Mahrwald - Modern Methods in Stereoselective Aldol Reactions

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The Editor

Prof. Dr. Rainer Mahrwald

Humboldt-Universitt Berlin

Institut fr Chemie

Brook-Taylor-Str. 2

12489

Berlin

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Preface

Stereoselectivity is one of the most important aspects for natural product chemists. Following the increasing possibility of detection and assignment of stereogenic centers, a tremendous increase in stereoselective methods of organic reactions, particularly aldol reactions, has been noticed. In the beginning of this development, only sporadic examples of stereoselective aldol reactions were described, mostly in the context of total syntheses of natural products. An outstanding early example is the R. B. Woodward's proline-catalyzed aldol addition in the total synthesis of erythronolide A at the Harvard University in 1981. In the following three decades, a vast arsenal of stereoselective aldol additions has been developed (see Figure).

This book provides a comprehensive review of modern aldol reactions, especially in the aspect of how to achieve high stereoselectivity diastereoselectivity as well as enantioselectivity. Stereoselection is discussed under several different aspects. One aspect is the deployment of different substrates acetate or propionate aldol reactions. Another aspect is the mode of action including metal enolate chemistry, Lewis acid as well as Lewis base catalysis, enzymatic catalysis, and organocatalysis. There are some overlappings of these aspects in the chapters covering the cross-cutting themes of vinyloguos Mukaiyama reaction or asymmetric inductions (e.g., compare Scheme ). These overlappings, however, are intentional in order to give a comprehensive insight into the techniques for installing required configurations during aldol reactions. The utility of the corresponding methods is shown in the context of total syntheses of natural products. All chapters are thoroughly well written by experts in the respective fields.

It is my pleasure to express profound gratitude to the 15 authors for their huge endeavor to organize and summarize this vast amount of material. It has been a great pleasure for me to work with this team of authors at all times. Finally, my special thanks go to Elke Maase and Bernadette Gmeiner at WILEY for their fine work in making this book a reality.

Berlin, Autumn 2012

Rainer Mahrwald

List of Contributors