Cycloaddition Reactions in Organic Synthesis (S. Kobayashi & K. A. Jorgensen).pdf

Cycloaddition Reactions in Organic Synthesis.

Edited by S. Kobayashi and K. A. Jorgensen

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

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

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

ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)

Editors

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.

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

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

Cover

The sculpture is

made by the Danish

glass artist Tchai Munch.

Weinheim (Germany), 2002

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

names, trademarks, etc. used in this book, even

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 betz-druck GmbH, Darmstadt

Bookbinding Wilhelm Osswald & Co., Neustadt

ISBN 3-527-30159-3

Cycloaddition Reactions in Organic Synthesis.

Edited by S. Kobayashi and K. A. Jorgensen

ISBNs: 3-527-30159-3 (Hardcover); 3-527-60025-6 (Electronic)

Contents

List of Contributors XIII

Introduction 1

References

Catalytic Asymmetric Diels-Alder Reactions

Yujiro Hayashi

1.1

Introduction 5

1.2

The Chiral Lewis Acid-catalyzed Diels-Alder Reaction 6

1.2.1

The Asymmetric Diels-Alder Reaction of

-Unsaturated Aldehydes

as Dienophiles

1.2.1.1

Aluminum 6

1.2.1.2

Boron 6

1.2.1.3

Titanium 18

1.2.1.4

Iron 20

1.2.1.5

Ruthenium 21

1.2.1.6

Chromium 21

1.2.1.7

Copper

1.2.2

The Asymmetric Diels-Alder Reaction of , -Unsaturated Esters

as Dienophiles

1.2.3

The Asymmetric Diels-Alder Reaction

of 3-Alkenoyl-1,3-oxazolidin-2-ones as Dienophiles

1.2.3.1

Aluminum 26

1.2.3.2

Magnesium 26

Copper

1.2.3.3

Iron 34

1.2.3.4

Nickel

1.2.3.5

Titanium 36

1.2.3.6

1.2.3.7

Zirconium 40

1.2.3.8

Lanthanides

1.2.4

The Asymmetric Diels-Alder Reaction of Other Dienophiles

1.3

The Asymmetric Catalytic Diels-Alder Reaction Catalyzed by Base

1.4

Conclusions

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