New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction
-
R. Keder
,
P. Drabina
Abstract
New chiral nitrogen ligands based on the substituted mono-and bis(imidazolyl)pyridines have been prepared and characterised. Their complexes with cupric acetate were used as catalysts in the nitroaldolisation reaction. In the case of optically pure complexes of mono(imidazolyl)pyridine, the isolated products were 2-nitro-1-(2-nitrophenyl)ethanols or 2-nitro-1-(4-nitrophenyl)ethanols in overall yields of 49–93 % and with the maximum enantiomeric excess of 15.6 %. The complexes of bis(imidazolyl)pyridine also catalyse the nitroaldol reaction, the yields being 64–90 %, but with zero enantioselective excess.
[1] Jacobsen, E. N., Pfaltz, A., and Yamamoto, H. (Eds.), Comprehensive Asymmetric Catalysis. Springer, Berlin, 1999. 10.1007/978-3-642-58571-5Search in Google Scholar
[2] Seyden-Penne, J., in Chiral Auxiliaries and Ligands in Asymmetric Synthesis. Wiley-VCH, New York, 1995. Search in Google Scholar
[3] Ojima, I. (Ed.), Catalytic Asymmetric Synthesis. 2nd Edition, Wiley-VCH, New York, 2000. 10.1002/0471721506Search in Google Scholar
[4] Davies, D. L., Fawcett, J., Garratt, S. A., and Russell, D. R., J. Chem. Soc., Dalton Trans. 2004, 3629. 10.1039/B408921ASearch in Google Scholar
[5] Desimoni, G., Faita, G., and Quadrelli, P., Chem. Rev. 103, 3119 (2003). http://dx.doi.org/10.1021/cr020004h10.1021/cr020004hSearch in Google Scholar
[6] Henry, L. C. R., Acad. Sci., Ser. C 1895, 1265. Search in Google Scholar
[7] Henry, L. C. R., Bull. Soc. Chim. Fr. 13, 999 (1895). Search in Google Scholar
[8] Ono, N., The Nitro Group in Organic Synthesis. Wiley-VCH, New York, 2001. 10.1002/0471224480Search in Google Scholar
[9] Patai, S. (Ed.), The Chemistry of Amino, Nitroso, Nitro and Related Groups. Wiley, Chichester, 1996. 10.1002/047085720XSearch in Google Scholar
[10] Feuer, H. and Nielsen, A. T. (Eds.), Nitro Compounds: Recent Advances in Synthesis and Chemistry. VCH, Weinheim, 1990. Search in Google Scholar
[11] Rosini, G. and Ballini, R., Synthesis 1895, 833. Search in Google Scholar
[12] Seebach, D., Colvin, E. W., Leher, F., and Weller, T., Chimia 33, 1 (1979). Search in Google Scholar
[13] Palomo, C., Oiarbide, M., and Mielgo, A., Angew. Chem., Int. Ed. Engl. 43, 5442 (2004). http://dx.doi.org/10.1002/anie.20046050610.1002/anie.200460506Search in Google Scholar
[14] Sasai, H., Suzuki, T., Arai, S., Arai, T., and Shibasaki, M., J. Am. Chem. Soc. 114, 4418 (1992). http://dx.doi.org/10.1021/ja00037a06810.1021/ja00037a068Search in Google Scholar
[15] Arai, T., Yamada, Y. M. A., Yamamoto, N., Sasai, H., and Shibasaki, M., Chem. Eur. J. 2, 1368 (1996). Search in Google Scholar
[16] Trost, B. M. and Yeh, V. S. C., Org. Lett. 16, 2621 (2002). http://dx.doi.org/10.1021/ol020077n10.1021/ol020077nSearch in Google Scholar
[17] Trost, B. M. and Yeh, V. S. C., Angew. Chem., Int. Ed. Engl. 41, 861 (2002). http://dx.doi.org/10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO;2-V10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO;2-VSearch in Google Scholar
[18] Christensen, C., Juhl, K., Hazell, R. G., and Jørgensen, K. A., J. Org. Chem. 67, 4875 (2002). http://dx.doi.org/10.1021/jo025690z10.1021/jo025690zSearch in Google Scholar
[19] Evans, D. A., Seidel, D., Rueping, M., Lam, H. W., Shaw, J. T., and Downey, C. W., J. Am. Chem. Soc. 125, 12692 (2003). http://dx.doi.org/10.1021/ja037387110.1021/ja0373871Search in Google Scholar
[20] Sasai, H., Watanabe, S., Suzuki, T., and Shibasaki, M., Org. Synth. Coll. 10, 571 (2004). Search in Google Scholar
[21] Palomo, C., Oiarbide, M., and Laso, A., Angew. Chem., Int. Ed. Engl. 44, 3881 (2005). http://dx.doi.org/10.1002/anie.20046307510.1002/anie.200463075Search in Google Scholar
[22] Luzzio, F. A., Tetrahedron 57, 915 (2001). http://dx.doi.org/10.1016/S0040-4020(00)00965-010.1016/S0040-4020(00)00965-0Search in Google Scholar
[23] Sedlák, M., Drabina, P., Císařová, I., Růžička, A., Hanusek, J., and Macháček, V., Tetrahedron Lett. 45, 7723 (2004). http://dx.doi.org/10.1016/j.tetlet.2004.08.08510.1016/j.tetlet.2004.08.085Search in Google Scholar
© 2006 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Influence of medium on the kinetics of oxidation of iron(II) ion with t-butyl hydroperoxide
- Synthesis of new thiazolo[2,3-b]pyrimidine derivatives of pharmaceutical interest
- Enthalpic analysis of the CaTiSiO5 system
- Kinetic, spectrophotometric determination of nanogram levels of manganese(II) using catalytic azo dye—potassium periodate—1,10-phenanthroline system
- Application of a ternary complex of tungsten(VI) with 4-nitrocatechol and thiazolyl blue for extraction-spectrophotometric determination of tungsten
- Determination of risperidone at picogram level in human urine by luminol—H2O2 chemiluminescence
- Electrochemical dissolution of chalcopyrite studied by voltammetry of immobilized microparticles
- Colon tissue concentrations of copper, iron, selenium, and zinc in colorectal carcinoma patients
- Structure of tetrakis(pyridinioacetate) neodymium(III) tetrahydrate perchlorate
- Thermally stable oligomer—Metal complexes based on oligo-ortho-aminophenol and oligophenylazomethinephenol
- Adsorption of SO2 on alumina
- One-pot, three-component synthesis of secondary amines and trisubstituted hydrazines from ketones
- Synthesis of α,α′-bis(R-benzylidene)cycloalkanones catalyzed by potassium hydrogen sulfate under solvent-free conditions
- Electrical conductivity of the molten KF—K2TaF7 system
- New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction
Articles in the same Issue
- Influence of medium on the kinetics of oxidation of iron(II) ion with t-butyl hydroperoxide
- Synthesis of new thiazolo[2,3-b]pyrimidine derivatives of pharmaceutical interest
- Enthalpic analysis of the CaTiSiO5 system
- Kinetic, spectrophotometric determination of nanogram levels of manganese(II) using catalytic azo dye—potassium periodate—1,10-phenanthroline system
- Application of a ternary complex of tungsten(VI) with 4-nitrocatechol and thiazolyl blue for extraction-spectrophotometric determination of tungsten
- Determination of risperidone at picogram level in human urine by luminol—H2O2 chemiluminescence
- Electrochemical dissolution of chalcopyrite studied by voltammetry of immobilized microparticles
- Colon tissue concentrations of copper, iron, selenium, and zinc in colorectal carcinoma patients
- Structure of tetrakis(pyridinioacetate) neodymium(III) tetrahydrate perchlorate
- Thermally stable oligomer—Metal complexes based on oligo-ortho-aminophenol and oligophenylazomethinephenol
- Adsorption of SO2 on alumina
- One-pot, three-component synthesis of secondary amines and trisubstituted hydrazines from ketones
- Synthesis of α,α′-bis(R-benzylidene)cycloalkanones catalyzed by potassium hydrogen sulfate under solvent-free conditions
- Electrical conductivity of the molten KF—K2TaF7 system
- New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction
