Stereoselective Heterocyclic Synthesis II PDF
Preview Stereoselective Heterocyclic Synthesis II
190 scipoT ni Current Chemistry Editorial Board A. de Meijere • K.N. Houk. J.-M. Lehn. S.V. Ley J. Thiem • B.M. Trost E • V6gtle • H. Yamamoto regnirpS Berlin Heidelberg New York anolecraB Budapest gnot-I Kong London Milan siraP Santa aralC eropagniS oykoT Stereoselective Heterocyclic Synthesis II Volume Editor: .P Metz With contributions by W. H. Chan, E Chiu, M. Lautens, A. W. M. Lee, .P Perlmutter, .S M. Weinreb r e g n~ i r p S This series presents critical reviews of the present position and future trends in modern chemical research. It is addressed to all research and industrial chemists who wish to keep abreast of advances in the topics covered. sA rule, a contributions are specially commissioned. The editors and publishers will, always however, be pleased to suggestions receive and supplementary information. Papers are accepted for" Topics in Current Chemistry" in English. In references Topics in Current Chemistry is abbreviated Curr. Chem. Top. and is cited as a journal. Springer WWW home page: http://www.springer.de Visit the CCT home page at led.regnirps.wwwll:ptth ISSN O340-1022 ISBN 3-540-627OO-6 Springer-Verlag Berlin Heidelberg New York Library of Congress Catalog Card Number 226446-47 This work subject is to copyright. llA rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction omni crofdms or in any other ways, and storage in data banks. Duplication of this publication orp arts thereof is ylno permitted under thep rovisions of the German Copyright Law of September ,9 ,5691 in its current version, and permission for use must always be obtained from Violations Springer-Verlag. are liable for prosecution under the German Copyright .waL Springer-Verlag © Berlin Heidelberg 7991 Printed in Germany The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. design: Cover Friedhelm Steinen-Broo, Barcelona Typesetting: Fotosatz-Service K6hler ,GHO Wtirzburg 97o84 :NIPS 61727501 t o 2 - - 66/3o2o 3 4 Printed 5 on acid-free paper Volume Editor Prof, Dr. Peter Metz Institut ftir Organische Chemie Technische Universit~it Dresden Mommsenstr. 13 D-01062 Dresden, Germany E-mail: metz@cochO l.ch m.tu-dresden.de Editorial Board Prof. Dr. Armin de Meijere Prof. K.N. Houk Institut fiir Organische Chemie Department of Chemistry and Biochemistry der Georg-August-Universit/it University of California Tammannstrat]e 2 504 Higard Avenue 77073-D G6ttingen, Germany soL Angeles, AC ,9851-42009 ASU E-mail: ed.negnitteog-inu@cocu E-mail: ude.alcu.mehc@kuoh Prof. Jean-Marie Lehn Prof. Steven .V Ley Institut de Chimie Chemical University Laboratory de Universit~ Strasbourg Road Lensfield 1 rue Pascal, Blaise .B .P Z 8R/692 2BC WE1 Britain Great Cambridge, 80076-F Strasbourg France Cedex, E-mail: svll .ca.mac.suc@00O uk E-mail: rf.gbsarts-u.eimihc@nhel Prof. Dr. Joachim Thiem Prof. Barry M. Trost Institut Organische fiir Chemie Department of Chemistry ti~tisrevinU Hamburg Stanford University Martin-Luther-King-Platz 6 Stanford, AC ,0805-50349 ASU 64102-D Hamburg, Germany E-mail: ude.drofnats.dnalel@tsortmb [email protected] E-mail: Pro£ Dr. Fritz V6gtle Prof. Hisashi Yamamoto Institut fiir Organische Chemie School of Engineering und Biochemie der ti~tisrevinU University Nagoya Gerhard-Domagk-St ehtar 1 10-464 Nagoya, Chikusa, Japan 12135-D Bonn, Germany :liam-E pj.ca.u-ayogan.cc.ccun@a88954j :liam-E ed.nnob-inu.eimehcLeimehcnS@eltgeov ecaferP Heterocycles play a central role in organic synthesis. Above all due to the in- teresting biological activities associated with a large number of these structurally diverse compounds, many heterocycles have been and will be challenging targets for total synthesis. Moreover, even if the final goal of a synthesis is not heterocyclic, at least a central intermediate or a key reagent used along the synthetic sequence most surely will be. This holds especially true if stereoselectivity is an important issue, as modern heterocyclic chemistry provides the synthetic organic chemist with an excellent arsenal of methods and strategies for the stereocontroUedc on- struction and elaboration (including the cleavage) of heterocycles. Recent years have witnessed exciting new findings in this field, and it is the aim of this two- volume set on"Stereoselective Heterocyclic Synthesis" within the series Topics in Current Chemistry to present a selection of these novel developments. As the guest editors I am very glad that leading researches in this area havec on- tributed highly inspiring accounts with up-to-date coverage to this compilation. Part I features chapters on "Hetero Diels-Alder Reactions in Orgnic Chemistry" by L.F. Tietze and .G Kettschau describing the state of the art for these useful [4 + 2] cycloadditions,w hich yield a wide variety of heterocycles and "Tandem sessecorP of Metallo Carbenoids for the Synthesis of Azapolycycles" by A. Padwa surveying attractive routes to complex ring systems based upon 1,3-dipolar cycloadditions. Part II comprises chapter on "Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis" by .2t Chiu and M.L autens focussing on the preparation and the synthetic utility of the versatile title compounds, "The Nucleophilic Addition/Ring Closure (NARC) Sequence for the Stereocontrolled Synthesis of Heterocycles" a powerful tactical combination disccussed by .P Perlmutter,"Chiral Acetylenic Sulfoxides and Related Compounds in Organic Synthesis" by A.W..M. Lee and .W .41 Chan emphasizing the use of sulfur-activated acetylenic and vinyl units for the efficient preparation of heterocycles, and "N-Sulfonyl Imines - Synthons Useful in Stereoselective Organic Synthesis" by S.M. Weinreb giving a comprehensive review on the chemistry of these valuablee lectron-deficient compounds. I hope that the articles collected in this two-volume set on "Stereoselective Heterocyclic Synthesis" will not only serve experts in the field but will also attract the interest of scientists not yet familiar with this fascinating research topic. Dresden, March 1997 Peter Metz elbaT of stnetnoC Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis .P Chiu, M. Lautens .............................. The Nucleophilic Addition/Ring Closure (NARC) Sequence fort he Stereocontrolled Synthesis of Heterocycles .P Perlmutter .................................. 87 Chixal Acetylenic Sulfoxides and Related Compounds in Organic Synthesis A. .W M. Lee, W. H. Chan ........................... 103 N-Sulfonyl Imines - Useful Synthons in Stereoselective Organic Synthesis .S M. Weinreb ................................. 131 Author Index Volumes - 151 190 ....................... 185 Table of Contents of Volume 189 Stereoselective I Heterocyclic Synthesis Volume Editor: P. Metz Hetero Diels-Alder Reactions in Organic Chemistry .L E Tietze, G. Kettschau Tandem Processes of Metallo Carbenoids for the Synthesis of Azapolycyles A. Padwa gnisU Ring-Opening Reactions of cilcycibaxO sdnuopmoC sa a Strategy ni Organic sisehtnyS Pauline Chiu 1 and Mark Lautens 2 1 Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong E-marl: [email protected] 2 Department of Chemistry, University of Toronto, Toronto, Canada SSM 1A1 E-marl: [email protected] This chapter discusses the various methods for the preparation of oxabicyclic compounds, with an emphasis on the stereo- and enantioselective synthesis of these substances. Methods to desymmetrize oxabicyclic compounds are also presented. The utility of these sub~ meso strates for organic synthesis is demonstrated by the many strategies available for ring-opening the bicyclic compounds to yield cyclic and acyclic structures. Examples demonstrating how this strategy has been incorporated into the efficient syntheses of many natural products are presented. .sdrowyeK Cycloaddition, oxabicyclic, ring opening, stereocontrol, natural products Table of Contents Introduction ............................ 3 Preparation of Oxabicyclic Substrates .............. 4 2.1 Cycloaddition with Furan Derivatives .............. 4 2.1.1 4 + 2 Cycloadditions with Dienophiles ............. 4 2.1.2 4 + 3 Cycloadditions with Oxyallyl Cations ........... 8 2.1.3 4 + 3 Cycloadditions with Allylic Cations ............ 12 2.1.4 4+4 Cycloadditions with Pyrones ................ 13 2.1.5 Cyclopropanation/Rearrangement of Furan Derivatives .... 14 2.2 5 + 2 Cycloadditions of Pyrylium Betaines ........... 15 2.3 Cycloadditions of Cyclic Carbonyl u ............. 18 2.4 Fragmentation of Cyclic Oxonium Intermediates ........ 20 2.5 Annulations of 1,3-Dinucleophiles with Dicarbonyl Compounds ...................... 21 2.6 Transannular Addition of Nucleophiles .............. 23 2.7 Miscellaneous Reactions ...................... 25 Survey of Functionalization Reactions of Oxabicyclic Substrates 26 3.1 Stereoselectivity of Functionalizations .............. 26 3.1.1 exo/endo Selectivity ......................... 26 3.1.2 Regioselectivity ........................... 30 3:2 Enantioselective Desymmetrization Reactions .......... 32 3.2.1 Desymmetrization of Oxabicyclo2.2.1 Substrates ....... 33 3.2.2 Desymmetrization of Oxabicyclo3.2.1 Substrates ....... 34 scipoT ni tnerruC ,yrtsimehC .loV 091 (cid:14)9 regnirpS galreV nilreB grebledieH 7991 2 E Chiu. .M Lautens Ring-Opening Reactions of Oxabicyclic Substrates ....... 35 4.1 Cleavage of Carbon-Carbon Bonds in the Oxabicyclic Framework ....................... 35 4.1.1 Oxidation of the Carbonyl Functionality ............. 35 4.1.2 Oxidative Cleavage ofVicinal Diols in the Carbon Framework 38 4.1.3 Oxidative Cleavage of the Carbon Framework .......... 39 4.1.4 Retro-Dieckmann/Retro-Aldol Reactions ............. 40 4.1.5 Photochemically-Induced Cleavage ................ 41 4.1.6 Electrochemical Cleavage ...................... 42 4.1.7 Acid-Induced Skeletal Rearrangements .............. 42 4.1.8 Miscellaneous Cleavage Reactions ................. 43 4.2 Cleavage of Carbon-Oxygen Bonds in the Oxabicyclic Framework ....................... 44 4.2.1 Oxygen Bridge Activation by an Electron-Donating Group at the Bridgehead Carbon ...................... 44 4.2.2 Generation of a Carbanion a to the Carbon-Oxygen Bond . . . 45 4.2.3 Generation of a Carbanion y to the Carbon-Oxygen Bond . . . 48 4.2.4 Heterolytic Cleavage Induced By Acids .............. 49 4.2.4.1 Protic Acids ............................. 49 4.2.4.2 Boron-Based Lewis Acids ...................... 52 4.2.4.3 Silyl Lewis Acids ........................... 54 4.2.4.4 Other Lewis Acids .......................... 55 4.2.5 Grob Fragmentation ......................... 56 4.2.6 Overall Addition of Hydride .................... 56 4.2.6.1 Hydrogen Addition ......................... 56 4.2.6.2 Single Electron Transfer Reductions ................ 57 4.2.6.3 Reductive Elimination ....................... 60 4.2.6.4 Metal Hydride Reductions ..................... 61 4.2.6.4.1 fl-Hydridic Organometallic Reagents ............... 61 4.2.6.4.2 Boranes and Borohydrides ..................... 62 4.2.6.4.3 Aluminum Hydrides ........................ 63 4.2.6.4.4 Tin Hydrides ............................. 67 4.2.6.5 Photochemical Reductions ..................... 68 4.2.7 Overall Addition of Alkyl/Aryl Groups .............. 69 4.2.7.1 Silyl Enol Ether and a Lewis Acid ................. 69 4.2.7.2 Organolithium Reagents ...................... 69 4.2.7.3 Organocuprate Reagents ...................... 75 4.2.7.4 Transition Metal-Catalyzed Alkylative Ring-Opening ...... 77 Conclusions and New Frontiers .................. 78 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79
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