Catalysis Letters

, Volume 45, Issue 1–2, pp 73–78

New enantioselective heterogeneous catalysts

  • G.V. Smith
  • J. Cheng
  • R. Song
Article

Abstract

A new enantioselective heterogeneous catalytic system has been made by partly decomposing (hydrogenolyzing) chiral silyl ethers in hydrogen over Pd black and differently dispersed Pd/SiO2. Preliminary hydrogenations of two prochiral C=C's have demonstrated the feasibility of the method which produced catalysts attaining ee's up to 22%. The chiral silyl ethers appear to hydrolyze off the surface, but in the absence of water, the new catalysts catalyze reproducible ee's.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    T. Sigimura, T. Osawa, S. Nakagawa, T. Harada and A. Tai, in: 11th Int. Congr. on Catalysis — 40th Anniversary, Studies in Surface Science and Catalysis, Vol. 101, eds. J.W. Hightower, W.N. Delgass, E. Iglesia and A.T. Bell (Elsevier, Amsterdam, 1996) p. 231.Google Scholar
  2. [2]
    H.-U. Blaser and M. Müller, in: Heterogeneous Catalysis and Fine Chemicals II, eds. M. Guisnet et al. (Elsevier, Amsterdam, 1991) p. 73; H.-U. Blaser, Tetrahedron: Asymmetry 2 (1991) 843; J.R.G. Perez, J. Malthete and J. Jackques, Compt. Rend. Acad. Sci. Paris Serie II (1985) 169.Google Scholar
  3. [3]
    S. Akabori, S. Sakurai, Y. Izumi and Y. Juji, Nature 178 (1956) 323.CrossRefGoogle Scholar
  4. [4]
    M. Bart_ok, G. Wittmann, G.B. Bart_ok and G. Göndös, J. Organomet. Chem. 384 (1990) 385.Google Scholar
  5. [5]
    Y.Nitta and K.Kobiro,Chem. Lett. (1996) 165.Google Scholar
  6. [6]
    T. Uemura, X. Zhang, K. Matsumura, N. Sayo, H. Kumobayashi, T. Ohta, K. Nozaki and H. Takaya, J. Org. Chem. 61 (1996) 5510.CrossRefGoogle Scholar
  7. [7]
    J. Cheng, MS Thesis, Enantioselective hydrogenation of CàC bonds over new chiral heterogeneous catalysts, Southern Illinois University at Carbondale,USA (1996).Google Scholar
  8. [8]
    A. Moln_ar, I. Bucsi, M. Bart_ok, F. Notheisz and G.V. Smith, J. Catal. 98 (1986) 386.CrossRefGoogle Scholar
  9. [9]
    S. Tjandra, D. Ostgard, G.V. Smith, M. Musoiu, T. Wiltowski, F. Notheisz, M. Bart_ok and J. Stoch, in: Catalysis of Organic Reactions, ed.W.E. Pascoe (Dekker, NewYork, 1992) p. 137.Google Scholar
  10. [10]
    G.V. Smith, J. Stoch, S. Tjandra and T. Wiltowski, in: Catalysis of Organic Reactions, eds. M.G. Scaros and M.L. Prunier (Dekker, NewYork, 1995) p. 403.Google Scholar
  11. [11]
    G.V. Smith, comment on: S. Yoshida, T. Kakehi, S. Matsumoto, T. Tanaka, H. Kanai and T. Funabiki, in: New Frontiers in Catalysis, eds. L. Guczi, F. Solymosi and P. T _et_enyi (Akad_emiai Kiad_o, Budapest, 1993) p. 990.Google Scholar
  12. [12]
    G.V. Smith, S. Tjandra, M. Musoiu, T. Wiltowski, F. Notheisz, M. Bart_ok, I. Hannus, D. Ostgard and V. Malhotra, J. Catal. 161 (1996) 441.CrossRefGoogle Scholar
  13. [13]
    D.I. Bradshaw, R.B. Moyes and P.B. Wells, J. Chem. Soc. Faraday I 76 (1980) 979.CrossRefGoogle Scholar
  14. [14]
    M.J. Hostetler, R.G. Nuzzo and G.S. Girolami, J. Am. Chem. Soc. 116 (1994) 11608.CrossRefGoogle Scholar
  15. [15]
    D.J. Ostgard, The carbon disulfide titration of olefin transformation sites on well characterized Pd and Pt catalysts, PhD Dissertation, Southern Illinois University at Carbondale, USA(1995).Google Scholar
  16. [16]
    G.V. Smith, F. Notheisz, A.G.Zsigmond, D. Ostgard, T. Nishizawa and M. Bart_ok, in: Proc. 9th Int. Congr. on Catalysis, Vol. 3, Calgary (The Chemical Institute of Canada, Ottawa, 1988); G.V. Smith, R. Song, M. Gasior and R.E. Malz, Jr., in: Catalysis of Organic Reactions, eds. T.A. Johnson and J.R. Kosak (Dekker, New York, 1994) p. 137.Google Scholar
  17. [17]
    F. Notheisz, _ A. Zsigmond, M. Bart_ok, Zs. Szegletes and G.V. Smith, Appl. Catal.A 99 (1994) 105.CrossRefGoogle Scholar
  18. [18]
    L.M.Gross and P.J.Rys, J. Org. Chem. 39 (1974) 2429.CrossRefGoogle Scholar
  19. [19]
    Y. Nitta, F. Sekine, J. Sasaki, T. Imanaka and S. Teranishi, J. Catal. 79 (1983) 211.CrossRefGoogle Scholar
  20. [20]
    A. Rives, E. Leclercq and R. Hubaut, in: Catalysis of Organic Reactions, ed. R.E. Malz Jr. (Dekker, New York, 1996) pp. 241–247.Google Scholar
  21. [21]
    G.V. Smith and J.A. Roth, J.Am. Chem. Soc. 88 (1966) 3879; H.W. Thompson and R.E. Naipawer, J. Am. Chem. Soc. 95 (1973) 6379.CrossRefGoogle Scholar
  22. [22]
    I. P_alink_o, F. Notheisz, D. Ostgard, G.V. Smith and M. Bart_ok, J.Mol. Catal. 57 (1990) 353.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1997

Authors and Affiliations

  • G.V. Smith
  • J. Cheng
  • R. Song

There are no affiliations available

Personalised recommendations