Catalytic Asymmetric Corey-Chaykovsky Cyclopropanation and Epoxidation Promoted by Heterobimetallic Catalyst

Abstract

The Corey-Chaykovsky reaction with utilizing sulfur ylide is one of the most reliable reactions in the cyclopropanation and the epoxidation of various carbonyl compounds. In our laboratory, the validity of heterobimetallic catalyst has been represented in the wide range of catalytic asymmetric reactions. Herein, we report the catalytic asymmetric version of Corey-Chaykovsky reaction. In catalytic asymmetric cyclopropanation of enones with dimethylsulfoxonium methylide, newly explored heterobimetallic catalyst having La and Li-Na mixed alkali metals afforded high yield and excellent enantioselectivity. In catalytic asymmetric epoxidation of methyl ketones, LLB-phoshine oxide complex catalyzed the addtion of ylide to give terminal epoxide successfully. The heterobimetallic catalysts were applicable to challenging substarates such as heteroaryl unit in both Corey-Chaykovsky reactions.