Enantioselective synthesis of aminobenzazepinones

Enantioselective synthesis of constrained trans-aminobenzazepinone utilizing palladium-mediated Jeffery-Heck reaction and rhodium(II) catalyzed asymmetric hydrogenation as key steps are described. Diverse functional groups such as alkyl, aryl, basic or amino acid moieties were introduced with minimal racemization.

Constrained trans-aminobenzazepinones (8a-e) were synthesized through a tandem palladium-mediated Jeffery-Heck reaction and rhodium(II) catalyzed asymmetric hydrogenation. Diverse functionalities were introduced at the amino terminus of aminobenzazepinone with minimal racemization.