Transition metal-catalyzed asymmetric cycloaddition reactions of a chiral (β-sulfinyl)vinylcyclopropane derivative: asymmetric synthesis of a cyclopentane derivative using a chiral sulfinyl functionality as the chiral source

Abstract

Asymmetric synthesis of a cyclopentane derivative using a chiral sulfinyl functionality as the chiral source has been successfully executed by a transition metal-catalyzed asymmetric cycloaddition reaction of a chiral (β-sulfinyl)vinylcyclopropane derivative with acrylonitrile. The effects of the catalysts, ligands, and solvent were examined. The degree of the asymmetric induction and the chemical yield were highly dependent on the catalyst and, especially, the ligand used. A plausible mechanism of the asymmetric induction is proposed.