title: Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.
abstract: Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Sau
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Ryan
authors.initials: R
authors.lastname: Williams
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Carlos
authors.initials: C
authors.lastname: Palo-Nieto
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Antonio
authors.initials: A
authors.lastname: Franconetti
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Sandra
authors.initials: S
authors.lastname: Medina
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: M Carmen
authors.identifier: 0000-0001-7307-2871
authors.initials: MC
authors.lastname: Galan
keywords: acetals; asymmetric catalysis; deoxyglycosides; glycosylation; palladium