Asymmetric Synthesis of α-Arylcyclohexenones Catalyzed by Diphenylprolinol Silyl Ether

A general methodology for the asymmetric synthesis of α-arylcyclohexeneones from arylacetones and α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether followed by p-TSA-mediated cyclization is developed. A variety of arylacetones and α,β-unsaturated aldehydes were successfully converted to α-arylcyclohexeneones in 34-67% yield, 10:1-100:0 dr, and 81-99% ee. The scalability of this methodology by a gram-scale synthesis and their utility by converting the product to the corresponding epoxide, alcohol, and diol are demonstrated.