title: Coordination compounds based on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.
abstract: Syntheses of 2,6-bis[((3S)-3-(methoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonyl]pyridine and its coordination compounds with Cu2+, Co2+, Co3+, or Fe3+ are described. By means of 1H- and 13C-NMR spectra it was proved that 2,6-bis[((3S)-3-(methoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-2-yl)carbonyl]pyridine as well as its coordination compound with Co3+ exist in the form of a mixture of three conformers, differing in the conformations at the two amide groups present. The prepared coordination compounds were tested in the enantioselective catalysis of the nitroaldol addition of nitromethane with 2-nitrobenzaldehyde or 4-nitrobenzaldehyde, and in the Michael addition of ethyl 2-oxocyclohexanecarboxylate to but-3-en-2-one.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nám. Cs. legií 565, 53210 Pardubice, Czech Republic. jansa@uochb.cas.cz
authors.forename: Petr
authors.initials: P
authors.lastname: Jansa
authors.forename: Vladimír
authors.initials: V
authors.lastname: Machácek
authors.forename: Petr
authors.initials: P
authors.lastname: Nachtigall
authors.forename: Vladimír
authors.initials: V
authors.lastname: Wsól
authors.forename: Markéta
authors.initials: M
authors.lastname: Svobodová
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D008968:Molecular Conformation; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
chemical_list: D008670:Metals; D044005:Tetrahydroisoquinolines; C031270:1,2,3,4-tetrahydroisoquinoline carboxylic acid