Cinchona alkaloids in synthesis and catalysis : ligands, immobilization and organocatalysis

This comprehensive review of cinchona-based chiralilty inducers and their applications covers every topic, including ligands, immobilization and organocatalysis. Each chapter summarizes the scope and limitations of the new methods and technologies, while the final chapter contains carefully selected working procedures of cinchona alkaloid-promoted reactions organized according to reaction type.
Invaluable reading for anyone wanting to learn about the current state of this hot topic.

Author Notes

Choong Eui Song has been a full Professor at Sungkyunkwan University since 2004. He received his B.S. in 1980 from Chungang University and obtained a Diploma (1985) and a Ph.D. (1988) at RWTH Aachen in Germany. After completing his Ph.D. he worked as a Principal Research Scientist at the Korea Institute of Science and Technology (KIST). In 2001 he was appointed as head of the national research laboratory for Green Chirotechnology in Korea. In 2004 he moved to his current position and in 2006 he was appointed as a director at the Research Institute of Advanced Nanomaterials and Institute of Basic Sciences in Sungkyunkwan University. His research interests focus on asymmetric catalysis, ionic liquid chemistry and nanochemistry. He received the Scientist of the Month Award from the Ministry of Science and Technology in Korea (2001).

An Overview of Cinchona Alkaloids in Chemistry

Brief History

Active Sites in Cinchona Alkaloids and Their Derivatives

Structural Information on Cinchona Alkaloids

How This Book is Organized

Part I Cinchona Alkaloid Derivatives as Chirality Inducers in Metal-Catalyzed Reactions

Cinchona Alkaloids As Chirality Transmitters In Metal-Catalyzed Asymmetric Reductions

Introduction

Homogeneous Systems for Ketone Reductions

Heterogeneous Pt and Pd Catalysts Modified with Cinchona Alkaloids

Industrial Applications

Conclusions

Cinchona Alkaloids As Chiral Ligands In Asymmetric Oxidations

Introduction

Asymmetric Dihydroxylation of Alkenes

Aminohydroxylation

Sulfur Oxidations

Summary

Cinchona Alkaloids And Their Derivatives As Chirality Inducers In Metal-Promoted Enantioselective Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions

Introduction

Nucleophilic Addition to Carbonyl or Imine Compounds

Miscellaneous Reactions

Cinchona-Based Chiral Ligands in C-F Bond Forming Reactions

Conclusions

Part II Cinchona Alkaloid Derivatives as Chiral Organocatalysts

Cinchona-Based Organocatalysts for Asymmetric Oxidations and Reductions

Introduction

Cinchona-Based Organocatalysts in Asymmetric Oxidations

Cinchona-Based Organocatalysts in Asymmetric Reductions

Conclusions

Cinchona-Catalyzed Nucleophilic Alpha-Substitution of Carbonyl Derivatives

Introduction

Organocatalytic Nucleophilic Alpha-Substitution of Carbonyl Derivatives

Cinchona Alkaloids in Asymmetric Organocatalysis

The Pioneer Works for Phase-Transfer Catalytic Alpha-Substitution

Alpha-Substitution of Alpha-Amino Acid Derivatives via PTC

Alpha-Substitution of Other Carbonyl Derivatives via PTC

Alpha-Heteroatom Substitution via PTC

Nucleophilic Alpha-Substitution of Carbonyl Derivatives via Non-PTC

Conclusions

Cinchona-Mediated Enantioselective Protonations

Introduction

Preformed Enolates and Equivalents

Nucleophilic Addition on Ketenes

Michael Additions

Enantioselective Decarboxylative Protonation

Proton Migration

Summary of Cinchona-Mediated Enantioselective Protonations

Cinchona-Catalyzed Nucleophilic 1,2-Addition to C=O and C=N Bonds

Introduction

Aldol and Nitroaldol (Henry) Reactions

Mannich and Nitro-Mannich Reactions

Aldol- and Mannich-Related Reactions

Cyanation Reactions

Trifluoromethylation

Friedel-Crafts Type Alkylation

Hydrophosphonylation

Conclusions

Cinchona-Catalyzed Nucleophilic Conjugate Addition To Electron-Deficient C=C Double Bonds

Introduction

Conjugate Reaction of Alpha,Beta-Unsaturated Ketones, Amides, and Nitriles

Conjugate Addition of Nitroalkenes

Conjugate Addition of Vinyl Sulfones and Vinyl Phosphates

Cyclopropanation and Other Related Reactions

Conclusions

Cinchona-Catalyzed Cycloaddition Reactions

Introduction

Asymmetric Cycloadditions Catalyzed by Quinuclidine Tertiary Amine

Asymmetric Cycloadditions Catalyzed by Bifunctional Cinchona Alkaloids

Asymmetric Cycloaddition Reactions Catalyzed by Cinchona-Based Primary Amines

Asymmetric Cycloaddition Catalyzed by Cinchona-Based Phase-Transfer Catalysts

Conclusion

Cinchona-Based Organocatalysts for Desymmetrization of Meso-Compounds and (Dynamic) Kinetic Resolution of Racemic Compounds

Introduction

Desymmetrization of meso-Compounds

(Dynamic) Kinetic Resolution of Racemic Compounds

Conclusions

Part III Organic Chemistry of Cinchona Alkaloids

Organic Chemistry of Cinchona Alkaloids

Introduction

Preparation of Quincorine and Quincoridine: Discovery of a Novel Cleavage Reaction of Cinchona Alkaloids

Transformations of the Quinoline Moiety

Basic Transformations of the Vinyl Side Chain

Selected Novel Transformations of the Quinuclidine Moiety of Cinchona Alkaloids

Nucleophilic Substitution at Carbon C9

Novel Rearrangements of the Azabicyclic Moiety

General Experimental Hints and Obstacles

Conclusions

Part IV Cinchona Alkaloid and Their Derivatives in Analytics

Resolution Of Racemates And Enantioselective Analytics By Cinchona Alkaloids and Their Derivatives

Introduction

Resolution of Racemates by Crystallization and Extraction of Diastereoisomers

Enantioselective Chromatography and Related Techniques

Cinchona Alkaloids as Chiral Solvating (Shift) Agents in NMR Spectroscopy

Cinchona-Based Sensors, Receptors, and Materials for Separation and Analytics

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Summary

Summary

Author Notes

Table of Contents