title: Cu (II)-catalyzed asymmetric henry reaction with a novel C1-symmetric aminopinane-derived ligand.
abstract: A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(-)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)2H2O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%-76% range.
authors: Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. liudmila.filippova@nmbu.no.
authors: Liudmila
authors: L
authors: Filippova
authors: Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. yngve.stenstrom@nmbu.no.
authors: Yngve
authors: Y
authors: Stenstrøm
authors: Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. t.v.hansen@farmasi.uio.no.|Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway. t.v.hansen@farmasi.uio.no.
authors: Trond Vidar
authors: TV
authors: Hansen
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D000081008:Bicyclic Monoterpenes; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001547:Benzaldehydes; D000081008:Bicyclic Monoterpenes; D008024:Ligands; D009595:Nitroparaffins; D013729:Terpenes; C030216:pinane; D003300:Copper; D008697:Methane; C008640:nitromethane; C032175:benzaldehyde