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.