Asymmetric Synthesis V3 - 1st Edition - ISBN: 9780125077033, 9780323145008

Asymmetric Synthesis V3

1st Edition

Editors: James Morrison
eBook ISBN: 9780323145008
Imprint: Academic Press
Published Date: 1st April 1984
Page Count: 592
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Asymmetric Synthesis, Volume 3: Stereodifferentiating Addition Reactions, Part B presents intensive investigations in leading academic and industrial laboratories on stereodifferentiating addition reactions. This book is divided into eight chapters and begins with a comprehensive review of the formation of chiral metal enolates and their stereoselective alkylation reactions. These topics are followed by discussions on chiral Aldol addition reactions and the many variations of asymmetric synthesis that may be carried out using chiral oxazolines. A chapter describes the alkylation of chiral hydrazones, a process that yields chiral-substituted aldehydes and ketones. Other chapters explore a variety of cyclization processes that form carbon-carbon and carbon-heteroatom bonds. The last chapters deal with the asymmetric cycloadditions and sigma-tropic rearrangements. Synthetic chemists and researchers will find this book invaluable.

Table of Contents

Contributors Preface

  1. Stereoselective Alkylation Reactions of Chiral Metal Enolates I. Prologue II. Selective Enolate Formation III. Enolate Structure IV. Transition-State Control Elements V. Intraannular Chirality Transfer VI. Chelate-Enforced Intraannular Chirality Transfer VII. Extraannular Chirality Transfer VIII. Conclusions References
  2. The Aldol Addition Reaction I. Simple Diastereoselection II. Diastereofacial Selectivity References
  3. Asymmetric Synthesis via Chiral Oxazolines I. Introduction II. (R)- and (S)-Dialkylacetic Acids III. (R)- or (S)-2-Substituted Butyrolactones and Valcrolactones IV. Optically Active ß-Hydroxy and ß-Methoxy Acids V. ß-Hydroxy Esters via Aldol Condensation VI. Optically Active 2-Methoxyalkanoic and 2-Chloroalkanoic Acids VII. Thiiranes VIII. Asymmetric Reductions IX. Chiral Grignard Reagents X. Kinetic Resolution of Racemic Alkyl Halides XI. Optically Active 2-Hydroxycarboxylic Acids XII. Chiral Phthalides XIII. (R)- and (S)-ß,ß-Dialkylpropionic Acids XIV. (R)- and (S)-ß-Substituted Valerolactones XV. α,ß,ß-Trisubstituted Propionic Acids XVI. (S)-4-Substituted 1,4-Dihydropyridines XVII. Chiral Binaphthyls References
  4. Alkylation of Chiral Hydrazones I. Introduction II. The SAMP-/RAMP-Hydrazone Method III. Asymmetric Carbon-Carbon Bond Formations α to the Carbonyl Group via SAMP-/RAMP- Hydrazones IV. Mechanistic Studies V. Applications of the SAMP-/RAMP-Hydrazone Method to Asymmetric Syntheses of Natural Products VI. Conclusion and Outlook References
  5. Olefin Cyclization Processes That Form Carbon-Carbon Bonds I. Introduction II. Ring Fusion: Relationship between Chiral Centers A and B III. Orientation of Adjacent Rings: Relationship between Ch


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© Academic Press 1984
Academic Press
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About the Editor

James Morrison

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