Asymmetric Synthesis V1

1st Edition - December 1, 1983
Editor: James Morrison
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 6 0 0 0 - 1

Asymmetric Synthesis, Volume 1: Analytical Methods covers the major analytical methods used to determine enantiomeric ratios. This volume contains chapters that discuss the… Read more

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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.

Contributors

Preface

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

References

2. Polarimetry

I. Introduction

II. Instrumentation

III. Advantages of Optical Rotation Measurements

IV. Requirements for Precision of Data

References

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

References

4. Isotope-Dilution Techniques

I. Introduction

II. History

III. Theory

IV. Errors

V. Examples

References

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

References

6. Separation of Enantiomers by Liquid Chromatographic Methods

I. Introduction and Background

II. General Considerations

III. Indirect Resolutions

IV. Direct Resolutions

V. Conclusions

References

7. Nuclear Magnetic Resonance Analysis Using Chiral Derivatives

I. Introduction

II. Application of Chemical Shift Nonequivalence

III. Application of Induced Chemical Shift Nonequivalence

References

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

References

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

References

Index