Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β′-Keto-β-Amino Esters via Dynamic Kinetic Resolution

An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of alpha-substituted beta-ketoesters via dynamic kinetic resolution is reported. The desired anti beta'-hydroxy-beta-amino esters were obtained in moderate to good yields (60-95%) with 72-99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100).

Automated summary

An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of alpha-substituted beta-ketoesters via dynamic kinetic resolution was reported. The desired anti beta'-hydroxy-beta-amino esters were obtained in moderate to good yields with high enantioselectivity and diastereoselectivity. This protocol is tolerant to various functional groups and can be easily conducted on gram scale with lower catalyst loading.