Synfacts 2019; 15(05): 0554
DOI: 10.1055/s-0037-1612479
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Cinchona Alkaloids in Organic Catalysis

Benjamin List
Oleg Grossmann
Fiske PS, Bredig G. * ETH Zürich, Switzerland
Durch Katalysatoren bewirkte asymmetrische Synthese.

Biochem. Z. 1912;
687: 7-23
Pracejus H. * Universität Rostock, Germany
Asymmetrische Synthesen mit Ketenen.

Justus Liebigs Ann. Chem. 1960;
634: 9-22
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15. April 2019 (online)



In 1912, Bredig and Fiske published the first example of asymmetric (nonenzymatic) (organo)catalysis. They reported the addition of HCN to benzaldehyde catalyzed by the pseudo­enantiomeric alkaloids quinine and quinidine, with low but reproducible enantioselectivities. About four decades later, Pracejus, for the first time, achieved reasonable enantioselectivities (74% ee) by using O-acetylquinine as an organocatalyst. This groundwork paved the way to a variety of cinchona-alkaloid-catalyzed asymmetric transformations in industry and academia.



Cinchona alkaloids are among the most privileged asymmetry inducers in the area of enantioselective catalysis. They possess a chiral skeleton that is easily modifiable. In the last century, methodologies were developed in which they were used as chiral bases, as chiral Lewis base catalysts, in ligand-accelerated catalysis, or as quaternized ammonium salts in phase-transfer catalysis, among others. Current research continues to showcase their importance and utility in asymmetric catalysis, for example by incorporating other privileged organic catalophores such as thioureas.