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A Visible‐Light‐Promoted O ‐Glycosylation with a Thioglycoside Donor
Author(s) -
Spell Mark L.,
Deveaux Kristina,
Bresnahan Caitlin G.,
Bernard Bradley L.,
Sheffield William,
Kumar Revati,
Ragains Justin R.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601566
Subject(s) - glycosylation , visible spectrum , chemistry , reagent , alcohol , acceptor , photochemistry , reactivity (psychology) , alkyl , electron donor , electron acceptor , inert , irradiation , organic chemistry , biochemistry , materials science , catalysis , medicine , optoelectronics , physics , alternative medicine , pathology , condensed matter physics , nuclear physics
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.