Principles of Asymmetric Synthesis - 1st Edition

Principles of Asymmetric Synthesis, Volume 14

1st Edition

Authors: R.E. Gawley J. Aubé
Imprint: Pergamon
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Table of Contents

Introduction. Why we do asymmetric synthesis. What is an asymmetric synthesis? Stereoselectivity: intraligand vs. interligand asymmetric induction. Selectivity: kinetic and thermodynamic control. Single and double asymmetric induction. Glossary of stereochemical terms. References. Analytical Methods. The importance of analysis, and which method to choose. Polarimetry, the old fashioned way. Nuclear magnetic resonance. Chromatography. Summary. References. Enolate, Azaenolate, and Organolithium Alkylations. Enolates and azaenolates. Chiral organolithiums. References. 1,2 and 1,4 Additions to Carbonyls. Cram's rule: open-chain model. Cram's rule: rigid, chelate, or cyclic model. Additions using chiral catalysts or chiral nucleophiles. Conjugate additions. References. Aldol and Michael Additions of Allyls and Enolates. 1,2-Additions of allyl metals and metalloids. Aldol additions. Michael additions. References. Rearrangements and Cycloadditions. Rearrangements. Cycloadditions. References. Reductions and Hydroborations. Reduction of carbon-heteroatom double bonds. Reduction of carbon-carbon bonds. Hydroborations. References. Oxidations. Introduction and scope. Epoxidation and related reactions. Dihydroxylations. Oxidation of enolates and enol ethers. Miscellaneous oxidations. References. Index.


The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion.

The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types.

After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers.

The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step.

In addition to tables of examples that show high selectivity, a transi


This book is intended for advanced undergraduate or graduate students needing a guide to the principles of asymmetric synthesis and stereoselective reactions, and for practicing chemists seeking a similar guide or who want leading references to the primary literature. The book could be used for a course in organic mechanisms, stereochemistry, reactions, or synthesis. It will also be a valuable reference source for the expert.


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About the Authors

R.E. Gawley Author

Affiliations and Expertise

Department of Chemistry and Biochemistry University of Arkansas 348 Arkansas Ave Fayetteville, AR 72701 USA

J. Aubé Author

Affiliations and Expertise

University of Kansas, Kansas, USA