Alkene-Zipper Catalyzed Selective and Remote Retro-ene Reaction of Alkenyl Cyclopropylcarbinol

Reminiscent of biological systems, the increasingly popular concept of remote activation allows a greater strategic synthetic flexibility for the development of novel synthetic organic methodologies. In this Communication, we report that commercially available ruthenium (II)-based “alkene zipper catalyst” enables the selective transformation of a large variety of ω-alkenyl cyclopropylcarbinols into stereodefined unconjugated (E)-acyclic aldehydes bearing a quaternary stereocenter through an isomerization followed by a retro-ene reaction. To unravel this peculiar catalytic property of the “alkene zipper” and shed some light on the mechanism, a series of control experiments were performed. (Figure presented.).