Chiral phosphoric acid directed regioselective acetalization of carbohydrate-derived 1,2-diols

Abstract

In control: A chiral phosphoric acid catalyst significantly enhances or completely overrides the inherent regioselective acetalization profiles exhibited by monosaccharide-derived 1,2-diol substrates. This study represents the first example of chiral-catalyst-directed regio- and enantioselective intermolecular acetalizations, which are complementary to existing methods for substrate-controlled functionalization of polyols.

Keywords: carbohydrates; organocatalysis; protecting groups; regioselectivity; synthetic methods.