Skip to main content
Log in

New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction

  • Short Communication
  • Published:
Chemical Papers Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. Jacobsen, E. N., Pfaltz, A., and Yamamoto, H. (Eds.), Comprehensive Asymmetric Catalysis. Springer, Berlin, 1999.

    Google Scholar 

  2. Seyden-Penne, J., in Chiral Auxiliaries and Ligands in Asymmetric Synthesis. Wiley-VCH, New York, 1995.

    Google Scholar 

  3. Ojima, I. (Ed.), Catalytic Asymmetric Synthesis. 2nd Edition, Wiley-VCH, New York, 2000.

    Google Scholar 

  4. Davies, D. L., Fawcett, J., Garratt, S. A., and Russell, D. R., J. Chem. Soc., Dalton Trans. 2004, 3629.

  5. Desimoni, G., Faita, G., and Quadrelli, P., Chem. Rev. 103, 3119 (2003).

    Article  PubMed  CAS  Google Scholar 

  6. Henry, L. C. R., Acad. Sci., Ser. C 1895, 1265.

  7. Henry, L. C. R., Bull. Soc. Chim. Fr. 13, 999 (1895).

    Google Scholar 

  8. Ono, N., The Nitro Group in Organic Synthesis. Wiley-VCH, New York, 2001.

    Google Scholar 

  9. Patai, S. (Ed.), The Chemistry of Amino, Nitroso, Nitro and Related Groups. Wiley, Chichester, 1996.

    Google Scholar 

  10. Feuer, H. and Nielsen, A. T. (Eds.), Nitro Compounds: Recent Advances in Synthesis and Chemistry. VCH, Weinheim, 1990.

    Google Scholar 

  11. Rosini, G. and Ballini, R., Synthesis 1895, 833.

  12. Seebach, D., Colvin, E. W., Leher, F., and Weller, T., Chimia 33, 1 (1979).

    CAS  Google Scholar 

  13. Palomo, C., Oiarbide, M., and Mielgo, A., Angew. Chem., Int. Ed. Engl. 43, 5442 (2004).

    Article  CAS  Google Scholar 

  14. Sasai, H., Suzuki, T., Arai, S., Arai, T., and Shibasaki, M., J. Am. Chem. Soc. 114, 4418 (1992).

    Article  CAS  Google Scholar 

  15. Arai, T., Yamada, Y. M. A., Yamamoto, N., Sasai, H., and Shibasaki, M., Chem. Eur. J. 2, 1368 (1996).

    CAS  Google Scholar 

  16. Trost, B. M. and Yeh, V. S. C., Org. Lett. 16, 2621 (2002).

    Article  Google Scholar 

  17. Trost, B. M. and Yeh, V. S. C., Angew. Chem., Int. Ed. Engl. 41, 861 (2002).

    Article  CAS  Google Scholar 

  18. Christensen, C., Juhl, K., Hazell, R. G., and Jørgensen, K. A., J. Org. Chem. 67, 4875 (2002).

    Article  PubMed  CAS  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).

    Article  PubMed  CAS  Google Scholar 

  20. Sasai, H., Watanabe, S., Suzuki, T., and Shibasaki, M., Org. Synth. Coll. 10, 571 (2004).

    Google Scholar 

  21. Palomo, C., Oiarbide, M., and Laso, A., Angew. Chem., Int. Ed. Engl. 44, 3881 (2005).

    Article  CAS  Google Scholar 

  22. Luzzio, F. A., Tetrahedron 57, 915 (2001).

    Article  CAS  Google Scholar 

  23. Sedlák, M., Drabina, P., Císařová, I., Růžička, A., Hanusek, J., and Macháček, V., Tetrahedron Lett. 45, 7723 (2004).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. Sedlák.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Keder, R., Drabina, P., Hanusek, J. et al. New substituted mono-and bis(imidazolyl)pyridines and their application in nitroaldolisation reaction. Chem. Pap. 60, 324–326 (2006). https://doi.org/10.2478/s11696-006-0059-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-006-0059-z

Keywords

Navigation