Rhodium-Catalyzed Homogeneous Asymmetric Hydrogenation of Naphthylamine Derivatives

The precise control of chemo-, regio- and enantioselectivity in the transition-metal-catalyzed hydrogenation of naphthylamine derivatives has remained a long-standing challenge, stemming from their inherent high aromaticity and the potential for catalyst poisoning by amine groups. Herein, we report the first highly efficient homogeneous hydrogenation of naphthylamine derivatives, enabled by a chiral tethered rhodium-diamine complex. This method provides direct and practical access to a broad range of valuable chiral 1,2,3,4-tetrahydronaphthylamine derivatives from readily available naphthylamine feedstocks. Its extensive synthetic utility is further demonstrated by the concise synthesis of several chiral drugs and bioactive molecules.