Principles of Asymmetric Synthesis


  • Robert Gawley, Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, USA
  • Jeffrey Aube, Department of Medicinal Chemistry, The University of Kansas, Lawrence, KS, USA

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, this book presents a detailed analysis of the factors that govern stereoselectivity in organic reactions.

After an explanation of the basic physical-organic principles governing stereoselective reactions, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Practical Aspects of Asymmetric Synthesis" provides a critical overview of the most common methods for the preparation of enantiomerically pure compounds, techniques for analysis of stereoisomers using chromatographic, spectroscopic, and chiroptical methods.

The authors then present an overview of the most important methods in contemporary asymmetric synthesis organized by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions, one chapter on reductions, and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). This organization allows the reader to compare the leading methods for asymmetric synthesis in an appropriate context.

A highlight of the book is the presentation and discussion of transition states at the current level of understanding, for important reaction types. In addition, extensive tables of examples are used to give the reader an appreciation for the scope of each reaction. Finally, leading references are provided to natural product synthesis that has been accomplished using a given reaction as a key step.

View full description


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 level of understanding 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.


Book information

  • Published: May 2012
  • Imprint: ELSEVIER
  • ISBN: 978-0-08-044860-2


"…we have a wonderful second edition that not only retains the spirit of the original book, but is also comprehensive and comprehendible…Gawley’s legacy…lives on, not just in his own independent research, but in the number of chemists that this book and its first edition have inspired and those it will no doubt continue to inspire."-- Chemistry World, July 2013

Table of Contents

1. Introduction, General Principles, and Terminology

2. Practical Aspects of Asymmetric Synthesis

3. Enolate, Azaenolate, and Organolithium Alkylations

4. 1,2 and 1,4 Additions to C=X Bonds

5. Aldol and Michael Additions of Allyls, Enolates, and Enolate Equivalents

6. Cycloadditions and Rearrangements

7. Reductions

8. Oxidations