Synlett · 2001 · 64 citations · 0 references
Natural SciencesChemistryCarbohydrate ChemistryCatalysisOrganic ChemistryCarbohydrate SynthesisGlycosidic Bond FormationGlycosylation PathwaysHeterocyclic ChemistryAmbient Temperature EffectsGlycal ChemistryGlycan SynthesisGlycoside SynthesisGlycosylation StereoselectivitySelectivityStereoselective GlycosylationStereoselective Synthesis
Iodine efficiently catalyzes the glycosidation of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in dichloromethane at ambient temperature to afford the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high α-selectivity.