title: Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst.
abstract: A derivative of diphenylborinic acid promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.
authors.affiliation: Department of Chemistry, University of Toronto, Ontario, Canada.
authors.forename: Christina
authors.initials: C
authors.lastname: Gouliaras
authors.forename: Doris
authors.initials: D
authors.lastname: Lee
authors.forename: Lina
authors.initials: L
authors.lastname: Chan
authors.forename: Mark S
authors.initials: MS
authors.lastname: Taylor
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D002241:Carbohydrates