A Visible-Light-Promoted O-Glycosylation with a Thioglycoside Donor
Mark L Spell1, Kristina Deveaux1, Caitlin G Bresnahan1
1Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
Abstract:
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.
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