title: Stereoselective C-glycoside formation by a rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acetylated enones derived from glycals.
abstract: [reaction: see text] A new method for the formation of C-glycosides has been developed employing a cationic rhodium(I)-catalyzed 1,4-addition of arylboronic acids to enones derived from glycals. The reaction is stereoselective for the alpha-anomer and is highly dependent on the nature of the rhodium catalyst.
authors.affiliation: MCR Research Inc., Chemistry and Computer Sciences Bldg., York University, 4700 Keele St., Toronto, Ontario, Canada M3J 1P3.
authors.forename: J
authors.initials: J
authors.lastname: Ramnauth
authors.forename: O
authors.initials: O
authors.lastname: Poulin
authors.forename: S S
authors.initials: SS
authors.lastname: Bratovanov
authors.forename: S
authors.initials: S
authors.lastname: Rakhit
authors.forename: S P
authors.initials: SP
authors.lastname: Maddaford
mesh_terms: D000107:Acetylation; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D006027:Glycosides; D007202:Indicators and Reagents; D012238:Rhodium