Imidazole-based potential bi- and tridentate nitrogen ligands: Synthesis, characterization and application in asymmetric catalysis

Molecules

Volumn 13, Issue 9, 2008, Pages 2326-2339

  Sívek, Roman ^a   Bureš, Filip ^a   Pytela, Oldřich ^a   Kulhánek, Jiří ^a  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

Asymmetric catalysis; Imidazole; Nitrogen ligands

Indexed keywords

IMIDAZOLE; IMIDAZOLE DERIVATIVE; LIGAND; NITROGEN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; IMIDAZOLES; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; STEREOISOMERISM;

EID: 53249084247     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13092326     Document Type: Article

References (31)

1. 1 Synthesis of enantiomerically pure 1-alkylimidazoles. J. Org. Chem. 1995, 60, 2008-2015.
2. Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Synthesis of amino acid-derived imidazoles from enantiopure N-protected α-amino glyoxals. Tetrahedron Lett. 2000, 41, 1275-1278.
3. Rucombining double acute accentther, T.; Done, M. C.; Cavell, K. J.; Peacock, E. J.; Skelton, B. W.; White, A. H. Novel methylpalladium(II) complexes bearing tridentate imidazole-based chelate ligands: synthesis, structural characterization, and reactivity. Organometallics 2001, 20, 5522-5531.
4. Bureš, F.; Kulhánek, J. Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids. Tetrahedron Asymmetry 2005, 16, 1347-1354.
5. Jiang, H.-Y.; Zhou, C.-H.; Luo, K.; Chen, H.; Lan, J.-B.; Xie, R.-G. Chiral imidazole metalloenzyme models: synthesis and enantioselective hydrolysis for α-amino acid esters. J. Mol. Catal. A: Chem. 2006, 260, 288-294.
6. Matsuoka, Y.; Ishida, Y.; Sasaki, D.; Saigo, K. Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols. Tetrahedron 2006, 62, 8199-8206.
7. Marek, A.; Kulhánek, J.; Ludwig, M.; Bureš, F. Facile synthesis of optically active imidazole derivatives. Molecules 2007, 12, 1183-1190.
8. Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. L.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Asymmetric hydroformylation of vinyl acetate: Application in the synthesis of optically active isoxazolines and imidazoles. Org. Lett. 2007, 9, 2665-2668.
9. Gulevich, A. V.; Balenkova, E. S.; Nenajdenko, V. G. The first example a diastereoselective Thio-Ugi reaction: A new synthetic approach to chiral imidazole derivatives. J. Org. Chem. 2007, 72, 7878-7885.
10. Mlostoń, G.; Mucha, P.; Urbaniak, K.; Broda, K.; Heimgartner, H. Synthesis of optically active 1-(1-phenylethyl)-1H-imidazoles derived from 1-phenylethylamine. Helv. Chim. Acta 2008, 91, 232-236.
11. Gerstenberg, B. S.; Lin, J.; Mimieux, Y. S.; Brown, L. E.; Oliver, A. G.; Konopelski, J. P. Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the β-lactam nucleus from an α-amino acid. Org. Lett. 2008, 10, 369-372.
12. De Luca, L. Naturally occurring and synthetic imidazoles: Their chemistry and their biological activities. Curr. Med. Chem. 2006, 13, 1-23.
13. Boiani, M.; González, M. Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini-Rev. Med. Chem. 2005, 5, 409-424.
14. Suwiński, J.; Szczepankeiwicz, W.; Świerczek, K.; Walczak, K. Synthesis of chiral imidazole derivatives as purine precursors. Eur. J. Org. Chem. 2003, 1080-1084.
15. Katsuki, I.; Motoda, Y.; Sunatsuki, Y.; Matsumoto, N.; Nakashima, T.; Kojima, M. Spontaneous resolution induced by self-organization of chiral self-complementary cobalt(III) complexes with achiral tripod-type ligands containing three imidazole groups. J. Am. Chem. Soc. 2002, 124, 629-640.
16. Nakamura, H.; Fujii, M.; Sunatsuki, Y.; Kojima, M.; Matsumoto, N. Cobalt(III) complexes of a tripodal ligand containing three imidazole groups: Properties and structures of racemic and optically active species. Eur. J. Inorg. Chem. 2008, 1258-1267.
17. Bureš, F.; Szotkowski, T.; Kulhánek, J.; Pytela, O.; Ludwig, M.; Holčapek, M. Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis. Tetrahedron Asymmetry 2006, 17, 900-907.
18. Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. A new imidazole-containing imidazolidinone catalyst for organocatalyzed asymmetric conjugate addition of nitroalkanes to aldehydes. Adv. Synth. Catal. 2007, 349, 740-748.
19. Kotsuki, H.; Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Synthesis of novel chiral diazole ligands for enantioselective addition of diethylzinc to benzaldehyde. Tetrahedron Asymmetry 1995, 6, 2665-2668.
20. Perl, N. R.; Leighton, J. L. Enantioselective Imidazole-Directed Allylation of Aldimines and Ketimines. Org. Lett. 2007, 9, 3699-3701.
21. 2: N,N′-bis(salicylidene) ethylene-1,2-diamine. Chem. Eur. J. 2007, 13, 4849-4858.
22. Gullotti, M.; Santagostini, L.; Pagliarin, R.; Granata, A.; Casella, L. Synthesis and characterization of new chiral octadentate nitrogen ligands and related copper(II) complexes as catalysts for stereoselective oxidation of catechols. J. Mol. Catal. A: Chem. 2005, 235, 271-284.
23. Hodgson, R.; Douthwaite, R. E. Synthesis and asymmetric catalytic application of chiral imidazollium-phosphines derived from (1R,2R)- trans-diaminocyclohexane. J. Organomet. Chem. 2005, 690, 5822-5831.
24. Sívek, R.; Pytela, O.; Bureš, F. Design and synthesis of optically active 2-phenylimdiazolecarboxamides featuring amino acid motive. J. Heterocyclic Chem. 2008, in press.
25. Paul, R.; Brockman, J. A.; Hallett, W. A.; Hanifin, J. W.; Tarrant, M. E.; Torley, L. W.; Callahan, F. M.; Fabio, P. F.; Johnson, B. D.; Lenhard, R. H.; Schaub, R. E.; Wissner, A. Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents. J. Med. Chem. 1985, 28, 1704-1716.
26. Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. Asymmetric alkylation using SuperQuat auxiliaries - an investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones. J. Chem. Soc., Perkin Trans. 1 1999, 387-398.
27. Luzzio, F. A. The Henry reaction: recent examples. Tetrahedron 2001, 57, 915-945.
28. Evans, D. A.; Seidel, D.; Rueping, M.; Hon, Wai Lam; Shaw, J. T.; Downey, C. W. A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction. J. Am. Chem. Soc. 2003, 125, 12692-12693.
29. Gan, C.; Lai, G.; Zhang, Z.; Wang, Z.; Zhou, M.-M. Efficient and enantioselective nitroaldol reaction catalyzed by copper Schiff-base complexes. Tetrahedron Asymmetry 2006, 17, 725-728.
30. Trost, B. M.; Yeh, V. S. C. A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction. Angew. Chem. Int. Ed. Engl. 2002, 41, 861-863.
31. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. Basic character of rare earth metal alkoxides. Utilization in catalytic C-C bond-forming reactions and catalytic asymmetric nitroaldol reactions. J. Am. Chem. Soc. 1992, 114, 4418-4420.