Nickel(II) chloride-mediated regioselective benzylation and benzoylation of diequatorial vicinal diols

Abstract

Ni(II)-chelates of monosaccharide vicinal diols were found to be useful intermediates in regioselective monobenzylation and monobenzoylation. It was observed that the substitution occurs exclusively at the position adjacent to the axially oriented substituent of the pyranose ring, for example, at C-2 of α-D-gluco and at C-3 of β-D-galacto.