Organocatalytic glycosylation by using electron-deficient pyridinium salts

Abstract

A new organocatalytic glycosylation method based on electron-deficient pyridinium salts is reported. At ambient temperature and catalyst loadings as low as 1 mol %, 2-deoxyglycosides were formed from benzyl- and silyl-protected glycals and primary or secondary glycosyl acceptors, with excellent yields and anomeric selectivity. Mechanistic investigations point to alcohol-pyridinium conjugates (1,2-addition products) as key intermediates in the catalytic cycle.

Keywords: acetals; anion binding; glycosylation; organocatalysis; pyridinium cations.