Iodine-Catalyzed Stereoselective Synthesis of Allylglycosides, Glycosyl Cyanides and Glycosyl azides

J. S. Yadav, B. V. Subba Reddy, Changqing Rao, Pratap K. Chand, A. R. Prasad

Synlett · 2001 · 64 citations · 0 references

Concepts

Abstract

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.