Transition-Metal-Mediated Cascade Reactions: <i>C</i>,<i>C</i>-Dicyclopropylmethylamines by Way of Double C,C-σ-Bond Insertion into Bicyclobutanes

Abstract

The organometallic multicomponent reaction of alkenyl zirconocene, alkynyl imine, and zinc carbenoid in the presence of dimethylzinc leads to novel C,C-dicyclopropylmethylamines. The formation of intermediate bicyclo[1.1.0]butanes represents the first synthetically useful example of a double C,C-sigma-bond insertion, and the increase in structural complexity from starting materials is highlighted by the formation of nine new C,C-bonds in the final product.