Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles

Abstract

A palladium(II)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported. The transformation proceeded through a typical aza-Wacker reaction mechanism to forge a new C–N bond with oxygen as the terminal oxidant. The desired fused heterocycles were obtained in moderate yields. The process is tolerant of a range of functional aryl groups under mild conditions.