Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium-Catalyzed Asymmetric Hydrogenation

Herein,we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand.The transformation shows good functional group tolerance,and gives the hydrogenated prod-ucts with excellent yields(up to 99%)and enantioselectivities(up to 98%ee).A gram-scale reaction was also carried out,and pro-vided the hydrogenated product in excellent yield with no erosion in enantioselectivity.Finally,the transformation of the hydrogen-ated product provided an efficient approach for the synthesis of the intermediate of a HIV protease inhibitor.