Synthesis of aryl enopyranones directly from glycals and aromatic halides to access 2-deoxy-β-C-aryl glycosides

Abstract

An efficient synthesis of aryl enopyranones via an oxidative Heck-type coupling reaction between ether protected D/L-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact via the Saegusa–Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-β-aryl-C-glycosides after Pd/C reduction.