Synfacts 2008(3): 0274-0274  
DOI: 10.1055/s-2008-1042680
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-2 Methylene Glycosides by AuCl3 Catalysis

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
S. Kashyap, S. R. Vidadala, S. Hotha*
National Chemical Laboratory, Pune, India
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Publication History

Publication Date:
21 February 2008 (online)


Prior to this study several methods for the preparation of C-2 methylene glycosides had been reported. These include Ferrier reaction using BF3×Et2O or InCl3 as well as similar strategies using Nafion-H, Montmorillonite K-10, and Pd(PPh3)4. The present paper utilizes the propargyloxy group as a leaving group in the presence of catalytic AuCl3 to effect SN2′ addition of various functionalized aglycones to propargyloxy­methyl glycals. C-2 Methylene glycosides are obtained in moderate yields with stereoselective formation of the α-glycoside.