Rhodium-catalysed β-selective 1,4-addition of arylboron compounds to glycals enabled by chiral diene ligands

Abstract

The rhodium-catalysed β-selective 1,4-addition of arylboron compounds to enones derived from glucal derivatives enabled by chiral diene ligands. The present catalytic system allows ligand-controlled anomeric selectivity, providing direct access to β-C-glycosyl arenes in good to high yields. The reaction exhibits broad substrate scope, proceeds efficiently on gram scale with low catalyst loading, and enables the synthesis of a 2-deoxy derivative of the SGLT2 inhibitor dapagliflozin.