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Tietze, Gordon Brasche, and Kersten M.. Gericke Domino Reactions in Organic Synthesis Domino Reactions in Organic Synthesis.. Tietze, Gordon Brasche, and Kersten M... Modern Aldol Reacti

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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

ISBN: 3-527-29060-5

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Lutz F Tietze, Gordon Brasche,

and Kersten M Gericke

Domino Reactions

in Organic Synthesis

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The Authors

Prof Dr Dr h.c Lutz Tietze

Inst f Organische Chemie

Georg-August-Universität

Tammannstr 2

37077 Göttingen

Dr Gordon Brasche

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

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>

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

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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

ISBN: 3-527-29060-5

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