Highly enantioselective and efficient organocatalytic aldol reaction of acetone and β,γ-unsaturated α-keto ester

Org Lett. 2010 Dec 17;12(24):5616-9. doi: 10.1021/ol102254q. Epub 2010 Nov 11.

Abstract

An effective organocatalytic asymmetric aldol reaction of acetone to β,γ-unsaturated α-keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.