Iridium-Catalyzed Enantioselective Ring Opening of Alkenyl Oxiranes by Unactivated Carboxylic Acids

An iridium-catalyzed enantioselective ring-opening of alkenyl oxiranes by unactivated carboxylic acids has been developed. The reaction undergoes at ambient conditions between an in-situ-generated chiral iridium-π-allyl complex and carboxylic acids to provide rapid access to valuable alkenyl diols in high yields. The synthetic utility of this method is demonstrated by the elaboration of the products into various medium and large ring-sized compounds that are part of biologically relevant molecules.