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A General Approach to 1,2-trans-C-Glycosides via Glycosyl Samarium(III) Compounds
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1998
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Carbonyl CompoundsCross-coupling ReactionEngineeringNatural SciencesDiversity-oriented SynthesisGlycobiologyGlycosyl Pyridyl SulfonesGlycosyl SamariumOrganic ChemistryStereoselective SynthesisChemistryNatural Product SynthesisCorresponding LithiumCarbohydrate-protein InteractionEnantioselective SynthesisBiomolecular EngineeringGlycosylation
A remarkable stereoselective coupling reaction is undergone by glycosyl pyridyl sulfones, such as 1, with carbonyl compounds affording 1,2-trans-C-glycosides. In contrast to the corresponding lithium counterparts the intermediate anomeric organosamarium reagent displays enhanced stability to β elimination of the C2-substituent.