Asymmetric Hydrogenation of Racemic α-Aryl-β-ethoxycarbonyl Cyclopentanones via Dynamic Kinetic Resolution and Its Application to the Synthesis of (+)-Burmaniol A.

Abstract

An efficient asymmetric hydrogenation of racemic α-aryl-β-ethoxycarbonyl cyclopentanones via dynamic kinetic resolution is reported. Via catalysis by a chiral iridium Ir-SpiroPAP catalyst, a range of racemic α-aryl-β-ethoxycarbonyl cyclopentanones were hydrogenated to the corresponding ester-functionalized chiral 2-arylcyclopentanols with three contiguous stereocenters in high yields with excellent enantio- and diastereoselectivities. This method was successfully applied in the enantioselective synthesis of cyclopentane-based γ-amino ester/alcohol derivatives and phenylpropanoid (+)-burmaniol A.