Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions

Carbohydrate as a kind of important chiral scaffold is widely recognized for its obvious advantages cheap and readily available. A new type of prolinamide organocatalysts, derived from carbohydrate, was synthesized in high yield, and the novel organocatalysts were applied to the direct asymmetric aldol reactions of cyclohexanone and various aromatic aldehydes. The corresponding aldol products were obtained in high yields (up to 99%) with excellent diastereoselectivities (up to >98:2 dr) and enantioselectivities (up to 97% ee) under mild reaction conditions. (C) 2013 The Authors. Published by Elsevier B.V. All rights reserved.