Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 22, Pages 6515-6519Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601566
Keywords
glycosylation; photochemistry; reaction mechanisms; sulfur
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Funding
- Louisiana Board of Regents [LEQSF-(2013-16)-RD-A-03]
- Louisiana State University
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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 beta-selectivity can be attained through neighboring-group participation.
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