Efficient Preparation of 1,3-Diol Derivatives with Three Contiguous Stereocenters by an Enantioselective Direct Aldol–Tishchenko Reaction

Abstract

1,3-Diol derivatives with three contiguous stereocenters were efficiently prepared by an enantioselective direct aldol–Tishchenko reaction catalyzed by dilithium 3,3′-diphenylbinaphtholate. The reactions of acyclic ketones as aldol donors gave 1,2- syn -1,3- anti -diol derivatives, whereas the reactions of cyclic ketones as aldol donors gave 1,2- anti -1,3- anti -diol derivatives. Sequential aldol–aldol–Tishchenko reactions gave a triol derivative with five consecutive chiral centers.