A Visible-Light-Promoted O-Glycosylation with a Thioglycoside Donor.

Autor:	Spell, Mark L., Deveaux, Kristina, Bresnahan, Caitlin G., Bernard, Bradley L., Sheffield, William, Kumar, Revati, Ragains, Justin R.
Předmět:	GLYCOSYLATION GLYCOSIDES IRRADIATION PHOTOCATALYSTS ELECTRONS
Zdroj:	Angewandte Chemie; 5/23/2016, Vol. 128 Issue 22, p6625-6629, 5p
Abstrakt:	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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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