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Mechanisms of Asymmetric Heterogeneous Catalysis1

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Abstract

Asymmetric catalysis plays an important role in present-day production of pharmaceuticals. It can be predicted that enantioselective catalysis will dominate in the future, replacing conventional stoichiometric methods. Heterogeneous catalysts offer several advantages compared to their homogeneous counterparts. In the present review mechanisms of asymmetric heterogeneous catalysis are discussed and the different ways of chirality transfer are addressed. Enantioselection is possible over chiral supports and chiral metals exhibiting intrinsic chirality, as well as over modified metal supported catalysts. The interactions between a reactant and a modifier are very specific being critical for achieving high enantioselectivities.

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REFERENCES

  1. Muller, G.W., Konnecke, W.E., Smith, A.M., et al., Org. Proc. Res. Dev., 1999, vol. 3, p. 139.

    Google Scholar 

  2. Takeuchi, Y., Shiragami, T., Kimura, K., et al., Org. Lett., 1999, vol. 1, p. 1571.

    Google Scholar 

  3. Stinson, S.C., Chem. Eng. News, 1994, vol. 72, p. 38.

    Google Scholar 

  4. Stinson, S.C., Chem. Eng. News, 2000, vol. 78, p. 55.

    Google Scholar 

  5. Blaser, H.-U., Spindler, F., and Studer, M., Appl. Catal., A, 2001, vol. 221, p. 119.

    Google Scholar 

  6. Sheldon, R.A., Chirotechnology, New York: Marcel Dekker, 1993.

    Google Scholar 

  7. Collins, A.N., Sheldrake, G.N., and Crosby, J., Chirality in Industry II, New Delhi: Thomson, 1997.

    Google Scholar 

  8. Blaser, H.-U. and Pugin, B., Chiral Reactions in Heterogeneous Catalysis, Jannes, G. and Dubois, V., Eds., New York: Plenum, 1995, p. 33.

    Google Scholar 

  9. Blaser, H.-U. and Müller, M., Stud. Surf. Sci. Catal., 1991, vol. 59, p. 73.

    Google Scholar 

  10. Blaser, H.-U., Tetrahedron Asymm., 1991, vol. 2, p. 843.

    Google Scholar 

  11. Feast, S., Rafiq, M., Siddiqui, H., et al., J. Catal., 1997, vol. 167, p. 533.

    Google Scholar 

  12. Fraile, J.M., Garcä, J.I., Mayoral, J.A., et al., J. Catal., 1999, vol. 186, p. 214.

    Google Scholar 

  13. Brunel, D., Sutra, P., and Fajula, F., Stud. Surf. Sci. Catal., 2000, vol. 129, p. 773.

    Google Scholar 

  14. Abramson, S., Lasperas, M., and Chiche, B., J. Mol. Catal. A: Chem., 2001, vol. 165, p. 231.

    Google Scholar 

  15. Heterogeneous Catalysis in Organic Chemistry, Smith, G.V. and Notheisz, F., Eds., New York: Academic, 1999, p. 97.

    Google Scholar 

  16. Baiker, A., J. Mol. Catal. A: Chem., 1997, vol. 115, p. 473.

    Google Scholar 

  17. Baiker, A. and Blaser, H.-U., Handbook of Heterogeneous Catalysis, Ertl, G., Knözinger, H., and Weitkamp, J., Eds., Weinheim: VCH, 1997, vol. 5, p. 2422.

    Google Scholar 

  18. Margitfalvi, J., Tälas, E., and Tfirst, E., Chim. Oggi/Chem. Today, 2000, p. 45.

  19. Izumi, Y., Adv. Catal., 1983, vol. 32, p. 215.

    Google Scholar 

  20. Tai, A. and Sugimura, T., Chiral Catalyst Immobilization and Recycling, De Vos, D.E., Vankelecom, I.F.J., and Jacobs, P.A., Eds., Weinheim: Wiley-VCH, 2000, p. 173.

    Google Scholar 

  21. Blaser, H.-U., Jalett, H.-P., Müller, M., et al., Catal. Today, 1997, vol. 37, p. 441.

    Google Scholar 

  22. Von Arx, M., Mallat, T., and Baiker, A., Top. Catal., 2002, vol. 19, p. 75.

    Google Scholar 

  23. Wells, P.B. and Wilkinson, A.G., Top. Catal., 1998, vol. 5, p. 39.

    Google Scholar 

  24. Baiker, A., J. Mol. Catal. A: Chem., 2000, vol. 163, p. 205.

    Google Scholar 

  25. Baiker, A., in A Molecular View of Heterogeneous Catalysis, Derouane, E.G., Ed., Paris: De Boeck Université, 1998, p. 165.

    Google Scholar 

  26. Blackmond, D.G., Cattech, 1998, vol. 6, p. 17.

    Google Scholar 

  27. Raval, R., Cattech, 2001, vol. 5, p. 12.

    Google Scholar 

  28. Humblot, V., Haq, S., Muryn, C., et al., J. Am. Chem. Soc., 2002, vol. 124, p. 503.

    Google Scholar 

  29. Ahmadi, A., Attard, G., Feliu, J., et al., Langmuir, 1999, vol. 15, p. 2420.

    Google Scholar 

  30. Stephenson, M.J. and Lambert, R.M., J. Phys. Chem. B, 2001, vol. 105, p. 12832.

    Google Scholar 

  31. Tungler, A., React. Kinet. Catal. Lett., 2001, vol. 74, p. 271.

    Google Scholar 

  32. Mäki-Arvela, P., Salmi, T., and Murzin, D.Yu., Stud. Surf. Sci. Catal., 2003 (in press).

  33. Sutyinszki, M., Szöri, K., Felföldi, K., et al., Catal. Commun., 2002, vol. 3, p. 125.

    Google Scholar 

  34. Wang, G.Z., Mallat, T., and Baiker, A., Tetrahedron Asymm., 1997, vol. 8, p. 2133.

    Google Scholar 

  35. Lindholm, A., Mäki-Arvela, P., Toukoniitty, E., et al., J. Chem. Soc., Perkin Trans. I, 2002, p. 2605.

  36. Huck, W.-R., Bürgi, T., Mallat, T., et al., J. Catal., 2002, vol. 205, p. 213.

    Google Scholar 

  37. Nitta, Y. and Kobiro, K., Chem. Lett., 1996, p. 897.

  38. Kun, I., Török, B., Felföldi, K., et al., Appl. Catal., A, 2000, vol. 293, p. 71.

    Google Scholar 

  39. Tungler, A. and Fogassy, G., J. Mol. Catal., A: Chem., 2001, vol. 173, p. 231.

    Google Scholar 

  40. Blaser, H.U., Jalett, H.P., Lottenbach, W., et al., J. Am. Chem. Soc., 2000, vol. 122, p. 12675.

    Google Scholar 

  41. Testa, A.C. and Augustine, R.L., Catalysis in Organic Reactions, New York: Dekker, 2001, vol. 82, p. 465.

    Google Scholar 

  42. Osawa, T., Hayashi, Y., Ozawa, A., et al., J. Mol. Catal. A: Chem., 2001, vol. 169, p. 289.

    Google Scholar 

  43. Toukoniitty, E., Mäki-Arvela, P., Kalantar Neyestanaki, A., et al., Stud. Surf. Sci. Catal., 2000, vol. 130, p. 3363.

    Google Scholar 

  44. Keane, M.A., Langmuir, 1997, vol. 13, p. 41.

    Google Scholar 

  45. Vargas, A., Bürgi, T., von Arx, M., et al., J. Catal., 2002, vol. 209, p. 489.

    Google Scholar 

  46. Huck, W.-R., Mallat, T., and Baiker, A., Catal. Lett., 2000, vol. 69, p. 129.

    Google Scholar 

  47. Gamez, A., Köhler, J., and Bradley, J., Catal. Lett., 1998, vol. 55, p. 73.

    Google Scholar 

  48. Toukoniitty, E., Mäki-Arvela, P., Kuusisto, J., et al., J. Mol. Catal. A: Chem., 2003, vol. 192, p. 135.

    Google Scholar 

  49. Baiker, A. and Blaser, H.-U., Handbook of Heterogeneous Catalysis, Ertl, G., Knözinger, H., and Weitkamp, K., Eds., Weinheim: VCH, 1997, vol. 5, p. 2422.

    Google Scholar 

  50. Kubicki, M., Borowiak, T., Gawron, M., et al., J. Cryst. Spectr. Res., 1990, vol. 20, p. 447.

    Google Scholar 

  51. Carley, A.F., Rajumon, M.K., Roberts, M.V., et al., J. Chem. Soc. Faraday Trans., 1995, vol. 91, p. 2147.

    Google Scholar 

  52. Ferri, D. and Bürgi, T., J. Am. Chem. Soc., 2001, vol. 123, p. 12074.

    Google Scholar 

  53. Kubota, J. and Zaera, F., J. Am. Chem. Soc., 2001, vol. 123, p. 11115.

    Google Scholar 

  54. Toukoniitty, E., Mäki-Arvela, P., Kalantar Neyestanaki, A., et al., Appl. Catal. A: Chem., 2002, vol. 235, p. 125.

    Google Scholar 

  55. Kukula, P. and Červený, L., Appl. Catal., A, 2001, vol. 210, p. 237.

    Google Scholar 

  56. Webb, G., Chiral Reactions in Heterogeneous Catalysis, Jannes, G. and Dubois, V., Eds., New York: Plenum, 1995, p. 61.

    Google Scholar 

  57. Lorenzo, M.O., Humblot, V., Murray, P., et al., J. Catal., 2002, vol. 205, p. 123.

    Google Scholar 

  58. Wolfson, A., Geresh, S., Landau, M.V., et al., Appl. Catal., A, 2001, vol. 208, p. 91.

    Google Scholar 

  59. Klabunovskii, E.I., Vedenyapin, A.A., Chankvetadze, B.G., et al., Proc. 8th Int. Congr. Catal., Berlin, 1984, vol. 5, p. 543.

    Google Scholar 

  60. Toukoniitty, E., Mäki-Arvela, P., Kuzma, M., et al., J. Catal., 2001, vol. 204, p. 281.

    Google Scholar 

  61. Toukoniitty, E., Ševíková, B., Mäki-Arvela, P., et al., J. Catal., 2003, vol. 213, p. 7.

    Google Scholar 

  62. Nitta, Y. and Shibata, A., Chem. Lett., 1998, p. 161.

  63. Kukula, P. and Červený, L., J. Mol. Catal. A: Chem., 2002, vol. 185, p. 195.

    Google Scholar 

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Murzin, D.Y., Mäki-Arvela, P. & Salmi, T. Mechanisms of Asymmetric Heterogeneous Catalysis1 . Kinetics and Catalysis 44, 323–333 (2003). https://doi.org/10.1023/A:1024438801008

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