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(from preface)Volume 45 of Advances in Heterocyclic Chemistry contains five contributions, all of which break new ground for this series. In the first article, Fujita and Nagao describe the use of heterocycles for the induction of chirality. Thiscontribution represents an example of the way in which our subject is making itself increasingly felt throughout the whole field of chemistry. The second article, by Tisler, covers heterocyclic quinones, including the many classes in which a heterocycle is fused to a 1,2- or 1,4-benzoquinone ring.In the third article, Porter describes the chemistry of thiophenium salts and ylids, to which he has contributed extensively. The chemistry of 1,4-diazocines is presented by Perlmutter; this article follows an earlier review by the same author on azocines in Volume 31 of Advances in Heterocyclic Chemistry. The final article of this volume, and the second contribution from Japan, is by Tsuge and Kanemasa and deals with recent advances in azomethine ylide chemistry.The cumulative index updates, as announced in the preface to Volume 40, will cover Volumes 41-45 and will appear in Volume 46. This will prevent a delay in the publication of Volume 45.
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Advances in Heterocyclic Chemistry Volume 45 Editorial Advisory Board R. A. Abramovitch, Clemson, South Carolina A. Albert, Canberra, Australia A. T. Balaban, Bucharest, Romania A. J. Boulton, Norwich, England H. Dorn, Berlin, G.D.R. J. Elguero, Madrid, Spain S. Gronowitz, Lund, Sweden T. Kametani, Tokyo, Japan 0. Meth-Cohn, South Africa C. W. Rees, FRS, London, England E. C . Taylor, Princeton, New Jersey M. TiSler, Ljubljana, Yugoslavia J. A. Zoltewicz, Gainesville, Florida Advances in HETEROCYCLIC CHEMISTRY Edited by ALAN R. KATRITZKY, FRS Kenan hfessor of Chemistry Department of Chemistry university of Florida Gainesville. Florida n Volume 45 ACADEMIC PRESS, INC. Harcourt Bmce Jovanovich, Publishers San Diego New York Berkeley Boston London Sydney Tokyo Toronto COPYRIGHT 0 1989 BY ACADEMIC PRESS, INC. All Rights Reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy. recording, or any information storage and retrieval system, without permission in writing from the publisher. ACADEMIC PRESS, INC. San Diego, California 92101 United Kingdom Edition published by ACADEMIC PRESS LIMITED 24-28 Oval Road, London NW I 7DX LIBRARY OF CONGRESS CATALOG CARD NUMBER: ISBN 0-12-020645-5 (alk. paper) PRINTED IN THE UNITED STATES OF AMERICA ~ Y Y ~ Y I 9Y n ~ 7 6 5 4 . 3 2 1 62-13037 Contents PREFACE ...................................................................... vii Chiral Induction Using Heterocycles EIICHIFUJITA AND YOSHIMIT~U NAGAO . I Introduction .......................................................... I1. Preparation of CCChiral Thiazolidine-2-thionesand Oxazolidine-2-thiones ... I11. C h i d Recognition in Aminolysis ........................................ IV Analytical Separation and Optical Resolution of Racemic Carboxylic Acids and Amino Acids .............................. V Highly Diastereoselective AldoL’Ilpe Reactions ............................ VI . Highly Selective Nonenzymatic Chiral Induction onto Prochiral a-Symmetric Dicarboxylic Acids ................................ VII Methylseleno-Promoted Ketene-Imine Cycloaddition Reaction ............... VIII Conclusion ........................................................... References ............................................................ . . . . 1 2 4 6 1 22 30 33 33 Heterocyclic Quinones MIHATISLER I. I1. 1