Catalytic activation of glycosyl phosphates for stereoselective coupling reactions

Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (K-m) to the H-bond donor and enhanced reactivity of the complex (k(cat)) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions.