title: Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands.
abstract: The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozinc and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.
authors.affiliation: Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747, AG Groningen, The Netherlands.
authors.forename: Maria Gabriella
authors.initials: MG
authors.lastname: Pizzuti
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005561:Formates / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry; D013452:Sulfonium Compounds / Q000737:chemistry; D014050:Toluene / Q000737:chemistry
chemical_list: D005561:Formates; D007097:Imines; D008024:Ligands; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D013451:Sulfonic Acids; D013452:Sulfonium Compounds; C434331:phosphoramidite; C030544:formic acid; D014050:Toluene; D003300:Copper; C005741:sulfamic acid