorporating Cucurbituril and Their Supramolecular Assemblies." VIII.C.7-10 Hennrich, G.; Anslyn, E.V. CEJ, 8, 2218, 2274. Concept: "l,3,5-2,4,6-Functionalized, Facially Segregated Benzenes---Exploitation of Sterically Predisposed Systems in Supramolecular Chemistry." VIII.C.7-11 Haddon, R.C., guest ed. ACR, 35, 997-1113. Reviews" "Carbon Nanotubules." VIII.C.7-13 Guldi, D.M. CSR, 31, 22. Review" "Fullerene-Porphyrin Architectures" Photosynthetic Antenna and Reaction Center Models."

ORGANIC SYNTHESISm2003

332

,VIII.D. Total Syntheses of Selected Natural Products

(see also VIII.B) VIII.D.-A Ku, Y.-Y. JACS, 124, 4282 Hanessian, S. JACS, 124, 4716 Frank, X. TL, 43, 1449 Singh, V. K. TL, 43, 5393 Barrero, A.F. TL, 43, 2793 Adamczyk, M. T, 58, 6951 Adamczyk, M. T, 58, 6951 Wong, Y.-S. CC, 686 Kibayashi, C. OL, 4, 2469 Wu, Y. JOC, 67, 3802 Feldman, K.S. JOC, 67 7096; JACS, Kim, S. JOC, 67, 3127 Russell, A.T. TL, 43, 8519 Brown, R.T. H, 56, 51 Takayama, H. CPB, 50, 1141 Witulski, B. CC, 2984 Toyooka, N. OL, 4, 1715 Aube, J. JACS, 124, 9974 Couladouros, E.A. CEJ, 8, 1795 Passarella, D. OL, 4, 2925 Passarella, D. OL, 4, 2925 Cook, J.M. OL, 4, 4237 Fukuda, Y. T, 58, 2513 Yamamoto, H. JACS, 124, 3647 Lee, E. AG(E), 41, 176 Marquet, A. CEJ, 8, 439 Pattenden, G. A G(E), 41,508 Maleczka, R.E., Jr. OL, 4, 2841 Trost, B.M. JACS, 124, 12420 Furstner, A. AG(E), 41, 4763 Amat, M. CC, 526 Blechert, S. EJOC, 2855 Morris, J.C. OL, 4, 631 Bonnet-Delpon, D. JOC, 67, 1253 Boger, D.L. JOC, 67, 7361 Doris, E. JOC, 67, 6571 Mori, M. JOC, 67, 224 Ogasawara, K. H, 56, 39 Nicolaou, K.C. AG(E), 41, 3701 Spinella, A. TL, 43, 1681 Spinella, A. TA, 13, 2071 Kigoshi, H. T, 58, 1075

A-240610-0 A-315675 Acaterin (-)-Acaterin Achilleol (S)-(-)-Acromelobic Acid (S)- (-)-Acromelobinic Acid Aculeatin A & B (-)-Adaline Aerangis Lactone 124, 9060 Agelastatin A & B AGI.7 AI.77.B (.).Ajmalicine (+)-Alangine Alcyopterosin E Alkaloid 223A Alkaloid 251F Alkannin (+)-Aloperine

6.epi.Aioperine

Alstonisine (+)-AM6898A & D (-)-Ambrox Ambruticin Amiclenomycin Amphidinolide A Amphidinolide A Amphidinolide A Amphidinolide T4 (-).Anabasine (-)-Anaferine Ancistrocladidine Anh y d rodi h y droa r t emisi n in Anh y drol yco rinone Anh y d rovi n blasti n e Anolignan A & B (-)-Aphanorphine Apicularen A Aplyolide B & D Aplyolide C & E Aplyronine A

SELECTED TOPICAL AREAS

Corey, E.J. OL, 4, 2441 Trost, B.M. OL, 4, 2621 Sibi, M.P. JOC, 67, 1738 Hansen, T.V. TA, 13, 547 Ley, S.V. OL, 4, 711; EJOC, 3995 Hsung, R.P. TL, 43, 8791 Omura, S. OL, 4, 367 Hsung, R.P. TL, 43, 3341, 3337 Hod, H. JOC, 67, 2355 Echavarren, A.M. JCS(P1) 1361 Quintero, L. TL, 43, 7639 Rawal, V.H. JACS, 124, 4628 Marino, J.P. JACS, 124, 13398 Katoh, T. TL, 43, 6929 Corey, E.J. JACS, 124, 7904 Theodorakis, E.A. JACS, 124, 12261 Spitzner, D. SL, 1712 Hayashi, Y. JACS, 124, 1 2 0 7 8

333

(+).8.Araneosene (-)-Arbutamine (.)-Arctigenin (R)-(-).Argentilactone Argyrin B (.)-Arisugacin A (+).Arisugacin A (:k)-Arisugacin A Artepillin C Ascididemin Aspergillamide B ( + ). A s p i d os p e rmi dine ( + )- Asp i d os p e r mi dine (+).Aureol (+)-Austamide Avarol (+)-Axenol (-)-Azaspirene

VIII.D.-B Roush, W.R. JACS, 124, 6981 Marshall, J.A. JOC, 67, 733 Pericas, M.A. TL, 43, 779 Depres, J.-P. JA CS, 124, 15313 Depres, J.-P. JA CS, 124, 15313

(.)-Bafilomycin A1 Bafilomycin V1 Baikiain (+).Bakkenolide A (-)-Bakkenolide III, B, C, H, L, V & X Nagasawa, K. OL, 4, 2921 Batzelladine D Boeckman, R.K., Jr. OL, 4, 2109 Bengamide B, E & Z Bengamide E Liu, W. TL, 43, 1373 James, K.D. S, 850 (R,S)-Bicalutamide Seki, M. H, 58, 125; TL, 43, 3269; JOC, 67, 5527 (+)-Biotin Hagiwara, H. JCS(P1) 895 a-Bisabol-l.one Wipf, P. CEJ, 8, 1670 Bistramide C Trost, B.M. OL, 4, 3513 (+).Boronolide Carda, M. JOC, 67, 6560 (+).Boronolide Kim, D. JOC, 67, 764, 772 (+).Brefeldin A Romo, D. OL, 4, 3231 (+).Brefeldin A Suh, Y.-G. JOC, 67, 4127 (+)-Brefeldin A Trost, B.M. JACS, 124, 9328 (+)-Brefeldin A Denmark, S.E. JA CS, 124, 15196 (+).Brasilenyne Deshpande, V.H. T, 58, 6615 (+_)-Brasiliquinone B Faber, K. CJC, 80, 362 (+).exo-B re vico rain Home, D.A. JOC, 67, 4498 Bromoaxinohydantoin Beria, I. TL, 43, 7323 Brostallicin Couture, A. JOC, 67, 5846 Buflavine Pfau, M. JOC, 67, 2252 Bufotenin Ovasaka, T. TL, 43, 1939 (+_).7-epi-~. B ulnesene

334

ORGANIC SYNTHESISm2003

VIII.D.-C Henegar, K.E. JOC, 67, 7147 Cabergoline Queguiner, G. JOC, 67, 3272 Caerulomycin B & C Sammakia, T. OL, 4, 2385 Caerulomyein C Trost, B.M. AG(E), 41, 841; JACS, 124, 10396 Callipeltoside A Evans, D.A. JACS, 124, 5654 Callipeltoside A Enders, D. OL, 4, 1023; CEJ, 8, 4272 (-)-Callystatin A Lautens, M. S, 1993 Callystatin A Marshall, J.A. JOC, 67, 2751 (-)-Callystatin A Lautens, M. S, 1993 C 19-epi-Callystatin A Enders, D. CEJ, 8, 4272 C 20-epi-Callystatin A Madsen, R. CC, 1106 Calystegnine B2, B3 & B4 Marco-Contelles, J. JOC, 67, 3705 (+)-Calystegnine B2 Sinay, P. CEJ, 8, 240 Calditol Taber, D.F. JOC, 67, 4821 (-)-Calicoferol B Bennasar, M.-L. JOC, 67, 7465 (+)-Camptothecin Knolker, H.-J. T, 58, 8937 Carazostatin Knolker, H.-J. S, 557 Carbazaquinocin C Ghosh, S.K. TL, 43, 7711 (+)-Carpamic Acid Jew, S. TA, 13, 715 (+)-Catechin Colbert, F. OL, 4, 1723 (-)-Centrolobine Rychnovsky, S.D. OL, 4, 3919 (-)-Centrolobine Mukai, C. T, 58, 5225 (+_)-Ceratopicanol Paquette, L.A. JA CS, 124, 9199 Ceratpicanol Nishiyama, S. BCJ, 75, 847 cis, cis.Ceratospongamide Deng, S. JA CS, 124, 916 cis, cis-Ceratospongamide Yokokawa, F. T, 58, 8127 Ce ratosp on gami de Argade, N.P. JOC, 67, 7131 Chaetomellic Acid Tadano, K. JOC, 67, 6690 (+)-Cheimonophyllal Tadano, K. JOC, 67, 6690 (+)-Cheimonophyllon E Marcos, I.S. TL, 43, 1243 (-)-Chettaphanin II Covey, D.F. JOC, 67, 4893 ent-Cholesterol Wu, Y.-L. JCS(P1), 1746 Chrycorin Krief, A. TL, 43, 6167, 7881 trans-Chrysanthemic Acid Hirama, M. OL, 4,4551 Ciguatoxin CTX3C Rizzacasa, M.A. JOC, 67, 4392 (.)-Cinatrin B Woerpel, K.A. OL, 4, 2945 Citreovirai Woerpel, K.A. OL, 4, 2945 5-epi.Citreoviral Marcos, J.S. SL, 105 Cladocoran A & B Banwell, M.G. JCS(PI), 22 (-)-Cladospolide A Fukuyama, Y. TL, 43, 6919 Ciusiparalicoline A Trost, B.M. JACS, 124, 14542 (.)-Codeine Lipshutz, B.H. JACS, 124, 14282 Coenzyme QlO Selvakumar, N. TL, 43, 9175 (• Nicolaou, K.C. AG(E), 41, 3276 Coleophomone B & C Nicolaou, K.C. CC, 2478 Coleophomone D O'Doherty, G.A. OL, 4, 4447 Colletodioi

SELECTED TOPICAL AREAS

Colletol O'Doherty, G.A. OL, 4, 4447 Conduritol Chung, S.-K. JOC, 67, 3327 (.).a-Conhydrine Enders, D. TA, 13, 285 (S).Coniine Davies, S.G. SL, 1146 Constanolactone A & B Falck, J.R. TL, 43, 3939 Coriolin Paquette, L.A. JA CS, 124, 9199 (.)-COTC Yakahashi, T. H, 56, 209 (+)-CP-99,994 Kibayashi, C. TL, 43, 7979 Kibayashi, C. TL, 43, 7979 (+)-CP-122,721 Nicolaou, K.C. JACS, 124, 2183, 2190, 2202 CP-225,917 Nicolaou, K.C. JACS, 124, 2183, 2190, 2202 CP.263,114 Crambescidin 359 Nagasawa, K. OL, 4, 177 (+)-Crocacin D Rizzacasa, M.A. OL, 4, 525 (+)-Crocacin D Chakraborty, T.K. TL, 43, 2645 Cryptophycin 1 Tius, M.A. OL, 4, 1637 Cryptophycin 52 Moher, E.D. OL, 4, 1813 Cucumin E Shindo, M. TL, 43, 5039 (+)-Curacin A Pattenden, G. JCS(P1), 2243 (+)-Curassanecine Dieter, R.K. TL, 43, 7725 Curcumene Hagiwara, H. JCS(P1) 895 Curcuphenol Hagiwara, H. JCS(P1) 895 Cuscohygrine B lechert, S. JOC, 67, 6456 Cycloheptepeptide Banaigs, B. TL, 43, 4041 Cyclomyctaylane-5a-ol Hagiwara, H. JCS(P1), 583 Cyciotheonamide E2 & E3 Wasserman, H.H. TL, 43, 3743 Cyclindrospermopsin Weinreb, S.M. JACS, 124, 3939 Cytostatin Waldmann, H. AG(E), 41, 1748 (+)-Cystothiazole A Akita, H. TL, 43, 643 Cycloviracin B1 Furster, A. JACS, 124, 10274 Cystothiazole A & C Bach, T. CEJ, 8, 5585 (-)-Cytorazone Carda, M. TA, 13, 1005 VIII.D.-D Smith, A.B., III OL, 4, 635; JACS, 124, 1102 (+)-Dactylolide ~-Damascone Vidari, G. TA, 13, 1245 Daphneticin Pan, X. TA, 13, 1799 (-)-Deacetylanisomycin Chandrasekhar, S. S, 1867 Deamido Bleomycin A2 Hecht, S.M. JACS, 124, 9476 Debromoaxinohydantoin Home, D.A. JOC, 67, 4498 Decumbenine B Larock. R.C. JOC, 67, 86 Deglycobleomycin Hecht, S.M. OL, 4, 1079 Dehyd ro- 16-E piaffinisine Cook, J.M. OL, 4, 4681 (+)-Dehydropentenomycin Pohmakotr, M. TL, 43, 7385 Deliquinione Kraus, G.A. JOC, 67, 5857 Demethylasterriquinone B! Pirrung, M.C. JOC, 67, 7919 Denbinobin Kraus, G.A. TL, 43, 9597 Dendroamide A Pattenden, G. H, 58, 521

335

336

ORGANIC SYNTHESISm2003

Trost, B.M. OL, 4, 2621 Shipman, M. CC, 150 Gerog, G.I. JOC, 67, 7140 Bennasar, M.-L. JOC, 67, 7465 Ramachandran, P.V. JOC, 67, 7547 Guillerm, G. TA, 13, 111 Corey, E.J. JACS, 124, 7904 Hudlicky, T. OL, 4, 115 Hudlicky, T. JOC, 67, 8726 Yang, B.-H. T, 58, 3267 Zard, S.Z. AG(E), 41, 1783 Isobe, M. JACS, 124, 7847 Miller, M.J. JACS, 124, 15001 Nicolaou, K.C. AG(E), 41, 3495 Home, D.A. TL, 43, 5135 Home, D.A. TL, 43, 5135 Ley, S.V. OL, 4, 3223 Martin, S.F. JOC, 67, 4200 Isobe, M. OL, 4, 2679 Taber, D.F. JOC, 67, 4501 Martin, S.F. OL, 4, 3243 Blechert, S. JOC, 67, 6456 Joseph-Nathan, P. T, 58, 1479 Jiang, B. TA, 13, 383 Kawasaki, T. TL, 43, 4245 Ogasawara, K. TL, 43, 1047 Hesse, M. HCA, 85, 161 Grigg, R. T, 58; 161 Kumar, P. T, 58, 1223 Yu, B. JOC, 67, 9099 Kita, Y. A G(E), 41, 348 Jiang, B. TA, 13, 383 Kawasaki, T. TL, 43, 4245 S toltz, B.M. JA CS, 124, 13179 Suzuki, K. TL, 43, 7753 Chamberlin, A.R. JOC, 67, 3194 Hanessian, S. JACS, 124, 13342

(-).Denopamine (+)-Deoxoprosophylline 13-Deoxybaccatin III (+)-20-Deoxycamptothecin (+)-9.Deoxygoniopypyrone 6-Deoxy-homoDMDP ( + )- D eoxy i s o a us t a mi de

epi-7-Deox ypancratista tin ent.7.Deoxypancratistatin

L-Deoxyribose (+). 13-Deoxyserratine 11-Deoxytetrodotoxin Desferrisalmycin B Diazonamide A Dibromoisophakellin Dibromophakellstatin (+)-Didemniserinolipid B 6,7-Dideoxysqualestatin H5 8,11-D ideoxytetrodotoxin trans- Dih y d rocon fe rti fo lin Dih y d rocorynan theoi ( + )-Dih yd r ocu sco h y g r in e Dihydroflustramine C Dihydrohamacanthin A Dihydrohamacanthin A ( + )- D i h y d ro me n is d a u ri i i d e ( +)-( S)-Di h y d ro p e ri ph yllin e Dihydropinidine (+)-Diolmycin A2 Dioscin Discorhabdin A Dragmacidin A Dragmacidin B & C Dragmacidin D Dryopteric Acid Dysiherbaine Dysinosin A

VIII.D.-E Mandal, A.K. OL, 4, 2043 Pena-Cabrera, E. JOC, 67, 1689 Fukuyama, T. JACS, 124, 6552 Sewald, N. AG(E), 41, 4267 Yamada, Y. TL, 43, 7773 Hagiwara, H. JCS(P1) 895 Sibi, M.P. JOC, 67, 1738 Cook, J.M. OL, 4, 4681

(-)-Ebelactone Echinochrome A Ecteinascidin 743 Efrapeptin C Elisabethin C Eluirol (-).Enterolactone 16-Epiaffinisine

SELECTED TOPICAL AREAS

337

Paquette, L.A. S, 2105 (+)-Epiafricanol Steel, P.G. OL, 4, 1 1 5 9 (+)-Epiasarinin White, J.D. JACS, 124, 4950 Epicyclindrospermopsin Weinreb, S.M. JACS, 124, 3939 7.Epicyclindrospermopsin Ramachandran, P.V. JOC, 67, 7547 (-)-8-Epigoniodiol Cheon, S.H. TL, 43, 4721 ( + )-E pi he r nan d ul cin Cook, J.M. OL, 4, 4681 16.E pinormacusine Pyne, S.G. TL, 43, 6047 (+_)-Epipentenomycin I & III Jung, M. OL, 4, 2763 6-Epiplakortolide E Wardrop, D.J. TL, 43, 737 (+)-Episordidin Dieter, R.K. TL, 43, 7725 (+)-S-Epitashiromine Kato, T. T, 58, 9213 dl- 12-Epiverticillol Bennasar, M.-L. TA, 13, 95 (+)- 16-E pivin ox ine Hayashi, Y. JOC, 67, 9443 Epolactaene Danishefsky, S.J. JACS, 124, 9825 Epothilone 490 Furstner, A. CC, 1057 Epothilone A & C Liu, Z.-Y. CEJ, 8, 3747 Epothilone A Sinha, S.C. AG(E), 41, 1381 Epothilone B Ermolenko, M.S. TL, 43, 2895 Epothilone B & D Taylor, R.J.K. TL, 43, 3573 epi-Epoxydon Porco, J.A., Jr. OL, 4, 3267 Epoxyquinoi A Hayashi, Y. AG(E), 41, 3192; TL, 43, 9155 (+)-Epoxyquinol A & B Srikrishna, A. TL, 43, 5261 (+)-10,11-E poxythapsan-I 0-ol Datta, A. T, 58, 9765 (S,S)-Ethambutol Bach, T. TL, 43, 9145 Eupomatenoid 3-6, 9 & 15 Miller, M.J. JOC, 67, 4759 Exochelin MN VIII.D.-F Estevez, R.J. TL, 43, 5323 Funk, R.L. OL, 4, 331 Bracher, F. EJOC, 2288 Imanishi, T. CC, 742 Falck, J.R. OL, 4, 969 Hatakeyama, S. CC, 3042 Joseph-Nathan, P. T, 58, 1479 Bracher, F. SL, 1742 Williams, R.M. A G(E), 41, 4683 Ciufolini, M.A. AG(E), 41, 4688 Evans, D.A. AG(E), 41, 1787 Sorensen, E.J. JACS, 124, 4552 Fukuyama, T. AG(E), 41, 4686 Trauner, D. AG(E), 41, 1569 Chenevert, R. TA, 13, 339 Ruiz, M. TA, 13, 1535 Snider, B,.B. OL, 4, 1087 Parrain, J.-L. SL, 743

Fagaronine (+)-Fasicularin Ficuseptine Fostriecin (+)-Fostriecin (+)-Fostriecin Flustramine E 6.nor.Fluvirucinin B (+)-FR66979 & (+)-FR900482 (+)-FR66979 (.).FR182877 (+)-FR182877 (+)-FR900482 (.).Frondosin B (-).Frontalin (+)-D-Fucosamine (-)-Fumiquinazoline C, E & H (+)- & (-)-Furocaulerpin

338

Trost, B.M. JA CS, 124 11616 Myers, A.G. JACS, 124, 4230

ORGANIC SYNTHESIS--2003

Furaquinocin E (-)-Fusaproliferin

VIII.D.-G Shinada, T. SL, 1341 Gabosine A-E (-)-Gabosine C Yakahashi, T. H, 56, 209 Davies, S. G. SL, 1637 D-Galactose Trost, B.M. AG(E), 41, 2795 (-)-Galanthamine Scivanti, A. TA, 13, 2193 Galaxolide Sasaki, M. OL, 4, 2981; JACS, 124, 14982 Gambierol Andrus, M.B. OL, 4, 3 5 4 9 (+)-Geldanamycin Danishefsky, S.J. TL, 43, 549, 545; JACS, 124, 9812 (+)Gelsemine Katoh, T. T, 58, 1289 (+).Geodin Smitt, O. SL, 1273 1 (10),5-Germacradien- 4- ol Nevalainen, N. JOC, 67, 1554 nor. 1,6- G e rma c radien.5- ol Vyvyan, J.R. JOC, 67, 2263 Gibbilimbol A.D Takacs, J.M. TL, 43, 8417 (-)-Gibboside Spitzner, D. T, 58, 4331 (-)-Gleenol Li, Y.-L. SC, 32, 1077 (+)-Glyflavanone-A Lin, G.-Q. SL, 1265 (+)-Goniodiol Banwell, M. G. JCS(P1), 1622 (+).Goniodiol Ramachandran, P.V. JOC, 67, 7547 (+)-Goniodiol Pan, X. JCR(S), 330 6-R-(+).Goniothalamin Yoda, H. SL, 1 5 3 2 (-)-Goniothalesdiol Gracza, T. TL, 43, 6 9 8 3 Goniothalesdiol O'Doherty, G.A. OL, 4, 4447 Grahamimycin A Murase, M. CPB, 50, 872 Granulatimide Danishefsky, S.J. AG(E), 41, 2188 Guanacastepene A VIII.D.-H Kitahara, T. H, 58, 99 A1-Mourabit, A. JOC, 67, 6474 Jiang, B. JOC, 67, 1396 Cetusic, J.R. OL, 4,11307 Macias, F.A. TL, 43, 6417 Dieter, R.K. TL, 43, 7725 Pilli, R.A. TL, 43, 2819 Furstner, A. JACS, 124, 7061 Srikrishna, A. SL, 340 Ghosh, S. TL, 43, 1313 Srikrishna, A. TL, 43, 151; SL, 340 Srikrishna, A. SL, 340 Srikrishna, A. TL, 43, 151 Cheon, S.H. TL, 43, 4721

(-).Halicholactone Haliclamine A Hamacanthin B Hectochlorin (+).Helibisabonol A (+).Heliotridane (+)-Herbarumin I H erbarumin I & II (+)-Herbertene (+)-Herbertene (_+)-Herbertenediol (+)-~- & 13-Herbertenol (+). 11-epi.H e r ber tenoli de (+)-Hernandulcin

SELECTED TOPICAL AREAS

Suh, Y.-G. TL, 43, 3825 Banwell, M.G. JCS(P1), 2439 Singh, V. TL, 43, 519 Holmes, A.B. JCS(P1), 1494 Holmes, A.B. JCS(P1), 1494 Ishikawa, T. TL, 43, 6751 Davies, S.G. SL, 1146 Davies, S.G. SL, 1146 Selvakumar, N. TL, 43, 9175 Corey, E.J. OL, 4, 2441 Izquierdo, T. TA, 13, 1581 Corey, E.J. JACS, 124, 7904 Sasaki, N.A. EJOC, 834 Barrero, A.F. JOC, 67, 2566 Mukai, C. OL, 4, 4301 Trost, B.M. CEJ, 8, 259 Paquette, L.A. JA CS, 124, 9199 Imamura, P.M. TL, 43, 3609

339

12(S)-HETE (.)-Hirsutene (+).Hirsutene (+)- & (.).Histrionicotoxin (-).Histrionicotoxin 235A (+)- H omoch eli don i ne (S)-Homopipecolic Acid (S)-Homoproline (+)-Horsfiline Humulene (+)-Hyacinthacine A3 (+).Hydratoaustramide 4-Hydroxyisoleucine ( + )- 3 ~- H y d r ox y r eyn o s i n (_+)-8~- H y droxys t re pt azol on e

C.L-epi-Hygromycin A

Hypnophilin (+). & (-)-Hyrtiosal

VIII.D.-I, .J Theodorakis, E.A. OL, 4, 819; JACS, 124, 12261 (.).Ilimaquinone R.(.)-Imperanene Eklund, P.C. JOC, 67, 7544 (S)-(+)-Imperanene Doyle, M.P. JOC, 67, 2954 (+).Indatraline Davies, H.M.L. TL, 43, 4951 (-).Indolizidine 167B Pereira, M.M.A. TL, 43, 455 (-).Indolizidine 167B Blechert, S. TL, 43, 6739 (.).Indolizidine 209B Sato, F. TL, 43, 8635 (+)-Ingenol Winkler, J.D. JACS, 124, 9726 T-Ionone Vidari, G. TA, I3, 1245 my o-Inositol tris & Chung, S.-K. JOC, 67, 5626 Tetrakisphosphane D-myo-Inositol-1- & Miller, S.J. JACS, 124, 11652 3-phosphate Ionomycin Lautens, M. OL, 4, 1879 ( + ). Isoai t h ola ct on e Pan, X. T, 58, 6796 (-)-Isoarctigenin Sibi, M.P. JOC, 67, 1738 Isocapnellenone (putative) Mehta, G. TL, 43, 8301 Isoiridomyrmecin Helmchen, G. S, 1953 (+)-Isokotanin A Bringmann, G. EJOC, 1096 A2 Isoprostane Zanoni, G. JOC~ 43, 4346 E1 & E2 Isoprostane Spur, B.W. TL, 43, 9249 15-F2 Isoprostane Snapper, M.L. JA CS, 124, 10998 (+).Isoretronecanol Dieter, R.K. TL, 43, 7725 Isoroquefortine C Joullie, M.M. JOC, 67, 620 (-).Isosemburin Ogasawara, K. SL, 334 (+)-Isostemonamide Kende, A.S. T, 58, 61 Isozonarone Seifert, K. T, 58, 4299

340

Padwa, A. OL, 4, 715 Paquette, L.A. JACS, 124, 6542

ORGANIC SYNTHESISm2003

(+).Jamtine Jatrophatrione

VIII.D.-K Wood, J.L. TL, 43, 379 Pan, X. JOC, 67, 5405 Watanabe, H. TL, 43, 857, 861 Yamada Y. TL, 43, 2227 Vidari, G. TA, 13, 1245 Vidari, G. TA, 13, 1245 Myers, A.G. AG(E), 41, 1062 Bach, T. SL, 1305 Koreeda, M. OL, 4, 3755 Kobayashi, S. SL, 601 Bringmann, G. JOC, 67, 5595 Magnus, P. T. 58, 3423 Magnus, P. T. 58, 3423

(+)-(7R)- & (-)-(7S)-K252a Kadsurenin C & L Kaitocephalin Kalihinene X Karahana Ether Karahana Lactone Kedarcidin aglycon (_+)-Kelsoene Kelsoene Khafrefungin Knipholone (_+)-Kopsidasine (+_). Kopsijasminilam

VIII.D..L Magnus, P. T. 58, 3423 Lee, E. JACS, 124, 384 Back, T.G. OL, 4, 1779 Nelson, S.G. JACS, 124, 13654 Mulzer, J. TL, 43, 3381 Williames, D.R. TL, 43, 4841 Wender, P.A. JACS, 124, 4956 Crimmins, M.T. JACS, 124, 5958 Boeckman, R.K., Jr. OL, 4, 3891 DeVoss, J.J. OL, 4, 3047 Schmidt, R.R. EJOC, 4137 Singh, V.K. JOC, 67, 4630 Kibayashi, C. A G(E), 41, 3017 Weinreb, S.M. JOC, 67, 4337 Wipf, P. CC, 2066 Carreira, E.M. AG(E), 41, 4098 Kozmin, S.A. JACS, 124, 13670 Porco, J.A., Jr. JACS, 124, 5650 Lebreton, J. JOC, 67, 9192 Kalaus, G. JOC, 67, 7255 Scherkenbeck, J. EJOC, 2350 Shair, M.D. JACS, 124, 773 Wood, J.L. OL, 4, 3087 Eggleston, I.M. JCS(P1), 1115 Dallavalle, S. TL, 43, 1835 Argade. N.P. S, 323

(+).Lahadinine B (-)-Lasonolide A (-)-Lasubine II (-)-Laulimalide (-).Laulimalide (.)-Laulimalide (-).Laulimalide (-)-Laulimalide (+)-Laurenyne Lauthisan ( + )- Len ti gin osi n e (+). & (-)-Lentiginosine (.).Lepadiformine Lepadiformine Leucascandrolide A Leucascandrolide A Leucascandrolide A Lobatamide C (-).Lobeline (-)-Lochnericine Loloatin A-C (-)-Longithorone A Luminacin D (+)-Lunarine Luotonine A Luotonin F

SELECTED TOPICAL AREAS

Hamada, Y. T, 58, 9737 Zard, S.Z. OL, 4, 1135 Yan, T.-H. T, 58, 7335 Shioiri, T. T, 58, 9445

341

(S)-(+).Lyeoperdic Acid (:l:)-~-Lycorane (+)-Lycoricidine Lyngbyabellin A & B

VIII.D.-M Cook, J.M. OL, 4, 687 Marino. J.P. JACS, 124, 1664 Sharma, G.V.M. TL, 43, 9159 Akita, H. TA, 13, 705 Kobayashi, Y. TL, 43, 4381 Omura, S. OL, 4, 501 Yen, C.-F. A G(E), 41, 4090 Le Quesne, P.W. H, 56, 221 Cook, J.M. OL, 4, 687 Honda, T. T, 58, 8929 Van Vranken, D.L. OL, 4, 2337 Batey, R.A. OL, 4, 2913 Batey, R.A. OL~ 4, 2913 Du Bois, J. JACS, 124, 12950 Whitehead, R.C.'JCS(P1), 476 Martin, S.F. JACS, 124, 8584 Ma, D. TL, 43, 9405 Meinwald, J. JOC, 67, 5896 Kalaus, G. JOC, 67, 7255 Crich, D. T, 58, 35 Pfau, M. JOC, 67, 2252 Perkins, M.V. OL; 4, 1655 de March, P. TA, 13,455 Ogasawara, K. TL, 43, 1047 de March, P. TA, 13, 455 Danishefsky, S.J. JACS, 124, 2080 Kulkami, M.G. TL, 43, 2297 Cook, J.M. OL, 4, 687 Kutschy, P. TL, 43, 9489 Kutschy, P. TL, 43, 9489 Srikrishna, A. TL, 43, 2765 Seeberger, P.H. OL, 4, 2965 Krief, A. S, 2019 Fukuyama, Y. TL, 43, 3829 Bennasar, M.-L. CC, 1166 Giner, J.-L. JOC, 67, 4856 van der Donk, W.A. OL, 4, 1335 Ogasawara, K. OL, 4, 4515 Hauser, F.M. OL, 4, 2237, 2241 Mukherjee, D. T, 58, 1765 Cook, J.M. OL, 4, 687

Macralstonidine (-)-Macrolactin A Macrosphelide A & E (+)-Macrosphelide C, F & G Macrosphelide H & G (+)-Madindolide A & B Magellanine Magnolamide (+)-Majvinine (.)-Malyngolide (_+)-Mandindoline A & B Martinellic Acid Martinelline Manzacidin A & C Manzamenone A, C & F Manzamine A (_+).Martinelline Mayolene.16 & 18 (.).Mehranine MEL A Melatonin (-)-Membrenone-A & C (+) & (-)-Menisdaurilide (+)-Menisdaurili de (+)-Rengyolone (+)-Merrilactone A (+)-Mesembrine ( + )- 10- Met h oxy a ffi n isi n e (+)-'l-Methoxyspirobrassinin (+)- 1- Met h oxyspi robrassinoi (+)-3-Methoxythaps.8-ene 8,10. di- O- M e th yl be r gen in Methyl trans.chrysanthemate 7-M eth yl de hydro pin gu isen ol (-).N(a)-Methylervitsine 2. Met h yl.D- eryt h ri tol Methyllanthionine (.)-O-Methylpallidinine (+).O-Methyl PD 116740 (+).O-Methyipisiferic Acid (+)-Na-Methylsarpagine

342

Kalaus, G. JOC, 67, 7255 Cossy, J. SL, 715 Carda, M. OL, 4, 3447 Gung, B.W. OL, 4, 2517 Mori, K. TL, 43, 5743 Deslongchamps, P. JOC, 67, 5269 hamattoor, D.M. TL, 43, 367 Lett, R. TL, 43, 3997, 4003 Taber, D.F. JACS, 124, 12416 Trost, B.M. JACS, 124, 14542 Ogasawara, K. CC, 1094 Panek. J.S. JACS, 124, 11368 Takahashi, S. AG(E), 41, 4751 Nakata, T. JOC, 67, 5739 Takahashi, S.TL, 43, 8661 Tamariz, J. H, 57, 259 Singh, V.K. TL, 43, 2773 Ley, S.V. CEJ, 8, 1621 Carda, M. EJOC, 2649 Ariza, X. TL, 43, 2691 Tadano, K. OL, 4, 2941 Kishi, Y. OL, 4, 647 Chida, N. BCJ, 75, 1927 Ham, W.-H. TL, 43, 9361 Bodo, B. TL, 43, 7565 Ito, M. JCS(P1) 1581

ORGANIC SYNTHESIS--2003

(-)-Na- Met hyl voa p h yllin e (+)-Methynolide Microcarpalide (-)-Minquartynoic Acid (_+)-Mispyric Acid (+)-Momilactone A Montiporyne A & B Monocillin I (-)-Morphine (-)-Morphine (-)-Morpholine (-)-Motuporin Mucocin Mucocin Muconin Mukonine (-)-Muricatacin Muricatetrocin C (-)-Muricatacine Musclide B Mycoepoxydiene Mycolactone A & B (+).Myriocin Myriocin Myrioxazine A & B Mytiloxanthin

VIII.D.-N Ohta, S. JCS(P1), 1061 Naamine C Theodorakis, E.A. JACS, 124, 12261 Nakijiquinone A Tatsuta, K. CL, 14 (+)-Napyradiomycin A1 Yan, T.-H. JOC, 67, 6954 (+)-Narciclasine Williams, R.M. JOC, 67, 6361 (+)-Negamycin Ma, D. TL, 43, 8511 Nelfinavir Mascarenas, J.L. CEJ, 8, 884 (+)-Nemorensic Acid Donohoe, T.J. JCS(PI), 1369 (+).Nemorensic Acid Hodgson, D.M. ,OL, 4, 1809 cis.Nemorensic Acid Sibi, M.P. JOC; 67, 1738 (-)-Nephrosteranic Acid Rodriguez, J.B. T, 58, 3129 (+)-Neplanocin F Hayashi, Y. T, 58, 9839 NG-391 Zwanenburg, B. EJOC, 810 Nijmegen.1 Ruchirawat, S. OL, 4, 2633 Ningalin C Perlmutter, P. JCS(P1), 2896 (+).Nonactic Acid Mane, R.B. TL:, 43, 4535 Norbisabolide Figueredo, M. TL, 43, 5583 Norpandamarilactonine A & B Gammon, D.W. TL, 43, 3141 Noviose

SELECTED TOPICAL AREAS

343

VIII.D.-O Gill, M. AJC, 55, 213 Barrero, A.F. JOC, 67, 2501 Panek, J.S. JACS, 124, 12806 Jung, G. AG(E), 41, 2307 Corey, E.J. JACS, 124, 11290 Carda, M. EJOC, 2649 Jin, Z. JACS, 124, 5676 Mehta, G. AG(E), 41, 2396 Mehta, G. OL, 4, 2881 Chu, C.K. OL, 4, 1147 Popsavin, V. TL, 43, 2281 Shibasaki, M. TL, 43, 8647

(R)-Ochratoxin Oidiolactone C Oleandolide Omphalotin A (+)-a-Onocerin (-).Osmundalactone OSW-1 Ottelione A & B epi.Ottelione A & B L.Oxetanocin (+)-Oxybiotin (S)-Oxybutynin

VIII.D.-P Thompson, D.H. JOC, 67, 6503 Palmitoyl Plasmenylcholine Lee, E. JACS, 124, 14655 Pamamycin-607 Kang, S.H. AG(E), 41, 1392 (+)-Pamamycin-607 Yadav, J.S. T, 58, 4955 Panaxydol Yadav, J.S. T, 58, 4955 Panaxytriol Kim, S. OL, 4, 1343 Pancratistatin Takatama, H. CPB, 50, 1303 (:i:).Pandamarilactonine A & C Figueredo, M. TL, 43, 5583 Pandamarilactonine A Feldman, K.S. JOC, 67, 8528; JACS, 124, 11600 Pareitropone Coelho, F. T, 58, 1647 (+)-Pathylactone A Magnus, P. T. 58, 3423 (+)-Pauciflorine B Woerpel K.A. JACS, 124, 11342 (5:)-Pe dun cula ri ne Katsumura, S. AG(E), 41, 1023 Peridinin Faber, K. TA, 13, 523 (+)-Pestalotin Giner, J.-L. JOC, 67, 4659 Petuniasterone D Rokach, J. TL, 43, 2801 iPF4~-VI Nicolaou, K.C. JACS, 124, 2183, 2190, 2202 Phomoidride A & B O'Doherty, G.A. TL, 43, 8195 Phomopsolide C Sekine, M. JOC, 67, 3290 Phosmidosine Omura, S. TL, 43, 1265 Pinellic Acid Kozmin, S.A. OL, 4, 3005 (-)-Pinolidoxin Mukherjee, D. T, 58, 1765 (:l:)-Pisiferic Acid Kitching, W. JACS, 124, 9718 Plakortone D Ley, S.V. AG(E), 41, 2194 (+)-Plicamine Sterner, O. TL, 43, 891 Podoscyphic Acid Steglich, W. OL', 4, 3287 Polycitone A & B Ley, S.V. AG(E), 41, 2786 Polycephalin C Akita, H. CPB, 50, 930 (+)-a- & ~-Polypodatetraene Kumar, P. T, 58, 6685 (+)- & (-)-Posticlure Joseph-Nathan, P. TA, 13, 1147 Prandiol

344

ORGANIC SYNTHESISm2003

Sterner, O. T, 58, ,2523 Fujiwara, K. SL; 1493 Barrett, A.G.M.:JOC, 67, 2735 Ubukata, M. T, 58, 7829 Cossy, J. JOC, 67, 1982 Mukherjee, D. T, 58, 6179 Li, W.-R. JOC, 67, 4702 Sata, N.U. TL, 43, 115 Nubbemeyer, U. EJOC, 3315, 3304 Kibayashi, C. JOC, 67, 5517 Srikrishna, A. TL, 43, 1109 Clive, D.L.J. CC, 2380 Quideau, S. OL, 4, 3975 Baldwin, J.E. OL, 4, 2125 Baldwin, J.E. TL, 43, 327 Ohta, S. JCS(P1), 1061 Overman, L.E. JACS, 124, 9008 .

.

.

.

.

.

.

.

(-)-Pregaliellalactone Prelaureatin (-)-Preussomerin G Procyanidin.B3 (-)-Prosophylline (+)-Pseu doclo v en e. B Pulchellalactam Pulcherrimine (+)-Pumiliotoxin 251D (+)-Pumiliotoxin A, B & 251D (-)-9-Pupukeanone (+)-Puraquinonic Acid (+)-Puupehenone Pyridovericin Pyrinodemin A Pyronaamidine Psycholeine

,,

VIII.D.-Q, -R Overman, L.E. JACS, 124, 9008 Ogasawara, K. TL, 43, 97 Rawal, V.H. JACS, 124, 4628 Andrus, M.B. OL, 4, 3549

Quadrigemine C ( + )-Q ueb ra c h ami ne (-)-Quebrachamine (.)-o.Quinogeldanamycin

Lett, R. TL, 43, 3997, 4003 Aoyama, T. H, 58, 471 Boger, D.L. JACS, 124, 5288 Bogcr, D.L. JACS, 124, 5288 Samos, D. dACS, 124, 6900 Pattcndcn, G. TL, 43, 493 White, J.D. JOC, 67, 7750 Bergman, J. T, 58, 2813 Yang, B.-H. T, 58, 3267 Fuch, P.L. OL, 4, 317 Sibi, M.P. JOC, 67, 1738 Yamamoto, T. TL. 43, 9077 Carreno, M.C. AG(E), 41, 2755 Rossi, R. TL, 43, 2023 Kim, K. TL, 43, 3993

Radicicol Radiosumin Ramoplanin A2 Ramoplanose Agycon (-)-Rhazinilam Rhizoxin D Rhizoxin D Rhopaladin A-D L-Ribose Ritterazine M (-)-Roccellaric Acid Rose Oxide Rubiginone A2 & C2 Rubrolide M Rutaecarpine

VIII.D.-S Paquette, L.A. JACS, 124, 4257 (-)-Sanglifehrin A Zhu, J. JACS, 124, 583 Sanjoinine GI Boeckman, R.K., Jr. JACS, 124, 190 (+)- & (-)-Saudin Cossy, J. JOC, 67, 1 9 8 2 (+)-Sedamine Lebreton, J. JOC, 67, 9192 (.).Sedamine

SELECTED TOPICAL AREAS

345

Ogasawara, K. SL, 334 (-).Semburin Pfau, M. JOC, 67, 2252 Serotonin Kim, S. JOC, 67, 3127 Sescandelin Danishefsky, S.J. AG(E), 41, 1434 Sesquicillin Vails, N. JOC, 67, 4945 SF608 Couladouros, E.A. CEJ, 8, 1795 Shikonin Koreeda, M. OL, 4, 3329 (-).Sibirione Calter, M.A. JACS, 124, 13127 Siphonarienedione Calter, M.A. JA CS, 124, 13127 Siphonarienolone Helmchen, G. S, 1953 a-Skytanthine Cossy, J. S, 951 (-)-Slaframine Jiang, B. OL, 4, 3951 Slagenin A-C Gurjar, M.K. OL, 4, 3569 Slagenin B & C Theodorakis, E.A. JACS, 124, 12261 Smenospongidine Makabe, H. OL, 4, 1083 cis.Solamin Brown, R.C.D. OL, 4, 3715 cis.Solamin Hagiwara, H. JOC, 67, 5969 Solanapyrone D & E Shioiri, T. TL, 43, 8673 Somamide A Aube, J. OL, 4, 2577 (+)-Sparteine Cook, G.R. TL, 43, 9027 D- & L-Sphinganine Chida, N. BCJ, 75, 1927 (-)-Sphingofungin E Chida, N. OL, 4, 151 Sphingofungin E Shiozaki, M. T, 58, 8779 Sphingofungin E Ham, W.-H. OE, 4, 4403 Sphingofungin F Chung, S.-K. TA, 13, 343 Sphingosine Chida, N. JOC, 67, 2874 Spicamycin Fuji, K. OL, 4, 249 Spirotryprostatin B Crimmins, M.T. JACS, 124, 5661 Spongistatin 1 & 2 Ohira, S. TL, 43, 4641 Sporochnol A-C Zhou, W.-S. T, 58, 10293 Squalamine Ko, S.Y. TL, 43, 639 Statine Kende, A.S. T, 58, 61 (+)-Stemonamide Padwa, A. OL, 4, 1515 (+).Stenine Mehta, G. TL, 43, 703 (+_)-Sterpurene Takayama, H. TL, 43, 8657 Strictifoline Zwanenburg, B. EJOC, 810 Strigolactone GR7 & GR24 Yadav, J.S. TL, 43, 1739 Strongylodiol A Moil, M. AG(E), 41, 1934 (-)-Strychnine Shibasaki, M. JACS, 124, 14546 (-)-Strychnine Carreira, E.M. JACS, 124, 14826 (+)-Strychnofoline Mehta, G. TL, 43; 3319 (-)-Suicatine G Pyne, S.G. JOC, 67, 7774 (-)-Swainsonine VIII.D.-T Rawa[, V.H. JACS, 124, 4628 Ho, T.-L. T, 58, 4969 Izquierdo, I. EJOC, 309

(+)-Tabersonine Tacamonine (-).Talaromycin C & E

346

Honda, T. TL, 43, 2411 Nagumo, S. T, 58, 9871, 4917 Honda, T. T, 58, 8929 O'Doherty, G.A. JOC, 67, 2682 Dieter, R.K. TL, 43, 7725 Georghiou, P.E. OL, 4, 2675 Papaioannou, D. TL, 43, 2597, 2593 Myers, A.G. JACS, 124, 4230 Montgomery, J. JACS, 124, 9366 Williams, R.M. JACS, 124, 2951 Townsend, C.A. OL, 4, 3859 Gill, M. JCS(P1), 938 Danishefsky, S.J. AG(E), 41,512 Chenevert, R. TL, 43, 7971 Trivedi, G.K. TL, 43, 5471 Kuhrnert, N. TA, 13, 123 Wipf, P. JACS, 124, 14848 Wu, Y.-L. TL, 43, 3529 Guo, Z. OL, 4, 2893

ORGANIC SYNTHESISm2003

(-)-TAN1251A (-)-TAN1251A (+)-Tanikolide Tarchonanthuslactone (:i:)-Tashiromine (-)-Tejedine Tenuilobine (-)-Terpestacin (+)-Testudinariol A (-)-Tetrazomine (SR)-Thiolactomycin Thysanone TMC-95A & 95B (S)-tx-Tocotrienol Triacetoxy-(-)-goniot riol Trianglimine (-)-T u b eroste monin e Typhoniside A Tyrocidine A

VIII.D.-U, -V, -Y, -Z Joullie, M.M. JACS, 124, 520

Ustiloxin D

Okada, K. TL, 43, 2385 Molina, P. TL, 43, 1005 Takabe, K. JCS(P1), 500 Kakinuma, K. JCS(P1), 949 Fukuyama, T. JA CS, 124, 2137 Bennasar, M.-L. TA, 13, 95 Stefani, H.A. SL, 1335 Williams, R.M. JACS, 124, 2556 Kalaus, G. JOC, 67, 7255 Fehr, C. CEJ, 8, 853

(-)-Vallesamidine Variolin B (__)-Vertinolide Vicenistatin (+)-Vinblastine (-)-Vinoxine (+)-Virol C (-)-VM55599 (-)-Voaphylline (-)-Vulcanolide

Allin, S.M. TL, 43, 4191 Furstner, A. AG(E), 41, 2097 Shibasaki, M. AG(E), 41, 4680

Withasomnine Woodrosin I Wortmannin

Hodgson, D.M. CC, 2436 Yu, B. JOC, 67, 9099 Davis, F.A. JOC, 67, 1290

(-)-Xialenon A Xiebai Saponin I (s)-(-)-Xylopinine

Seifert, K. T, 58, 4299

Yahazunol

Smith, A.B., III JACS, 124, 1102 Ley, S.V. Jcs(P1), 874 Mukherjee, D. T, 58, 1773 Villamizar, J. JCR(S), 395 Seifert, K. T, 58, 4299

(+)-Zampanolide i3-Zearalenol (+_)-Zizaene (+)-Zonarone Zonarone

SELECTED TOPICAL AREAS

347

VIII.E.1 Reactions in Polar Media VIII.E.1 Reactions in Aqueous Media

VIII.E.I-1 Barbas, C.F., Ill et al. CC, 3024 "Direct Organocatalytic Aldol Reactions in Buffered Aqueous Media." -

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i,

i

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VIII.E.1-2 Aggarwal, V.K. et al. JOC, 67, 510. "Rate Acceleration of the Baylis-Hillman Reaction in Polar Solvents (Water and Formamide). ,,

,,,,

i,i

VIII.E.1-3 Cheng, J.-P. et al. TL, 43, 7389. "Aqueous Baylis-Hillman Reactions of Cyclopent-2.enone Using Imidazole as Catalyst." ,

t,,

,,

VIII.E.1-4 Batra, S. et al. SL, 1819. "Baylis-Hiilman Chemistry in Aqueous Media" A Fast and Practical Approach to the Azides of Baylis.Hillman Adducts in Solution and on Solid Phase." VIII.E.I-5 Akiyama, T. et al. SL, 1269. "Mannich-Type Reaction Catalyzed by HBF4 in Water: Effect of the Loading of Surfactant." .

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VIII.E.1-6 Wurz, R.P.; Charette, A.B. OL, 4, 4531. "Transition Metal-Catalyzed Cyclopropanation of Alkenes in Water: Catalyst Efficiency and in situ Generation of the Diazo Reagent." VIII.E.I-7 Leadbeater, N.E.; Marco,M. OL, 4, 2973. "Ligand-Free Palladium Catalysis of the Suzuki Reaction in Water Using Microwave Heating." VIII.E.1-8 Uozumi, Y.; Nakai, Y. OL, 4, 2997. "An Amphiphilic Resin-Supported Palladium Catalyst for High-Throughput Cross-Coupling in Water." :

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VIII.E.1-9 Kobayashi, S. et al. SL, 483. "Ligand-Accelerated Cadmium.Catalyzed Allylation of Aldehydes and Ketones in Aqueous Media."

348

ORGANIC SYNTHESIS--2003

VIII.E.I-10 Jang, D.O.; Cho, D.H. SL, 631. "A Radical Carbon-Carbon Bond Forming Reaction: Indium Mediated Radical Addition to [3-Substituted Conjugated Alkenes in Aqueous Media." ,,

V I I I . E . I - l l Wang, D.; Li, C.-T. et al. TL, 43, 7789. "Rhodium-Catalyzed Reacrions of Arylbismuth and Aryllead Reagents with a Chiral Glyoxylate Hydrate in Air and Water: Water-Promoted Diastereoselectivity Enhancement." ,

,,

VIII.E.I-12 Sinou, D. et al. TL, 43, 7397. "Glucosamine-Based Phosphines. Efficient Ligands in the Suzuki Cross-Coupling Reaction in Water." VIII.E.I-13 Zhang, Y. et al. TL, 43, 6787. "A Novel Method for the Synthesis of Vicinal Disulfonamides Promoted by Metallic Samarium in Aqueous Media." VIII.E.I-14 Barbas, C.F., III et al. TL, 43, 6743. "Amine-Catalyzed Direct Self Diels-Alder Reactions of a,13Unsaturated Ketones in Water" Synthesis of Pro-Chiral C y cloh exan on es." V I I I . E . I - 1 5 Li, C.-J. et al. TL, 43, 5731. "Cu(I)Br Mediated Coupling of Alkynes with N-Acylimine and N-Acyliminium Ions in Water." VIII.E.I-16 Welch, J.T. et al. TL, 43, 5801. "Indium-Mediated Allylation Reaction of Difluoroacetyltrialkylsilanes in Aqueous Media." VIII.E.I-17 Jang, D.O.; Cho, D.H. TL, 43, 5921. "Radical Deoxygenation of Alcohols and Vicinal Diols with NEthylpiperidine Hypophosphite in Water." VIII.E.I-18 Wang, Z. et al. TL, 43, 5097. "Gallium-Mediated Allylation of Carbonyl Compounds in Water." VIII.E.I-19 Suarez, R.M.; Sestelo, J.P.; Sarandeses, L.A. SL, 1435. "Diastereoselective Ultrasonically Induced Zinc-Copper Conjugate Addition to Chiral a,13-Unsaturated Carbonyl Systems in Aqueous Media."

SELECTED TOPICAL AREAS

349

VIII.E.1-20 Naito, T. et al. OL, 4, 131. "Indium-Mediated Intermolecular Alkyl Radical Addition to Electron-Deficient C=N Bond and C=C Bond in Water." ,

VIII.E.I-21 Oshima, K. et al. CL, 2. "Allylation of Carbonyl Compounds with Allylic Gallium Reagents." ,,,

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VIII.E.1-22 Kabalka, G.W.; Wang, L. TL, 43, 3067 "Ligandless Palladium Chloride-Catalyzed Homo-Coupling of Arylboronic Acids in Aqueous Media." ,

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....

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VIII.E.1-23 Wang, M.; Li, C.-J. TL, 43, 3589. "Aldol Reaction via In Situ Olefin Migration in Water." ,

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VIII.E.1-24 Huang, T.; Li, C.-J. TL, 43, 403. "Palladium-Catalyzed Coupling of Aryl Halides with Arylhalosilanes in Air and Water." VIII.E.1-25 Moil, A. et al. CL, 756. "Sonogashira Coupling with Aqueous Ammonia." ,,,

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VIII.E.1-26 Wang, Z. et al. OL, 4, 1683. "Application of Tin and Nanometer Tin in Allylation of Carbonyl Compounds in Tap Water." .

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VIII.E.1-27 Jang, D.O.; Cho, D.H. SL, 1523. "N-Ethylpiperidene Hypophosphite Mediated Intermolecular Radical Carbon-Carbon Bond Forming Reaction in Water." ,

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VIII.E.1-28 Chung, Y.K.; Hyeon, T. et al. OL, 4, 277. "The First Intramolecular Pausen-Khand Reaction in Water Using Aqueous Colloidal Nanoparticles as Catalysts." .

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VIII.E.1-29 Botella, L.; Najera, C. AG(E), 41, 179. "A Convenient Oxime-Carbapalladacycle-Catalyzed Suzuki Cross-Coupling of Aryl Chlorides in Water." .

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VIII.E.2-30 Amengual, R.; Michelet, V.; Genet, J.-P. TL, 43, 5905. "New Studies of Rh-Catalyzed Addition of Boronic Acids Under Basic Conditions in Aqueous Medium."

350

ORGANIC SYNTHESIS--2003

VIII.E.1-31 Oshima, K. et al. SL, 674. Account" "Synthetic Radical Reactions in Aqueous Media." VIII.E.1-32 Lindstrom, U.M. CRV, 102, 2751. Review" "Stereoselective Organic Reactions in Water." ,

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VIII.E.1-33 Akiya, N.; Savage, P.E. CRV, 102, 2725. Review: "Roles of Water for Chemical Reactions in HighTemperature Water." VIII.E.2 Reactions in Ionic Media VIII.E.2-1 Yanada, R.; Takemoto, Y. TL, 43, 6849; see also" Branco, L.C.; Afonso, C.A.M. CC, 3036; Song, C.E. et al. CC, 3038; Yao, Q. OL, 4, 2197. "OsO4-Catalyzed Dihydroxylation of Olefins in Ionic Liquid [emin]BF4" A Recoverable and Reusable Osmium." ,,

..L

i

VIII.E.2-2 Jacobs, P.A. et al. TL, 43, 8107. "Aerobic Oxidation of Alcohols with Ruthenium Catalysts in Ionic Liquids." VIII.E.2-3 Toma, S. et al. CC, 2510. "Proline-Catalyzed Asymmetric Aldol Reaction in the Room Temterature Ionic Liquid [bmin]BF~i." VIII.E.2-4 Mehnert, C.P. et al. CC, 3010. "Supported Ionic Liquid Catalysis Investigated for Hydrogenation Reactions." VIII.E.2-5 Ren, R.X. et al. TL, 43, 387. "Catalytic Rosenmund-von Braun Reaction in Halide-Based Ionic Liquid." .

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VIII.E.2-6 Schotteen, T. et al. S, 1607. "Transfer hydrogenation in Ionic Liquids under Microwave Irradiation." VIII.E.2-7 Hemeon, I.; Singer, R.D. CC, 1884. "Silylstannation of Terminal Alkynes Using a Recyclable Palladium(0) Catalyst lmmobilised in an Ionic Liquid."

SELECTED TOPICAL AREAS

351

VIII.E.2-8 Haddleton, D.M. et al. CC, 2850. "Unprecedented Solvent-Induced Acceleration of Free-Radical Propagation of Methyl Methacrylate in Ionic Liquids." J

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VIII.E.2-9 Yorimitsu, H.; Oshima, K. BCJ, 75, 853. "Triethylborane-Induced Radical Reactions in Ionic Liquids." i

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H.,

ii

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VIII.E.2-10 Welton, T. et al. JOC, 67, 8855. "Nucleophilicity in Ionic Liquids. Cation Effects on Halide Nucleophilicity in a Series of Bis(trifluoromethylsulfonyl)imide Ionic Liquids." i|

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VIII.E.2-11 Eckert, C.A. et al. CC, 887. "Ionic Liquids as Catalytic Green Solvents for Nucleophilic Displacement Reactions." ,

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, ...,i

VIII.E.2-12 Judch, Z.M.A. et al. TL, 43, 9381. "A Facile and Efficient Nucleophilic Displacement Reaction at Room Temperature in Ionic Liquids." ,.

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,,

, ,

VIII.E.2-13 Dcng, Y. et al. TL, 43, 8145. "The Syntheses o f Carbamates from Reactions of Primary and Secondary Aliphatic Amines with Dimethyl Carbonate in Ionic Liquids." VIII.E.2.14 Song, C.E.; Choi, J.H. et al. CC, 1122. "Ionic Liquids as Powerful Media in Scandium Triflate Catalyzed Diels-Alder Reactions" Significant Rate Acceleration, Selectivity Improvement and easy Recycling of Catalyst." .

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, , .

VIII.E.2-15 Itoh, T. r al. TL,, 43, 3041. "Cycloaddition of Styrene Derivatives with Quinone Catalyzed by Ferric Ion" Remarkable Acceleration in an Ionic Liquid Solvent System." VIII.E.2.16 Singer, R.D. ct al. SL, 1815. "Endo Selecti,ve Dieis-Alder Reactions of Furan in Ionic Liquids." VIII.E.2-17 Dixneuf, P.H. ct al. CC, 146. "Alkene Metathesis Catalysis in Ionic Liquids with Ruthenium AIlenyidene Salts."

352

ORGANIC SYNTHESIS--2003

VIII.E.2-18 Ranu, B.C. et al. JCS(P1), 1520. "Catalysis by Ionic Liquids: Solvent-Free Efficient Transthioacetalisation of Acetals by Molten Tetrabutylammonium Bromide." .

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.t,

.,

J

J

VIII.E.2.19 Wasserscheid, P.; Gordon, C.M. et al. CC, 1186. "Ionic Liquids: Polar, but Weakly Coordinating Solvents for the First Biphasic Oligomerisation of Ethene to Higher ~Olefins with Cationic Ni Complexes." VIII.E.2-20 DuPont, J. et al. TL, 43, 753. "Carbonylation of AIkynols Catalyzed by Pd(II)/2-PyPPh2 Dissolved in Organic Solvents and in Ionic Liquids: A Facile Entry to ~.Methylene T- and 8-Lactones." VIII.E.2-21 Nacci, A. et al. JOM, 645, 152. "Pd-Benzothiazole Carbene Catalyzed Carbonylation of Aryl Halides in Ionic Liquids." .,

,,,

VIII.E.2-22 Bccheanu, A.; Laschat, S. SL, 1865. "Intermolecular Colbalt-Mediated Pauson-Khand Reactions in Ionic Liquids." VIII.E.2-23 Ryu, I. et al. OL, 4, 1691. "A Copper-Free Sonogashira Coupling Reaction in Ionic Liquids and Its Application to a Microflow System for Efficient Catalyst Recycling." VIII.E.2-24 Srinivasan, K.V. et al. CC, 616. "Ultrasound Promoted Suzuki Cross-Coupling Reactions ill Ionic Liquid at Ambient Conditions." VIII.E.2-25 Revell, J.D.; Ganesan, A. OL, 4, 3071. "Ionic Liquid Acceleration of Solid.Phase Suzuki.Miyaura Cross-Coupling Reactions." VIII.E.2-26 Yokoyama, C. ct al. TL, 43, 7115. "Heck Reactions in a Non-Aqueous Ionic Liquid Using Silica Supported Palladium Complex Catalysts." VIII.E.2-27 Beller, M. ct al. OL, 4, 3031. "New Palladium Carbene Catalysts for the Heck Reaction of Aryl Chlorides in Ionic Liquids."

SELECTED TOPICAL AREAS

353

VIII.E.2-28 Cacchi, S. et al. TL, 43 5537. "The [(E,E,E)- 1,6,11-Tris(p-toluenesulfonyl)-l,6 ,11triazacyclopentadeca-3,8,13.triene]Pd(0) Complex in the Hydroarylation of Alkenes in Ionic Liquids. An Approach to Quinolines." VIII.E.2-29 Laali, K.K.; Borodkin, G.I. JCS(P2), 953; see also: Plaquevent, J.-C. et al. TL, 43, 6573. "First Application of Ionic Liquids in Electrophilic Fluorination of Arenes: Selectfluor~, (F-TEDA-BF4)for 'Green' Fluorination." ,,.,., . . . . .

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VIII.E.2-30 Chiappe, C. ct al. EJOC, 2831. "Bromination of Alkynes in Ionic Liquids---A Kinetic Investigation." .....

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VIII.E.2-31 Salunkhe, M.M. et al. TL, 43, 1127. "Lewis Acidic Ionic Liquids for the Synthesis of Electrophilic Alkenes via the Knoevenagel Condensation." VIII.E.2-32 Yadav, J.S. et al. JCS(P1), 2390. "Dy(OTf)3-Immobilized in Ionic Liquids: A Novel and Recyclable Reaction Media for the Synthesis of 2,3. Unsaturated Glycopyranosides." VIII.E.2-33 Khandekar, A.C.; Khadilkar, B.M. SL, 152. "Pechmann Reaction in Chloroaluminate Ionic Liquid." VIII.E.2-34 Yeung, K.-S. ct al. TL, 43, 5793. "Friedel-Crafts Acylation of Indoles in Acidic Imidazolium Chloroaluminate Ionic Liquid at Room Temperature." ,

,

VIII.E.2-35 Judeh, Z.M.A. et al. TL, 43, 5089. "The First Bischler.Napieralski Cyclization in a Room Temperature Ionic Liquid." VIII.E.2-36 Li, C.-J. et al. TL, 43, 4993. "Direct Formation of Tetrahydropyranols via Catalysis in Ionic Liquid." VIII.E.2-37 Dzyuba, S.V.; Bartsch, R.A. TL, 43, 4657. "Expanding the Polarity Range of Ionic Liquids.'

354

ORGANIC SYNTHESIS--2003

VIII.E.2-38 Engel, R.; Cohen, J.I. et al. S, 1530. "Polycations. The Synthesis of Liquid Ionic Phosphates (LIPS) from Mono- and Polycationie Ammonium Halides." VIII.E.2-39 Chen, Z.-C. et al. S, 1505. "Organic Reactions in Ionic Liquids: Ionic Liquid Accelerted Cyciocondensation of a-Tosyloxyketones with 2. Aminopyridine." VIII.E.2-40 Namboodiri, V.V.; Varma, R.S. TL, 43, 5381 and OL, 4, 3161. "An Improved Preparation of 1,3-Dialkylimidazolium Tetrafluoroborate Ionic Liquids Using Microwaves." VIII.E.2.41 Deelman, B.-J. et al. OL, 4, 3851. "A Highly Fluorous Room.Temperature Ionic Liquid Exhibiting Fluorous Biphasic Behavior and Its Use in Catalyst Recycling. VIII.E.2-42 Shreeve, J.M. et al. TL, 43, 9497. "New Dense Fluoroalkyl-Substituted Imidazolium Ionic Liquids." VIII.E.2-43 Gathergood, N" Scammells, P.J. AJC, 55, 557. "Design and Preparation of Room.Temperature Ionic Liquids Containing Biodegradable Side Chains." VIII.E.2-44 Afonso, C.A.M. et al. CEJ, 8, 3671. "Preparation and Characterization Of New Room Temperature Ionic Liquids." VIII.E.2-45 Saigo, K. et al. CC, 2240. "Design and Synthesis of a Novel Imidazolium-Based Ionic Liquid with Planar Chirality." .

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VIII.E.2-46 Shreeve, J.M. et al. JOC, 67, 9340. "Synthesis of 1-Aikyl-l,2,4-triazines and the Formation of Quaternary 1-Alkyi.4-polyfluoroalkyl-l,2,4-triazolium Salts Leading to Ionic Liquids." VIII.E.2-47 Saigo, K. et al. CC, 2240. "Design and Synthesis of a Novel Imidazolium-Based Ionic Liquid with Planar Chirality."

SELECTED TOPICAL AREAS

VIII.F. Combinatorial

355

Chemistrv

VIII.F.1 Suvoorts. Linkers and Protecting Groups VIII.F.I-1 Reger, T.S.; Janda, K.D. BCML, 12, 837; see also: Hwang, J.-J.; Tour, J.M. T, 58, 10387. "Parallel Suspension Polymerization for High.Throughput Resin Synthesis." VIII.F.I.2 Pinson, J.; Pulicani, J.-P. et al. JOC, 67, 8513. "Surface-Modified Carbon Felts" Possible Supports for Combinatorial Chemistry." VIII.F.1.3 Tornoe, C.W.; Meldal, M. TL, 43, 6409. "EXPO3oo0---A New Expandable Polymer for Synthesis and Enzymatic Assays." VIII.F.1-4 Janda, K.D. et al. JOC, 67, 3045. "Preparation of New Microgel Polymers and Their Application as Supports in Organic Synthesis." VIII.F.1.5 Guillemin, J.C. et al. SL, 316. "Preparation of Soluble Polymeric Supports with a Functional Group for Liquid-Phase Organic Synthesis." VIII.F.I-6 Sutherland, A.J. et al. JOC, 67, 4847. "Synthesis and Evaluation of Poly(oxyethyleneglycol) Polymer (POP) Supports." VIII.F.I-7 Wang, B. et al. TL, 43, 6339. "Catechol Pendant Polystyrene for Solid-Phase Synthesis." VIII.F.1-8 Guo, M.-J.; Varady, L. TL, 43, 3677, 5611; see also: Furst, M.; Ruck-Braun, K. SL, 1991; Subra, G. et al. TL, 43, 9221. "2-(3-Aminopropyi)-4-pentenoic Acid as a BioCompatible/Cleavable Linker for Solid-Phase Organic Synthesis." VIII.F.1-9 Lusinchi, M. et al. T, 58, 5715. "Xanthates and Solid-Phase Chemistry. A New Soluble Polymer Analogue of Wang Resin."

356

ORGANIC SYNTHESISm2003

VIII.F.I-10 Yaylayan, V.A. et al. TL, 43, 9023. "Microwave-Assisted PEGylation of Merrifield Resins." VIII.F.l-11 Arseniyadis, S.; Wagner, A.; Mioskowski, C. TL, 43, 9717. "A Straightforward Preparation of Amino-Polystyrene Resin from Merrifield Resin." VIII.F.I-12 Wagner, M.; Kunz, H. AG(E), 41, 317; Brown, R.C.D. et al. TL, 43, 6023. "The (2-Phenyl-2-trimethylsilyl)ethyl-(PTMSEL) Linker--A Novel Linker for the Solid-Phase Synthesis of Protected Peptides and Glycopeptides Cleavable with Fluoride." VIII.F.I-13 Ingenito, R. et al. OL, 4, 1187. "Efficient Loading of Suifonamide Safety-Catch Linkers by Fmoc Amino Acid Fluorides." VIII.F.l-14 Lamaty, F. et al. EJOC, 2308. "A New Soluble Polymer-Supported Sulfonyl Linker-Application to the Synthesis of Cyclic tx-Amino Acids." VIII.F.I-15 Poiri'er, D. et al. BMCL, 12, 2833. "A Multidetachable Sulfamate Linker Successfldly Used in a Solid-Phase Strategy to Generate Libraries of Sulfamate and Phenol Derivatives." VIII.F.l-16 Hwang, S.H.; Kurth, M.J. JOC, 67, 6564; Cheng, W.-C.; Kurth, M.J. JOC, 67, 4387. "Versatile 'Tracerless' Sulfone Linker for SPOS: Preparation of lsooxazolinopyrrole-2-carboxylates." VIII.F.I-17 Balasubramanian, S. et al. JOC, 67, 129. "Practical Synthesis of a Dithiane-Protected 3',5'Dialkoxybenzoin Photolabile Safety-Catch Linker for SolidPhase Organic Synthesis." VIII.F.I-18 Zhang, Z.; Lepore, S.D. TL, 43, 7375. "Synthesis of Cyclopentadienylmanganese Tricarbonyl Resins as Potential Olefin Tracerless Supports."

SELECTED TOPICAL AREAS

357

VIII.F.2 Supported Reagents. Catalysts. Ligands and Scavengers VIII.F.2-1 Ley, S.V. et al. SL, 1641. "Application of Polymer.Supported Enzymes and Reagents in

the Synthesis of ~,-Aminobutyric Acid (GABA) Analogues."

VIII.F.2-2 Ley, S.V. et al. SL, 516. "A Polymer-Supported Iridium Catalyst for the Stereoselective Isomerization of Double Bonds." VIII.F.2-3 Ley, S.V. et al. SL, 775. "A Clean Conversion of Aldehydes to Nitriles Using a SolidSupported Hydrazine." VIII.F.2-4 Ley, S.V. et al. JCS(P1), 1850. "A Concise Synthesis of Carpanone Using Solid-Suppported Reagents and Scavengers." VIII.F.2-5 Lindsey, C.W. et al. TL, 43, 4225, 6319; see also: Curran, D.P.; Furukawa, T. OL, 4, 2233; van Boom, J.H. TL, 43, 7809. "Fluorous-Tethered Quenching Reagents for Solution Phase Parallel Synthesis." VIII.F.2-6 Barrett, A.G.M.; de Miguel, Y.R. T, 58, 3785. "Synthesis and Characterization of a New Polymer Support for a Metallocene Catalyst." VIII.F.2-7 Grela, K. et al. TL, 43, 9055. "A PS-DES Immobilized Ruthenium Carbene: A Robust and Easily Recyclable Catalyst for Olefin Metathesis." VIII.F.2-8 Faita, G.; Pasini, D. et al. TA, 13, 333. "A Soluble Polymer-Bound Evans' Chiral Auxiliary: Synthesis, Characterization and Use in Cycloaddition Reactions." VIII.F.2-9 Botta, M.; Corelli, F. et al. TL, 43, 6507 and H, 56, 369; Kirschning, A. et al. TL, 43, 1401. "An Improved Synthesis of Solid.Supported Reagents (SSRs) for Selective Acylation of Amines by Microwave Irradiation."

358

ORGANIC SYNTHESISm2003

VIII.F.2-10 Luis, S.V.; Martens, J. eta. OL, 4, 2002; see also: Deshpande, V.H.; Bedekar, A.V. et al. TL, 43, 5587; Mayoral, J.A. et al. OL, 4, 3927; Trost, B.M. et al. A G(E), 41,4691; Weissberg, A.; Portnoy, M. SL, 247. "New Supported 13-Amino Alcohols as Efficient Catalysts for the Enantioselective Addition of Diethylzinc to Benzaldehyde under Flow Conditions." VIII.F.2-11 Chen, J.J. et al. TL, 43, 4083; Kennedy, A.L. et al. OL, 4, 1167. "The Universal Rink-lsonitrile Resin" Applications in Ugi Reactions." VIII.F.2-12 Barrett, A.G.M. et al. TL, 43, 1081. "ROMPgel-Supported Biphenyl and Naphthalene: Reagents for Lithiation Reactions with Minimal Purification." VIII.F.2-13 Huang, X.; Xu, W. TL, 43, 5495; Qian, H.; Huang, X. TL, 43, 1059. "Polystyrene-Supported Benzyi Selenide: An Efficient Reagent for Highly Stereocontrolled Synthesis of Olefins and Allylic Alcohols." VIII.F.2-14 Luo, G. et al. TL, 43, 8909. "A Novel, Solid-Phase Chlorinating Reagent for the Synthesis of Acyi Chlorides." VIII.F.2-15 Janda, K.D. et al. BMCL, 12, 2047. "Preparation of Soluble and Insoluble Polymer Supported IBX Reagents." VIII.F.2-16 Mukaiyama, T. et al. CL, 250. "Polymer-Supported Sulfinimidoyl Chloride as a Useful Reagent for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds." VIII.F.2-17 Faita, G.; Quadrelli, P. et al. EJOC, 1175. "Solid-Supported Nitrile Oxides as Stable and Valuable Reactive Intermediates." VIII.F.2-18 Sodeoka, M. et al. OL, 4, 3923. "Solution-Phase Parallel Synthesis of Carbamates Using Polymer-Bound N-Hydroxysuccinimide."

SELECTED TOPICAL AREAS

359

VIII.F.2-19 Ikegami, S. et al. SL, 2031; Ali, M.H.; McDermott, M. TL, 43, 6271. "Oxidation of Amines and Sulfides Catalyzed by an Assembled Complex of Phosphotungstate and Non-CrossLinked Amphiphilie Polymer." VIII.F.2-20 Zhang, J.-L.; Che, C.-M. OL, 4, 1911. "Soluble Polymer-Supported Ruthenium Porphyrin Catalysts for Epoxidation, Cyclopropanation, and Aziridation of Alkenes." VIII.F.2.21 Chandrasekhar, S. et al. TL, 43, 8335. "Direct Condensation of Carboxylic Acids with Polyethylene Glycols Catalyzed by Sc(OTf)3." VIII.F.2-22 Linclau, B. et al. OL, 4, 1035. "Polymer-Supported O.Methylisourea: A New Reagent for the O-Methylation of Carboxylic Acids." VIII.F.2-23 Hinklin, R.J.; Kiessling, L.L. OL, 4, 1131. "p-Methoxybenzyl Ether Cleavage by Polymer-Supported Sulfonamides." VIII.F.2-24 Stien, D. et al. TL, 43, 1693~ "A New High-Loading Water-Soluble Scavenger for Anhydrides, Acid Chlorides and Isocyanates." VIII.F.2-25 Bergbreiter, D.E. et al. OL, 4, 737. "Soluble Polymer-Supported Catalysts Containing Azo Dyes." VIII.F.2-26 Barlos, K. et al. TL, 43, 3419. "Resin-Bound Mercapto Acids: Synthesis and Application." VIII.F.3 Solid-Phase Heterocvclic Svnthesis VIII.F.3-1 Deng, Y.; Hlastra, D.J. OL, 4, 4017. Azoles VIII.F.3-2 Yun, Y.K. et al. SL, 739; Huang, K.-T.; Sun, C.-M. BMCL, 12, 1001; Wu, C.-Y.; Sun, C.-M. TL, 43, 1529. Benzimidazoles

360

ORGANIC SYNTHESISm2003

VIII.F.3-3 Collins, J.L. et al. OL, 4, 323.

Benzopyranoisoxazoles

VIII.F.3-4 Makino, S. et al. TL, 43, 8401. 1,2,4-Benzothiadiazine 1,1-Dioxides VIII.F.3-5 Chang, J.; Zhao, K.; Pan, S. TL, 43, 951. 2-Arylbenzoxazoles VIII.F.3-6 Wu, T.Y.H.; Schultz, P.G. OL, 4, 4033. 13-Carbolines and Tryptamines I.F.3-7 Houghten, R.A. et al. T, 58, 221 and TL, 43, 1157. Dih y droimi da zo !es VIII.F.3-7 Righi, P.; Zwanenburg, B. et al. OL, 497. Dih y d rois oxa zol es VIII.F.3-8 David, M. et al. JCS(P1), 2234. Dih y d ro py ri da zi n- 3 ( 2H)- on es VIII.F.3-9 Rodriguez, H.; Suarez, M.; Martin, N. et al. TL, 43, 439. Dihydropyridones VIII.F.3-10 Kundu, B. et al. T, 58, 10469. Furans VIII.F.3-11 Bueno, J.M. et al. TL, 43, 4741. Fu razano [3,4- b ] pyrazi nes VIII.F.3-12. Lai, J.Y.Q.; Payne, H.J. et al. TL, 43, 7557; Capretta, A. et al. TL, 43, 7687. Imidazoles VIII.F.3-12 Cheng, J.-F. et al. TL, 43, 4571; Yang, K. et al. TL, 43, 4463; Lange, U.E.W. TL, 43, 6857. 2- & 4.Imidazolones VIII.F.3-13 Houghten, R.A. et al. T, 58, 3349 and TL, 43, 2343. lmi d azoli din- 4- on es

SELECTED TOPICAL AREAS

361

VIII.F.3-14 Lain, Y. et al. OL, 4, 3935; Jaramillo, C. et al. SL, 1544. Imidazo[1,2-a]pyridines VIII.F.3-15 Yamazaki, K.; Kondo, Y. CC, 210; Yasuhara, A.; Sakamoto, T. et al. TL, 43, 6579; Wacker, D.A.; Kasireddy, P. TL, 43, 5189; Willoughby, C.A. et al. BMCL, 12, 93; Hartley, R.C. et al. OL, 4, 75. Indoles VIII.F.3-16 Alvarez-Builla, J. et al. SL, 343. 1H-Isoin dole. 1,3- dion es VIII.F.3-17 Shang, Y.-J.; Wang, Y.G. TL, 43, 2247; Shang, Y.-J.; Wang, Y.-G. S, 1663; Kurth, M.J. et al. OL, 4, 741. lsoxazoles VIII.F.3-18 Makara, G.M. et al. TL, 43, 5043. 1,2,4- O xa di azoi es VIII, F.3-19 Clapham, B.; Janda, K.D. et al. TL, 43, 5407. Oxazoles VIII.F.3-20 Kundu, B. et al. TL, 43, 8327. Oxazolidin-2-ones VIII.F.3-21 Cheng, J.-F. et al. TL, 43, 6293; Figueroa-Perez, S. et al. SL, 1085; Balasubramanian, S. et al. TL, 43, 2439. 2-Oxopiperazines

VIII.F.3-22 Rutjes, F.P.J.T.; Hiemstra, H. et al. EJOC, 3133; Barluenga, J. et al. OL, 4, 3667; Hanessian, S.; Seid, M.; Nilsson, I. TL, 43, 1991; Hanessi'an, S.; Nilsson, I. et al. TL, 43, 1995. Piperidines VIII.F.3-23 A1-Obeidi, F. et al. TL, 43, 6169; Legraverend, M. et al. T, 58, 7911. Purines VIII.F.3-24 Haruta, M. et al. H, 58, 79; Smith, D.B.; Talamas, F.X. et al. TL, 43, 8071. Pyrimidines

362

ORGANIC SYNTHESIS--2003

VIII.F.3-25 Bergauer, M.; Gmeiner, P. S, 274; Gmeiner, P. et al.

BMCL, 12, 1937; Kobayashi, N. et al. BMCL, 12, 1747; Bleicher, K.H. et al. BMCL, 12, 3073; Quinn, R.J. et al. AJC, 55, 789. Pyrroles

VIII.F.3-26 Komatsu, M. et al. OL, 4, 3505; Hanessian, S.; Bayrakdarian, M. TL, 43, 9441; Pyrrolidines VIII.F.3-27 Cordero, F.M.; Brandi, A. et al. TL, 43, 5711. Pyrrolizidines VIII.F.3-28 O'Mahony, D.J.R.; Krchnak, V. TL, 43, 939; Houghton, R.A. et al. JOC, 67, 5831; Kundu, B. et al. TL, 43, 5579; Weber, C. et al. TL, 43, 2931. Q uin azol in- 4 (3 H) -on es VIII.F.3-29 Hulme, C. et al. TL, 43, 1637. Quinoxalinones VIII.F.3-30 Shuttleworth, S.J. et al. TL, 43, 6661. T etrah y d r o- 13-ca r b ol in es VIII.F.3-31 Benaglia, M. et al. EJOC, 1184. Tetrahydroquinolines VIII.F.3-32 Kilburn, J.P. et al. TL, 43, 3309. 1,3,4-T hia d ia z! n e s VIII.F.3-33 Berteina,-Roboin, S. et al. TL, 43, 3193; Kodomari, M. et al. TL, 43, 1717. Thiazoles VIII.F.3-34 Blass, B.E. et al. TL, 43, 4059. 1,2,3-Triazoles VIII.F.3-35 Graybill, T.L. et al. TL, 43, 5305; Makara, G.M. et al. OL, 4, 1751; Park, K.-H.; Cox, L.J. et al. TL, 43, 3899. 1,2,4-Triazoles

SELECTED TOPICAL AREAS

363

VIII.F.3-36 Blass, B.E. et al. TL, 43, 8165. 1,2,4- T riazin- 6-on es VIII.F.3-37 Purandare, A.V. et al. TL, 43, 3903. "Solid-Phase Synthesis of 'Diverse' Heterocycles." VIII.F.3-38 Elkaim, L. et al. SL, 352. "The Mannich Reaction of Hydrazones Amenable to Solid Phase Synthesis: A Powerful Tool for Heterocycle Preparation." VIII.F.3-39 Xia, M. Wang, Y.-G. TL, 43, 7703. "Soluble Polymer-Supported Synthesis of Bignineili Compounds." YIII.F.4 Solid.Supt~orted ......Organic Reaction Processes VIII.F.4-1 W e i g a n d , K; Pelka, S. OL, 4, 4689; Kondo, Y. et al.

JCS(P1), 2137.

"Palladium-Catalyzed Amination of Aryi Halides on Solid Support."

VII1.F.4-2 Duboc, R.; Savignac, M.; Genet, J.-P. JOM, 643-644, 512; Lutz, C.; Bleicher, K.H. TL, 43,2211; Miyaura, N. et al. T, 58, 5779; Shimizu, K. et al. TL, 43, 5653. "Palladium Cross.Coupling Reactions on Solid Support Using a New Silylated Linker." VIII.F.4-3 Morphy, J.R. et al. TL, 43, 5973. "Low Dilution Procedures in Solid-Phase Organic Synthesis: Diels-Alder and Heck Reactions." VIII.F.4-4 Henkel, B.; Weber, L. SL, 1877; Lou, B. et al. TL, 43, 8467; Fullop, F. et al. OL, 4, 1967; Hulme, C. et al. TL, 43, 3681; Nixey, T.; Hulme, C. TL, 43, 6833. "A Novel Four-Component Synthesis of N-Substituted Amino Acid Esters." VIII.F.4-5 Wright, D.L. et al. TL, 43, 943. "Studies on the Sequential Multi-Component Coupling/DielsAlder Cycloaddition Reaction."

364

ORGANIC SYNTHESISm2003

VIII.F.4-6 Blankespoor, R.L. et al. JOC, 67, 2677. "Photochemical Synthesis of Aldehydes in the Solid-Phase." VIII.F.4-7 Lazny, R.; Michalak, M. SL, 1931; Takahashi, T. et al. SL, 1427. "Application of Piperazine.Derived Hydrazone Linkers for Alkylation of Solid-Phase Immobilized Ketones." VIII.F.4-8 Tice, C.M.; Albericio, F. et al. TL, 43, 7491; Albericio, F.; Michelotti, E.L. et al. TL, 43, 7495; Royo, M.; Albericio, F. et al. TL, 43, 2029. "Solid Phase Synthesis of ct-Acylamino-t~,~-disubstituted Ketones." VIII.F.4-9 Lizarzaburu, M.E.; Shuttleworth, S.J. TL, 43, 2157. "Synthesis of Aryl Ethers from Aminoalcohols Using Polymer-Supported Triphenylphosphine." VIII.F.4-10 Liang,, X.; Bols, M. JCS(P1), 503; Baruah, M.; Bols, M.

JCS(P1), 509.

"Solution-Phase Combinatorial Synthesis Using Multicomponent Grignard Reagents."

VIII.F.4-11 Raghavan, S.; Anuradha, K. TL, 43, 5181. "Solid-Phase Synthesis of 1,4-Diketones by Thiazolium Salt Promoted Addition of Aldehydes to Chalcones." VIII.F.4-12 Toru, T. et al. TL, 43, 2381; see also: Cheng, S.; Comer, D.D. TL, 43, 1179. "Asymmetric Conjugate Addition Reactions of PolymerSupported Highly Enantioenriched 13-(Trimethylsilyl)ethyl Sulfoxides." VIII.F.4-13 Fukase, K. et al. TL, 43, 8867; for other amine syntheses, see also: A1-Obeidi, F. et al. TL, 43, 3555; Jonsson, D.; Unden, A. TL, 43, 3125; Lowden, C.T.; Mendoza, J.S. TL, 43, 979; Fukuyama, T. et al. SL, 1338. "Reactivity Switching on Solid Support: Solid-Phase Synthesis of Tertiary Amines by Reduction of Tertiary Amides with LiAIH4." VIII.F.4-14 Ray, N.C. et al. OL, 4, 597. "A Solid-Phase Route to N-Cyanoamides."

SELECTED TOPICAL AREAS

365

VIII.F.4-15 Kurth, M.J. et al. TL, 43, 2967; Gennari, C. et al. TL, 43, 761; Zhang, Z. et al. TL, 43, 4347. "Dimsyl Anion in the Monoalkylation of Solid-Phase Alkyi Sulfones." VIII.F.4-16 Morphy, J.R. et al. TL, 43, 6413. "One-Pot Hofmann Eiimination-Transesterification/Amidation Reactions on REM Resin Using Perfluorous Solvents." VIII.F.4-17 Chang, S. et al. TL, 43, 7445. "A Short and Efficient Synthetic Approach to Hydroxy (E)Stilbenoids via Solid-Phase Cross Metathesis." VIII.F.4-18 Jung, K.W. et al. T, 58, 3329; Fernandez-Forner, D. et al.

TL, 43, 3543.

"Efficient Cs2CO3-Promoted Solution and Solid Phase Synthesis of Carbonates and Carbamates in the Presence of TBAI."

VIII.F.4-19 Pastor, J. et al. TL, 43, 7105; Kilburn, J.P. et al. T, 58, 1739. "A Novel, Facile Methodology for the Synthesis of N,N'bis(tert.Butoxycarbonyl).Protected Guanidines Using Polymer-Supported Carbodiimide." VIII.F.4-20 Bradley, M. et al. TL, 43, 7 2 0 1 . "Solid Phase-Mediated Synthesis of Isonitriles." VIII.F.4-21 Esteve, C.; Vidal, B., TL, 43, 1019. "Solid-Phase Synthesis of Sulfamides." VIII.F.4-22 Ruhland, T. et al. JOC, 67, 5257. "Iron-Assisted Nucleophilic Aromatic Substitution on Solid Phase." VIII.F.4-23 Scott, W.L.; O'Donnell, M.J. et al. JOC, 67, 2960. "A Solid-Phase Synthetic Route to Unnatural Amino Acids with Diverse Side-Chain Substituents." VIII.F.4-24 Rabanal, F.; Giralt, E. et al. OL, 4, 3831. "A New Method for the Preparation of Unprotected Peptides on Biocompatible Resins with Application in Combinatorial Chemstry."

366

ORGANIC SYNTHESIS--2003

VIII.F.4-25 Corbett, A.D.; Gleason, J.L. TL, 43, 1369. "Preparation of Active Esters on Solid Support for AqueousPhase Peptide Coupling." VIII.F.4-26 Janda, K.D. et al. TL, 43, 37. "Solid Phase Peptide Synthesis on JandaJel TM Resin." VIII.F.4-27 Kodadek, T. et al. OL, 4, 4057. "Microwave.Assisted Solid-Phase Synthesis of Peptoids." VIII.F.4-28 Flitsch, S.L. et al. JACS, 124, 10988. "Protease-Catalyzed Peptide Synthesis on Solid Support." VIII.F.4-29 Rose, K. et al. TL, 43, 8693. "Covalent Captive Purification of Polypeptides after SPPS via a Linker Removable Under Very Mild Conditions." VIII.F.4.30 Boons, G.J. et al. TL, 43, 4691. "Demixing Libraries of Saccharides Using a Multi-Linker Approach in Combination with a Soluble Polymeric Support." vIIi.F.4-31 Warriner, S.L. et al. AG(E), 41, 1215. "Peptide-Templated Saccharide Synthesis on a Solid Support." VIII.F.4.32 Nicotra, F. et al. TL, 43, 1355; Jimenez-Barbero, J.; Nicotra, F. et al. CEJ, 8, 3976. "Polycyclic Scaffolds from Fructose." VIII.F.4.33 Takahashi, T. et al. SL, 867; Jacobson, M.; Ellervik, U. TL, 43, 6549; Crich, D.; Smith, M. JACS, 124, 8867; Hunt, D.K.;, Seeberger, P.H. OL, 4, 2751. "Solid-Phase Synthesis of Aryi O-Glycoside Using Aqueous Base and Phase-Transfer Catalyst." VIII.F.4-34 Fukase, K. et al. SL, 1409; Jensen, K.J.; Withers, S.G. et al. JOC, 67, 4143; Ruttens, B.; Van der Eycken, J. TL, 43, 2215. "Solid-Phase Synthesis of Oligosaceharides Using Novel Alkyne-Type Linkers" Selection of Reactive Sites on the Support by Sonogashira Reaction."

SELECTED TOPICAL AREAS

367

VIII.F.5 Targeted Library Svnthesis VIII.F.5-1 Aldrich, J.V. et al. JMC, 45, 3820. "Solid Phase Synthesis and Evaluation of Tyr-Tic-Phe-Phe(pNHCOCH2Br)([Phe(p-bromoacetamide)4]TIPP), a Potent Affinity Label for 8-Opiod Receptors." VIII.F.5-2 Bertozzi, C.R. et al. BMCL, 12, 329. "Tyrosylprotein Sulftransferase Inhibitors Generated by Combinatorial Target-Guided Ligand Assembly." VIII.F.5-3 Betra, S. et al. BMCL, 12, 1905. "Combinatorial Synthesis and Biological Evaluation of Isoxazole-Based Libraries as Antithrombic Agents." VIII.F.5-4 Bleicher, K.H. et al. BMCL, 12, 2519. "Parallel Solution- and Solid-Phase Synthesis of Spirohydantoin Derivatives as Neurokinin-Receptor Ligands." VIII.F.5-5 Boger, D.L. et al. JACS, 124, 544. "Erythrpoietin Mimetics Derived from Solution Phase Combinatorial Libraies." VIII.F.5-6 Brown, P.J. et al. BMCL, 12, 1225. "Identification of a Subtype Selective Human PPARa Agonist Through Parallel-Array Synthesis." VIII.F.5-7 Chauhan, P.M.S. et al. BMCL, 12, 667. "Synthesis of Novel Antimycobacterial Combinatorial Libraries of Structurally Diverse Substituted Pyrimidines by Three-Component Solid-Phase Reactions." VIII.F.5-8 Couladouros, E.A.;, Strongilos, A.T. AG(E), 41, 3677. "Generation of Libraries of Pharmacophoric Structures with Increased Complexity and Diversity by Employing Polymorphic Scaffolds." VIII.F.5-9 Gilbert, I.H. et al. EJMC, 883. "Design, Synthesis and Evaluation of Peptide Libraries as Potential Anti.HIV Compounds, via Inhibition of gpl20/Cell Membrane Interractions, Using the gp 120/cd 4/fab 17 Crystal Structure."

368

ORGANIC SYNTHESISm2003

VIII.F.5-10 Chen, L. et al. BMCL, 12, 1679. "Focused Library Approach for Identification of New NAcylphenylalanines as VCAM/VLA-4 Antagonists." VIII.F.5-11 Cheng, Y. et al. BMCL, 12, 529; Raghavan, S. et al.

BMCL, 12, 2855.

"A Combinatorial Library of lndinavir Analogues and Its In Vitro and In Vivo Studies."

VIII.F.5-12 Huang, L.; Ellman, J.A. BMCL, 12, 2993; Ellamn, J.A. et al. JOC, 67,910. "General Solid.Phase Method to Prepare Novel Cyclic Ketone Inhibitors of the Cysteine Protease Cruzain." VIII.F.5-13 Gray, N.S.; Schultz, P.G. et al. JACS, 124, 1594; Tripathy, R. et al. TL, 43, 217; Norskov-Lauritsen, L. et al. BMCL, 12, 1525. "A Combinatorial Scaffold Approach Toward Kinase-Directed Heterocycle Libraries." VIII.F.5-14 Haque, T.S. et al. JMC, 45, 4669. "Parallel ,Synthesis of Potent, Pyrazole-Based Inhibitors of Helicobacter pylori Dihdroorotate Dehydrogenase." VIII.F.5-15 Hori, H. et al. BMCL, 12, 951. "Design and Synthesis of Antiangiogenic/Heparin-Binding Arginine Dendrimer Mimicking the Surface of Endostatin." VIII.F.5-16 Houghton, R.A. et al. TL, 43, 4103. "An Expedient Method for the Solid-Phase Synthesis of c~. Aminoalkyl Phosphonopeptides." VIII.F.5-17 Kilbum, J.D. et al. CEJ, 8, 1300. "Synthesis of Guanidiniuni Receptor Libraries and Screening for Selective Peptide Receptors in Water." VIII.F.5-18 Kitas, E.A. et al. BMCL, 12, 1727. "Syntheis of Triazole-Tethered Pyrrolidine Libraries: Novel ECE lnhibitors." VIII.F.5-19 Ley, S.V. et al. OL, 4, 3793. "Synthesis of the [32 Agonist (R)-Salmetrol Using a Sequence of Supported Reagents and Scavenging Agents."

SELECTED TOPICAL AREAS

369

VIII.F.5-20 Krutzik, P.O.; Chamberlin, A.R. BMCL, 12, 2129; Kamal, A. et al. TL, 43, 2103. "Rapid Solid-Phase Synthesis of DNA-Binding PyrroleImidazole Polyamides." .

.

.

.

.

.

.

.

.

.

.

VIII.F.5-21 Kundu, B. et al. BMCL, 12, 1473. "Identification of Novel Antifungal Nonapeptides Through the Screening of Combinatorial Peptide Libraries Based on a Hexapeptide Motif." VIII.F.5-22 Kundu, B. et al. BMCL, 12, 2803; Sergheraert, C. BMCL, 12, 2595. "Solid-Phase Synthesis and Bioevaluation of Lupeol-Based Libraries as Antimalarial Agents." VIII.F.5-23 Lee, B.H. et al. BMCL, 12, 353. "Generation of a Small Library of Cyclodepsipeptide PF 1022A Analogues Using a Cyclization-Cleavage Method with Oxime Resin." VIII.F.5-24 Malkinson, J.P.; Falconer, R.A. TL, 43, 9549. "Solid-Phase Synthesis of C-Terminal Thio-Linked Glycopeptides." VIII.F.5-25 Meldal, M. et al. JACS, 124, 11046 and JCS(P1), 682; St Hilaire, P.M.; Meldal, M. et al. JMC, 45, 1971. "A Solid-Phase Approach to Mouse Melanocortin Receptor Agonists Derived from a Novel Thioether Cyclized Peptidomimetic Scaffold." VIII.F.5-26 Myers, A.G.; Lanman, B.A. JACS, 124, 12969. "A Solid-Supported Enantioselective Synthesis Suitable for the Rapid Preparation of Large Numbers of Diverse Structural Analogues of (-)-Saframycin A." VIII.F.5-27 Ohtake, N. et al. JMC, 45, 984. "Cyclohexylmethylpiperidinyltriphenylpropioamide: A Selective Muscarinic M3 Antagonist Discriminating Against the Other Receptor Subtypes." VIII.F.5-28 Roe, M.B. et al. T, 58, 5741. "Solid and Solution Phase Synthesis of the 2Cyanopyrrolidide DPP-IV Inhibitors NVP-DPP728."

370

ORGANIC SYNTHESISm2003

VIII.F.5-29 Rew, Y.; Goodman, M. JOC, 67, 8820. "Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the FukuyamaMitsunobu Reaction." VIII.F.5-30 Smith, R.A. et al. BMCL, 12, 2875. "Solid.Phase Synthesis and Investigation of Benzofurans as Selective Estrogen Receptor Modulators." VIII.F.5-31 Stromgaard, K. et al. JMC, 45, 5745. "Solid-Phase Synthesis of Polyamine Toxin Analogues" Potent and Selective Antagonists of Ca2§ AMPA Receptors." VIII.F.5-32 Verdine, G.L. et al. JACS, 124, 13352. "High-Affinity Mu Opiod Receptor Ligands Discovered by the Screening of an Exhaustively Stereodiversified Library of 1,5-Enediols." VIII.F.5-33 Volonterio, A.; Zanda, M. et al. EJOC, 428 and CCC, 67, 1305. "Solution/Solid.Phase Synthesis of Partially Modified Retroand Retro.lnverso-~g[NHCH(CF3)]2 Peptidyl Hydroxamates and Their Evaluation as MMP-9 Inhibitors." VIII.F.5-34 Waldmann, H. et al. JACS, 124, 5954, 13171 and AG(E), 41, 307, 3616. "Solid-Phase Syntheis of Lipidated Peptides." VIII.F.5-35 Wilson, L.J. et al. BMCL, 12, 1149; Jefferson, E.A. et al.

JMC, 45, 3430.

"The Identification and Characterization of Hydrazine UreaBased Antibacterial Agents Through Combinatorial Chemistry."

VIII.F.5.36 Xu, P. et al. S, 1017. "Synthesis of a Peptidomimetic HCMV Protease Inhibitor Library." VIII.F.5-37 Chang, Y.-T.; Chung, S.-K.; Schultz, P.G. et al. JACS, 124, 1856. "The Synthesis and Biological Characterization of a Ceramide Library."

SELECTED TOPICAL AREAS

371

VIII.F.5-38 Yasukata, T. et al. BMCL, 12, 3033. "An Efficient and Practical Method for Solid.Phase Synthesis of Tripeptide-Bearing Glycopeptide Antibiotics: Combinatorial Parallel Synthesis of Carboxamide Derivatives of Chloroorienticin B." VIII.F.6 Novel Techniques in Combinatorial Chemistry VIII.F.6-1 Lam, K.S. et al. JACS, 124, 7678. "A Novel Peptide-Based Encoding System for 'One-Bead One-Compound' Peptidomimetic and Small Molecule Combinatorial Libraries." VIII.F.6-2 Trau, M. et al. AJC, 54, 649 (2001). "Multi-Fluorescent Silica Colloids for Encoding Large Combinatorial Libraries." VIII.F.6-3 Wong, C.-H. et al. JACS, 124, 14397. "Synthesis of Sugar Arrays in Microtiter Plate." VIII.F.6-4 Manabe, S. Ito, Y. JACS, 124, 12638. "On-Resin Real.Time Reaction Monitoring of Solid-Phase Oligosaccharide Synthesis." VIII.F.6-5 Smietana, M.; Kool, E.T. AG(E), 41, 3704; Gait, M.J. et al. OL, 4, 3259. "Efficient and Simple Solid-Phase Synthesis of Short Cyclic Oligodeoxynucleotides Bearing a Phosphorothioate Linkage." VIII.F.6-6 Micalizio, G.C.; Schreiber, S.L. AG(E), 41, 152. "A Boronic Ester Annulation Strategy for Diversity-Oriented Organic Synthesis." VIII.F.6-7 Storm, O.; Luning, U. CEJ, 8, 793; Hodge, P. et al. JCS(P 1), 629. "How to Synthesize Macrocycles Efficiently by Using Virtual Combinatorial Libraries." VIII.F.6-8 Schreiber, S.L. et al. JACS, 124, 13402. "Skeletal Diversity via a Branched Pathway: Efficient Synthesis of 29,400 Discrete, Polycycllc Compounds and Their Arraying into Stock Solutions."

372

ORGANIC SYNTHESISm2003

VIII.F.6-9 Schreiber, S.L. et al. JACS, 124, 1354. "Diversity-Oriented Synthesis of Biaryl-Containing Medium Rings Using a One Bead/One Stock Solution Platform." VIII.F.6-10 Stevenson, J.D.; Benkovic, S.J. JCS(P2), 1483. "Combinatorial Approaches to Engineering Hybrid Enzymes." VIII.F.6-11 Bauerle, P. et al. CC, 2762. "Combinatorial Parallel Synthesis and Automated Screening of a Novel Class of Liquid Crystalline Materials." VIII.F.6-12 Eliseev, A.V. et al. JOC, 67, 59. "Synthesis and Mass Spectrometry Studies of Branched Oxime Ether Libraries." VIII.F.6-13 Quinn, R.J. et al. AJC, 54, 355 (2001). "The Synthesis of a Combinatorial Library Using a Tambjamine Natural Product Template.' VIII.F.6-14 Mason, S.J.; Balasubramanian, S. OL, 4, 4261. "Solid-Phase Catch Activate and Release Synthesis of Cyanine Dyes." VIII.F.7 Reviews VIII.F.7-1 Grzybowski, B.A. et al. ACR, 35, 261. Review: "From Knowledge.Based Potentials to Combinatorial Lead Design in Silico." VIII.F.7-2 Schweizer, F. AG(E), 41, 231. Review" "Glycosamino Acids: Building Blocks for Combinatorial Synthesis--Implications for Drug Discovery." VIII.F.7-3 Waldmann, H. et al. AG(E), 41, 2878. Review" "From Protein Domains to Drug Candidates-NatUral Products as Guiding Principles in the Design and Synthesis of Compound Libraries." VIII.F.7-4 ~(~chn',a_k,V.; Holladay, M.W. CRV, 102, 61. Review" "Solid Phase Heterocyclie Chemistry."

SELECTED TOPICAL AREAS

VIII.F.7-5 Janda, K.D., ed. BMCL, 12, 1791-1884. Symposia "Polymer Supported Catalysts and Reagents in in-Print: Synthetic Organie Chemistry." VIII.F.7-6 Grigg, R. et al. CRV, 102, 2607. Review: "Traceless Solid-Phase Organic Synthesis." VIII.F.7-7 Manimala, J.C.; Anslyn, E.V. EJOC, 3909. Microreview: "Solid-Phase Synthesis of Guanidinium Derivatives from Thiourea and Isothiourea Fun c t ionali ties." VIII.F.7-8 Winder, R. CI(L), 20. Comment: "Combinatorial Chemistry."

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AUTHOR INDEX Alsters, L. 104 Alterman, M. 86, 239 Alvarez, M. 81 Alvarez-Builla, J. 361 Alvarez-Ibarra, C. 188 Alvaro, G. 32 Amat, M. 35, 143, 332 Amedjkouh, M. 234 Anderson, J.C. 82 Anderson, K. 83 Andersson, P.G. 232, 280 Andrade, C.K.Z. 24, 31 Andrus, M.B. 82, 92, 109, 239, 284, 338, 344 Andrusziewicz, R. 198 Angle, S.R. 151,179 Angyal, S.J. 297 Anslyn, E.V. 259, 373 Anson, M.S. 111 Antonioletti, R. 154 Antsypovitch, S.I. 300 Aoyama, T. 157, 344 Appendino, G. 249, 310 Arai, S. 37, 114, 135 Arai, T. 314 Aran, V.J. 191 Arcadi, A. 152 Ardisson, J. 276 Areces, P. 90 Argade, N.P. 110, 340, 334 Ariga, M. 169, 192 Arimura, T. 317 Ariza, X. 197, 342 Arjona, O. 52 Armarol, N, 315 Armaroli, N. 310 Armstrong, A. 113, 296 Arnaiz, F.J 270

Abele, E. 210 Abell, A.D. 50, 205 Abiko, A. 17 Abrahim, W.-R. 210 Adam, W. 114, 206, 284, 299 Adamczyk, M. 332 Adams, J.P. 303 Adolfsson, H. 20, 121 Advincula, R.C. 316 Afonso, C.A.M. 350, 354 Agami, C. 304 Agarwal, S. 292 Ager, D.J. 285 Aggarwal, V.K. 21, 35, 51, 135, 136, 194, 347 Ahlberg, P. 132 Airaksinen, A.J. 162 Aitken, R.A. 61 Akagi, M. 247 Aki, S. 77 Akiba, K. 262 Akita, H. 92, 147, 335, 341,343 Akiyama, T. 31,347 A1-Mourabit, A. 338 A1-Obeidi, F. 201,361,364 Alajarin, M. 172, 327 Alami, M. 273 Albaneze-Walker, J. 126 Albericio, F. 313, 364 Alcaide, B. 25, 90, 141, 194, 214, 282 Alcalde, E. 328 Aldrich, J.V. 367 Alexakis, A. 31, 39, 40, 49, 65,278 Ali, M.H. 359 Allegretti, M. 124 Allin, S.M. 79, 346 Almendros, P. 282 Alper, H. 91, 92 375

376

Arnold, D.R. 282 Arsenyan, P. 180 Asakawa, M. 324 Asfari, Z. 323 Ashram, M. 317 Athey, P.S. 204 Aube, J. 144, 332, 345 Aubert, C. 290, 310 Auge, J. 26, 207 Aumann, R. 69, 96 Aurrecoechea, J.M. 161 Autino, J.C. 222 Avenoza, A. 167 Avery, M.A. 186, 219 Azzena, U. 8 Baba, A. 2, 23, 38, 131,255 Bach, T. 75, 81, 83, 142, 182, 229, 335,337, 340 Back, T.G. 340 Backinowsky, L.V. 313 Backvall, J.-E. 12, 105, 124, 249, 290 Badham, N.F. 230 Bagley, M.C. 169, 205 Bailey, P.D. 167 Bailey, W.F. 213 Baird, M.S. 58 Bajwa, J.S. 253 Baker, R.W. 27 Bakulev, V.A. 204 Balasubramanian, K.K. 228 Balasubramanian, S. 356, 361,372 Baldwin, J.E. 40, 174, 285,344 Balicki, R. 126 Balker, A. 121 Ballini, R. 36, 54, 232 Balme, G. 85, 159 Banaigs, B. 335 Bandini, M. 27, 41 Banik, B.K. 126, 216, 217 Banks, H.D. 319 Bannwarth, W. 274

AUTHOR INDEX

Bansal, S.S. 314 Banthia, A.K. 314 Banwell, M.G. 79, 310, 334, 338,339 Barbakella, G. 83 Barbas, C.F., III 19, 68, 146, 242, 247, 347, 348 Bargon, R.M. 271 Barlos, K. 359 Barluenga, J. 62, 64, 96, 110, 166, 167, 176, 231,240, 361 Barrero, A.F. 176, 332, 339, 343 Barrett, A.G.M. 77, 344, 357, 358 Barriault, L. 99 Bartlett, P.A. 190 Bartolini, O. 113 Bartsch, R.A. 318, 319, 353 Basak, A. 140, 141,160 Basavaiah, D. 22, 120, 143 Baskaran, S. 133 Basu, B. 239 Bates, R.W. 290, 296 Batey, R.A. 24, 207, 341 Bathini, Y. 189 Batra, S. 18, 347 Bauer, T. 22 Bauerle, P. 193, 372 Bazan, G.C. 328 Beak, P. 21, 36 Beaton, G. 170 Beaucage, S.L. 226 Beccalli, E.M. 142 Beck, G. 276 Beckert, R. 207 Bedekar, A.V. 358 Bedford, R.B. 81, 82, 84, 164 Beer, P.D. 318 Begtrup, M. 161 Begue, J.-P. 113 Behar, V. 23, 85 Beletskaya, I.P. 8 Bellassoued, M. 17

AUTHOR INDEX

Beller, M. 81, 82, 92, 127, 238, 282, 352 Bellina, F. 96 Belot, F. 248 Benaglia, M. 270, 362 Benati, L. 141 Bencini, A. 329 Bendorf, H.D. 180 Benhida, R. 264 Benhide, R. 264 Benkovic, S.J. 372 Bennasar, M.-L. 95, 334, 336, 337, 341,346 Benner, S.A. 264 Benshafrut, R. 325 Benvegnu, T. 325 Beresnev, D.G. 213 Bergbreiter, D.E. 359 Bergman, J. 193, 206, 344 Bergman, R.G. 168 Bergmeier, S.C. 303 Beria, I. 333 Bernard, A.M. 177 Berteina,-Roboin, S. 362 Berthelette, C. 271 Bertozzi, C.R. 50, 367 Bertram, J.S. 295 Beshore, D.C. 214 Betra, S. 367 Bhide, B.H. 149 Bianchi, A. 329 Biehl, E. 158 Bilodeau, M.T. 237 Bjorsvik, H.-R. 118 Black, S.StC. 319 Blakemore, P.R. 283 Blankespoor, R.L. 364 Blass, B.E. 303,362, 363 Blechert, S. 49, 50, 161, 332, 335,336, 339 Bleicher, K.H. 362, 363,367 Blum, J. 59

377

Boaz, N.W. 127 Bochet, C.G. 222, 275 Bodo, B. 342 Bodwell, G.J. 70 Boeckman, R.K., Jr. 333,340, 344 Boger, D.L. 156, 301,332, 344, 367 Bohmer, V. 320 Bolm, C. 22, 121,130, 193,201 Bols, M. 246, 364 Bonacorso, H.G. 168 Bondarev, O.G. 10 Bonin, M. 114, 187 Bonini, C. 115,284 Bonjoch, J. 160 Bonnet, M.C. 120 Bonnet-Delpon, D. 113, 136, 332 Booker-Milburn, K.L. 75 Boons, G.J. 366 Borham, B. 229 Bosch, J. 35 Bose, A.K. 274 Bose, D.S. 149, 256 Botes, A.L. 122 Boto, A. 243 Botta, M. 357 Boudjouk, P. 267 Boumendjel, A. 85 Bouwman, E. 302 Bouzide, A. 128 Bowman, W.R. 173,212 Boyd, D.R. 110 Boyd, M.K. 226 Boykin, D.W. 82, 239 Bracher, F. 337 Braddock, D.C. 328 Bradley, M. 315, 365 Braga, A.L. 22, 26, 38, 57 Brana, M.F. 315 Branchaud, B.P. 79 Brandi, A. 362 Brase, S. 32 Braun, T. 293

378

Brel, V.K. 138 Brenna, E. 230, 295 Breslow, R. 109 Brimble, M.A. 18 Bringmann, G. 280, 339, 340 Brisbois, R.G. 59 Brisdon, A.K. 26 Brown, H.C. 120 Brown, J.M. 55 Brown, P.J. 367 Brown, R.C.D. 115, 150, 154, 345 Brown, R.T. 332 Brueggemeier, R.W. 178 Brummond, K.M. 90 Brun, P. 148 Brunner, H. 121 Bryce, M.R. 89 Bu, X.R. 27 Buchwald, S.L. 82, 83, 86, 90, 128, 160, 237, 239, 252, 269 Budnikova, Y.H. 275 Bueno, J.M. 360 Buisson, D. 122 Bujoli, B. 121 Bullington, J.L. 162 Bunce, R.A. 159, 165 Burger, K. 31,221 Burgess, K. 113 Buriak, J.M. 127 Burke, S.D. 50, 145 Burke, T.R., Jr. 245 Bumell, D.J. 143 Burstyn, J. 303 Burton, D.J. 56, 83 Buscemi, S. 205 Buszek, K.R. 149 Butenschon, H. 76, 94 Butters, T.D. 298 Cabiddu, S. 156 Cacchi, S. 82, 152, 190, 208, 210, 211,270, 353

AUTHOR INDEX

Caddick, S. 55, 272 Cai, D. 87 Cai, M.-Z. 55, 97, 261 Cain, G.A. 130 Calhorda, M.J. 10 Calo, V. 193 Calter, M.A. 156, 345 Caminade, A.-M. 81, 313 Campagne, J.-M. 129 Campos, K.R. 2 Campos, P.J. 161,261 Cao, X. 48, 314 Capparelli, M.V. 267 Capretta, A. 360 Carboni, B. 56, 82 Carda, M. 30, 169, 333,335, 342, 343 Carreira, E.M. 26, 30, 296, 340, 345 Carreno, M.C. 41,344 Carretero, J.C. 6 Casey, M. 79, 184 Castedo, L. 217 Castro, A.M.M. 11 Cava, M.P. 157, 207 Cerero, S. de la M. 310 Cerichelli, G. 2 Cesare, V. 139 Cetusic, J.R. 338 Cha, J.K. 14, 35, 64, 182 Chakraborti, A.K. 224 Chakraborty, T.K. 245, 335 Chamberlin, A.R. 336, 369 Chan, A.S.C. 26, 38, 121,127, 265 Chan, K.S. 114, 266 Chan, W.L. 26 Chandrasekaran, S. 291 Chandrasekhar, S. 126, 130, 172,217,335,359 Chandrasekhar, V. 82 Chang, H.S. 106 Chang, N.-C. 124, 143 Chang, S. 94, 105, 365 Chang, Y.-T. 370

AUTHOR INDEX

Chapleur, Y. 115 Charbonniere, L.J. 257 Charette, A.B. 62, 347 Chatani, N. 54, 79, 142 Chattopadhyay, A. 263 Chattopadhyay, S.K. 55 Chaudhari, R.V. 240 Chauhan, P.M.S. 367 Chauhan, S.M.S. 112 Chaumeil, H. 82 Chavan, S.P. 107 Che, C.-M. 105, 112, 137, 316, 359 Chelucci, G. 278 Chemla, F. 137, 162, 244, 304 Chen, C.-T. 80 Chen, F.-E. 257 Chen, J.J. 358 Chen, K. 136 Chen, L. 368 Chen, L.-C. 169 Chen, M.-Y. 225 Chen, Q. 320 Chen, Q.-Y. 17, 63 Chen, S.T. 143 Chen, Y.-J. 78 Chen, Z.-C. 354 Chenault, J. 187 Chenevert, R. 337, 346 Cheng, C.-H. 84, 89, 94, 95, 149, 232, 273 Cheng, J.-F. 360, 361 Cheng, J.-P. 318, 347 Cheng, S. 364 Cheng, Y. 165,368 Cheon, S.H. 337, 338 Chi, D.Y. 168, 255 Chiacchio, U. 38, 156 Chiang, L.Y. 306 Chida, N. 342, 345 Chin, C.S. 291 Cho, B.T. 120, 279 Cho, C.-G. 56, 70, 81

379

Cho, C.S. 2, 148, 174 Cho, Y.S. 179 Choi, J.H. 351 Choi, M.C.K. 127 Chong, J.M. 22, 32, 123 Chopa, A.B. 272 Chou, S.-S.P. 8, 167 Choudary, B.M. 31, 115 Christie, S.D.R. 289 Christoffers, J. 109 Christopherson, R.I. 300 Chu, C.K. 343 Chung, S.-K. 335, 339, 345, 370 Chung, W.-S. 70 Chung, Y.K. 90, 349 Chupakhin, O.N. 213 Cignarella, G. 212 Cintrat, J.-C. 96 Ciufolini, M.A. 159, 170, 337 Clapham, B. 361 Clark, A.J. 287 Clarke, P.A. 179, 249 Clayden, J. 13, 88 Clennan, E.L. 115 Clive, D.L.J. 71, 97, 273,344 Clivio, P. 77 Coates, G.W. 140,275 Coates, R.M. 27 Coelho, F. 343 Cohen, J.I. 354 Cohen, T. 43 Colacot, T.J. 84 Colbert, F. 334 Coldham, I. 9, 158 Collins, I. 211 Collins, J.L. 360 Colobert, F. 82, 255 Colombo, L. 100 Comasseto, J.V. 266 Cominos, D.L. 75 Comins, D.L. 197 Compernolle, F. 143

380

Concellon, J.M. 47, 62, 128, 132 Conde-Frieboes, K. 198 Cook, G.R. 345 Cook, J.M. 332, 335, 336, 337, 341 Cooke, A. 99 Cordero, F.M. 362 Cordham, I. 183 Corelli, F. 357 Corey, E.J. 26, 67, 108, 283, 333,336, 339, 343 Cortes, D. 108 Cossy, J. 50, 102, 116, 122, 173, 180, 231,232, 290, 342, 344, 345 Costa, P.R.R. 36, 119 Costa,M. 196 Couladouros, E.A. 332, 345, 367 Cousins, R.P.C. 176 Couture, A. 22, 333 Couturier, M. 226 Couty, F. 100, 139 Covey, D.F. 334 Cozzi, P.G. 41, 78 Crabtree, R.H. 59, 121 Cragg, P.J. 320 Credi, A. 316 Crich, D. 86, 248, 270, 341,366 Crimmins, M.T. 340, 345 Cristau, H.J. 286 Cristea, I. 114 Cristoph, G. 42 Crotti, P. 227 Crouch, R.D. 225 Crousse, B. 136 Csaky, A.G. 42, 188 Csuk, R. 263 Cunha, S. 259 Cunico, R.F. 34, 237 Curini, M. 135, 215, 235 Curran, D.P. 170, 171, 231, 274, 357 Custelcean, R. 326

AUTHOR INDEX

Dahanukar, V.H. 12 Dahl. R. 174 Dai, W.-M. 45, 152, 165 Dal Piaz, V. 212 Dal Pozzo, A. 242 Dalko, P.I. 232 Dalla, V. 138 Dallavalle, S. 340 Dallemagne, P. 157, 167 Dang, Q. 166 Danheiser, R.L. 87 Danishefsky, S.J. 50, 51, 52, 88, 150, 222, 337, 338, 341,345, 346 Daran, J.-C. 6 Darcy, R. 330 Darses, S. 38 Das, B. 249, 256 Das, N.B. 218 Datta, A. 337 Dauban, P. 137 Davenport, R.J. 144 David, M. 360 Davies, H.M.L. 42, 62, 70, 243, 339 Davies, S.G. 4, 98, 235, 245, 335,338,339 Davis, F.A. 243, 346 de Azevedo, C.G. 290 De Brabander, J.K. 15 De Clecq, P.J. 71 De Kimpe, N. 65, 209 de la Pradilla, R.F. 99, 112 de Lederkremer, R.M. 248 de Lijser, H.J.P. 217 de March, P. 183, 341 de Meijere, A. 64, 67, 163 de Mendoza, J. 323 De Nino, A. 119 De Schryuer, F.C. 312 de Vries, J.G. 91 De, A. 156 Deaton-Rewolinski, M.V. 220 Dechoux, L. 171

AUTHOR INDEX

Decout, J.-L. 299, 304 Decurtins, S. 193 Deelman, B.-J. 354 Dehaen, W. 204, 313 Delgado, A. 22 Deligoz, H. 319 Delogu, G. 120 Demir, A.S. 84, 115, 161,230 Demuth, M. 10 Deng, J.-G. 122 Deng, L. 251,269 Deng, M. 83 Deng, M.-Z. 89, 128 Deng, S. 334 Deng, Y. 351 Deng. J.-G. 316 Deniaud, D. 184 Denmark, S.E. 15, 24, 56, 81, 113, 282, 283,333 Denny, W.A. 160 Depres, J.-P. 333 Depreux, P. 223 Desai, R.C. 82 DeSantis, G. 230 Deshmukh, A.R.A.S. 246 DeShong, P. 96, 231 Deshpande, V.H. 333, 358 Desiraju, G.R. 325,327 Deslongchamps, P. 18, 46, 342 Desmaele, D. 55 DeVoss, J.J. 340 Dhar, T.G.M. 198 Dhimane, H. 68 Di Fabio, R. 32 Dias, H.V.R. 80, 136 Dias, L.C. 15, 68, 113 Diederich, F. 301 Dieguez, M. 6, 121, 129 Dieter, R.K. 335, 337, 338, 339, 346 Dietrich-Buchecker, C. 81 Diez, D. 66, 154 Ding, B. 208

381

Ding, J. 93 Ding, K. 6, 167, 176 Dinnell, K. 82 Dinsmore, C.J. 213 Diver, S.T. 50, 185 Dixneuf, P.H. 351 Dixon, R.A. 120 Dobbs, A.P. 179 Dodd, R.H. 137 Dolbier, W.R., Jr. 13, 17, 22, 261 Dolenc, D. 106 Dolphin, D. 66 Dominguez, E. 2, 181 Domling, A. 140 Dondoni, A. 188, 305, 319 Donohoe, T.J. 5, 114, 116, 125, 175,283, 342 Dordick, J.S. 106 Doris, E. 128, 132, 332 Doucet, H. 55, 81, 82 Dowden, J. 117 Doye, S. 160, 239, 261,266 Doyle, M.P. 55, 62, 339 Drueckhammer, D.G. 8 Du Bois, J. 137, 341 Dubreuil, D. 247 Duchene, A. 57, 93 Dufresne, C. 80 Duggan, P.J. 275 Dujardin, G. 174 Dulcere, J.-P. 67 Dumazet-Bonnamour, I. 319 Dunach, E. 117, 191,203 Duncton, M.A.J. 164 DuPont, J. 352 Dussau, P.H. 232 Dvorak, D. 10, 84 Dwek, R.A. 298 Dyson, P.J. 126 Eames, J. 202, 280 Eberhard, M.R. 59

382

Echavarren, A.M. 94, 333 Eckert, C.A. 351 Eggleston, I.M. 340 Eibracht, P. 151 Eklund, P.C. 339 E1 Ashry, S.H. 204 E1 Gaied, M.M. 18, 252 E1 Kaim, L. 204 E1-Qisairi, A.K. 109 E1-Rady, E.A. 205 Eliseev, A.V. 372 Elkaim, L. 363 Ellervik, U. 248, 366 Elliot, M.C. 211 Ellman, J.A. 16, 245, 279, 368 Elsevier, C.J. 129 Enders, D. 1, 8, 17, 29, 30, 33, 37, 40, 45, 140, 196, 200, 202, 240, 284, 334, 335 Engberts, J.B.F.N. 73 Engel, R. 354 Engman, L. 160 Epifano, F. 235 Erdik, E. 241 Erhardt, P.W. 294 Ermolenko, M.S. 337 Ernst, H. 294 Eschavarren, A.M. 292 Esmaili, A.A. 182 Estevez, R.J. 337 Evans, D.A. 15, 17, 147, 253, 334, 337 Evans, D.H. 176 Evans, P. 90 Evans, P.A. 94 Evans, W.J. 292 Faber, K. 136, 333, 343 Fahti, R. 151 Fairbanks, A.J. 228 Fairfax, D.J. 189 Faita, G. 357, 358 Falck, J.R. 48, 80, 153,335, 337

AUTHOR INDEX

Faller, J.W. 59, 73, 121,129 Familoni, O.B. 289 Fan, Q-H. 128 Fang, J.-M. 77 Fang, W.-S. 311 Farras, J. 264 Fathi, R. 82, 151 Fearnley, S.P. 71 Fedorov, A.Y. 175 Fehr, C. 346 Feit, B.-A. 83 Feiters, M.C. 330 Feldman, K.S. 83, 332, 343 Feng, J.-C. 217 Feng, X. 27, 176 Fensterbank, L. 58, 65, 279 Fenteany, G. 225 Feringa, B.L. 18, 39, 127 Fernandez, J.M. 297 Fernandez-Forner, D. 365 Fernandez-Lafuente, R. 230 Feroci, M. 234 Ferraz, H.M.C. 43, 115, 178, 295 Ferreira, P.M.T. 162 Fiandanese, V. 57 Fields, S.C. 218 Figueredo, M. 342, 343 Figueroa-Perez, S. 361 Filippone, P. 186 Finet, J.-P. 175 Fink, M.J. 266 Finney, N.S. 105 Fioravanti, S. 137 Firouzabadi, H. 120, 125, 216, 217, 256, 272 Fischer, B. 265 Fisera, L. 263 Fleet, G.W.J. 130 Fleming, F.F. 16, 37, 47, 286 Fleming, S.A. 76 Fletcher, N.C. 278 Flitsch, S.L. 366

AUTHOR INDEX

Floreancig, P.E. 179 Florent, J.-C. 50 Flores, A.F.C. 186 Florio, S. 9, 49, 64 Fogagnolo, M. 113 Fogg, D.E. 49 Fokin, A.A. 286 Fokin, V.V. 203 Forsyth, C.J. 175 Fort, Y. 81, 87, 131,209, 239, 240 Fraga, C.A.M. 160, 194 Frank, X. 332 Fraser-Reid, B. 229 Frechet, J.M.J. 312 Freeman, S. 302 Frejd, T. 86, 122 Frey, J. 81 Fry, A.J. 126 Fryatt, R. 289 Fu, G.C. 29, 38, 69, 75, 81, 89, 94, 121,139, 141,235,291 Fu, X. 86 Fuchs, B. 315 Fuchs, P.L. 108, 132, 344 Fuentes, J. 264 Fuji, K. 345 Fujii, N. 10, 245 Fujita, K. 106, 131,168 Fujita, M. 69, 281 Fujiwara, K. 180, 344 Fujiwara, S. 92 Fukase, K. 330, 364, 366 Fukuda, Y. 332 Fukumoto, Y. 257 Fukuyama, T. 118, 163, 181, 194, 336, 337, 346, 364 Fukuyama, Y. 334, 341 Fullop, F. 363 Funabiki, K. 11 Funk, R.L. 337 Furber, M. 204

383

Furstner, A. 81, 85, 129, 328, 332, 335,337, 338, 346 Furstoss, R. 150 Fustero, S. 245 Fyles, T.M. 329 Gais, H.-J. 21, 39, 271 Gait, M.J. 371 Gallagher, T. 82, 83 Gallos, J.K. 195 Gammon, D.W. 342 Gan, L. 307, 308 Ganem, B. 124, 196 Ganesan, A. 12, 84, 352 Ganguly, N.C. 217 Gansauer, A. 42 Garcia, H. 286 Garcia, J. 197 Garcia-Mera, X. 263 Garcia-Valverde, M. 108, 202 Garrett, C.E. 234 Gasfaldi, S. 273 Gauthier, D.R., Jr. 83 Gautier, A. 48 Gavezzotti, A. 301 Gawley, R.E. 312 Genet, J.-P. 38, 121,153, 349, 363 Gennari, C. 365 Georghiou, P.E. 317, 346 Gerasko, O.A. 281 Gerog, G.I. 336 Gerrard, J.A. 284 Gerusz, V. 85 Gervay-Hague, J. 228 Geuorgyan, V. 267 Geyer, A. 248 Ghosez, L. 67 Ghosh, A.K. 17, 119 Ghosh, C.K. 170 Ghosh, S. 338 Ghosh, S.K. 334 Giacomelli, G. 223, 234, 255

384

Giannis, A. 107 Gibson, S.E. 90, 277, 329 Gielen, H. 259 Gilbert, A.M. 185 Gilbert, I.H. 367 Gill, M. 343,346 Gimbert, Y. 102, 311 Gin, D.Y. 183 Giner, J.-L. 341,343 Giorgi, C. 329 Giorgi-Renault, S. 168 Giralt, E. 313,365 Gladysz, J.A. 254, 274, 275 Glass, T.E. 321 Glatzhofer, D.T. 251 Gleason, J.L. 5,366 Gleiter, P. 207 Glorius, F. 142 Gmeiner, P. 142, 362 Goeldner, M. 226 Gomaa, M.A.-M. 67 Gomez, A.M. 89 Gomez, M. 6, 120 Gonda, J. 184 Gong, L. 6 Gong, Y. 82 Gonzalez, C. 217 Gonzalez, J. 139 Gonzalez-Muniz, R. 139 Gonzalez-Nogal, A.M. 186 Gooben, L.J. 84 Goodman, J.M. 18 Goodman, M. 370 Goodson, F.E. 89 Goosen, L.J. 29, 55 Gopalan, A.S. 178 Gordon, C.M. 352 Gorwa-Grauslund, M.F. 122 Gotor, V. 122, 230, 250, 275 Gottardo, C. 59 Gottlich, R. 168 Gottschalk, K.-E. 301

AUTHOR INDEX

Gouverneur, V. 293 Gowda, D.C. 132, 258 Gracza, T. 338 Graham, D. 126 Grandas, A. 264 Grande, M. 141 Gray, N.S. 368 Graybill, T.L. 362 Grayson, D.H. 154 Gree, R. 104, 293 Greene, A.E. 102, 311 Grela, K. 60, 180, 357 Gribble, G.W. 85, 87 Grieco, P.A. 59 Griesbeck, A.G. 278 Grigg, R. 142, 158, 160, 164, 181, 194, 336, 373 Grignon-Dubois, M. 42 Grimmes, S. 42 Grinstaff, M.W. 264, 303 Gross, P.H. 42 Grossman, R.B. 37 Groth, U. 33, 91 Grotjahn, D.B. 186 Groziak, M.P. 264 Grubbs, R.H. 23, 50, 52 Grushin, V.V. 293 Gryko, D.T. 209 Grzybowski, B.A. 372 Gu, Y.G. 158 Guarna, A. 245 Guibe, F. 64, 142 Guicharo, G. 109 Guillaumet, G. 82 Guillemin, J.C. 355 Guillerm, G. 336 Guiry, P.J. 6, 239 Guisan, J.M. 230 Guiso, M. 55 Guldi, D.M. 306, 326, 331 Gung, B.W. 342 Guo, M.-J. 355

AUTHOR INDEX

Guo, Q.-X. 26 Guo, Z. 346 Gurjar, M.K. 3, 82, 180, 345 Gutsche, C.D. 317 Ha, H.-J. 210 Haag, R. 274 Haas, R. 82 Habibi, M.H. 249 Haddad, N. 186 Haddleton, D.M. 351 Haddon, R.C. 331 Hagiwara, H. 51,333,335, 336, 345 Hahn, H.-G. 201 Haider, N. 70, 212 Hajipour, A.R. 111, 217, 223,255, 270 Halcomb, R.L. 23 Hale, K.J. 244 Haley, M.M. 185, 304, 324 Hall, D.G. 145 Hallberg, A. 86 Ham, W.-H. 342, 345 Hamachi, I. 326 Hamada, Y. 23, 244, 341 Hamama, W.S. 214 Hamilton, A.D. 325 Hamilton, D.G. 331 Hammond, G.B. 67 Han, H. 6 Han, L.-B. 265 Hanamoto, T. 92 Hanessian, S. 120, 158, 248, 332, 336, 361,362 Hanna, I. 52 Hannon, M.J. 326 Hansch, C. 276 Hansch, M. 15 Hansen, T.V. 333 Hanson, P.R. 51 Hanzawa, Y. 38 Haque, T.S. 368 Hara, S. 89, 254

385

Harada, T. 15 Haraguchi, K. 263 Harayama, T. 83, 142 Harmata, M. 53 Haroutounian, S.A. 33 Harrity, J.P.A. 195 Harrowven, D.C. 55 Hartley, R.C. 291,361 Hartung, J. 284, 287 Hartwig, J.F. 83, 159, 239, 261,262 Haruta, M. 361 Harvey, D.F. 62 Harvey, R.G. 113 Harwood, L.M. 68 Hasegawa, E. 33 Hashihayata, T. 159 Hashimoto, K. 161 Hashimoto, M. 223 Hashimoto, S. 15, 150, 271 Hassner, A. 234 Haswell, S.J. 274 Hatakeyama, S. 337 Hatcher, M.A. 99 Hattori, T. 221 Haufe, G. 68, 230 Hauser, F.M. 248, 341 Hayashi, M. 116 Hayashi, T. 18, 26, 38, 42, 50, 82, 84, 114, 267 Hayashi, Y. 18, 333, 337, 342 Hayes, C.J. 145, 242 Hazarkhani, H. 256 Heasley, V.L. 253 Heathcock, C.H. 118, 158 Hecht, S.M. 335 Hedenstrom, E. 250 Hedrick, J.L. 249 Hedstrom, L. 299 Hegedus, L.S. 6, 263 Hekmatshoar, R. 122, 256 Helal, C.J. 184

386

Heldmann, D.K. 224 Hell, Z. 198 Hellberg, J. 330 HeUer, B. 167 Helmchen, G. 11,339, 345 Henegar, K.E. 334 Henichart, J.-P. 168, 170 Henkel, B. 363 Heravi, M.M. 218 Herdewijn, P. 300 Hermitage, S.A. 184 Hernandez, R. 243 Herndon, J.W. 69 Herranz, R. 246 Herrmann, W.A. 82, 287 Hesse, M. 336 Heydari, A. 260, 274 Hibert, M. 239 Hibino, S. 170, 220 Hidai, H. 61 Hidai, M. 177 Hiegel, G.A. 255 Hiemstra, H. 32, 361 Hiersemann, M. 100, 283 Higashiyama, K. 137 Hilt, G. 57, 69, 282 Hioki, H. 317 Hirama, M. 82, 296, 334 Hirao, T. 42, 82, 326 Hiratani, K. 324 Hiroi, K. 150 Hirota, K. 131 Hiroya, K. 165 Hirsch, A. 307 Hitchcock, S.R. 17 Hiyama, T. 95, 237, 283, 291 Hlastra, D.J. 359 Hlavaty, J. 60 Ho, T.-I. 192 Ho, T.-L. 345 Hodge, P. 371 Hodgetts, K.J. 196

AUTHOR INDEX

Hodgson, D.M. 9, 49, 268, 289, 342, 346 Hofmann, R.V. 119, 199 Holmes, A.B. 81, 82, 339 Holten, D. 208 Honda, T. 209, 341,346 Hong, B.-C. 74 Hong, J.H. 50 Hoornaert, G.J. 157 Hopfl, H. 328 Hoppe, D. 9, 42 Hori, H. 333, 368 Horiguchi, Y. 169 Horiuchi, C.A. 195 Home, D.A. 333, 335, 336 Horvath, I.T. 80, 303 Hoshi, M. 89 Hoshino, O. 90, 135, 183 Hosokawa, T. 55 Hosomi, A. 15, 178, 253 Hossain, M.M. 62 Hosseini, M.W. 321 Hosseinzadeh, R. 104, 217, 239 Hou, X.-L. 6, 20, 137, 240 Houghten, R.A. 185, 362, 360, 368 House, D. 209 Hoveyda, A.H. 27, 38, 39, 44, 51, 153, 169 Howell, A.R. 214 Hrebabecky, H. 263 Hruby, V.J. 82, 127, 202, 245 Hsung, R.P. 100, 142, 167, 170, 333 Hu, L. 18, 221 Hu, Q.S. 315 Hu, X.E. 169 Hu, Y. 22 Huang, H.-C. 279 Huang, X. 35, 46, 107, 148, 171,260, 358 Huang, Z.-T. 14 Huang, Z.-Z. 46 Hudlicky, T. 336

AUTHOR INDEX

Hughes, A.B. 242 Hughes, D.L. 7 Hulme, A.N. 17 Hulme, C. 362, 363 Humphrey, M.G. 316 Husson, H.-P. 168 Hutchings, G.J. 113 Hwang, G.T. 318 Hyeon, T. 82, 349 Iadonisi, A. 228 Ibrahim, Y.A. 49 Ibrahim-Ouali, M. 71,180 Ichikawa, Y. 48 Igglessi-Markopoulou, O. 148 Ihara, M. 44, 71,160, 292 Ikariya, T. 122, 135 Ikeda, S. 54, 95 Ikegami, S. 89, 359 Ikemoto, N. 29 Ikunaka, M. 245 Ila, H. 79, 85, 101 Imamoto, T. 165 Imamura, P.M. 339 Imanishi, T. 337 Imperiali, B. 242 Inanaga, J. 138 Indolese, A.F. 84, 92 Inesi, A. 234 Ingenito, R. 356 Inomata, K. 194 Inoue, Y. 38 Iqbal, J. 49, 170 Iqbal, M.A. 220 Iranpoor, N. 120, 125, 216, 256, 272 Isaacs, L. 330 Ishar, M.P.S. 75 Ishibashi, H. 45, 286 Ishihara, H. 266 Ishii, Y. 42, 92, 252, 258 Ishikawa, T. 277, 339

387

Ishino, Y. 21, 25 Ishiyama, T. 56, 262 Ishizaki, M. 90, 135, 183 Isobe, M. 78, 336 Itami, K. 91 Ito, K. 317, 320 Ito, M. 121,342 Ito, O. 306 Ito, Y. 179, 224, 262, 298, 371 Itoh, A. 116 Itoh, K. 67, 171 Itoh, T. 189, 351 Iwasa, S. 105 Iwasawa, N. 75, 86, 158 Iyengar, D.S. 224 Izawa, K. 135 Izquierdo, I. 345, 339 Jabin, I. 145 Jackson, J.E. 326 Jackson, R.F.W. 36, 145, 164 Jacobi, P.A. 96 Jacobs, P.A. 350 Jacobsen, E.N. 19, 27, 34, 148, 174,231,235 Jagannadh, B. 172 Jalon, F.A. 127 James, K.D. 333 Janda, K.D. 19, 314, 355, 358, 361,366, 373 Jang, D.O. 348, 349 Janin, Y.L. 82 Janssen, R.A.J. 83 Jaramillo, C. 361 Jarosz, S. 279 Jaskolski, M. 325, 327 Jedlinski, Z. 213 Jefferson, E.A. 370 Jenks, C.W. 187 Jenner, G. 27, 301 Jensen, K.J. 298, 366 Jeong, I.H. 25

388

Jeong, J.H. 22 Jerschow, A. 276 Jessop, P.G. 235 Jew, S. 3, 244, 334 Jia, G. 127 Jiang, B. 26, 90, 156, 170, 193, 240, 336, 338, 345 Jiang, X. 234, 253 Jiang, Y. 27, 127, 176 Jikai, L. 294 Jimenez-Barbero, J. 366 Jin, M.-J. 6 Jin, T.-S. 188, 223 Jin, Z. 56, 343 Johannsen, M. 267 Johnson, J.S. 27 Johnston, J.N. 160 Jonczyk, A. 86 Jones, S. 277 Jonsson, D. 364 Jorgensen, K.A. 16, 19, 36, 197, 236, 240, 242, 244 Joseph-Nathan, P. 336, 337, 343 Joshi, N.N. 195, 231,252 Joullie, M.M. 339, 346 Judeh, Z.M.A. 351,353 Jun, C.-H. 79, 93, 94 Jung, G. 343 Jung, K.W. 80, 82, 95,238, 365 Jung, M. 337 Jung, M.E. 68, 103, 176 Junjappa, H. 79, 85, 101 Jurczak, J. 22, 26, 112 Jursic, B.S. 27 Kabalka, G.W. 22, 349 Kaberdin, R.V. 214 Kadouri-Puchot, C. 245 Kagan, H.B. 250, 292 Kai, H. 195 Kaimal, T.N.B. 249 Kakinuma, K. 346

AUTHOR INDEX

Kakiuchi, K. 91 Kalaus, G. 340, 341,342, 346 Kalbaka, G.W. 34 Kalchenko, V.I. 320 Kalesse, M. 17, 296 Kamal, A. 119, 133, 134, 215, 216, 369 Kambe, N. 11, 92 Kamimura, A. 18, 141,155, 195, 269 Kanakahara, T. 78 Kanbara, T. 321 Kaneda, K. 107 Kaneko, S. 227 Kanemasa, S. 36, 194, 214 Kang, J. 237 Kang, S.-K. 25, 91, 94, 161,237 Kang, S.H. 343 Kanger, T. 198 Kann, N.C. 96 Kanth, J.V.B. 289 Kantlehner, W. 232 Kappe, C.O. 69, 266 Karami, B. 270 Karikomi, M. 154 Karimi, B. 192, 215, 216, 222, 270 Karlsson, S. 194 Karoyan, P. 162 Katayama, H. 188 Kato, K. 92, 300 Kato, S. 87 Kato, T. 337 Katoh, T. 333, 338 Katritzky, A.R. 9, 14, 18, 30, 162, 172, 181,184, 189, 192, 195, 202, 203,206, 209 Katsuki, T. 111, 112, 146, 222 Katsumura, S. 343 Katti, S.B. 202 Kaufman, T.S. 120 Kaufmann, D.E. 85 Kawada, A. 258 Kawahara, N. 79, 154

AUTHOR INDEX

Kawamura, Y. 177 Kawanami, Y. 38 Kawano, T. 82, 327 Kawasaki, T. 336 Kay, K.-Y. 309 Kaye, P.T. 149, 178 Kazemi, F. 222 Kazmaier, U. 100, 273 Keck, G.E. 29, 123, 179 Keese, R. 208 Keller, P.A. 307 Kelly, T.R. 169 Kende, A.S. 68, 339, 345 Kennedy, A.L. 358 Kerr, M.A. 78 Keuthe, J.T. 120 Khadilkar, B.M. 105, 353 Khan, A.T. 215,216 Khan, F.A. 116 Khazaei, A. 217 Khlebnikov, A.F. 66 Khodaei, M.M. 217 Khurana, J.M. 134 Kiasat, A.R. 222 Kibayashi, C. 332, 335, 340, 344 Kidwai, M. 188 Kielbasinski, P. 250 Kiesman, W.F. 68 Kiessling, L.L. 50, 359 Kigoshi, H. 332 Kikugawa, Y. 257 Kilburn, J.D. 281,368 Kilburn, J.P. 362, 365 Kim, B.H. 320 Kim, D. 333 Kim, D.Y. 254 Kim, G.-J. 121 Kim, H.R. 154 Kim, J.N. 7, 85, 93, 173, 272 Kim, K. 187, 200, 324, 325, 331,344 Kim, M.-J. 122 Kim, S. 5, 256, 332, 343,345

389

Kim, S.S. 105, 111 Kim, T.H. 4,235 Kim, Y.G. 114, 229, 236 Kim, Y.H. 38, 132 Kimura, M. 168 Kinder, F.R., Jr. 297 King, A.S.H. 302 King, S.B. 195 Kinoshita, H. 46 Kinston, D.G.I. 296 Kirihara, M. 250 Kirmse, W. 285 Kirsch, G. 157 Kirschleger, B. 175 Kirschning, A. 21, 50, 357 Kirwin, S.K. 65 Kise, N. 42 Kishi, Y. 10, 342 Kita, T. 80 Kita, Y. 68, 81,250, 336 Kitade, Y. 263 Kitahara, T. 338 Kitamura, M. 221,238 Kitamura, T. 149 Kitas, E.A. 368 Kitching, W. 343 Kiyooka, S. 15 Klebe, G. 281 Klumpp, D.A. 78 Knight, D.W. 154, 159 Knight, J.G. 143 Knizhnikov, V.A. 291 Knochel, P. 11, 31, 83, 87, 97, 127, 165, 238, 240, 265, 289 Knolker, H.-J. 209, 334 Knowles, W.S. 278 Ko, S.Y. 345 Kobayashi, N. 362 Kobayashi, S. 15, 19, 49, 186, 249, 252, 274, 277, 340, 347 Kobayashi, Y. 10, 11, 82, 341 Koch, G. 17, 100

390

Koch, T. 265 Kodadek, T. 366 Kodomari, M. 362 Kohler, K. 82, 84 Kohnke, F.H. 317, 320 Koike, T. 168 Kojima, S. 47 Koketsu, M. 266 Kokotos, G. 242, 314 Komatsu, K. 306 Komatsu, M. 92, 136, 159, 362 Kondo, Y. 361,363 Konno, H. 143 Konno, T. 10, 59 Konopelski, J.P. 83 Konwar, D. 256 Kool, E.T. 264, 301, 371 Koreeda, M. 248, 340, 345 Koshima, H. 204 Kotha, S. 82, 285 Kouklovsky, C. 194 Kouznetsov, V. 166, 212 Kovalev, V. 319 Kozbwski, M.C. 107 Kozhevnikov, I.V. 77 Kozlowski, M.C. 24, 70 Kozmin, S.A. 340, 343 Krafft, M.E. 91 Krakowiak, K.E. 213 Krapcho, A.P. 213 Kraszewski, A. 264 Kraus, G.A. 28, 68, 78, 88, 335 Krause, N. 38, 153,279 Krawczyk, H. 41 Krchnak, V. 372 Krief, A. 334, 341 Krische, M.J. 18, 41 Krishnamurthy, D. 33 Krohn, K. 295 Kroulik, J. 180 Kruchok, I.S. 47 Ku, Y.-Y. 332

AUTHOR INDEX

Kuethe, J.T. 167 Kuhrnert, N. 346 Kukushkin, V.Y. 289 Kulinkovich, O.G. 47 Kulkarni, M.G. 341 Kumar, K. 299 Kumar, N.A. 300 Kumar, P. 336, 343 Kumar, S. 24, 82 Kume, M. 150 Kundig, E.P. 74, 194 Kundu, B. 360, 361,362, 369 Kunishima, M. 218 Kuniyasu, H. 282 Kunz, H. 221,356 Kunzer, A. 236 Kurasawa, Y. 212 Kurihara, T. 45 Kurosu, M. 26 Kurth, M.J. 195, 213, 244, 299, 356, 361,365 Kusano, G. 298 Kutschy, P. 341 Kwan, M.L. 47 Kwochka, W.R. 328 La Ferta, B. 298 Laali, K.K. 353 Lacour, J. 114 Lahuerta, P. 62 Lai, J.Y.Q. 360 Lai, Y.-H. 327 Laine, P. 324 Lakouraj, M.M. 111,229, 268 Lallemand, J.-Y. 66 Lam, K.S. 371 Lam, Y. 361 Lamaty, F. 356 Lambert, J.B. 302 Lamberth, C. 299 Lammertsma, K. 208 Landais, Y. 43

AUTHOR INDEX

Langa, F. 308 Lange, M. 186 Lange, U.E.W. 360 Langer, P. 50, 162, 286 Langlois, Y. 194 Lapidus, A.L. 92 Lappert, M.F. 288, 292 Larcheveque, M. 132 Larhed, M. 82 Larock, R.C. 13, 86, 87, 92, 94, 149, 158, 171,173, 335 Lasammertsma, K. 287 Laschat, S. 90, 127, 352 Lash, T.D. 320 Lasperas, M. 22 Lassaltta, J.M. 139 Lattanzi, A. 112, 154 Lattman, M. 323 Lattuada, L. 238 Lau, J.F. 167 Laufer, S. 185 Lautens, M. 89, 181,240, 290, 334, 339 Lavilla, R. 211 Lawrence, D.S. 223 Lawrence, N.J. 86 Lazny, R. 364 Le Merrer, Y. 50 Le Quesne, P.W. 341 Le Roux, C. 292 Leadbeater, N.E. 347 Lebel, H. 47 Lebreton, J. 122, 340, 344 Lectka, T. 19, 139, 277 Lee, A.S.-Y. 145, 225 Lee, B.H. 369 Lee, C. 253 Lee, C.-H. 321 Lee, D. 34, 180 Lee, D.G. 108 Lee, E. 152, 332, 340, 343 Lee, J.C. 108, 118, 251

391

Lee, P.H. 57, 58 Lee, W.S. 187 Leger. S. 193 Legraverend, M. 361 Legzdins, P. 303 Lehn, J.-M. 324, 325 Leighton, J.L. 26, 92 Leitner, W. 57 Lemaire, M. 82, 121,289 Lemiere, G.L.F. 212 Lepore, S.D. 356 Lequeux, T. 180 Lesma, G. 167 Lete, E. 30 Lett, R. 82, 150, 342, 344 Leumann, C.J. 35 Leung, M. 59 Levacher, V. 120 Levai, A. 186, 211 Ley, S.V. 17, 99, 107, 333, 336, 342, 343, 346, 357, 368 Lhommet, G. 68 Li, C. 95, 104, 112 Li, C.-J. 15, 30, 38, 53, 85, 170, 348, 349, 353 Li, C.-S. 176 Li, C.-T. 348 Li, G. 18, 184 Li, G.Y. 81, 82 Li, J.J. 152 Li, K. 202 Li, R. 158 Li, W. 262 Li, W.-D.Z. 15 Li, W.-R. 344 Li, Y. 121,305 Li, Y.-L. 338 Li, Z. 109 Li, Z.M. 170 Liao, C.-C. 70, 302 Liao, Y. 151 Liebeskind, L.S. 270

392

Liebscher, J. 4 Liese, A. 231 Lievre, C. 46 Lightner, D.A. 189 Lin, C.-C. 121,225, 227, 248 Lin, C.-H. 247 Lin, G.-Q. 27, 146, 338 Lin, W. 316 Linclau, B. 251,359 Linde, C. 112 Lindell, S.D. 87 Lindsey, C.W. 357 Lindsey, J.S. 208 Lindsley, C.W. 134 Lindstrom, U.M. 350 Liotta, D.C. 19 Lipshutz, B.H. 12, 121,334 Liskamp, R.M.J. 234, 245 List, B. 20, 236, 280 Liu, B. 200 Liu, J. 29 Liu, L. 26 Liu, R.-S. 141, 152 Liu, W. 333 Liu, Z.-Y. 337 Livinghouse, T. 160 Llera, J.M. 139 Lloyd, D. 302 Lloyd-Jones, G.C. 6, 292 Lo, L.-C. 230 Lobo, A.M. 98, 212 Loh, T.-P. 19, 20, 24, 98, 177, 179 Loiseleur, O. 17 Lopez, F.J. 87 Lopez, J.C. 89 Lou, B. 363 Lou, J.-D. 104, 105 Louie, J. 149 Lovely, C.J. 136, 158 Lowary, T.L. 238, 248 Lowden, C.T. 364 Lu, G.-Y. 321

AUTHOR INDEX

Lu, J. 188 Lu, T.-J. 243 Lu, X. 67, 197 Lu, Z.-H. 125 Luh, T.-J. 118 Luh, T.-Y. 83, 288 Luis, S.V. 358 Lukashev, N.V. 80 Lukes, I. 317 Lukevics, E. 210 Luna, D. 198 Luning, U. 371 Luo, G. 358 Lusinchi, M. 355 Luthman, K. 119 Lutzen, A. 83 Lygo, B. 3, 113 Ma, D. 19, 79, 156, 341,342 Ma, J. 320 Ma, S. 58, 79, 83, 85, 147, 153, 160, 178, 250 Ma, Y. 63 Macias, F.A. 338 MacMillan, D.W.C. 19, 40, 68 Maddaluno, J. 165, 174 Madsen, R. 334 Madsen, U. 38, 88 Maes, B.U.W. 239 Magnus, P. 90, 195, 340, 343 Mahajan, M.P. 189, 302 Maier, M.E. 50, 71, 72, 97, 101,178 Maison, W. 190,245 Majoral, J.-P. 81, 313, 316 Majumdar, K.C. 211 Makabe, H. 345 Makara, G.M. 234, 361,362 Makino, S. 360 Makosza, M. 156, 241 Malachowski, W.P. 140 Malacria, M. 9, 43, 58, 65, 271, 279, 290, 310

AUTHOR INDEX

Maleczka, R.E., Jr. 131,332 Malhotra, S.V. 274 Mali, R.S. 178 Malinakova, H.C. 175 Malkinson, J.P. 369 Mallakpour, S.E. 111, 217, 223 Malmstrom, E. 6 Mancini, P. 68 Mandal, A.K. 336 Mane, R.B. 342 Mangeney, P. 16 Mann, A. 59, 159 Manoharan, M. 264 Mantyla, A. 265 Marcacchini, S. 191 Marcantoni, E. 47 Marchand, A.P. 283 Marciniec, B. 50 Marco, J.A. 30, 169 Marco-Contelles, J. 65, 334 Marcos, I.S. 334 Marcotullio, M.C. 261 Marek, I. 37, 57, 65, 97, 287, 288 Marinelli, F. 169 Marinetti, A. 121,209 Marino, J.P. 267, 333, 341 Marko, I.E. 4, 63, 167, 179 Marks, T.J. 160 Marquet, A. 332 Marsella, M.J. 330 Marshall, J.A. 333, 334 Marson, C.M. 101 Marsura, A. 325 Martens, J. 358 Martin, M.T. 269 Martin, N. 306, 307, 360 Martin, S.E. 104 Martin, S.F. 49, 245, 284, 294, 336, 341 Martinez, A.G. 22, 310 Martinez-Alvarez, R. 190 Martins, M.A.P. 189

393

Maruoka, K. 3, 105, 176 Masaguer, C.F. 188 Mascarenas, J.L. 50, 74, 174, 342 Masuda, Y. 267 Mata, E.G. 139 Mataka, S. 103 Mathey, F. 72 Mathias, L.J. 235 Mathieu, A. 323 Matos, K. 120 Matsubarg, S. 54 Matsuda, I. 1, 94 Matsuda, T. 122 Matsui, M. 11 Matsumoto, K. 19, 230 Matsumoto, T. 231 Matsumura, Y. 7 Matsuo, K. 239 Matteson, D.S. 241 Mauquez, V.E. 263 May, B.C.H. 205 Mayano, S. 221 Maycock, C.D. 138 Mayoral, J.A. 358 McDonald, F.E. 11, 151, 174 McEachern, E.J. 126 McGrath, D.V. 314 Mclntosh, M.C. 100, 282 McLeod, M. 18 McLeod, M.D. 285 McMorris, T.C. 120 McNab, H. 302 McNeill, K. 162 McNulty, J. 82 McWilliams, J.C. 269 Meanwell, N.A. 302 Medebielle, M. 23 Meffre, P. 59 Mehnert, C.P. 350 Mehta, G. 50, 114, 287, 294, 309, 311,339, 343, 345 Meier, H. 329

394

Meier, M.S. 307 Meierhenrich, U.J. 278 Meinwald, J. 341 Meldal, M. 203, 355,369 Melguizo, M. 258 Menichetti, S. 52 Merour, J.-Y. 183 Meth-Cohn, O. 165 Metz, P. 202 Metzner, P. 9, 100, 135 Meunier, B. 295 Meyers, A.I. 37, 38 Mezzetti, A. 127 Mi, A. 133 Michelet, V. 153, 349 Michelotti, E.L. 364 Michl, J. 81 Micouin, L. 114, 279 Mihovilovic, M.D. 285 Mikami, K. 20, 255, 277, 331 Mikolajczyk, M. 122, 266 Miller, J.A. 56 Miller, M.J. 336, 337 Miller, S.J. 246, 279, 339 Minakata, S. 136 Minami, T. 175 Mineo, T. 222 Mioskowski, C. 48, 153, 249, 267, 272, 356 Mirkhani, V. 138 Mitsuda, T. 94, 268 Mitsudo, T. 160 Mitzel, T.M. 21 Miura, M. 85,260 Miyashita, M. 11, 71, 74 Miyaura, N. 49, 56, 88, 89, 363 Miyawa, N. 262 Mizuno, T. 197 Mlosten, G. 207 Moberg, C. 6, 8 Moeller, K.D. 154, 178 Moghimi, A. 326

AUTHOR INDEX

Mohammadpoor-Baltork, I. 222, 250 Mohan, R.S. 26, 216, 292 Moher, E.D. 335 Moise, C. 49 Molander, G.A. 3, 59, 73, 82, 95, 144 Molina, P. 22, 346 Moloney, M.G. 7, 56 Molteni, G. 186 Molteni, V. 186 Mongin, F. 81, 88 Monsees, A. 127 Montchamp, J.-L. 265 Monteiro, A.L. 82 Montgomery, J. 26, 39, 346 Monti, H. 311 Monti, S. 276 Moody, C.J. 30, 99, 106, 219 Moore, J.S. 327 Morales-Morales, D. 6 Mori, A. 62, 349 Moil, H. 92 Mori, K. 342 Mori, M. 24, 26, 92, 94, 160, 161,169, 332, 345 Morimoto, T. 91 Morita, C. 43 Morken, J.P. 99, 140 Morphy, J.R. 363,365 Morrill, T.C. 260 Morris, J.C. 102, 332 Mortier, J. 88 Mortishire-Smith, R.J. 181 Morwick, T. 198 Moser, W.H. 15 Moss, R.A. 303 Motherwell, W.B. 22 Motoyama, Y. 37, 196 Movassagh, B. 111,229 Moyano, A. 6, 90 Muathen, H.A. 255 Mudryk, B. 251 Mukai, C. 90, 334, 339

AUTHOR INDEX

Mukaiyama, T. 15, 106, 228, 310, 358 Mukherjee, D. 341,343, 344, 346 Muller, G. 6 Muller, M. 135, 299 Muller, T.J.J. 171 Mulzer, J. 340 Mura, M. 83 Murahashi, S.-I. 19 Murai, A. 68, 180, 220 Murai, S. 22, 85, 282 Murakami, M. 89, 94, 97 Murakami, T. 23 Murase, M. 338 Murata, M. 267 Murata, S. 306 Murphy, P.J. 41, 161 Muthusamy, S. 36, 150, 215, 287 Muzart, J. 105 Myers, A.G. 55,338, 340, 346, 369 Nacci, A. 352 Nagao, Y. 46, 143 Nagaoka, H. 310 Nagasawa, K. 2, 3, 33, 333, 335 Nagumo, S. 79, 147, 154, 346 Nair, V. 69, 149, 151,155, 191,193, 203, 305 Naito, T. 124, 349 Najera, C. 3, 8, 27, 59, 82, 111, 299, 349 Nakada, M. 71 Nakagawa, M. 50 Nakajima, M. 253 Nakamura, E. 285, 305, 323 Nakamura, K. 122, 230 Nakamura, Y. 163 Nakano, H. 68 Nakata, T. 178, 181,342 Namy, J.-L. 25 Nangia, A. 115 Narasaka, K. 160, 163 Naso, F. 270

395

Navarro, M. 80 Nazih, A. 235 Negishi, E. 57, 149, 283 Negrete, G.R. 68 Nelson, A. 247 Nelson, D.P. 262 Nelson, S.G. 13, 340 Nematollahi, D. 189 Nemoto, H. 50, 71 Nenajdenko, V.G. 53, 185 Neumann, R. 104 Neunhoeffer, H. 172 Nevalainen, N. 338 Newkome, G.R. 313 Newman, P.D. 265 Nguyen, S.T. 121 Nicholas, K.M. 163, 241 Nicolaou, K.C. 39, 51, 117, 166, 198, 200, 206, 237, 252, 284, 301,332, 334, 335, 336, 343 Nicotra, F. 297, 366 Nielsen, P. 50, 264 Nierengarten, J.-F. 308, 310, 315 Night, D.W. 159 Nilsson, I. 361 Nishida, A. 37, 161 Nishikiori, S. 325 Nishimura, J. 306, 328 Nishimura, K. 268 Nishiwaki, K. 239 Nishiwaki, N. 169, 192 Nishiyama, K. 32 Nishiyama, S. 176, 294, 334 Nishiyama, Y. 42, 69, 120, 180, 266 Nishizawa, M. 233 Niwayama, S. 230 Nixey, T. 363 Node, M. 104, 269 Nogueras, M. 167 Nolan, S.P. 49, 59, 82, 83, 95, 239,249

396

Norskov-Lauritsen, L. 368 Noyori, R. 276 Nozaki, K. 237 Nubbemeyer, U. 244, 344 Nugent, W.A. 128 Nutaitis, C.F. 130 Nyerges, M. 158 Nyori, R. 121 O'Brian, P. 136, 280 O'Brien, D.F. 330 O' Doherty, G.A. 334, 335, 338, 343,346 O'Donnell, M.J. 242, 365 O'Mahony, D.J.R. 362 O'Shea, D.F. 82 Oba, M. 32 Oberborsch, S. 19 Occhiato, E.G. 56 Ochiai, M. 232 Oda, K. 144 Odom, A.L. 261 Ogasawara, K. 166, 332, 336, 339, 341,342, 344, 345 Ogasawara, M. 50 Ogawa, A. 122 Oh, C.H. 82, 89 Ohe, K. 63, 86, 127 Ohfune, Y. 16 Ohira, S. 345 Ohkata, K. 68 Ohmori, N. 74 Ohsawa, A. 124 Ohta, S. 342, 344 Ohtake, N. 369 Oi, S. 38 Ojima, I. 311 Okada, K. 346 Okano, T. 1 Okuyama, T. 69 Olah, G.A. 219, 239, 254 Olivo, H.F. 16, 17, 212

AUTHOR INDEX

Ollevier, T. 241 Olofson, R.A. 255 Olsson, R. 49, 158 Omura, S. 333, 341,343 Onaka, M. 93 Ong, C.W. 162 Ordonez, M. 119 Orfanopoulos, M. 305, 306 Organ, M.G. 176 Oriyama, T. 26, 222 Orsini, F. 23 Ortiz, F.L. 207, 208 Ortuno, R.M. 263 Osakada, K. 267 Osborn, H.M.I. 211 Oscarson, S. 248 Oshima, K. 2, 10, 18, 34, 44, 54, 55, 57, 66, 81, 96, 152, 190, 233, 349, 351 Osman, F.H. 302 Otaka, A. 10 Otera, J. 250 Otsuba, T. 206 Ouchi, A. 306 Outurquin, F. 257 Ovasaka, T. 333 Overman, L.E. 41, 88, 101, 184, 196, 344 Ozawa, F. 96, 267 Ozgun, B. 104 Padwa, A. 38, 71, 72, 137, 214, 237, 340, 345 Page, P.C.B. 113 Pagenkopf, B.L 91 Pal, M. 86 Palacios, F. 138, 162, 166, 189, 198, 213 Pale, P. 22, 59 Paley, R.S. 288 Palmieri, G. 30 Palomo, C. 68, 281

AUTHOR INDEX

Pamies, O. 249 Pan, S. 360 Pan, X. 335, 338, 339, 340 Pancrazi, A. 276 Pandey, G. 168 Pandey, P.S. 328 Panek, J.S. 59, 97, 342, 343 Pansare, S.V. 24 Panunzio, M. 199 Panza, L. 48, 250 Papaioannou, D. 346 Papini, A.M. 3 Pappalardo, S. 320 Paquette, L.A. 49, 127, 334, 335,337, 339, 340, 344 Pardo, D. 173 Pare, P.W. 29 Parilli, M. 225 Parisi, M.F. 320 Park, B.S. 77 Park, H. 3, 244 Park, J. 105, 122 Park, K.-H. 362 Park, K.K. 329 Park, Y.J. 187 Parrain, J.-L. 337 Parrot-Lopez, H. 318 Parsons, A.F. 42, 76, 154, 183,287 Pasini, D. 357 Passacantilli, P. 143, 195 Passarella, D. 332 Pastor, J. 365 Patel, B.K. 107, 216 Patel, I. 167 Paterson, I. 15 Pathak, T. 300 Pattenden, G. 332, 335, 344 Patti, A. 120 Patzel, M. 63 Paul, S. 184 Paulvannan, K. 167 Pavlik, J.W. 186

397

Pavlov, V.A. 278 Pawlas, J. 172 Payne, H.J. 360 Pearson, W.H. 74 Pedersen, H.L. 267 Pedro, J.R. 35 Pedrosa, R. 108, 158 Pei, J. 83 Pelinski, L. 120 Pellacani, L. 137 Pelletier, J.C. 238 Pelliciari, R. 245 Pellissier, H. 38, 282, 296 Pena-Cabrera, E. 336 Peng, S. 167 Peng, Z. 313 Peppe, C. 254 Peregrina, J.M. 167 Pereira, M.M.A. 339 Pereira, V.L.P. 36 Perez, P.J. 243 Perez-Castells, J. 50, 90 Perez-Perez, M.-J. 185 Perez-Prieto, J. 62 Periasamy, M. 116, 280 Pericas, M.A. 6, 28, 90, 333 Perillo, I.A. 191 Perkins, M.V. 341 Perlmutter, P. 342 Perrio, S. 111 Perumal, P.T. 77, 170, 178 Petasis, N.A. 239 Pete, J.-P. 75 Petrini, M. 17, 32 Petrus, L. 297 Pettus, T.R.R. 116, 174, 287 Pfaltz, A. 127 Pfau, M. 333, 341,345 Pfeffer, M. 291 Phillips, A.J. 17, 52 Piancatelli, G. 143, 195 Pielichowski, J. 135

398

Piers, W.E. 313 Pieters, R.J. 314 Pietrusiewicz, K.M. 232 Piettre, S.R. 48, 68 Pigge, F.C. 328 Pihlaja, K. 193 Pilli, R.A. 32, 338 Pinheiro, S. 20, 38, 119 Pinho e Melo, T.M.V.D. 162, 191 Pinson, J. 355 Pinto, B.M. 180 Piras, P.P. 79, 177 Pirrung, M.C. 36, 164, 335 Piva, O. 75, 76 Pizzano, A. 127 Pizzo, F. 285 Plaquevent, J.-C. 353 Pleixats, R. 82 Plobeck, N. 33 Plumet, J. 52 Podesta, J.C. 262, 273 Podlech, J. 22 Pohmakotr, M. 335 Poirier, D. 356 Poli, G. 96 Pollini, G.P. 162 Polniaszek, R.P. 196 Pombeiro, A.J.L. 289 Pomerantz, M. 80 Pons, M. 313 Popsavin, M. 264 Popsavin, V. 343 Porco, J.A., Jr. 118, 337, 340 Porta, O. 122 Porter, M.J. 203 Portlock, D.E. 244 Portnoy, M. 90, 358 Porzi, G. 243 Posner, G.H. 99 Postema, M.H.D. 50 Potkin, V.I. 214 Poupat, C. 22

AUTHOR INDEX

Pourjavadi, A. 47 Pozzi, G. 105 Prabhakar, S. 98, 140 Prakash, G.K.S. 33, 219, 239, 254 Prandi, C. 56 Prashad, M. 55 Prato, M. 308 Procopio, A. 216, 225 Procopioli, P.A. 119 Procter, D.J. 5, 23, 34 Proenca, M.F. 184 Prunet, J. 40, 224 Pu, L. 22, 26 Puddephatt, R.J. 324 Pulicani, J.-P. 355 Pulpoka, B. 321 Purandare, A.V. 363 Pushechnikov, A.O. 78 Py, S. 28 Pyne, S.G. 161,246, 307, 337, 345 Qian, C. 170 Qing, F. 244 Quadrelli, P. 358 Queguiner, G. 81, 188, 334 Quideau, S. 159, 344 Quinn, R.J. 362, 372 Quintero, L. 333 Quirante, J. 160 Quirion, J.-C. 1 Quiroga, J. 167 Raap, J. 264 Rabanal, F. 365 Raghavan, S. 115, 364, 368 Raghunathan, R. 158 Ragnarsson, U. 238 Ragoussis, V. 15 Raines, R.T. 245 Rainier, J.D. 296 RajanBabu, T.V. 57 Rajender, R.S. 275

AUTHOR INDEX

Ram, R.N. 249 Ramachandran, P.V. 18, 120, 289, 336, 337, 338 Ramalingam, T. 215 Ramig, K. 251 Ramos, J.H.R. 69 Ranu, B.C. 19, 49, 127, 215, 243, 269, 352 Rao, A.R.R. 205 Rao, P.N. 103 Rao, P.S. 126 Rao, T.S. 218 Rasmussen, S.C. 191 Raston, C.L. 319, 320 Rathore, R. 55 Rault, S. 156 Ravasio, N. 121 Ravikanth, M. 164 Ravina, E. 80 Rawal, V.H. 57, 60, 67, 174, 333, 344, 345 Ray, N.C. 364 Raymo, F.M. 316 Rayner, C.M. 18 Reddy, B.M. 222 Reddy, P.S.N. 214 Reese, C.B. 300 Reetz, M.T. 277 Reginato, G. 96 Regnouf-de-Vains, J.-B. 318, 319 Rein, T. 156,285 Reinhoudt, D.N. 326 Reiser, O. 19 Reissig, H.-U. 55, 172, 195, 244 Ren, R.X. 350 Renard, P.-Y. 272 Renaud, P. 41, 43, 103, 183 Reutrakul, V. 49 Reynolds, J.R. 193 Richards, C.J. 196 Richert, C. 264 Richter-Addo, G.B. 303

399

Riera, A. 50 Rigby, J.H. 141 Righi, G. 15,253 Righi, P. 194,360 Ripin, D.H.B. 262 Risch, N. 238 Risitano, F. 167 Rizzacasa, M.A. 334, 335 Roberts, S.M. 280 Robina, I. 248 Robins, M.J. 263, 264 Robinson, B. 210 Rodinovskaya, L.A. 157 Rodrigo, R. 92 Rodriguez, H. 360 Rodriguez, J.B. 342 Rodriguez, M.A. 161, 261 Roe, M.B. 369 Roglans, A. 82 Rokach, J. 343 Roland, S. 32 Romea, P. 4, 15 Romeo, G. 38, 156 Romero, D.L. 179 Romo, D. 5,333 Roschangar, F. 216 Rose, K. 366 Rosini, G. 154 Rossi, R. 344 Rossi, R.A. 77, 262, 265 Rossiter, S. 47 Roth, H.D. 286 Roush, W.R. 41, 67, 71,228, 333 Rousseau, B. 131 Roussel, C. 186 Routier, S. 219 Rovis, T. 22, 41 Rowan, J. 301 Roy, R. 115 Roy, S. 258 Roy, S.C. 154, 215, 216 Royo, M. 313, 364

400

Rozen, S. 255 Ruano, J.L.G. 11, 69, 158 Rubin, Y. 307 Ruchirawat, S. 342 Ruck-Braun, K. 355 Rudkevich, D.M. 331 Ruhland, T. 365 Ruiz, M. 167, 337 Rulev, A.Y. 302 Russell, A.T. 332 Rutjes, F.P.J.T. 361 Rybak-Akimova, E.V. 326 Rychnovsky, S.D. 334 Rykowski, A. 172 Ryu, I. 92, 352 Saa, J.M. 27 Sabitha, G. 170, 247 Sackus, A. 201 Sadekov, I.D. 291 Saicic, R.N. 147 Saidi, M.R. 29, 30, 32 Saigo, K. 308, 354 Sajiki, H. 131 Sakai, N. 78 Sakamoto, T. 361 Saladino, R. 113 Salamonczyk, G.M. 315 Salaskar, A. 263 Salehi, P. 217 Saljoughian, M. 275 Salter, M.M. 153 Salunkhe, M.M. 353 Samat, A. 80 Sames, D. 57, 344 Sammakia, T. 334 Sanders, J.K.M. 331 Sandhu, J.S. 125 Sannicolo, F. 211 Sano, S. 46 Sandri, S. 243 Santelli, M. 38, 55, 71, 81, 82, 180

AUTHOR INDEX

Sanz, R. 270 Sarandeses, L.A. 85, 110 Saricirtci, N.S. 306 Sarkar, A. 49, 99 Sarkar, T.K. 69 Sasaki, M. 338 Sasaki, N.A. 339 Sasaki, Y. 197 Sata, N.U. 344 Sato, F. 12, 23, 42, 53, 71, 94, 146, 339 Sato, N. 257 Sato, T. 216 Satoh, T. 58 Sauvage, J.-P. 323 Savage, P.B. 299 Savignac, M. 363 Savoia, D. 288 Sawada, M. 329 Sawamura, M. 305 Scammells, P.J. 354 Scanlon, E.M. 141 Schafer, H.J. 42 Schalley, C.A. 323 Schanze, K.S. 330 Schecter, H. 246, 259 Scherkenbeck, J. 340 Schlaf, M. 224, 227 Schlosser, M. 87 Schluter, A.D. 281, 312 Schmalz, H.-G. 9, 66, 87, 92 Schmidt, B. 25 Schmidt, R.R. 221,248, 340 Schneider, C. 38, 209, 280 Schneider, D.F. 222 Schneller, S.W. 263 Schore, N.E. 120 Schotteen, T. 350 Schrader, T. 277 Schreiber, S.L. 49, 371,372 Schreier, P. 299 Schreiner, P.R. 286

AUTHOR INDEX

Schrock, R.R. 51, 153, 169 Schubert, U.S. 81 Schultz, E. 6 Schultz, P.G. 360, 368, 370 Schuster, D.I. 326 Schweizer, F. 372 Scivanti, A. 338 Scobie, M. 244 Scorrano, G. 309 Scott, P. 136 Scott, W.L. 365 Sebesta, R. 22 Secen, H. 246 Seebach, D. 22 Seeberger, P.H. 248, 297, 298, 341,366 Seifert, K. 339, 346 Seki, K. 98, 99 Seki, M. 184, 333 Sekine, M. 343 Selegue, J.P. 192 Sels, B.F. 303 Selvakumar, N. 199, 334, 339 Selvam, P. 126 Semmelhack, M.F. 27 Senanayake, C.H. 33, 125,208 Sener, A. 186 Sener, B. 294 Senge, M.O. 164 Sengupta, S. 167, 315 Senning, A. 207 Sergheraert, C. 369 Servi, S. 187 Sessler, J.L. 321 Sestelo, J.P. 85 Seth, P.P. 185 Severin, K. 288 Sewald, N. 39, 298, 336 Sha, Y. 314 Shaabani, A. 108, 155,236 Shah, S.T.A. 252 Shair, M.D. 340

401

Sharghi, H. 234, 253, 256 Sharifi, A. 217, 239 Sharma, G.V.M. 252, 341 Sharpless, K.B. 114, 203, 205, 276 Shaw, B.R. 264 Shea, K.J. 145 Sheldon, R.A. 105 Shen, Y. 183 Shen, Y.-C. 311 Sherburn, M.S. 56 Sherman, J.C. 327 Sherman, T. 330 Sherrington, D.C. 267 Shi, D. 52, 93 Shi, M. 20, 29, 53, 196 Shi, Y. 113, 233, 259 Shibasaki, M. 26, 27, 36, 37, 117, 277, 343, 345, 346 Shibata, I. 38 Shibata, N. 200, 237 Shibata, T. 70, 91, 94, 160 Shieh, W.-C. 84, 251 Shiina, I. 78, 98, 150 Shim, S.C. 2, 148 Shimada, S. 82 Shimizu, K. 19, 363 Shimizu, M. 18, 33, 143, 241 Shimizu, T. 194, 324 Shinada, T. 16, 338 Shindo, M. 53, 194, 335 Shinmyozu, T. 327 Shinohara, H. 309 Shinokubo, H. 18, 44, 190 Shioiri, T. 47, 114, 135,341,345 Shiozaki, M. 345 Shipman, M. 233, 336 Shirahama, H. 161 Shirakawa, E. 89, 95,291 Shirini, F. 104, 217 Shishido, K. 50 Shizuma, M. 329 Sholl, D.S. 309

402

Shreeve, J.M. 27, 254, 293,354 Shuto, S. 60, 66 Shuttleworth, S.J. 362, 364 Shvo, Y. 105 Sibi, M.P. 41,259, 279, 333, 336, 339, 342, 344 Sickle, E.S. 295 Sierra, M.A. 53 Sigman, M.S. 105, 198 Silva, L.F., Jr. 115, 285 Simig, G. 5 Simpkins, N.S. 4, 38 Sinay, P. 49, 334 Singer, R.D. 350, 351 Singh, G. 297 Singh, H.B. 288 Singh, V. 68, 294, 339 Singh, V. K. 332 Singh, V.K. 104, 249, 340, 342 Singleton, D.A. 22 Sinha, S.C. 337 Sinou, D. 175, 348 Six, Y. 229 Skalski, B. 77 Skarzewski, J. 111 Skerlj, R.T. 97 Skrydstrup, T. 159 Sliwa, W. 210, 330 Slugovc, C. 51 Smaliy, R.V. 256 Smith, A.B., III 9, 107, 335, 346 Smith, B.O. 323 Smith, D.B. 361 Smith, D.K. 313 Smith, N.D. 162 Smith, R.A. 370 Smith, S.C. 98 Smith, W.E. 126 Smitt, O. 338 Smyth, T.P. 270 Snaith, J.S. 167 Snapper, M.L. 27, 175, 339

AUTHOR INDEX

Snider, B.B. 42, 194, 337 Snow, R.J. 143 Snyder, J.K. 73 Soai, K. 22, 315 Sodeoka, M. 254, 358 Soderberg, B.C.G. 159 Soga, T. 311 Solladie, G. 68 Somanathan, R. 27 Somfai, P. 138, 241 Sonada, N. 92 Song, C.E. 6, 114, 255, 350, 351 Song, G. 234 Song, J. 252 Sonoda, N. 42, 69, 120, 180, 266 Sorensen, E.J. 133, 337 Sosnovskikh, V.Y. 178, 188 Sotelo, E. 82 Souma, Y. 92 Spagnolo, P. 141 Spencer, J.B. 100 Speranza, M. 318 Spindler, F. 127 Spinella, A. 332 Spitzner, D. 333, 338 Spivey, A.C. 295 Spur, B.W. 38, 339 Spyroudis, S. 68 Srebnik, M. 25 Srikrishna, A. 63, 311,337, 338, 341,344 Srinivasan, K.V. 352 Srirangam, J.K. 238 Srivastava, R.S. 239 Srogi, J. 270 St Hilaire, P.M. 369 Staas, D.D. 17 Stahl, S.S. 160 Stajer, G. 210 Stalick, W.M. 33 Stanetty, P. 212 Stanforth, S.P. 80

AUI HOH INI.)I:X

Stang, P.J. 281 Stavber, S. 110, 255 Steed, J.W. 327 Steel, P.G. 337 Stefani, H.A. 346 Steglich, W. 343 Sterner, O. 343,344 Steudel, R. 304 Stevens, C.V. 64, 244 Stevens, M.F.G. 82 Stevenson, P.J. 68, 173 Stien, D. 273,359 Stockman, R.A. 182 Stoddart, J.F. 313, 323, 324 Stoltz, B.M. 102, 336 Stoodley, R.J. 176 Strazzari, S. 141 Streicher, H. 298 Stromgaard, K. 370 Studer, A. 199, 286 Studer, M. 84 Su, W. 190, 236 Suarez, E. 159, 229 Suarez, M. 360 Subra, G. 355 Suda, K. 117 Suffert, J. 60 Suginome, M. 179, 262 Sugiura, M. 165 Suh, Y.-G. 333,339 Sulikowski, G.A. 109 Sun, C.-M. 171,359 Sun, J.-S. 264 Sundararajan, G. 36 Sung, P.-J. 210, 211 Sutbeyaz, Y. 246 Sutherland, A.J. 355 Suzuki, H. 205,258 Suzuki, K. 101,102, 336 Svete, J. 204, 212 Svetlik, J. 186 Sweeney, J.B. 209, 211

403

Swenson, R.E. 168 Syvret, R.G. 255 Szabo, K.J. 179 Szeimies, G. 70 Szendi, Z. 123 Szymoniak, J. 28, 64 Taber, D.F. 26, 63, 334, 336, 342 Tadano, K. 334, 342 Taguchi, T. 38, 48, 67, 71,236 Tahmassebi, D.C. 264 Tai, H.-M. 124 Taillefer, M. 286 Tajbakhsh, M. 104, 217 Tajima, Y. 310 Takabe, K. 119, 346 Takacs, J.M. 14, 338 Takadoi, M. 68 Takaguchi, Y. 315 Takahashi, S. 92, 164, 342 Takahashi, T. 2, 85, 93, 97, 171,175, 250, 251,364, 366 Takahata, H. 218 Takai, K. 23 Takamiya, K. 206 Takamura, H. 27 Takasu, K. 71,160 Takata, T. 323, 324 Takayama, H. 332, 343, 345 Takeda, K. 73 Takeda, T. 23, 54, 63, 64, 96 Takemoto, M. 80 Takemoto, Y. 3 Takeuchi, R. 92, 291 Takeuchi, Y. 210 Takikawa, H. 154 Talamas, F.X. 361 Talanov, V.S. 318 Tale, R.H. 201,246 Talukdar, A. 256 Tam, W. 59 Tamamura, H. 245

404

Tamao, K. 283 Tamariz, J. 342 Tamaru, Y. 168 Tamioka, K. 45 Tanabe, Y. 148 Tanaka, A. 249 Tanaka, F. 68 Tanaka, H. 80 Tanaka, K. 153 Tanaka, M. 82, 265 Tanaka, O. 304 Tanaka, T. 58 Tang, J. 82 Tang, Y. 36, 45, 63 Tani, K. 48 Tanino, K. 74 Tanner, D. 273 Tanyeli, C. 1,109 Tardella, P.A. 137 Tatsuta, K. 342 Taylor, C.M. 244 Taylor, D.K. 65, 148 Taylor, R. 307, 308, 309 Taylor, R.E. 195 Taylor, R.J.K. 45, 242, 250, 257, 337 Teobald, B.J. 284 Tepe, J.J. 78, 184 Termin, A.P. 194 Thamattoor, D.M. 342 Thayumanavan, S. 314 Theil, F. 250 Theodorakis, E.A. 72, 224, 333, 339, 342, 345 Therisod, M. 110 Thiel, W.R. 113 Thiemann, T. 210 Thompson, D.H. 343 Threadgill, M.D. 329 Tice, C.M. 364 Tiecco, M. 201,260 Tietze, L.F. 6, 82

AUTHOR INDEX

Tilve, R.D. 255 Timmerman, P. 326 Tito, A. 158 Tius, M.A. 42, 295, 335 Toda, F. 281 Todd, M.H. 276 Togo, H. 109, 294 Tokitoh, N. 268 Tokuda, M. 131 Tokunaga, Y. 324 Toma, S. 350 Tome, A.C. 306, 308 Tominaga, Y. 213 Tomioka, K. 6, 38, 41, 114, 269 Toniolo, C. 310 Tor, Y. 288 Torres, T. 208 Torroba, T. 179 Toru, T. 9, 29, 364 Tour, J.M. 328, 355 Townsend, C.A. 346 Toyooka, N. 50, 332 Toyota, M. 292 Trau, M. 371 Trauner, D. 96, 99, 337 Traveras, A.G. 164 Tripathy, R. 368 Trivedi, G.K. 346 Trofimov, B.A. 213 Troin, Y. 167 Troisi, L. 98 Trost, B.M. 1, 4, 6, 7, 19, 54, 129, 150, 168, 174, 278, 332, 333, 334, 336, 338, 339, 342, 358 Truesdale, L. 130 Tsolomitis, A. 201 Tsoungas, P.G. 214 Tsuboi, S. 78 Tsuji, T. 331 Tsuji, Y. 95, 261 Tsukamoto, T. 20 Tu, Y.Q. 101,103

AUTHOR INDEX

Tucker, J.H.R. 276 Tung, C.-H. 74 Tuntulani, T. 318 Turro, N.J. 266, 326 Twyman, L.J. 302 Tykwinski, R.R. 301,325 Tyman, L. 330 Tyrrell, E. 9 Uang, B.-J. 27, 58, 80, 112 Ubukata, M. 344 Ueda, I. 82, 327 Ueda, M. 294 Uemura, M. 13 Uemura, S. 39, 61, 63, 86, 106, 127, 177 Ueno, K. 188 Uguen, D. 43 Uhlig, F. 273 Umani-Ronchi, A. 27, 41, 78 Uneyama, K. 9, 47, 137, 245 Uozumi, Y. 8, 82, 347 Uriarte, E. 69 Urpi, F. 4 Vadakkan, J.J. 106 Valeur, B. 319 Vallee, Y. 28, 61 Valls, N. 345 van Boom, J.H. 50, 272, 357 van der Donk, W.A. 42, 341 van der Eycken, J. 68, 69, 366 van der Gen, A. 293 van Koten, G. 3, 316 van Leeuwen, P.W.N.M. 82, 91 Van Vranken, D.L. 47, 341 Vaquero, J.J. 81 Varadarajan, R. 320 Vargas, M.D. 181 Vargas-Berenguel, A. 312 Varlamov, A. 166 Varma, R.S. 222, 224, 354

405

Vasapollo, G. 308 Vatele, J.-M. 224 Vaultier, M. 289 Vedejs, E. 226 Vedso, P. 81,172 Venkataraman, D. 152, 269 Venkateswaran, R.V. 128 Venkateswarlu, Y. 225, 228 Verardo, G. 238 Verdine, G.L. 370 Verkade, J.G. 18, 27, 37, 82 Veronese, A.C. 264 Verpoort, F. 49 Viala, J. 105 Vicens, J. 321,323 Vidal, B. 365 Vidari, G. 115, 147, 335, 339, 340 Viehe, H.G. 183 Vilar, E.T. 22 Villamizar, J. 346 Villar, H. 64 Voelter, W. 252, 268 Vogel, P. 271 Vogtle, F. 313 Voitekhovich, S.V. 214 Vollhardt, K.P.C. 290 Volonterio, A. 9, 370 von Itzstein, M. 298 Voskressensky, L.G. 214 Vrudhula, V.M. 310 Vyvyan, J.R. 295, 338 Wacker, D.A. 361 Wada, A. 59 Wada, M. 124, 253 Wagner, A. 249, 267, 356 Wai, C.M. 126 Wakatsuki, Y. 233 Wakharkar, R.D. 216 Wakselman, C. 267 Waldmann, H. 39, 219, 335, 370, 372 Waldvogel, S.R. 42, 80

406

Wallace, D.J. 82 Walsh, P.J. 22, 26, 115, 243 Walton, J.C. 141 Wang, B. 3, 355 Wang, D. 15, 78, 348 Wang, E.-C. 180 Wang, G. 272 Wang, J. 36, 98, 163 Wang, J.-X. 53 Wang, J.-Y. 117 Wang, K.K. 164 Wang, L. 269 Wang, M. 112 Wang, M.-X. 242 Wang, P.G. 149, 181 Wang, Q. 203 Wang, T. 77, 164 Wang, Y.-L. 117 Wang, Y.G. 361 Wang, Z. 270, 271,348, 349 Wardrop, D.J. 151,337 Warnmark, K. 87 Warren, S. 202, 209 Warriner, S.L. 366 Wasserman, H.H. 294, 335 Wasserscheid, P. 352 Watanabe, H. 340 Waymouth, R.M. 249 Weaver, G.W. 183 Weber, C. 362 Weck, M. 327 Wei, A. 247 Weidenbruch, M. 289 Weinreb, S.M. 142, 335,337, 340 Weissensteiner, W. 10, 127 Welch, J.T. 47, 348 Weller, A.S. 127 Welton, T. 351 Wendeborn, S. 264 Wender, P.A. 74, 182, 340 Wengel, J. 297 Wessjohan, L.A. 24

AUTHOR INDEX

West, F.G. 45, 183, 303 Westcott, S.A. 197 Wheelhouse, R.T. 164 White, J.D. 337, 344 Whitehead, R.C. 341 Whiting, A. 295 Widenhoefer, R.A. 44, 94, 283 Widhalm, M. 10 Wiemer, D.F. 50, 133, 264 Willard, P.G. 162 Wille, U. 286 William, A.D. 38 Williames, D.R. 340 Williams, D.J. 320, 324 Williams, J.A.G. 82 Williams, J.M.J. 46, 250 Williams, R.M. 3, 175, 209, 296, 312, 337, 342, 346 Williard, P.G. 48 Willis, M.C. 199, 240 Willoughby, C.A. 361 Wills, M. 121,122, 150, 278 Wilson, L.J. 307, 370 Wilson, S.R. 309 Winder, R. 373 WinNer, J.D. 339 Wipf, P. 22, 290, 333, 340, 346 Wirsching, P. 314 Withers, S.G. 248, 366 Witulski, B. 332 Wnuk, S.W. 263 Woerpel, K.A. 15, 151,208, 267, 334, 343 Wojciechowski, K. 210 Wolf, C. 22 Wong, C.-H. 48, 177, 216, 246, 247, 371 Wong, K.-T. 157, 262 Wong, Y.-S. 332 Woo, L.K. 62 Wood, J.L. 72, 340 Woodward, S. 26, 277

AUTHOR INDEX

Wrackmeyer, B. 268 WrackmVI.F-3 .i.Le Bideau, F. 268 Wright, D.L. 363 Wrodnigg, T.M. 297 Wu, C.-T. 318 Wu, H. 93, 133 Wu, M.-J. 144, 153 Wu, S.-H. 248 Wu, Y. 217, 224, 332 Wu, Y.-J. 239 Wu, Y.-L. 233, 334, 346 Wu, Y.-Q. 259 Wulff, G. 281 Wurthner, F. 319 Wyatt, P.B. 245 Xi, F. 134 Xi, Z. 93 Xia, M. 363 Xiaozhong, L. 91 Xu, J. 136, 138 Xu, J.-H. 139, 305 Xu, P. 370 Xu, X.-H. 266 Yadav, J.S. 26, 27, 31, 38, 42, 69, 77, 97, 122, 170, 177, 178, 187, 215, 219, 221,228, 236, 240, 247, 256, 270, 343, 345, 353 Yadav, L.D.S. 138, 139, 199 Yakahashi, T. 335,338 Yamabe, S. 94 Yamada, S. 234 Yamada, T. 194 Yamada, Y. 296, 336, 340 Yamago, S. 228 Yamaguchi, M. 1, 56, 78 Yamaguchi, R. 106, 131, 168 Yamamoto, A. 29 Yamamoto, H. 2, 80, 256, 259, 303,332 Yamamoto, T. 321,344

407

Yamamoto, Y. 1, 87, 93, 95, 97, 146, 165, 181,203, 205, 241, 252, 260, 262 Yamamura, S. 294 Yamano, T. 22 Yamasaki, K. 304 Yamashita, Y. 59 Yamato, T. 106, 327 Yamauchi, M. 195 Yamazaki, S. 94 Yamazaki, T. 11 Yan, T.-H. 195, 341,342 Yanada, R. 153, 350 Yang, B.-H. 336, 344 Yang, D. 64, 253 Yang, K. 360 Yang, R. 330 Yang, S.-C. 191 Yang, Z. 82, 151 Yao, C.-F. 175 Yao, Q. 350 Yao, Z.-J. 147, 244, 248 Yashima, E. 308 Yasuhara, A. 165, 361 Yasukata, T. 371 Yavari, I. 156, 200 Yaylayan, V.A. 356 Yee, N.K. 2 Yen, C.-F. 341 Yeung, C. 121 Yeung, K.-S. 296, 353 Yilmaz, M. 317 Yin, D. 225, 311 Yin, J. 239 Yoda, H. 33,338 Yokokawa, F. 334 Yokoyama, C. 352 Yokozawa, T. 26 Yonezawa, N. 257 Yongzhou, H. 203 Yoo, B.W. 29, 125, 126 Yoon, C.K. 133

408

Yoon, C.M. 216, 225 Yoon, N.S. 168 Yoon, Y.-J. 187, 235 Yoshida, J. 41, 91,228, 267, 286 Yoshida, M. 44 Yoshimatsu, M. 13, 52, 61 Yoshimitsu, T. 310 Yoshimura, T. 137 Young, D.W. 14, 188, 190 Yu, B. 336, 346 Yu, C.-M. 24, 179 Yu, W.-Y. 105 Yuan, Y.-J. 311 Yudin, A.K. 84, 136 Yue, T.-Y. 128 Yun, Y.K. 359 Yus, M. 28, 293 Yusubov, M.S. 233 Zaitsu, K. 314 Zakrzewski, J. 77 Zaleska, B. 189 Zanatta, N. 219 Zanda, M. 9, 370 Zanoni, G. 147, 339 Zaragoza, F. 6 Zard, S.Z. 59, 60, 141, 164, 256, 261,336, 341 Zatsepin, T.S. 300 Zavialov, I.A. 12 Zaworotko, M.J. 325

AUTHOR INDEX

Zecchi, G. 194 Zeng, X. 318 Zeynizadeh, B. 270 Zhan, Y. 165 Zhang, A. 206 Zhang, H.G. 168 Zhang, J. 80 Zhang, N. 248 Zhang, S. 268 Zhang, T.Y. 142 Zhang, W. 252 Zhang, X. 34, 61, 62, 76, 97, 127, 146, 153, 234 Zhang, Y. 28, 31, 42, 52, 80, 172, 188, 348 Zhang, Z. 365 Zhang, Z.-Z. 318 Zhao, G. 119 Zhao, K. 360 Zhao, Y.F. 264 Zhdankin, V.V. 293 Zheng, Z. 6, 112 Zhou, W.-S. 345 Zhu, J. 126, 141,164, 170, 344 Zhu, Q. 82 Zhu, S. 31 Ziessel, R.F. 257 Zimmerman, H. 275 Zolfigol, M.A. 258 Zubin, E.M. 300 Zubkov, F. 166 Zwanenburg, B. 342, 345, 360