Synthesis of <i>C</i>-Alkynyl Glycosides by Photoredox-Catalyzed Reductive Coupling of Alkynyl Bromides with Glycosyl Bromides
Liwen Xia, Maolu Jin, Yi Jiao, Shouyun Yu
Abstract
A general, convenient, and highly α stereoselective approach to access C-alkynyl glycosides via the photoredox-catalyzed reductive coupling of alkynyl bromides and glycoside bromides has been developed. Cheap and small-load eosin Y is used as the photocatalyst, and organic base N,N-diisopropylethylamine serves as the reducing reagent. This strategy features readily available starting materials, diverse substrates, mild conditions, and high α stereoselectivity. Moreover, a glycoconjugated peptide could also be achieved using this strategy.
Topics & Concepts
ChemistryStereoselectivityReagentGlycosylCatalysisCombinatorial chemistryGlycosideAlkyneBase (topology)Organic chemistryMathematical analysisMathematicsCarbohydrate Chemistry and SynthesisRadical Photochemical ReactionsChemical Synthesis and Analysis