ACS Catalysis · 2018 · 59 citations · 44 references
Natural SciencesChemistryMedicinal ChemistryCatalysisComputational ChemistryOrganic ChemistryGlycosidic Bond FormationGlycosylation PathwaysArylation ReactionsC-glycoside SynthesisGlycoside SynthesisGlycosylation StereocontrolStereochemistry Of GlycosidesStereoselective GlycosylationStereoselectivityStereoselectivity Control
We report herein the diastereoselective C(sp 3 )–H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.
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