Direct asymmetric aldol reaction of hydroxyacetone promoted by chiral tertiary amines

The tertiary amine-catalyzed direct asymmetric aldol reaction of hydroxyacetone with a variety of aromatic aldehydes is developed. Using 5-10 mol % of quinidine as catalyst, the direct aldol condensation products were obtained in reasonable yields and with asymmetric induction (up to 47% ee). The present approach is extended to asymmetric organocatalytic strategies for the preparation of 1,2-diols. (C) 2009 Elsevier Ltd. All rights reserved.