Indium-mediated alkynylation of sugars: synthesis of C-glycosyl compounds bearing a protected amino alcohol moiety

The coupling of glycals with an alkynyl iodide bearing a protected amino alcohol moiety was achieved in the presence of metallic indium under Barbier conditions. It gave functionalized C-glycosyl compounds, precursors of C-glycosyl amino acids with alpha configuration. (C) 2010 Elsevier Ltd. All rights reserved.