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Coordination Compounds Based on 1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic Acid
Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nám. Čs. legií 565, 53210 Pardubice, Czech Republic
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 16610 Praha 6, Czech Republic
Department of Biochemical Sciences, Faculty of Pharmacy, Charles University, Heyrovského 1203, 50005 Hradec Králové, Czech Republic
* Author to whom correspondence should be addressed.
Received: 27 March 2007; in revised form: 11 May 2007 / Accepted: 11 May 2007 / Published: 21 May 2007
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.
Keywords: (S)-1; 2; 3; 4-Tetrahydroisoquinoline-3-carboxylic acid; chiral Tic acid derivatives; enantioselective catalysis; 2; 6-bis[((3S)-3-(methoxycarbonyl)-1; 2; 3; 4-tetra- hydroisoquinolin-2-yl)carbonyl]pyridine
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Jansa, P.; Macháček, V.; Nachtigall, P.; Wsól, V.; Svobodová, M. Coordination Compounds Based on 1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic Acid. Molecules 2007, 12, 1064-1079.
Jansa P, Macháček V, Nachtigall P, Wsól V, Svobodová M. Coordination Compounds Based on 1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic Acid. Molecules. 2007; 12(5):1064-1079.
Jansa, Petr; Macháček, Vladimír; Nachtigall, Petr; Wsól, Vladimír; Svobodová, Markéta. 2007. "Coordination Compounds Based on 1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic Acid." Molecules 12, no. 5: 1064-1079.