Catalytic oxidation-phosphorylation of glycals: rate acceleration and enhancement of selectivity with added nitrogen ligands in common organic solvents

Abstract

The first general catalytic oxidation of glycals has been developed to afford useful glycosyl phosphates in high yield and selectivity in a domino process with the use of catalytic methyltrioxorhenium, urea hydrogen peroxide, stoichiometric dibutyl phosphate as nucleophile, and a substoichiometric amount of nitrogen ligands, such as pyridine or imidazole, in organic solvents. [Structure: see text]