Oxidative cyclization of active methylene amides: efficient synthesis of functionalized 3-azabicyclo[n.1.0]alkanes

Abstract

An efficient one-pot method has been developed for the stereoselective synthesis of functionalized 3-azabicyclo[n.1.0]alkanes from N-allyl/homoallyl-malonamates, using CuBr₂ as the oxidant at room temperature. This method is versatile and provides cyclopropane-fused lactams in very good yields. This reaction is further shown in the short synthesis of the tetracyclic core of cycloclavine.