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Synlett 2001; 2001(10): 1638-1640
DOI: 10.1055/s-2001-17438
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Iodine-Catalyzed Stereoselective Synthesis of Allylglycosides, Glycosyl Cyanides and Glycosyl azides

J. S. Yadav* , B. V. S. Reddy, C. Venkateshwar Rao, Pratap. K. Chand, A. R. Prasad
  • *Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India; Fax + 91(04)7 17 05 12; E-mail: yadav@iict.ap.nic.in
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Publikationsdatum:
27. September 2001 (online)

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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.

Ferrier rearrangement - glycals - iodine - C-glycosides