Imidazole-based Potential Bi- and Tridentate Nitrogen Ligands: Synthesis, Characterization and Application in Asymmetric Catalysis

doi:10.3390/molecules13092326

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Molecules 2008, 13(9), 2326-2339; doi:10.3390/molecules13092326

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Imidazole-based Potential Bi- and Tridentate Nitrogen Ligands: Synthesis, Characterization and Application in Asymmetric Catalysis

Roman Sívek, Filip Bureš* , Oldřich Pytela and Jiří Kulhánek

Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, nám. Čs. legií 565, Pardubice, CZ-532 10, Czech Republic

* Author to whom correspondence should be addressed.

Received: 2 September 2008; in revised form: 10 September 2008 / Accepted: 12 September 2008 / Published: 25 September 2008

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Abstract: Twelve new imidazole-based potential bi- and tridentate ligands were synthesized and characterized. Whereas in the first series the α-amino acid and imidazole moieties were linked by an amino bond, in the second series the tridentate ligands, containing two imidazole groups, were separated by an amide bond. The first series was obtained by the reductive amination of 2-phenylimidazole-4-carboxaldehyde with α-amino acid esters. The tridentate ligands were prepared from 2-phenylimidazole-4-carboxylic acid and chiral amines. In the Henry reaction, the amines were revealed as a more reactive species than the less nucleophilic amides, however the enantiomeric excesses were generally poor.

Keywords: Imidazole; Nitrogen ligands; Asymmetric catalysisq

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MDPI and ACS Style

Sívek, R.; Bureš, F.; Pytela, O.; Kulhánek, J. Imidazole-based Potential Bi- and Tridentate Nitrogen Ligands: Synthesis, Characterization and Application in Asymmetric Catalysis. Molecules 2008, 13, 2326-2339.

AMA Style

Sívek R, Bureš F, Pytela O, Kulhánek J. Imidazole-based Potential Bi- and Tridentate Nitrogen Ligands: Synthesis, Characterization and Application in Asymmetric Catalysis. Molecules. 2008; 13(9):2326-2339.

Chicago/Turabian Style

Sívek, Roman; Bureš, Filip; Pytela, Oldřich; Kulhánek, Jiří. 2008. "Imidazole-based Potential Bi- and Tridentate Nitrogen Ligands: Synthesis, Characterization and Application in Asymmetric Catalysis." Molecules 13, no. 9: 2326-2339.

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