Issue 33, 2013

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.

Graphical abstract: Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system

Supplementary files

Article information

Article type
Communication
Submitted
09 May 2013
Accepted
12 Jul 2013
First published
23 Jul 2013

Org. Biomol. Chem., 2013,11, 5409-5412

Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system

D. Lee and M. S. Taylor, Org. Biomol. Chem., 2013, 11, 5409 DOI: 10.1039/C3OB40981C

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