Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis

K. Kacprzak; J. Gawroński

doi:10.1055/s-2001-14560

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Synthesis 2001(7): 0961-0998
DOI: 10.1055/s-2001-14560

REVIEW

Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis

K. Kacprzak, J. Gawroński*
Department of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8658008; e-Mail: gawronsk@chem.amu.edu.pl;

Further Information

Publication History

Received 14 February 2001
Publication Date:
30 September 2004 (online)

Abstract
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Abstract

Cinchona alkaloids and their derivatives can catalyze an amazing array of synthetically important reactions, providing access to chiral products of high enantiopurity. A review of such asymmetric reactions, comprising the work reported in the last two decades, is presented here. Cinchona alkaloids-derived catalysts and ligands, either in monomeric form or attached to a polymeric support, are included in this review.

1 Introduction
2 Carbon-Carbon Bond Formation
2.1 Alkylation
2.1.1 Alkylation of Carbonyl Compounds
2.1.2 Alkylation of Schiff Bases: Synthesis of a-Amino Acids
2.2 Additions to Carbonyl Compounds
2.2.1 Aldol Reaction
2.2.2 Indium-Promoted Additions
2.2.3 Darzens Reaction
2.2.4 Baylis-Hillmann Reaction
2.2.5 Diethyl Zinc Addition
2.2.6 Michael Addition
2.2.7 Other Additions
2.3 Cycloadditions
2.3.1 Synthesis of β-Lactones
2.3.2 Synthesis of β-Lactams
2.3.3 Diels-Alder Reaction
2.4 Claisen Rearrangement
3 Carbon-Oxygen Bond Formation
3.1 Epoxidation of Enones and cis-Olefins
3.2 Asymmetric Dihydroxylation (AD)
3.3 Asymmetric Aminohydroxylation (AA)
3.4 α-Hydroxylation of Ketones
4 Hydrogenations and Reductions
4.1 Heterogeneous Hydrogenation of Activated Ketones
4.2 Heterogeneous Hydrogenation of Other Substrates
4.3 Homogeneous Reductions
5 Carbon-Heteroatom (N,P,S,F) Bond Formation
5.1 Chiral Aziridines and 2H-Azirines
5.2 Chiral α-Hydroxyphosphonate Esters
5.3 Chiral Sulphur Compounds
5.4 Chiral α-Fluorinated Carbonyl Compounds
6 Miscellaneous Reactions
6.1 Desymmetrization of Cyclic Anhydrides
6.2 Decarboxylation
7 Supported Cinchona Alkaloid Catalysts
7.1 Insoluble Polymer-Bound Cinchona Alkaloids
7.1.1 Homopolymers Derived from Cinchona Alkaloids
7.1.2 Copolymers of Cinchona Alkaloids with Acrylonitrile and Acrylates
7.1.3 Polymers of Cinchona Alkaloids with Added Spacers
7.1.4 Cinchona Alkaloids Catalysts Supported on Merrifield Resin
7.2 Cinchona Alkaloids Catalysts Immobilized on Silica Gel
7.3 Soluble Polymer-Bound Cinchona Ligands
7.4 Concluding Remarks
Acknowledgement
References

Key words

Cinchona alkaloids - asymmetric synthesis - catalysis - ligands

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