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Cycloaddition Reactions in Organic Synthesis.
Edited by S. Kobayashi and K. A. Jorgensen
Copyright © 2001 Wiley-VCH Verlag GmbH
ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)
Shu Kobayashi
Karl Anker Jørgensen (Eds.)
Cycloaddition Reactions
in Organic Synthesis
Cycloaddition Reactions in Organic Synthesis.
Edited by S. Kobayashi and K. A. Jorgensen
Copyright © 2001 Wiley-VCH Verlag GmbH
ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)
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Cycloaddition Reactions in Organic Synthesis.
Edited by S. Kobayashi and K. A. Jorgensen
Copyright © 2001 Wiley-VCH Verlag GmbH
ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)
Cycloaddition Reactions in Organic Synthesis
Edited by
Shu Kobayashi and Karl Anker Jørgensen
Cycloaddition Reactions in Organic Synthesis.
Edited by S. Kobayashi and K. A. Jorgensen
Copyright © 2001 Wiley-VCH Verlag GmbH
ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)
Editors
Shu Kobayashi
Graduate School of Pharmaceutical Sciences
University of Tokyo
The Hongo, Bunkyo-Ku
113-0033 Tokyo
Japan
Karl Anker Jørgensen
Department of Chemistry
Aarhus University
Langelandsgade 140
8000 Aarhus C
Denmark
n
This book was carefully produced. Nevertheless,
editors, authors and publisher do not warrant the
information contained therein to be free of er-
rors. Readers are advised to keep in mind that
statements, data, illustrations, procedural 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.
Die Deutsche Bibliothek – CIP-Cataloguing-in-
Publication Data
A catalogue record for this publication is available
from Die Deutsche Bibliothek
© WILEY-VCH Verlag GmbH
Weinheim (Germany), 2002
All rights reserved (including those of translation
in other languages). No part of this book may be
reproduced in any form – by photoprinting, mi-
crofilm, or any other means – nor transmitted or
translated into machine language without written
permission from the publishers. Registered
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when not specifically marked as such, are not to
be considered unprotected by law.
printed in the Federal Republic of Germany
printed on acid-free paper
Typesetting
K+V Fotosatz GmbH, Beerfelden
Printing
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Bookbinding
Wilhelm Osswald & Co., Neustadt
ISBN
3-527-30159-3
Cover
The sculpture is
made by the Danish
glass artist Tchai Munch.
Cycloaddition Reactions in Organic Synthesis.
Edited by S. Kobayashi and K. A. Jorgensen
Copyright © 2001 Wiley-VCH Verlag GmbH
ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)
V
Contents
List of Contributors
Introduction
1
3
XIII
References
1
1.1
1.2
1.2.1
1.2.1.1
1.2.1.2
1.2.1.3
1.2.1.4
1.2.1.5
1.2.1.6
1.2.1.7
1.2.2
Catalytic Asymmetric Diels-Alder Reactions
5
1.2.3
1.2.3.1
1.2.3.2
1.2.3.3
1.2.3.4
1.2.3.5
1.2.3.6
1.2.3.7
1.2.3.8
1.2.4
1.3
1.4
Yujiro Hayashi
Introduction
5
The Chiral Lewis Acid-catalyzed Diels-Alder Reaction
6
The Asymmetric Diels-Alder Reaction of
a, b-Unsaturated
Aldehydes
as Dienophiles
6
Aluminum
6
Boron
6
Titanium
18
Iron
20
Ruthenium
21
Chromium
21
Copper
21
The Asymmetric Diels-Alder Reaction of
a, b-Unsaturated
Esters
as Dienophiles
23
The Asymmetric Diels-Alder Reaction
of 3-Alkenoyl-1,3-oxazolidin-2-ones as Dienophiles
24
Aluminum
26
Magnesium
26
Copper
27
Iron
34
Nickel
34
Titanium
36
Zirconium
40
Lanthanides
40
The Asymmetric Diels-Alder Reaction of Other Dienophiles
43
The Asymmetric Catalytic Diels-Alder Reaction Catalyzed by Base
46
Conclusions
48
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