Transition-metal-mediated cascade reactions: C,C-dicyclopropylmethylamines by way of double C,C-sigma-bond insertion into bicyclobutanes.
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.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. pwipf@pitt.edu
Stephenson
Corey R J
CR
Okumura
Kazuo
K