Skip to main content
SpringerLink
Log in

Enantioselective Hydrogenation of Trifluoromethylcyclohexyl Ketone on Cinchona Alkaloid Modified Pt-Alumina Catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0–10 mmol/l), hydrogen pressure (1–100 bar), temperature (273–301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48% in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. I. Ojima, J.R. McCarthy and J.R. Welch, Biomedical Frontiers of Fluorine Chemistry (ACS Books, Washington, 1996).

    Google Scholar 

  2. M.W. Walter, A. Felici, M. Galleni, R.P. Soto, R.M. Adlington, J.E. Baldwin, J.M. Freŕe, M. Gololobov and C.J. Schofield, Bioorg. Med. Chem. Letters 6 (1996) 2455.

    Google Scholar 

  3. V.A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-Organic Compounds (Wiley, Chichester, 1999).

    Google Scholar 

  4. W.H. Pirkle and M.S. Hoekstra, J. Org. Chem. 39 (1974) 3904.

    Google Scholar 

  5. P.V. Ramachandran, A.V. Teodorevic and H.C. Brown, Tetrahedron 49 (1993) 1725.

    Google Scholar 

  6. M. Bucciarelli, A. Forni, I. Moretti and G. Torre, Synthesis 11 (1983) 897.

    Google Scholar 

  7. R. Noyori and R. Ohkuma, Angew. Chem. Int. Ed. 40 (2001) 40.

    Google Scholar 

  8. P. Gamez, F. Fache and M. Lemaire, Tetrahedron: Asymmetry 6 (1995) 705.

    Google Scholar 

  9. M. Studer, H.-U. Blaser and Ch. Exner, Adv. Synth. Catal. 345 (2003) 45.

    Google Scholar 

  10. T. Mallat, M. Bodmer and A. Baiker, Catal. Lett. 44 (1997) 95.

    Google Scholar 

  11. K. Balaźsik, B. Török, K. Felföldi and M. Bartók, Ultrason. Sonochem. 5 (1999) 149.

    Google Scholar 

  12. M. Bodmer, T. Mallat and A. Baiker, Chem. Ind. 75 (1998) 75.

    Google Scholar 

  13. M. von Arx, T. Mallat and A. Baiker, J. Catal. 193 (2000) 161.

    Google Scholar 

  14. M. von Arx, T. Mallat and A. Baiker, Tetrahedron: Asymmetry 12 (2001) 3089.

    Google Scholar 

  15. M. von Arx, T. Bürgi, T. Mallat and A. Baiker, Chem. Eur. J. (2002) 1430.

  16. M. von Arx, T. Mallat and A. Baiker, Catal. Lett. 78 (2002) 267.

    Google Scholar 

  17. A. Vargas, T. Bürgi and A. Baiker, New J. Chem. 26 (2002) 807.

    Google Scholar 

  18. B. Török and G.K. Prakash, Adv. Synth. Catal. 345 (2003) 165.

    Google Scholar 

  19. R. Hess, F. Krumeich, T. Mallat and A. Baiker, Catal. Lett. 92 (2004) 141.

    Google Scholar 

  20. R. Hess, S. Diezi, T. Mallat and A. Baiker, Tetrahedron: Asymmetry 15 (2004) 251.

    Google Scholar 

  21. T. Varga, K. Felföldi, P. Forgoánd M. Bartók, J. Mol. Catal. A-Chem. 216 (2004)181.

    Google Scholar 

  22. B.Török, K. Felföldi, G. Szakonyi, K. Balázsik and M. Bartók, Catal. Lett. 52 (1998) 81.

    Google Scholar 

  23. X. Zuo, H. Liu, D. Guo and X. Yang, Tetrahedron 55 (1999) 7787.

    Google Scholar 

  24. F.E. Herkes and D.J. Burton, J. Org. Chem. 32 (1967) 1311.

    Google Scholar 

  25. M. Bartók, Gy. Szöllösi, K. Balázsik and T. Bartók, J. Mol. Catal. A-Chem. 177 (2002) 299.

    Google Scholar 

  26. M. Bartók, K. Balázsik, Gy. Szöllösi and T. Bartók, J. Catal. 205 (2002) 168.

    Google Scholar 

  27. M. Bucciarelli, A. Forni, I. Moretti and G. Torre, J. Chem. Soc., Chem. Commun. (1978) 457.

  28. M.L.M. Schilling, H.D. Roth and W.C. Herndon, J. Am. Chem. Soc. 102 (1980) 4271.

    Google Scholar 

  29. B. Török, K. Balázsik, K. Felföldi and M. Bartók, Stud. Surf. Sci. Catal. 130 (2000) 3381.

    Google Scholar 

  30. M. Bartók, K. Balázsik, T. Bartók and Z. Kele, Catal. Lett. 87 (2003) 235.

    Google Scholar 

  31. M. Garland, and H-U. Blaser, J. Am. Chem. Soc. 112 (1990) 7048.

    Google Scholar 

  32. J.U. Köhler and J.S. Bradley, Catal. Lett. 45 (1997) 203.

    Google Scholar 

  33. M. Sutyinszki, K. Szöri, K. Felföldi and M. Bartók, Catal. Commun. 3 (2002) 125.

    Google Scholar 

  34. von M. Arx, N. Dummer, D.J. Willock, S.H. Taylor, R.P.K. Wells, P.B. Wells and G.J. Hutchings, Chem. Commun. (2003) 1926.

  35. E. Toukoniitty, B. Sevciková, P. Maki-Arvela, J. Warna, T. Salmi and D.Yu. Murzin, J. Catal. 213 (2003) 7.

    Google Scholar 

  36. M. Bartók, M. Sutyinszki, K. Felföldi and Gy. Szöllösi, Chem. Commun. (2002) 1130.

  37. S. Diezi, A. Szabó, T. Mallat and A. Baiker, Tetrahedron: Asymmetry 14 (2003) 2573.

    Google Scholar 

  38. G. Vayner, K.N. Houk and Y.K. Sun, J. Am. Chem. Soc. 126 (2004) 199.

    Google Scholar 

  39. A. Gamez, J. Köhler and J. Bradley, Catal. Lett. 55 (1998) 73.

    Google Scholar 

  40. X. Li, R.P.K. Wells, P.B. Wells, G.J. Hutchings, J. Catal. 221 (2004) 653.

    Google Scholar 

  41. K. Szöri, M. Sutyinszki, K. Felföldi and M. Bartók, Appl. Catal. A-Gen. 237 (2002) 275.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720, Szeged, Hungary

    Károly Felföldi, Tibor Varga & Péter Forgó

Authors
  1. Károly Felföldi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tibor Varga
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Péter Forgó
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mihály Bartók
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Felföldi, K., Varga, T., Forgó, P. et al. Enantioselective Hydrogenation of Trifluoromethylcyclohexyl Ketone on Cinchona Alkaloid Modified Pt-Alumina Catalyst. Catalysis Letters 97, 65–70 (2004). https://doi.org/10.1023/B:CATL.0000034289.64347.c1

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:CATL.0000034289.64347.c1

Search

Navigation