Asymmetric Synthesis V3
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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 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?
References
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
References
7. Asymmetric Cycloaddition Reactions
I. Introduction
II. Intermolecular Diels-Alder Reactions
III. Intramolecular Diels-Alder Processes
IV. [2 + 2] Cycloadditions
V. [3 + 2] Cycloadditions
References
8. Chirality Transfer via Sigmatropic Rearrangements
I. Introduction
II. 3,3-Sigmatropic Rearrangements
III. 2,3-Sigmatropic Rearrangements
IV. Summary
References
Index
Product details
- No. of pages: 592
- Language: English
- Copyright: © Academic Press 1984
- Published: April 1, 1984
- Imprint: Academic Press
- eBook ISBN: 9780323145008