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R. Mahrwald (Ed.)
Modern Aldol Reactions
Vol. 1: Enolates,
Organocatalysis,
Biocatalysis and Natural
Product Synthesis
Modern Aldol Reactions. Vol. 1: Enolates, Organocatalysis, Biocatalysis and Natural Product Synthesis.
Edited by Rainer Mahrwald
Copyright 8 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
ISBN: 3-527-30714-1
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Rainer Mahrwald (Ed.)
Modern Aldol Reactions
Vol. 1: Enolates, Organocatalysis, Biocatalysis
and Natural Product Synthesis
1081921026.048.png 1081921026.049.png
 
9
PD Dr. Rainer Mahrwald
Department of Organic Chemistry
Humboldt University
Brook-Taylor-Str. 2
12489 Berlin
Germany
This book was carefully produced.
Nevertheless, editor, authors and
publisher do not warrant the
information contained therein to be
free of errors. 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.
Bibliographic information published by
Die Deutsche Bibliothek
Die Deutsche Bibliothek lists this
publication in the Deutsche
Nationalbibliografie; detailed
bibliographic data is available in the
Internet at http://dnb.ddb.de
( 2004 WILEY-VCH Verlag GmbH &
Co. KGaA, Weinheim
All rights reserved (including those of
translation in other languages). No part
of this book may be reproduced in any
form – by photoprinting, microfilm, or
any other means – nor transmitted or
translated into machine language with-
out written permission from the pub-
lishers. 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 Asco Typesetters, Hong
Kong
Printing Strauss Gmbh, Morlenbach
Bookbinding Litges & Dopf
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ISBN 3-527-30714-1
v
Foreword
Historically, the stimulus for the development of a particular reaction has
been interconnected with a class of natural products whose synthesis would
be greatly facilitated by the use of that particular bond construction. For ex-
ample, the steroid synthesis challenges proved instrumental in the develop-
ment of the Diels–Alder reaction. So too the synthesis challenges associated
with the macrolide antibiotics have provided the motivation for the devel-
opment of the full potential of the aldol addition reaction. R. B. Woodward’s
1956 quote on the ‘‘hopelessly complex’’ architecture of the erythromycins
was probably stimulated, in part, by the fact that the aldol reaction existed in
a completely underdeveloped state five decades ago.
O
Me
Me
Me
OH
OH
Me
Me
OH
O
The erythromycin-A structure, as viewed
by Woodward in the ’50s
‘‘Erythromycin, with all of our
advantages, looks at present quite
hopelessly complex, particularly in view
of its plethora of asymmetric centers.’’
R. B. Woodward in Perspectives in
Organic Chemistry; Todd, A. Ed.; Wiley-
Interscience, New York, 1956, page 160.
Me
Et
O
O
NMe 2
H
OH
O
O
Me
O
H
Me
Me
MeO
OH
The challenges associated with the development of this reaction are also
embodied in the more general goals of acyclic stereocontrol that have been
under active investigation for nearly twenty-five years. In these studies, the
goal of understanding pi-face selectivity at trigonal carbon centers for a
multitude of organic transformations has been the ultimate objective. From
these research activities, a host of stereochemical models have evolved, such
as the Felkin–Anh model for carbonyl addition and the Zimmermann–
Traxler aldol stereochemical model for aldol diastereoselection.
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