LiO^tBu-Promoted trans-Stereoselective and β-Regioselective Hydroboration of Propargyl Alcohols

Abstract

A convenient and efficient trans-stereoselective and β-regioselective hydroboration of propargyl alcohols was achieved simply with LiO t Bu as the base and (Bpin) 2 as the boron reagent in dimethyl sulfoxide at room temperature. Both terminal and internal propargyl alcohols with diverse structures and functional groups underwent the transformation smoothly to produce β-Bpinsubstituted (E)-allylic alcohols, of which the synthetic potentials were demonstrated by the downstream conversions of boronate, alkenyl, and hydroxyl groups.