title: Highly stereoselective synthesis of C-vinyl pyranosides via a Pd0-mediated cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols.
abstract: Oct-2-enitols undergo a Pd(0)-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.
authors.affiliation: Colgate University, 13 Oak Drive, Hamilton, NY 13347, USA. Electronic address: enolen@colgate.edu.
authors.forename: Ernest G
authors.initials: EG
authors.lastname: Nolen
authors.affiliation: Colgate University, 13 Oak Drive, Hamilton, NY 13347, USA.
authors.forename: Vivian C
authors.initials: VC
authors.lastname: Ezeh
authors.affiliation: Colgate University, 13 Oak Drive, Hamilton, NY 13347, USA.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Feeney
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D006027:Glycosides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: D006027:Glycosides; D013402:Sugar Alcohols; D010165:Palladium
keywords: 1,2-Dideoxy-hept-1-enitols; 2,3-Dideoxy-oct-2-enitols; C-Glycosides; C-Vinyl pyranosides; Cycloetherification; Pd(0)-mediated