title: Stereoselective, electrophilic α-C-sialidation.
abstract: 5-N-Acetyl-5-N,4-O-oxazolidinone protected α- and β-sialyl phosphates react with allyltributylstannane and a variety of trimethylsilyl enol ethers to give α-sialyl C-glycosides in high yield and excellent selectivity. Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
authors.forename: Amandine
authors.initials: A
authors.lastname: Noel
authors.forename: Bernard
authors.initials: B
authors.lastname: Delpech
authors.forename: David
authors.initials: D
authors.lastname: Crich
mesh_terms: D004583:Electrons; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D023303:Oxazolidinones; D019158:N-Acetylneuraminic Acid