Asymmetric Synthesis V2 - 1st Edition - ISBN: 9780125077026, 9780323157360

Asymmetric Synthesis V2

1st Edition

Editors: James Morrison
eBook ISBN: 9780323157360
Imprint: Academic Press
Published Date: 1st December 1983
Page Count: 292
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Asymmetrie Synthesis, Volume 2: Stereodifferentiating Addition Reactions, Part A is concerned with asymmetric addition reactions.

This volume contains chapters that cover B-H additions across carbon-carbon and carbon-oxygen double bonds; carbonyl reductions using chiral modifications of lithium aluminum hydride and chiral dihydropyridines; additions of achiral and chiral nucleophiles to chiral and achiral aldehydes and ketones; organometal additions to chiral vinylic sulfoxides; and description of imine and enamine alkylations.

Chemists will find the book interesting.

Table of Contents



1. Asymmetric Hydroboration

I. Introduction

II. Diisopinocampheylborane

III. Dilongifolylborane

IV. Limonylborane

V. Monoisopinocampheylborane

VI. Conclusion


2. Reductions with Chiral Boron Reagents

I. Introduction

II. Chirally Modified Boranes

III. Chirally Modified Borohydrides


3. Reductions with Chiral Modifications of Lithium Aluminum Hydride

I. Introduction

II. Alcohol-Modified Lithium Aluminum Hydride

III. Amine-Modified Lithium Aluminum Hydride

IV. Amino Alcohol-Modified Lithium Aluminum Hydride

V. Aminodiol-Modified Lithium Aluminum Hydride

VI. Conclusions


4. Reductions with Chiral Dihydropyridine Reagents

I. Introduction

II. Summary of the Mechanistic Studies of NADH Model Reactions

III. Asymmetric Reductions with Chiral NADH Model Compounds

IV. Factors Affecting Product Stereochemistry in Asymmetric Reductions with Chiral NADH Model Compounds

V. Approach to Chiral NADH Models of Higher Stereoselectivity

VI. Simulation of Enzyme Active Site Composed of Peptide Chain

VII. Concluding Remarks


5. Application of Cram's Rule: Addition of Achiral Nucleophiles to Chiral Substrates

I. Introduction

II. Variation of Reaction Conditions

III. Application of Cram's Rule to Asymmetric Synthesis

IV. Remote Stereochemical Control


6. Addition of Chiral Nucleophiles to Aldehydes and Ketones

I. Introduction

II. Organometallic Reagents Used in a Chiral Environment

III. Addition of Carbanions a to a Chiral Sulfoxide Group

IV. Chiral Ester Enolates


7. Noncatalytic Additions to α,β-Unsaturated Carbonyl Compounds

I. Introduction

II. Conjugate Additions of Chiral α,β-Unsaturated Carbonyl Derivatives

III. Conjugate Additions with Chiral Nucleophiles


8. Addition of Organometallic Reagents to Chiral Vinylic Sulfoxides

I. Introduction

II. 1-Alkenyl Sulfoxides

III. 2-Alkenyl Sulfoxides

IV. 2-Cycloalkenone Sulfoxides

V. Conclusion


9. Alkylation of Imine and Enamine Salts

I. Introduction

II. Formation of Azaallyl Metal Reagents and Enamines

III. Structure of Azaallyl Metal Reagents

IV. Electrophilic Substitution of Azaallyl Metal Regents and Enamines

V. Asymmetric Syntheses Employing Chiral Azaallyl Metal Reagents

VI. Asymmetric Syntheses Employing Chiral Enamines




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© Academic Press 1983
Academic Press
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About the Editor

James Morrison

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