Topics in Current Chemistry
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1 Topics in Current Chemistry Editorial Board: A. de Meijere K.N. Houk H. Kessler J.-M. Lehn S.V. Ley S.L. Schreiber J. Thiem B. M. Trost - F. Vogtle H. Yamamoto
2 Springer Berlin ~eidelberg New York Barcelona Hung Kong Loridon Milan Paris Singapore Tokyo
3 Stereoselective Heterocyclic Synthesis Ill Volume Editor: Peter Metz With contributions by A. Hassner, I. N. N. Namboothiri, U. Nubbemeyer, S. D. Rychnovsky, C. J. Sinz, P. ten Holte, B. Zwanenburg Springer
4 The series Topics in Current Chetnistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage includes all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the nonspecialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to a larger scientific audience. As a rule, contributions are specially commissioned. The editors and publishers will, however, always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics in Current Chemistry in English. 111 references Topics in Current Chemistry is abbreviated Top. Curr. Chem. and is cited as a journal. Springer WWW home page: Visit the TCC home page at or ISSN ISBN X Springer-Verlag Berlin Heidelberg New York Library of Congress Catalog Card Number This work is subject to copyright.al1 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 on microfilm or in any other ways, and storage in data banks. 1)uplication of this publication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9,1965, in its current version, and permission for use must always he obtained from Springer- Verlag.Vio1ation.s are liable for prosecution under the German Copyright Law. Springer-Verlag Berlin Heidelberg New York a member of BertelsmannSpringer Science+Business Media GmbH O Springer-Verlag Berlin Heidelberg 2001 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. Cover design: Friedhelm Steinen-Broo,Barcelona; MEDIO, Berlin Typesetting: Fotosatz-Service K'ohler GmbH, Wiirzburg SPIN: ra Printed on acid-free paper
5 Volume Editor Prof. Dr. Peter Metz Institut fiir Organische Chemie Technische Universitat Dresden Mommsenstraf3e Dresden, Germany Editorial Board Prof. Dr. Armin de Meijere lnstitut fur Organische Chemie der Georg-August-Universitat Tammannstrde GGttingen, Germany Prof. Dr. Horst Kessler Institut fiir Organische Chemie TC Munchen Lichtenbergstrde Garching, Germany kessler@ch.tum.de Prof. K.N. Houk Department of Chemistry and Biochemistry University of California 405 Hilgard Avenue Los Angeles, CA , USA houk@chem.ucla.edu Prof. Jean-Marie Lehn Institut de Chimie UniversitC de Strasbourg 1 rue Blaise Pascal, B. P.Z 296lR Strasbourg Cedex, France lehn@chimie.u-strasbsfr Prof. Steven V. Ley University Chemical Laboratory Lensfield Road Cambridge CB2 lew, Great Britain sv11000@cus.cam.ac.uk Prof. Stuart L. Schreiber Chemical Laboratories Harvard University 12 Oxford Street Cambridge, MA , USA sls@slsiris.harvardedu Prof. Dr. Joachim Thiem Institut fur Organische Chemie Prof. Barry M. Trost Universitit bur^ Department of Chemistry Martin-Luther-King-Platz 6 Stanford University Hamburg, Germany Stanford, CA , USA thiem@chemie.uni-hamburg.de bmtrost@leland.stanford.edu Prof. Dr. Fritz Vogtle Prof. Hisashi Yamamoto Kekule-Institut fiir Organische Chemie School of Engineering und Biochemie der Universitat Bonn Xagoya Cniversity Gerhard-Domagk-Strai3e 1 Chikusa, Nagoya , Japan Bonn, Germany j45988a@nucc.cc.nagoya-u.ac.jp voegtmuni-burtn.de
6 Topics in Current Chemistry Now Also Available Electronically For all customers with a standing order for Topics in Current Chemistry we offer the electronic form via LINK free of charge. Please contact your librarian who can receive a password for free access to the full articles by registration at: If you do not have a standing order you can nevertheless browse through the table of contents of the volumes and the abstracts of each article at: There you will also find information about the - Editorial Board - Aims and Scope - Instructions for Authors
7 Preface Keeping up with the advances in modern heterocyclic chemistry is essential for many of our colleagues in academia and industry. It is the aim of this series on "Stereoselective Heterocyclic Synthesis" to assist the chemical community in this respect by presenting a selection of exciting recent developments. As it was for the first two volumes (1997), the stereoselective synthesis of - or with the aid of - heterocycles is the common motif for all the chapters in this third volume. I am very glad that again leading researchers in this area have contributed highly stimulating accounts with up-to-date coverage. "Stereoselective Heterocyclic Synthesis 111" features chapters on "Stereoselective Intramolecular J,3-Dipolar Cycloadditions" by I.N.N. Nambothiiri and A. Hassner giving an in depth survey of the generation and synthetic application of valuable 1,3-dipoles,"4-Acetoxy- and 4-Cyano-12-dioxanes in Synthesis" by C. J. Sinz and S.D. Rychnovsky presenting a comprehensive summary of the utility of the versatile title compounds in natural products synthesis,"the Synthetic Potential of Three-Membered Ring Aza-Heterocycles" by B. Zwanenburg and l? ten Holte highlighting the fascinating chemistry of aziridine and azirine carboxylic esters, and '(Synthesis of Medium-Sized Ring Lactams" by U. Nubbemeyer discussing a wide range of modern strategies for the stereoselective preparation of these important heterocycles. I wish to express my thanks to all contributors for their dedicated effort and to Mrs. Kollmar-Thoni, Springer-Verlag, for her continuous support. Dresden, March 2001 Peter Metz
8 Contents Stereoselective Intramolecular 1. 3.Dipolar Cycloadditions I.N.N. Namboothiri. A. Hassner Acetoxy- and 4-Cyano-1J-dioxanes in Synthesis C.J.Sinz.S.D.Rychnovsky The Synthetic Potential of Three-Membered Ring Aza-Heterocycles B. Zwanenburg. P. ten Holte Synthesis of Medium-Sized Ring Lactams U. Nubbemeyer Author IndexVolumes
9 Contents of Volume 189 Stereoselective Heterocyclic Synthesis I Volume Editors: P. Metz ISBN Hetero Diels-AIder Reactions in Organic Chemistry L.F. Tietze, G. Kettschau Tandem Processes of Metallo Carbenoids for the Synthesis of Azapolycycles A. Pawda Contents of Volume 190 Stereoselective Heterocyclic Synthesis I I Volume Editors: P. Metz ISBN Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis P. Chiu, M. Lautens The Nucleophilic AdditionlRing Closure (NARC) Sequence for the Stereocontrolled Synthesis of Heterocycles P. Perlmutter Chiral Acetylenic Sulfoxides and Related Compounds in Organic Synthesis A.W.M. Lee, W.H. Chan N-Sulfonyl Imines - Useful Synthons in Stereoselective Organic Synthesis S. M. Weinreb
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