European Journal of Organic Chemistry · 2013 · 179 citations · 250 references
Life SciencesBiochemistryChemistryCarbohydrate BiochemistryCarbohydrate ChemistryCatalysisCarbohydrate DerivatizationCarbohydrate SynthesisGlycan BiosynthesisGlycan StructureGlycosylation PathwaysN-linked GlycosylationAllylic SubstitutionGlycal ChemistryGlycoconjugate SynthesisGlycopeptide SynthesisGlycoside SynthesisRearrangement ReactionsRearrangement Techniques
Abstract Glycals (1,2‐unsaturated, cyclic carbohydrate derivatives) readily undergo (catalyzed) substitution reactions at C‐1 accompanied by allylic rearrangement. This reaction, currently named Ferrier rearrangement, or the Ferrier I reaction, has established itself as a useful synthetic tool for carbohydrate transformations. By means of this reaction, glycals can be converted into highly useful 2,3‐unsaturated glycosides. This review summarizes recent developments in the use of promoters for the Ferrier rearrangement of O‐, N‐, C‐ and S‐nucleophiles with glycals.
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Christian W. Tornøe, Caspar Christensen, Morten Meldal · The Journal of Organic Chemistry · 2002 · 8.5K citations