Skip to main content
Log in

Asymmetric Epoxidation of Styrene on the Heterogenized Chiral Salen Complexes Prepared from Organo-Functionalized Mesoporous Materials

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Organosilane-modified mesoporous materials have been prepared under mild and acidic conditions by a solvent evaporation method using C16TMABr surfactant as a template. The mesoporous samples synthesized in ethanol solvent by using this evaporation method showed a fully disordered pore system, but those obtained under hydrothermal conditions had highly ordered pores. The chiral salen Mn(III) complexes were immobilized on these organosilane-functionalized mesoporous silicas by a grafting method. The catalysts used in the asymmetric epoxidation of styrene and cis-stilbene and the effect of different mesoporous structures on the reactivity was investigated. Similar enantioselectivities were observed by using these heterogenized salen complexes as compared with reaction under homogeneous conditions.

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.

Similar content being viewed by others

References

  1. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli and J.S. Beck, Nature 359 (1992) 710.

    Google Scholar 

  2. J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins and J.L. Schlenker, J. Am. Chem. Soc. 114 (1992) 10834.

    Google Scholar 

  3. R. Ryoo and J.M. Kim, Chem. Commun. (1995) 711.

  4. H.S. Roh, J.S. Chang and S.E. Park, Korean J. Chem. Eng. 16 (1999) 331.

    Google Scholar 

  5. G.-J. Kim and D.-W. Park, Catal. Today 63 (2000) 537.

    Google Scholar 

  6. L. Sierra, B. Lopez, J. Gil and J.L. Guth, Adv. Mater. 11 (1999) 307.

    Google Scholar 

  7. S.S. Kim, T.R. Pauly and J. Pinnavaia, Chem. Commun. 21 (2000) 835.

    Google Scholar 

  8. E.N. Jacobson, W. Zhang, A.R. Muci, J.R. Ecker and L. Deng, J. Am. Chem. Soc. 113 (1991) 7063.

    Google Scholar 

  9. M. Palucki, P.J. Pospisil, W. Zhang and E.N. Jacobson, J. Am. Chem. Soc. 116 (1994) 9333.

    Google Scholar 

  10. R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron Lett. 31 (1990) 7345.

    Google Scholar 

  11. F. Minutolo, D. Pini and P. Salvadori, Tetrahedron Lett. 37 (1996) 3375.

    Google Scholar 

  12. M.J. Sabater, A. Corma, A. Domenech, V. Fornes and H. Garcia, Chem. Commun. (1997) 1285.

  13. S.B. Ogunwumi and T. Bein, Chem. Commun. (1997) 901.

  14. G.-J. Kim and J.-H. Shin, Tetrahedron Lett. 40 (1999) 6827.

    Google Scholar 

  15. L. Frunza, H. Kosslick, H. Landmesser, E. Hoft and R. Fricke, J. Mol. Catal. 123 (1997) 179.

    Google Scholar 

  16. S.L. Burkett, D.D. Sims and S. Mann, Chem. Commun. (1996) 1367.

  17. K. Tsuji, C.W. Jones and M.E. Davis, Micropor. Mesopor. Mater. 33 (1999) 223.

    Google Scholar 

  18. R. Ryoo, J.M. Kim, C.H. Shin and J.Y. Lee, Stud. Surf. Sci. Catal. 105 (1997) 45.

    Google Scholar 

  19. K.B.M. Janssen, I. Laquiere, W. Dehaen, R.F. Parton, I.F.J. Vankelecom and P.A. Jacobs, Tetrahedron: Asymmetry 8 (1997) 3481.

    Google Scholar 

  20. K.M. Spencer, S.J. Cianciosi, J.E. Baldwin, T.B. Freedman and L.A. Nafie, 44 (1990) 235.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Park, DW., Choi, SD., Choi, SJ. et al. Asymmetric Epoxidation of Styrene on the Heterogenized Chiral Salen Complexes Prepared from Organo-Functionalized Mesoporous Materials. Catalysis Letters 78, 145–151 (2002). https://doi.org/10.1023/A:1014945926583

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1014945926583

Navigation