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.