A Hydrogenation/Oxidative Fragmentation Cascade for Synthesis of Chiral 4,5-Dihydro‑1H‑benzo[d]azepin-1-ones

An iridium-catalyzed asymmetric hydrogenation/oxidative fragmentation of 6-substituted 5H-benzo­[d] benzofuro­[3,2-b]­azepines has been developed, providing an efficient access to optically active 4-substituted 4,5-dihydro-1H-benzo­[d]­azepin-1-ones with up to 91% ee. A possible reaction pathway includes the asymmetric hydrogenation to furnish chiral cyclic amines and oxidative fragmentation under an air atmosphere.