title: Diastereoselective metal-catalyzed synthesis of C-aryl and C-vinyl glycosides.
abstract: Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)(3)]/tmeda (acac = acetylacetonate, tmeda = N,N'-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1-3:1.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 Rue Vauquelin-75231 Paris Cedex 05, France.
authors.forename: Lionel
authors.initials: L
authors.lastname: Nicolas
authors.forename: Patrick
authors.initials: P
authors.lastname: Angibaud
authors.forename: Ian
authors.initials: I
authors.lastname: Stansfield
authors.forename: Pascal
authors.initials: P
authors.lastname: Bonnet
authors.forename: Lieven
authors.initials: L
authors.lastname: Meerpoel
authors.forename: Sébastien
authors.initials: S
authors.lastname: Reymond
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D009942:Organometallic Compounds; D003035:Cobalt; D007501:Iron