Monofunctional primary amine: A new class of organocatalyst for asymmetric Aldol reaction

Abstract

A new class of organocatalysts involving a primary amine as the only functional group is developed for catalytic asymmetric aldol reaction of cyclohexanone/cyclopentanone with various aryl aldehydes in the presence of benzoic acid as an additive at −10∘C. In an unexpected observation, the primary amine catalyzed reactions gave excellent yield and good to excellent stereoselectivity, while secondary amines were found to have little or no reactivity under similar reaction conditions. A new class of aminocatalysts with a primary amine as the only catalytically active functional group was developed for catalytic asymmetric aldol reaction of cyclohexanone/cyclopentanone with various aryl aldehydes in the presence of benzoic acid as an additive at -10oC under neat conditions.