Asymmetric Synthesis V1 - 1st Edition - ISBN: 9780125077019, 9780323160001

Asymmetric Synthesis V1

1st Edition

Editors: James Morrison
eBook ISBN: 9780323160001
Imprint: Academic Press
Published Date: 1st December 1983
Page Count: 216
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Asymmetric Synthesis, Volume 1: Analytical Methods covers the major analytical methods used to determine enantiomeric ratios.

This volume contains chapters that discuss the methods used to obtain chiral compounds and shows how to evaluate the chiral efficiency of an asymmetric synthesis. Analytical methods such as polarimetry, competitive reaction methods, isotope dilution, gas and liquid chromatography, and nuclear magnetic resonance methods are also discussed.

Chemists and researchers in the field of pharmaceutical will find the book very useful.

Table of Contents



1. A Summary of Ways to Obtain Optically Active Compounds

I. Introduction

II. Obtaining Chiral Compounds by the FRN Method

III. Isolating Chiral Compounds from Natural Sources

IV. Resolution of Racemic Modifications by the Physical Separation of Intermediate Diastereomers

V. Asymmetric Transformations

VI. Kinetic Resolution

VII. Asymmetric Synthesis


2. Polarimetry

I. Introduction

II. Instrumentation

III. Advantages of Optical Rotation Measurements

IV. Requirements for Precision of Data


3. Competitive Reaction Methods for the Determination of Maximum Specific Rotations

I. Introduction

II. Principles of Kinetic Resolution

III. Calculation of the Specific Rotation of an Enantiomer by Means of a Method Using Asymmetric Destruction of the Corresponding Racemic Mixture

IV. Calculation of the Specific Rotation of an Enantiomer by Means of a Method Using Two Reciprocal Kinetic Resolutions

V. Conclusion


4. Isotope-Dilution Techniques

I. Introduction

II. History

III. Theory

IV. Errors

V. Examples


5. Gas Chromatographic Methods

I. Introduction

II. Direct Resolution of Derivatized Enantiomers on Chiral Stationary Phases by Gas Chromatography

III. Direct Resolution of Underivatized Enantiomers on Metal-Containing Chiral Stationary Phases by Complexation Gas Chromatography

IV. Precision of Analysis and Practical Considerations

V. Conclusions


6. Separation of Enantiomers by Liquid Chromatographic Methods

I. Introduction and Background

II. General Considerations

III. Indirect Resolutions

IV. Direct Resolutions

V. Conclusions


7. Nuclear Magnetic Resonance Analysis Using Chiral Derivatives

I. Introduction

II. Application of Chemical Shift Nonequivalence

III. Application of Induced Chemical Shift Nonequivalence


8. Nuclear Magnetic Resonance Analysis Using Chiral Solvating Agents

I. Introduction

II. Principles

III. Chiral Solvating Agents, Solutes, and Association Interactions

IV. Practical Experimental Considerations

V. Comparison with the Chiral Lanthanide Shift Reagent Method

VI. Conclusions


9. Nuclear Magnetic Resonance Analysis Using Chiral Shift Reagents

I. Introduction

II. General Features of Shift Reagents

III. Structural Isomerism in Chiral Shift Reagents

IV. Variations in Structure

V. Mechanism of Action

VI. Uses of Chiral Shift Reagents

VII. Experimental Procedures




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© Academic Press 1983
Academic Press
eBook ISBN:

About the Editor

James Morrison

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