title: Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system.
abstract: The combination of a boronic acid and a Lewis base, both employed in substoichiometric amounts, enables the regioselective silylation of cis-diol groups in alkylpyranoside substrates. The proposed mode of activation involves the formation of a tetracoordinate adduct that displays enhanced nucleophilicity at the boron-bound alkoxide groups.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Doris
authors.initials: D
authors.lastname: Lee
authors.forename: Mark S
authors.initials: MS
authors.lastname: Taylor
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D058115:Lewis Bases / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D058115:Lewis Bases; D011714:Pyrans; D012821:Silanes