Principles of Asymmetric Synthesis

Principles of Asymmetric Synthesis, 2nd Edition

Principles of Asymmetric Synthesis, 2nd Edition,Robert Gawley,Jeffrey Aube,ISBN9780080448602






234 X 155

This text provides an analysis of stereoselectivity in organic reactions and also acts as an ideal reference guide to the literature.

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Key Features

  • Authoritative glossary to aid understanding of stereochemical terminology
  • Explanations of the key factors influencing stereoselectivity with numerous examples, organized by reaction type
  • A handy reference guide to the literature of asymmetric synthesis for practitioners in the field


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.


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.

Robert Gawley

Affiliations and Expertise

Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, USA

Jeffrey Aube

Department of Medicinal Chemistry, University of North Carolina, USA

Affiliations and Expertise

Department of Medicinal Chemistry, The University of Kansas, Lawrence, KS, USA

Principles of Asymmetric Synthesis, 2nd Edition




Chapter 1. Introduction, General Principles, and Glossary of Stereochemical Terms

1.1 Why We Do Asymmetric Syntheses

1.2 What is an Asymmetric Synthesis?

1.3 Stereoselectivity, and What It Takes to Achieve It

1.4 Selectivity: Kinetic and Thermodynamic Control

1.5 Entropy, the Isoinversion Principle, and the Effect of Temperature on Selectivity

1.6 Single and Double Asymmetric Induction

1.7 Kinetic Resolution

1.8 The Curtin–Hammett Principle

1.9 Asymmetric Transformations and Dynamic Resolutions

1.10 Asymmetric Catalysis and Nonlinear Effects

1.11 Glossary of Stereochemical Terms22


Chapter 2. Practical Aspects of Asymmetric Synthesis

2.1 Choosing a Method for Asymmetric Synthesis

2.2 How to Get Started

2.3 General Considerations for Analysis of Stereoisomers

2.4 Chromatography

2.5 Nuclear Magnetic Resonance

2.6 Chiroptical Methods

2.7 Summary


Chapter 3. Enolate, Azaenolate, and Organolithium Alkylations

3.1 Enolates and Azaenolates1

3.2 Chiral Organolithiums


Chapter 4. 1,2- and 1,4-Additions to CimageX Bonds

4.1 Cram’s Rule: Open-Chain Model

4.2 Cram’s Rule: Rigid, Chelate, or Cyclic Model

4.3 Chiral Catalysts and Chiral Auxiliaries

4.4 Conjugate Additions


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

5.1 1,2-Allylations and Related Reactions

5.2 Aldol Additions5

5.3 Michael Additions15


Chapter 6. Cycloadditions and Rearrangements

6.1 Cycloadditions

6.2 Rearrangements


Chapter 7. Reductions and Hydroborations

7.1 Reduction of Carbon–Heteroatom Double Bonds

7.2 Reduction of Carbon–Carbon Bonds

7.3 Hydroborations


Chapter 8. Oxidations

8.1 Epoxidations and Related Reactions

8.2 Asymmetric Dihydroxylation (AD) Reaction

8.3 α-Functionalization of Carbonyl Groups and Their Equivalents

8.4 Miscellaneous Oxidations that Necessitate Differentiation of Enantiotopic Groups



Quotes and reviews

"…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

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