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

Two-step, ring-opening 1,3-carbothiolation of donor-acceptor (D-A) cyclopropanes employing alkyl halides and in situ generated dithiocarbamates (from amines and CS 2 ) 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.