Trapping rhodium vinylcarbenoids with aminochalcones for the synthesis of medium-sized azacycles

A rhodium carbenoid initiated cascade has been developed for the stereoselective synthesis of medium-sized azacycles. The cascade approach utilizes readily accessible N-benzyl protected aminochalcones and vinyldiazo compounds to access 9-membered azacycles through a carbene- nitrogen insertion/aldol/oxy-Cope sequence. The cascade reaction has proven general with a range of N-benzyl protected aminochalcones and vinyldiazos to provide diverse medium-sized azacycles.