Coordination compounds based on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.
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.
Jansa
Petr
P
Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nám. Cs. legií 565, 53210 Pardubice, Czech Republic. jansa@uochb.cas.cz
Machácek
Vladimír
V
Nachtigall
Petr
P
Wsól
Vladimír
V
Svobodová
Markéta
M
D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D008968:Molecular Conformation; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
D008670:Metals; D044005:Tetrahydroisoquinolines; C031270:1,2,3,4-tetrahydroisoquinoline carboxylic acid