Simmons-Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates):Stereoselective Access to Functionalized Cyclopropyl Derivatives

A Simmons-Smith stereodefined procedure for thesynthesis of cyclopropyl-1,2-bis(boronates) has been developedstarting from the corresponding alkenes. The resulting compoundswere then subjected to regioselective Suzuki-Miyaura couplings toproduce diversely tri- or tetra-substituted arylcyclopropanes in goodyields. Further functionalization with 2-lithiothiophene provided 1,2-bis(aryl)cyclopropanes.