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I Lutz F. Tietze, Gordon Brasche, and Kersten M. Gericke Domino Reactions in Organic Synthesis Domino Reactions in Organic Synthesis. Lutz F. Tietze, Gordon Brasche, and Kersten M. Gericke Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 3-527-29060-5 II Related Titles Berkessel, A., Gröger, H. Asymmetric Organocatalysis From Biomimetic Concepts to Applications in Asymmetric Synthesis Mahrwald, R. (ed.) Modern Aldol Reactions, 2 Vol. 2004 ISBN 3−527-30714−1 2005 ISBN 3−527-30517−3 Nicolaou, K. C., Snyder, S. A. Zhu, J., Bienaymé, H. (eds.) Multicomponent Reactions 2005 Classics in Total Synthesis II More Targets, Strategies, Methods 2003 ISBN 3−527-30685−4 ISBN 3−527-30806−7 Eicher, T., Hauptmann, S. de Meijere, A., Diederich, F. (eds.) Metal-Catalyzed Cross-Coupling Reactions 2004 ISBN 3−527-30518−1 Beller, M., Bolm, C. (eds.) Transition Metals for Organic Synthesis, 2 Vol. Building Blocks and Fine Chemicals 2004 ISBN 3−527-30613−7 The Chemistry of Heterocycles Structure, Reactions, Syntheses, and Applications 2003 ISBN 3−527-30720−6 III Lutz F. Tietze, Gordon Brasche, and Kersten M. Gericke Domino Reactions in Organic Synthesis IV The Authors Prof. Dr. Dr. h.c. Lutz Tietze Inst. f. Organische Chemie Georg-August-Universität Tammannstr. 2 37077 Göttingen Dr. Gordon Brasche Inst. f. Organische Chemie Georg-August-Universität Tammannstr. 2 37077 Göttingen All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, pro cedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Dr. Kersten Matthias Gericke Inst. f. Organische Chemie Georg-August-Universität Tammannstr. 2 37077 Göttingen Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Intern et at <http://dnb.ddb.de>. © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form − by photoprinting, microfilm, or any other means − nor transmitted or translated in to a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Typesetting primustype Robert Hurler GmbH Printing betz-Druck GmbH, Darmstadt Binding Litges & Dopf Buchbinderei GmbH, Heppenheim Cover Design Adam Design, Weinheim Printed in the Federal Republic of Germany Printed on acid-free paper ISBN-13: 978-3-527-29060-4 ISBN-10: 3-527-29060-5 V Table of Contents Introduction 1 Classification 7 1 Cationic Domino Reactions 11 1.1 Cationic/Cationic Processes 12 1.1.1 Cationic/Cationic/Cationic Processes 33 1.2 Cationic/Pericyclic Processes 39 1.3 Cationic/Reductive Processes 42 2 Anionic Domino Reactions 48 2.1 Anionic/Anionic Processes 48 2.1.1 Anionic/Anionic/Anionic Processes 104 2.1.2 Fourfold and Higher Anionic Processes 135 2.1.3 Two- and Threefold Anionic Processes Followed by a Nonanionic Process 142 2.2 Anionic/Radical Processes 156 2.3 Anionic/Pericyclic Processes 160 2.3.1 Anionic/Pericyclic Processes Followed by Further Transformations 185 2.4 Anionic/Transition Metal-Catalyzed Processes 191 2.5 Anionic/Oxidative or Reductive Processes 194 3 Radical Domino Reactions 219 3.1 Radical/Cationic Domino Processes 223 3.2 Radical/Anionic Domino Processes 224 3.3 Radical/Radical Domino Processes 225 3.3.1 Radical/Radical/Anionic Domino Processes 252 3.3.2 Radical/Radical/Radical Domino Processes 253 3.3.3 Radical/Radical/Pericyclic Domino Processes 272 3.3.4 Radical/Radical/Oxidation Domino Processes 273 3.4 Radical/Pericyclic Domino Processes 275 4 Pericyclic Domino Reactions 280 4.1 Diels−Alder Reactions 282 Domino Reactions in Organic Synthesis. Lutz F. Tietze, Gordon Brasche, and Kersten M. Gericke Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 3-527-29060-5 Thank you for evaluating Wondershare PDF to Word. You can only convert 5 pages with the trial version. To get all the pages converted, you need to purchase the software from: http://cbs.wondershare.com/go.php?pid=417&m=db . paper ISBN -13 : 978-3-527-29060-4 ISBN -10 : 3-527-29060-5 V Table of Contents Introduction 1 Classification 7 1 Cationic Domino Reactions 11 1. 1 Cationic/Cationic Processes 12 1. 1 .1 Cationic/Cationic/Cationic. 33 1. 2 Cationic/Pericyclic Processes 39 1. 3 Cationic/Reductive Processes 42 2 Anionic Domino Reactions 48 2 .1 Anionic/Anionic Processes 48 2 .1. 1 Anionic/Anionic/Anionic Processes 10 4 2 .1. 2. Anionic Processes 13 5 2 .1. 3 Two- and Threefold Anionic Processes Followed by a Nonanionic Process 14 2 2.2 Anionic/Radical Processes 15 6 2.3 Anionic/Pericyclic Processes 16 0 2.3 .1 Anionic/Pericyclic