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An Efficient Nucleophilic Carbene Catalyst for the Asymmetric Benzoin Condensation

Dieter Enders*, Ulrike Kallfass

*Institut für Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen (Deutschland), Email:

D. Enders, U. Kallfass, Angew. Chem. Int. Ed., 2002, 41, 1743-1745.

DOI: 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO;2-Q


The development of a triazolium salt as an efficient precatalyst for the asymmetric benzoin condensation is described. The high asymmetric inductions in benzoin condensations are a result of the conformational rigidity of the bicyclic nucleophilic carbene catalyst and the shielding of the Breslow intermediate by the sterically demanding tert-butyl group.

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postulated transition-state

Key Words

acyloins, asymmetric catalysis, benzoin condensation, carbenes, triazolium salts, organocatalysis

ID: J06-Y2002-980