Lanthanide(III) Catalyzed Aldol Reactions of Glyceraldehyde Acetonide with Ketene Silyl Acetals: Catalytic Asymmetric Route to Monosaccharides

Article abstract of DOI:10.1016/S0957-4166(00)86145-5

The Pr-, Eu- and Ho(dppm)3 catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals are described, where remarkably high anti-diastereofacial selection is achieved.Thus, the asymmetric synthesis of 2-deoxy-D-ribonolactone and formal synthesis of 2-amino-2-deoxy-D-pentose by the lanthanide(III) catalyzed aldol reaction with ketene silyl acetals of acetate and α-chloroacetate, respectively are described.