<i>In Situ</i> Generation of Zinc Carbenoids from Diazo Compounds and Zinc Salts: Asymmetric Synthesis of 1,2,3-Substituted Cyclopropanes

Abstract

The first enantioselective cyclopropanation of alkenes using zinc carbenoids generated in situ from diazo compounds and zinc salts is reported. This new method allows the highly enantio- and diastereoselective synthesis of 1,2,3-substituted cyclopropanes via aryl-substituted carbenoids. The first Simmons-Smith reaction using a catalytic amount of zinc to generate enantioenriched cyclopropane is also reported.