Ring-Opening 1,3-Carbothiolation of Donor–Acceptor Cyclopropanes Using Alkyl Halides and In Situ Generated Dithiocarbamates

Abstract

Two-step, ring-opening 1,3-carbothiolation of donor–acceptor (D–A) cyclopropanes employing alkyl halides and in situ generated dithiocarbamates (from amines and CS2) has been demonstrated under mild conditions. The reaction is operationally simple and works with good functional group compatibility. Three new bonds including C–N, C–S, and C–C are formed in this 1,3-bifunctionalization strategy. Electron-poor olefins can also be used as electrophiles instead of alkyl halides. The use of enantiomerically pure D–A cyclopropane afforded enantiopure 1,3-carbothiolated product, thus demonstrating the stereospecificity of the reaction.