InCl3-catalyzed stereoselective synthesis of C-glycosyl heteroaromatics

Glycals react smoothly with furan in the presence of a catalytic temperature amount of indium trichloride at ambient to afford predominantly the C-3-substituted glycals in high yields. Other heteroaromatics including 2-benzyloxymethylfuran. thiophene and N-Boc protected indole afford exclusively C-I-glycosides in good yields with high beta-selectivity under similar reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved,