First example of the carbon-Ferrier rearrangement of glycals with isocyanides: a novel synthesis of C-glycosyl amides

Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl3 under mild reaction conditions to provide C-glycosyl amides in good yields with high alpha-selectivity. The use of FeCl3 makes this method simple, convenient and cost-effective. This is the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles. (C) 2008 Elsevier Ltd. All rights reserved.