Rhodium-Catalyzed Asymmetric Hydrogenation of All-Carbon Aromatic Rings

摘要

Compared with heteroarenes,homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control.Herein,we report the rhodium/diphosphine-catalyzed asymmetric hydrogenation of all-carbon aromatic rings,affording a series of axially chiral cyclic compounds with high enantioselectivity through desym-metrization or kinetic resolution.In addition,the central-chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group.The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties.The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom.