Title

A visible-light-promoted O-glycosylation with a thioglycoside donor

Document Type

Article

Publication Date

5-23-2016

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Visible-light irradiation of 4-p-methoxyphenyl-3-butenylthioglucoside donors in the presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O-glycosylation. Visible-light photocatalysts are not required for activation, and alkyl- and arylthioglycosides not bearing the p-methoxystyrene are inert to these conditions. Experimental and computational evidence for an intervening electron donor-acceptor complex, which is necessary for reactivity, is provided. Yields with primary, secondary, and tertiary alcohol acceptors range from moderate to high. Complete β-selectivity can be attained through neighboring-group participation. Visible-light irradiation of 4-p-methoxyphenyl-3-butenylthioglucoside donors in the presence of Umemoto's reagent serves as an exceptionally mild and orthogonal approach to O-glycosylation. Alkyl- and arylthioglycosides not containing the p-methoxystyrene moiety are inert under these conditions, and evidence suggests that an intervening electron donor-acceptor complex is necessary for reactivity.

Publication Source (Journal or Book title)

Angewandte Chemie - International Edition

First Page

6515

Last Page

6519

This document is currently not available here.

Share

COinS