Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from ω-alkynals via intramolecular 1-alkenylzinc/aldehyde additions

The omega -alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot reaction sequence involving alkyne monohydroboration, boron to zinc transmetalation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring closure to the aldehyde function. A general study of this macrocyclization methodology is presented with respect to ligand type, size, and nature of the formed rings.