Handbook of Reagents for Organic Synthesis Chiral Reagents for Asymmetric Synthesis.pdf

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Handbook of Reagents

for Organic Synthesis

Chiral Reagents for

Asymmetric Synthesis

Edited by

Leo A. Paquette

The Ohio State University, Columbus, OH, USA

The Atrium, Southern Gate,

Chichester, West Sussex

PO19 8SQ, England

Telephone (+44) 1243 779777

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Library of Congress Cataloguing-in-Publication Data

Handbook of reagents for organic synthesis,

p. cm.

Includes bibliographical references.

Contents: [1] Reagents, auxiliaries, and catalysts for C-C bond

formation / edited by Robert M. Coates and Scott E. Denmark

[2] Oxidising and reducing agents / edited by Steven D. Burke and

Riek L. Danheiser [3] Acidic and basic reagents / edited by

Hans J. Reich and James H. Rigby [4] Activating agents and

protecting groups / edited by Anthony J. Pearson and William R. Roush

[5] Chiral Reagents for Asymmetric Synthesis / edited by Leo A. Paquette

ISBN 0-471-97924-4 (v. 1). ISBN 0-471-97926-0 (v. 2)

ISBN 0-471-97925-2 (v. 3) ISBN 0-471-97927-9 (v. 4)

ISBN 0-470-85625-4 (v. 5)

1. Chemical tests and reagents. 2. Organic compounds-Synthesis.

QD77.H37 1999

547'.2 dc 21

98-53088

CIP

British Library Cataloguing in Publication Data

A catalogue record for this book is available from the British Library

ISBN 0 470 85625 4

Typeset in 9^/1

pt Times Roman by Thomson Press (India) Ltd., New Delhi

Printed and bound in Great Britain by Antony Rowe, Chippenham, Wiltshire

This book is printed on acid-free paper responsibly manufactured from sustainable forestry

in which at least two trees are planted for each one used for paper production.

e-EROS Editorial Board

Editor-in-Chief

Leo A. Paquette

The Ohio State University, Columbus, OH, USA

Executive Editors

David Crich

University of Illinois, Chicago, IL, USA

Philip L. Fuchs

Purdue University, West Lafayette, IN, USA

Peter Wipf

University of Pittsburgh, Pittsburgh, PA, USA

EROS 1 Print Edition Editorial Board

Editor-in-Chief

Leo A. Paquette

The Ohio State University, Columbus, OH, USA

Editors

Steven D. Burke

University of Wisconsin

at Madison,

WI, USA

Scott E. Denmark

University of Illinois

at Urbana-Champaign,

IL, USA

Dennis C. Liotta

Emory University, Atlanta,

CA, USA

Robert M. Coates

University of Illinois

at Urbana-Champaign,

IL, USA

David J. Hart

The Ohio State University,

Columbus, OH, USA

Anthony J. Pearson

Case Western Reserve University,

Cleveland, OH, USA

James H. Rigby

Wayne State University, Detroit,

MI, USA

Rick L. Danheiser

Massachusetts Institute of

Technology, Cambridge,

MA, USA

Lanny S. Liebeskind

Emory University, Atlanta,

GA, USA

Hans J. Reich

University of Wisconsin at Madison,

WI, USA

William R. Roush

Indiana University, Bloomington,

IN, USA

Assistant Editors

James P. Edwards

Mark Volmer

Ligand Pharmaceuticals, San Diego,

Emory University, Atlanta,

CA, USA

GA, USA

Leon A. Ghosez

Universite Catholique

de Louvain, Belgium

Chun-Chen Liao

„

. TT - i ^

University, Hsinchu, Taiwan

Ryoji Noyori

Nagoya University, Japan

Pierre Potier

CNRS, Gif-sur-Yvette, France

Hishashi Yamomoto

Nagoya University, Japan

International Advisory Board

Jean-Marie Lehn

Universite Louis Pasteur,

Strasbourg, France

• X ** J

Lewis N. Mander

Australian National University,

^ i

Canberra, Australia

Gerald

Steven V. Ley

University of Cambridge,

r*- - -KK A

Giorgio Modena

Universitd di Padua,

r i

Italy

Edward Piers

University of British Columbia,

Vancouver, Canada

Ekkehard Winterfeldt

Universitdt Hannover,

Germany

Pattenden

University of Nottingham,

W. Nico Speckamp

Universiteit van Amsterdam,

The Netherlands

Preface

As stated in its Preface, the major motivation for our

undertaking publication of the

Encyclopedia of Reagents for

Organic Synthesis

was "to incorporate into a single work a

genuinely authoritative and systematic description of the

utility of all reagents used in organic chemistry." By all

accounts, this reference compendium succeeded admirably

in approaching this objective. Experts from around the

globe contributed many relevant facts that define the various

uses characteristic of each reagent. The choice of a masthead

format for providing relevant information about each entry,

the highlighting of key transformations with illustrative

equations, and the incorporation of detailed indexes

serve in tandem to facilitate the retrieval of desired

information.

Notwithstanding these accomplishments, the editors came

to recognize that the large size of this eight-volume work and

its cost of purchase often deterred the placement of copies of

the

Encyclopedia

in or near laboratories where the need for this

type of information is most critical. In an effort to meet this

demand in a cost-effective manner, the decision was made to

cull from the major work that information having the highest

probability for repeated consultation and to incorporate the

same into a set of handbooks. The latter would also be

purchasable on a single unit basis.

The ultimate result of these deliberations was the

publication of the

Handbook of Reagents for Organic

Synthesis,

the first four volumes of which appeared in 1999:

Reagents, Auxiliaries, and Catalysts for C-C Bond

Formation

edited by Robert M. Coates and Scott E. Denmark

Oxidizing and Reducing Agents

edited by Steven D. Burke and Rick L. Danheiser

Acidic and Basic Reagents

edited by Hans J. Reich and James H. Rigby

Activating Agents and Protecting Groups

edited by Anthony J. Pearson and William R. Roush

Each of the volumes contains a selected compilation of those

entries from the original

Encyclopedia

that bear on the specific

topic. Ample listings can be found to functionally related

reagents contained in the original work. For the sake of current

awareness, references to recent reviews and monographs have

oeen included, as have relevant new procedures from

Organic

Syntheses.

The present volume entitled

Chiral Reagents for Asym-

metric Synthesis

constitutes the fifth entry into a continuing

series of utilitarian reference works. As with its predecessors,

:his handbook is intended to be an affordable, enlightening

:ompilation that will hopefully find its way into the labora-

:ories of all practicing synthetic chemists. Every attempt has

Deen made to be of the broadest possible relevance and the

expectation is that my colleagues will share in this opinion.

Leo A. Paquette

Department of Chemistry

The Ohio State University

Columbus, OH, USA

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