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Catalytic Asymmetric Synthesis
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Вернуться на страницу книги Catalytic Asymmetric Synthesis
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Страница 1
Table of Contents
List of Tables
List of Illustrations
Guide
Pages
Страница 7
Страница 8
PREFACE
PREFACE TO THE FIRST EDITION
LIST OF CONTRIBUTORS
Страница 12
1 ASYMMETRIC ENAMINE AND IMINIUM ION CATALYSIS
1.1. INTRODUCTION
1.2. REPRESENTATIVE ORGANOCATALYSTS 1.2.1. Introduction
1.2.2. Reactivity of Diphenylprolinol Silyl Ether Catalyst and MacMillan’s Catalyst
1.2.3. Cinchona Amine‐Based Catalysts
1.3. ENAMINE 1.3.1. Aldol Reaction
1.3.2. Mannich Reaction
1.3.3. Other Functionalization of the α‐Position of Carbonyl Groups
1.3.4. Michael Reaction
1.3.5. Dienamine and Trienamine as an Intermediate [33]
1.4. IMINIUM ION 1.4.1. Introduction of an Iminium Ion
1.4.2. Two Reaction Paths
1.4.3. Diels‐Alder Type Reaction
1.4.4. Michael Reaction
1.5. DOMINO REACTION 1.5.1. Introduction of Domino (Cascade and Tandem) Reactions
1.5.2. Enders’ Work
1.6. DOMINO REACTION AND TOTAL SYNTHESIS
1.6.1. Steroid Skeleton
1.6.2. α‐Skytanthine and Quinine
1.6.3. (+)‐Lycoposerramine Z
1.6.4. Estradiol Methyl Ether
1.6.5. MacMillan’s Alkaloid Synthesis
1.6.6. Prostaglandin E
1
Methyl Ester
1.6.7. Corey Lactone
1.7. COMBINATION OF TWO CATALYSTS
1.7.1. Combination of Two Organocatalysts
1.7.2. Combination of Organocatalyst and Metal Catalyst
1.7.2.1. Enamine and Metal Catalyst
1.7.2.2. Iminium Ion and Transition Metal Catalyst
1.7.3. Two Chiral Catalysts
1.8. CONCLUSION
REFERENCES
2 ASYMMETRIC ACID ORGANOCATALYSIS
2.1. INTRODUCTION
2.2. FEATURES OF CHIRAL BRØNSTED ACIDS
2.2.1. Acidity of Chiral Brønsted Acids
2.2.2. Mode of Activation of Chiral Phosphoric Acids and Related Compounds
2.2.3. Effect of Metal Salts
2.3. NUCLEOPHILIC REACTIONS 2.3.1. Reactions with Imines and Iminium Salts
2.3.2. Reactions with Carbonyl Compounds and Oxonium Salts
2.4. CYCLOADDITION REACTIONS 2.4.1. Diels‐Alder Reactions
2.4.2. Aza‐Diels‐Alder Reactions
2.4.3. Oxa‐Diels‐Alder Reactions
2.4.4. Other Cycloaddition Reactions
2.4.5. Nazarov Cyclizations
2.5. MICHAEL REACTIONS
2.6. REDUCTION 2.6.1. Reduction of Imines
2.6.1.1. Transfer Hydrogenation of Ketimines
2.6.2. Reduction of Ketones
2.6.3. Reduction of Alkenes
2.7. ADDITION TO ALKENES
2.8. SUBSTITUTION REACTIONS
2.9. REARRANGEMENT REACTIONS
2.10. MISCELLANEOUS REACTIONS
2.11. CONSTRUCTION OF AXIALLY, PLANAR, AND HELICALLY CHIRAL COMPOUNDS
2.12. COMBINATION WITH TRANSITION METAL CATALYSTS [25–27]
2.13. COMBINATION WITH PHOTOREDOX CATALYST
2.14. CONCLUSION
ACKNOWLEDGMENTS
REFERENCES
3 ASYMMETRIC BASE ORGANOCATALYSIS
3.1. INTRODUCTION
3.2. CHIRAL TERTIARY AMINE CATALYSTS: CHIRAL ACID–BASE BIFUNCTIONAL CATALYSIS
3.2.1. Application of Designed Pronucleophiles
3.2.2. Carbon‐Heteroatom Bond Formations
3.2.3. Other Applications
3.3. CHIRAL GUANIDINE CATALYSTS
3.4. OTHER CHIRAL UNCHARGED ORGANOBASE CATALYSTS: CHIRAL ORGANOSUPERBASES
3.4.1. Chiral Cyclopropenimine Catalysts
3.4.2. Chiral Triaryliminophosphorane Catalysts
3.4.3. Chiral P1‐Phosphazene Catalysts
3.4.4. Chiral Higher‐Order Phosphazene Catalysts
3.5. CONCLUSION AND OUTLOOK
REFERENCES
4 ASYMMETRIC PHASE‐TRANSFER AND ION‐PAIR ORGANOCATALYSES
4.1. INTRODUCTION
4.2. CHIRAL CATION 4.2.1. Chiral Cation Phase‐Transfer Catalysis
4.2.1.1. Alkylation
4.2.1.2. Addition to Michael Acceptors
4.2.1.3. Addition to Carbonyls and Imines
4.2.1.4. Arylation
4.2.1.5. Carbon‐Heteroatom (C‐X) Bond Formation
4.2.2. Transition‐Metal/Chiral Cation Dual Catalysis
4.2.3. Cation‐Binding Catalysis
4.3. CHIRAL‐ANION
4.3.1. Iminium
4.3.2. Oxocarbenium
4.3.3. Carbocation
4.3.4. Miscellaneous
4.3.5. Chiral‐Anion Phase Transfer
4.3.5.1. Halogenation
4.3.5.2. Amination
4.3.5.3. Miscellaneous Transformations
4.3.6. Transition‐Metal/Chiral‐Anion Dual Catalysis
4.3.7. Anion‐Binding Catalysis
4.3.7.1. Nonaromatic Cations
4.3.7.2. Cationic Heterocycles
4.3.7.3. Asymmetric Ring Opening of Strained Heterocycles
4.4. CONCLUSION
REFERENCES
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