Principles and Applications of Asymmetric Synthesis

Guo-Qiang Lin, Yue-Ming Li, Albert S.C. Chan

ISBNs: 0-471-40027-0 (Hardback); 0-471-22042-6 (Electronic)

PRINCIPLES AND

APPLICATIONS OF

ASYMMETRIC SYNTHESIS

PRINCIPLES AND

APPLICATIONS OF

ASYMMETRIC SYNTHESIS

Guo-Qiang Lin

Yue-Ming Li

Albert S. C. Chan

A JOHN WILEY & SONS, INC., PUBLICATION

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Dedicated to Professors

Chung-Kwong Poon and Wei-Shan Zhou

CONTENTS

Preface

xiii

Abbreviations

1 Introduction

1.1 The Signi®cance of Chirality and Stereoisomeric

Discrimination

1.2 Asymmetry

1.2.1 Conditions for Asymmetry

1.2.2 Nomenclature

1.3 Determining Enantiomer Composition

1.3.1 Measuring Speci®c Rotation

1.3.2 The Nuclear Magnetic Resonance Method

1.3.3 Some Other Reagents for Nuclear Magnetic

Resonance Analysis

1.3.4 Determining the Enantiomer Composition of Chiral

Glycols or Cyclic Ketones

1.3.5 Chromatographic Methods Using Chiral Columns

1.3.6 Capillary Electrophoresis with Enantioselective

Supporting Electrolytes

1.4 Determining Absolute Con®guration

1.4.1 X-Ray Di¨raction Methods

1.4.2 Chiroptical Methods

1.4.3 The Chemical Interrelation Method

1.4.4 Prelog's Method

1.4.5 Horeau's Method

1.4.6 Nuclear Magnetic Resonance Method for Relative

Con®guration Determination

1.5 General Strategies for Asymmetric Synthesis

1.5.1 ``Chiron'' Approaches

1.5.2 Acyclic Diastereoselective Approaches

1.5.3 Double Asymmetric Synthesis

1.6 Examples of Some Complicated Compounds

1.7 Some Common De®nitions in Asymmetric Synthesis and

Stereochemistry

1.8 References

vii

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