Asymmetric Synthesis V3

Asymmetric Synthesis V3

1st Edition - April 1, 1984

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  • Editor: James Morrison
  • eBook ISBN: 9780323145008

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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


    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


    2. The Aldol Addition Reaction

    I. Simple Diastereoselection

    II. Diastereofacial Selectivity


    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


    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


    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 Chiral Centers A and C

    IV. Effect of a Substituent on Ring 1 on the Chirality of Cyclization: Influence of Chiral Center D

    V. Effect of a Substituent on Ring 2 on the Chirality of Cyclization: Influence of Chiral Center E

    VI. Stereochemistry of Termination: Relationship between Chiral Center F and the Others

    VII. Chiral Auxiliaries

    VIII. Mechanistic Conclusions: Are the Cyclizations Concerted or Stepwise?


    6. Olefin Cyclization Processes That Form Carbon-Heteroatom Bonds

    I. Introduction

    II. Formation of Oxygen Heterocycles

    III. Formation of Nitrogen Heterocycles

    IV. Formation of Sulfur Heterocycles


    7. Asymmetric Cycloaddition Reactions

    I. Introduction

    II. Intermolecular Diels-Alder Reactions

    III. Intramolecular Diels-Alder Processes

    IV. [2 + 2] Cycloadditions

    V. [3 + 2] Cycloadditions


    8. Chirality Transfer via Sigmatropic Rearrangements

    I. Introduction

    II. 3,3-Sigmatropic Rearrangements

    III. 2,3-Sigmatropic Rearrangements

    IV. Summary



Product details

  • No. of pages: 592
  • Language: English
  • Copyright: © Academic Press 1984
  • Published: April 1, 1984
  • Imprint: Academic Press
  • eBook ISBN: 9780323145008

About the Editor

James Morrison

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