Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals
Carlos Palo‐Nieto, Abhijit Sau, Robin Jeanneret, Pierre‐Adrien Payard, Aude Salamé, Maristela Braga Martins-Teixeira, Ivone Carvalho, Laurence Grimaud, M. Carmen Galán
Abstract
We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both “armed” and “disarmed” type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that Cu I is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.
Topics & Concepts
ChemistryStereoselectivityReactivity (psychology)NucleophileCatalysisCounterionCombinatorial chemistryGlycosylationStereochemistryOrganic chemistryIonMedicineBiochemistryAlternative medicinePathologyCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchChemical Synthesis and Analysis