Synthesis of 1,4-epoxy-2-aryltetrahydro-1-benzazepines via rhodium(III)-catalyzed C-H allylation/intramolecular 1,3-dipolar cycloaddition.

ABSTRACT

Herein, we report a new synthetic route to 1,4-epoxy-2-aryltetrahydro-1-benzazepine derivatives with high efficiency, namely the Rh(III)-catalyzed C-H allylation of nitrones with allyl precursors, followed by subsequent intramolecular 1,3-dipolar cycloaddition, to deliver the title compounds. This reaction is regio- and stereo-selective, generating the cis-isomer with a broad substrate scope and good functional group tolerance.