Palladium-Catalyzed Glycosylation: Novel Synthetic Approach to Diverse<i>N</i>-Heterocyclic Glycosides

Abstract

An efficient and highly stereoselective method for the construction of N-heterocyclic glycosides is reported. This method is based on a palladium-catalyzed allylation which proceeded to provide N-heterocyclic glycosyl compounds in good-to-excellent yields with β- or α-selectivity. Various N-nucleophiles were examined for this reaction and selected N-glycosyl isatin substrates were further elaborated to bis-indole sugars which have potential as antiproliferative drugs.