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

An efficient asymmetric hydrogenation of racemic alpha-aryl-beta-ethoxycarbonyl cyclopentanones via dynamic kinetic resolution is reported. Via catalysis by a chiral iridium Ir-SpiroPAP catalyst, a range of racemic alpha-aryl-beta-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 gamma-amino ester/alcohol derivatives and phenyl-propanoid (+)-burmaniol A.

Automated summary

An efficient asymmetric hydrogenation via dynamic kinetic resolution was reported for the synthesis of chiral 2-arylcyclopentanols from a variety of racemic alpha-aryl-beta-ethoxycarbonyl cyclopentanones. The method, catalyzed by a chiral iridium Ir-SpiroPAP catalyst, showed high yields and excellent enantio- and diastereoselectivities, making it applicable for the synthesis of diverse chiral products.