
Principles of Asymmetric Synthesis
Description
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
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 C
X 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
Product details
- No. of pages: 568
- Language: English
- Copyright: © Elsevier 2012
- Published: May 29, 2012
- Imprint: Elsevier
- eBook ISBN: 9780080914138
- Paperback ISBN: 9780080448602
About the Authors
Robert Gawley
Affiliations and Expertise
Jeffrey Aubé
Affiliations and Expertise
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