Site-Selective Activation and Stereospecific Functionalization of Bis(boronic Esters) Derived from 2-Alkenes: Construction of Propionates and Other 1,2-Difunctional Motifs.

Non-directed regioselective activation of bis(boronic esters), followed by functionalization, is reported. A bulky activator is shown to selectively activate the less hindered boronic ester enabling it to undergo stereospecific cross-coupling to a variety of electrophiles. This steric-based regioselectivity provides a simple and efficient method to prepare highly functionalized, enantiomerically enriched products starting from simple alkenes.