A mild and efficient Zn-catalyzed C-glycosylation: synthesis of C(2)–C(3) unsaturated C-linked glycopyranosides

Abstract

A highly efficient C-glycosylation method was developed by using catalytic Zn(OTf)₂ for the synthesis of 2,3-unsaturated C-glycosides. The scope of the protocol was well illustrated with different substituted glycals and nucleophiles comprising allyltrimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide, trimethylaluminum, trimethylsilyl phenylacetylene and heterocycles such as thiophene and furan. The present method is mild enough to incorporate C-glycoside linkages in a disaccharide donor as well.