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

A Simmons–Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis­(boronates) has been developed starting from the corresponding alkenes. The resulting compounds were then subjected to regioselective Suzuki–Miyaura couplings to produce diversely tri- or tetra-substituted arylcyclopropanes in good yields. Further functionalization with 2-lithiothiophene provided 1,2-bis­(aryl)­cyclopropanes.