Asymmetric Synthesis of Chiral Cyclopropanes from Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex.

Abstract

An enantioselective cyclopropanation reaction of sulfoxonium ylides with β,γ-unsaturated ketoesters catalyzed by a chiral rhodium catalyst has been realized. A variety of optically pure 1,2,3-trisubstituted cyclopropanes was synthesized in 48-89% yields, with up to 99% ee, and with dr >20:1. Furthermore, research shows that a weak coordination between the chiral rhodium catalyst and β,γ-unsaturated ketoesters was responsible for the high diastereoselectivity and enantioselectivity of the corresponding products.