Principles of Asymmetric Synthesis - 2nd Edition - ISBN: 9780080448602, 9780080914138

Principles of Asymmetric Synthesis

2nd Edition

Authors: Robert Gawley Jeffrey Aube
Paperback ISBN: 9780080448602
eBook ISBN: 9780080914138
Imprint: Elsevier
Published Date: 31st May 2012
Page Count: 568
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Description

Dedication

Foreword

Preface

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

References

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

References

Chapter 3. Enolate, Azaenolate, and Organolithium Alkylations

3.1 Enolates and Azaenolates1

3.2 Chiral Organolithiums

References

Chapter 4. 1,2- and 1,4-Additions to CX 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

References

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

References

Chapter 6. Cycloadditions and Rearrangements

6.1 Cycloadditions

6.2 Rearrangements

References

Chapter 7. Reductions and Hydroborations

7.1 Reduction of Carbon–Heteroatom Double Bonds

7.2 Reduction of Carbon–Carbon Bonds

7.3 Hydroborations

References

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

References

Index

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

Readership

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.

Table of Contents

Dedication

Foreword

Preface

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

References

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

References

Chapter 3. Enolate, Azaenolate, and Organolithium Alkylations

3.1 Enolates and Azaenolates1

3.2 Chiral Organolithiums

References

Chapter 4. 1,2- and 1,4-Additions to CX 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

References

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

References

Chapter 6. Cycloadditions and Rearrangements

6.1 Cycloadditions

6.2 Rearrangements

References

Chapter 7. Reductions and Hydroborations

7.1 Reduction of Carbon–Heteroatom Double Bonds

7.2 Reduction of Carbon–Carbon Bonds

7.3 Hydroborations

References

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

References

Index

Details

No. of pages:
568
Language:
English
Copyright:
© Elsevier 2012
Published:
Imprint:
Elsevier
eBook ISBN:
9780080914138
Paperback ISBN:
9780080448602

About the Author

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

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