Enantioselective Organocatalyzed Reactions I Enantioselective Oxidat
Organocatalysis has emerged as one of the hot topics in organic chemistry in recent years, as confirmed by the rapid-growing interest that researchers have shown in this field. Enantioselective Organocatalyzed Reaction Volume I and II provides a critical
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Rainer Mahrwald Editor
Enantioselective Organocatalyzed Reactions I Enantioselective Oxidation, Reduction, Functionalization and Desymmetrization
Editor Prof. Dr. Rainer Mahrwald Institut für Chemie der Humboldt-Universität zu Berlin Brook-Taylor-Str. 2 12 489 Berlin Germany [email protected]
ISBN 978-90-481-3864-7 e-ISBN 978-90-481-3865-4 DOI 10.1007/978-90-481-3865-4 Springer Dordrecht Heidelberg London New York Library of Congress Control Number: 2011933564 © Springer Science+Business Media B.V. 2011 No part of this work may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission from the Publisher, with the exception of any material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com)
Foreword
It is part of the human experience to wonder and marvel at the beauty of life in the world around us. An astronomer might look up in awe and question the size, shape and age of the universe. A biologist might pay keen attention to the anatomical features unique to a given organism and see the beauty in the organism’s adaptability. The organic chemist, however, tends to look deeper and ponder the actual molecules, focusing on the unique mechanisms that create a wide array of complex molecules that in turn conspire to create life itself. This is as true today as it was more than a century ago when the great organic chemist Emil Fischer stated “If we wish to catch up with Nature, we shall need to use the same methods as she does, and I can foresee a time in which physiological chemistry will not only make greater use of natural enzymes, but will actually resort to creating synthetic ones.”1 Fischer foresaw that if we could understand how Nature’s enzymes catalyze reactions, we could create our own synthetic catalysts. Indeed, it was in recreating Nature’s aldolase enzymes that we were led to re-examine the chemistry of Hajos and Parrish in a new light. Through experimentation, we realized that the simple amino acid proline could recapitulate the ‘complex’ chemistry of an aldolase enzyme thereby providing a stunningly simple solution to the direct asymmetric aldol, Michael, Mannich and other reactions. Indeed, catalytic activity of amino acids, particularly in enamine and iminium chemistry, is not restricted to the amino acid proline but rather is a feature that most, if not all, amino acids have in common. A decade has now passed since the studies of my laboratory and those of David MacMillan’s refocused the considerable attention of the community on the profound potential of small organic molecules to catalyze asymmetric reactions. In this time, the scope of organocatalysis has enlarged considerably with respect both to the type of reactions catalyzed (aldol, cycloaddition, redox, asym
