Skip to main content

Design of Chiral Hybrid Organic-Inorganic Mesoporous Materials as Enantioselective Epoxidation and Alkylation Catalysts

  • Chapter
Nanostructured Catalysts

Part of the book series: Nanostructure Science and Technology ((NST))

Abstract

The nineties have seen important advances in the synthesis of hybrid organicinorganic mesoporous materials based on the functionalization of the surface of new micelle-templated mineral oxides such as MCM-41 type silicates.1 The major advantages of these new supports are their large surface area, their regular system of monodisperse mesopores and homogeneity of chemical surface properties, which allow the preparation of well-defined mesoporous hybrid materials. Nevertheless, asymmetric catalysts grafted on supports are generally less enantioselective than their homogeneous counterparts. This chapter deals mainly with the design of more efficient supported catalysts using MCM-41-type silica for enantioselective epoxidation and C-C bond formation reactions. This design is based on control of the different modification steps in order to improve both catalytic dispersion and mineral surface coverage. Keeping these factors in mind, a new generation of catalysts can be prepared that display enantioselectivity equal to homogeneous catalysts.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Corma, A. Chem. Rev. 1997, 97, 249

    Article  Google Scholar 

  2. Moller, K.; Bein, T. Chem. Mater. 1998, 10, 2950.

    Article  CAS  Google Scholar 

  3. Brunei, D. Micropor. Macropor. Mater. 1999, 27, 329.

    Article  Google Scholar 

  4. Chiral Catalyst Immobilization and Recycling, De Vos, D. E.; Vankelecom, I. F. J.; Jacobs, P.A. Eds, Wiley-VCH: New York, 2000.

    Google Scholar 

  5. Baiker, A. J. Mol. Catal 1997, 175, 473.

    Article  Google Scholar 

  6. Itsuno, S.; Frechet, J.M.J. J. Org. Chem, 1987, 52, 4140.

    Article  CAS  Google Scholar 

  7. Zengpu, Z.; Hodge, P.; Stratford, P.W. React. Polymers 1991, 15, 71.

    Article  Google Scholar 

  8. Soai, K.; Niwa, S.; Watanabe, M. J. J. Org. Chem. 1988, 53, 927.

    Article  CAS  Google Scholar 

  9. De, B.B.; Lohray, B.B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymmetry 1995, 6, 2105.

    Article  CAS  Google Scholar 

  10. Minutolo, F.; Pini, D.; Petri, A.; Salvatori, P. Jet. Lett. 1996, 37, 3375.

    CAS  Google Scholar 

  11. Canali, L.; Cowan, E.; Deleuze, H.; Gibson, C.L.; Sherrington, D. C. Chem. Commun. 1998, 2561.

    Google Scholar 

  12. Breysse, E.; Pinel, C.; Lemaire, M. Tetrahedron: Asymmetry 1998, 9, 897.

    Article  CAS  Google Scholar 

  13. Nagel, U.; Kinzel, E. J. Chem. Soc., Chem. Comm., 1986, 1098.

    Google Scholar 

  14. Pugin, B. J. Mol. Catal. A. 1996, 107, 273.

    Article  CAS  Google Scholar 

  15. Collman, J. P.; Belmont, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1983, 105, 7288.

    Article  CAS  Google Scholar 

  16. Battioni, P.; Lallier, J.-P.; Barloy, L.; Mansuy, D. J. Chem. Soc., Chem. Comm. 1989, 1149.

    Google Scholar 

  17. Martinez-Lorente, M. A.; Battioni, P.; Kleemiss, W.; Bartoli, J. F.; Mansuy, D. J. Mol. Catal. A 1996, 113, 343.

    Article  CAS  Google Scholar 

  18. Prado-Manso, C.M.C.; Vidoto, E.A.; Vinhado, F.S.; Sacco, H.C.; Ciuffi, K.J.; Martins, P.R.; Ferreira, A.G.; Lindsay-Smith, J.R.; Nascimento, O.R.; Iamamoto, Y. J. Mol. Catal. A 1999, 150, 251.

    Article  CAS  Google Scholar 

  19. Sorokin, A. B.; Tuel, A. New J. Chem. 1999, 23, 473.

    Article  CAS  Google Scholar 

  20. Corma, A.; Iglesias, M.; del Pino, C.; Sanchez, F. J. Chem. Soc., Chem. Commun. 1991, 1253.

    Google Scholar 

  21. Sanchez, F. Iglesias, M; Corma, A.; del Pino, C. J. Mol. Catal. 1991, 70, 369.

    Article  CAS  Google Scholar 

  22. Corma, A; Iglesias, M.; del Pino, C.; Sanchez, F. J. Organomet. Chem. 1992, 431, 233.

    Article  CAS  Google Scholar 

  23. Corma, A.; Iglesias, M; Mohino, F.; Sanchez, F. J. Organomet. Chem. 1997, 544, 147.

    Article  CAS  Google Scholar 

  24. Romanovsky, B.V. Proc. 8 th Congr. Catal. Verlag Chemie: Weinhein, 1984, 4, 657.

    Google Scholar 

  25. Herron, N.; Stucky, G. D.; Tolman, C. A. J. Chem. Soc., Chem. Comm. 1986, 1521.

    Google Scholar 

  26. Kimura, T.; Fukuoka, A.; Ichikawa, M. Catal. Lett. 1990, 4, 279.

    Article  CAS  Google Scholar 

  27. Bowers, C.; Dutta, P. K. J. Catal 1990, 122, 271.

    Article  CAS  Google Scholar 

  28. Parton, R. F.; Uytterhoeven, L.; Jacobs, P. A. Stud. Surf. Sci. Catal. 1991, 59, 395.

    Article  CAS  Google Scholar 

  29. Knops-Gerrits, P. P.; De Vos, D., Thibault-Starzyk, F.; Jacobs, P. A. Nature, 1994, 369, 543.

    Article  CAS  Google Scholar 

  30. Corma, A. Top. Catal. 1997, 4, 249.

    Article  Google Scholar 

  31. Ying, J. Y.; Mehnert, C. P.; Wong, M. S., Angew. Chem. Chem. Int. Ed., 1999, 38, 56.

    Article  CAS  Google Scholar 

  32. Tron On, D.; Desplantier-Giscard, D.; Danumah, C.; Kaliaguine, S. Appl. Catal. A 2001, 222, 299.

    Article  Google Scholar 

  33. Sayari, A.; Hamoudi, S. Chem. Mater. 2001, 13, 3151.

    Article  CAS  Google Scholar 

  34. Brunei, D.; Blanc, A. C.; Galarneau, A.; Fajula, F. Catal. Today 2002, 73, 139.

    Article  Google Scholar 

  35. Kresge, C.T.; Leonowicz, M.E.; Roth, W. J.; Vartuli, J. C. Nature, 1992, 359, 710.

    Article  CAS  Google Scholar 

  36. Beck, S.; Chu, C. T.-W.; Chu, I. D.; Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C. WO. Pat. 1991, 91/1 1390.

    Google Scholar 

  37. Cauvel, A.; Brunei, D.; Di Renzo, F.; Fubini, B.; Garrone, E. Langmuir, 1997, 13, 2773.

    Article  CAS  Google Scholar 

  38. Sutra, P.; Fajula, F.; Brunei, D.; Lentz, P.; Daelen, G.; Nagy, J. B. Colloid Surf. 1999, 158, 21.

    Article  CAS  Google Scholar 

  39. Zhao, X. S.; Lu, G. Q. J. Phys. Chem. B 1998, 102, 1556.

    Article  CAS  Google Scholar 

  40. Thomas, J. M. J. Mol. Catal. 1999, 146, 77.

    Article  CAS  Google Scholar 

  41. Johnson, B. F. G.; Raynor, S. A.; Shephard, D. S.; Mashmeyer, T.; Thomas, J. M.; Sankar, G.; Bromley, S.; Oldroyd, R.; Gladden, L.; Mantle, M. D. Chem. Commun. 1999, 1167.

    Google Scholar 

  42. Thomas, J. M.; Mashmeyer, T.; Johnson, B. F. G.; Shephard, D. S. J. Mol. Catal. 1999, 141,139.

    Article  CAS  Google Scholar 

  43. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.

    Article  Google Scholar 

  44. Johnson, R. A.; Sharpless, K. B., in “Catalytic Asymmetric Synthesis” Ojima, I. Ed., VCH: New York, 1993.

    Google Scholar 

  45. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S.Y.; Masumune, H.; Sharpless, K. B., J. Am. Chem. Soc., 1987, 109, 5765.

    Article  CAS  Google Scholar 

  46. Canali, L.; Karjalainen, D. C.; Sherrington, D. C.; Horni, O. E. O., Chem. Commun. 1997, 123.

    Google Scholar 

  47. Karjalainen, D.C.; Horni, O.E.O.; Sherrington, D.C. Tetrahedron: Asymm. 1998, 9, 2019.

    Article  CAS  Google Scholar 

  48. Farral, M. J.; Alexis, M.; Tracarten, M. New J. Chem. 1983, 7, 449.

    Google Scholar 

  49. Choudary, B. M.; Valli, V. L. K.; Prasad, A. D. D. J. Chem. Soc., Chem. Comm. 1990, 1186.

    Google Scholar 

  50. Ikeda, N.; Arai, L; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483.

    Article  CAS  Google Scholar 

  51. Guo, H.; Shi, X.; Quiao, Z.; Hou, S.; Wang, M. Chem. Commun. 2002, 118.

    Google Scholar 

  52. Meunier, D; Piechaczyk. A.; de Mallmann, A.; Basset, J.-M. Angew. Chem. Int. Ed., 1999, 38, 3540.

    Article  CAS  Google Scholar 

  53. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.

    Article  CAS  Google Scholar 

  54. Sabater, M.J.; Corma, A.; Domenech, A.; Fornés, V.; Garcia, H. Chem. Commun. 1997, 1285.

    Google Scholar 

  55. Ogunwumi, S.B.; Bein, T. Chem. Commun. 1997, 901.

    Google Scholar 

  56. Frunza, L.; Kosslick, H.; Landmesser, H.; Höft, E.; Fricke, R. J. Mol. Catal. 1997, 123, 179.

    Article  CAS  Google Scholar 

  57. Piaggio, P.; McMorn, P.; Langham, C.; Bethel, D.; Buman-Page, P. C.; Hancock, F. E.; Hutchings, G. J. New J. Chem. 1998, 1167.

    Google Scholar 

  58. Piaggio, P; Langham, C.; McMorn, P.; Bethel, D.; Bulman-Page, P. C.; Hancock, F. E.; Sly, C.; Hutchings, G. J. J. Chem. Soc., Perkin Trans. 2 2000, 143.

    Google Scholar 

  59. Piaggio, P; McMorn, P.; Murphy, D.; Bethel, D.; Bulman-Page, P. C.; Hancock, F. E.; Sly, C.; Kerton, O. J.; Hutchings, G. J. J. Chem. Soc., Perkin Trans. 2 2000, 2008.

    Google Scholar 

  60. Kim, G.-J.; Shin, J.-H. Catal. Lett. 1999, 63, 83.

    Article  CAS  Google Scholar 

  61. Corma, A.; Iglesias, M.; Obispo, J.R.; Sanchez, F. in Chiral Reactions in Heterogeneous Catalysis, Jannes, G.; Dubois, V. Eds., Plenum: New York, 1995.

    Google Scholar 

  62. Pini, D.; Mandoli, A.; Orlandi, S.; Salvadori, P. Tetrahedron: Asymm. 1999, 10, 3883.

    Article  CAS  Google Scholar 

  63. Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293.

    Article  CAS  Google Scholar 

  64. Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Li, S.-G.; Li, L. S.; Che, C.-M. Chem. Commun. 1999, 1789.

    Google Scholar 

  65. Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. Chem. Commun. 1997, 67.

    Google Scholar 

  66. Kim, G.-J.; Shin, J.-H. Catal. Lett. 1999, 63, 205.

    Article  CAS  Google Scholar 

  67. Kim, G.-J.; Shin, J.-H. Tet. Lett. 1999, 40, 6827.

    Article  CAS  Google Scholar 

  68. Kim, G.-J.; Park, D.-W. Catal. Today 2000, 63, 537.

    Article  CAS  Google Scholar 

  69. Baleizao, C.; Gigante, B.; Sabater, M.J.; Garcia, H.; Corma, A. App. Catal. A 2002, 228, 279.

    Article  CAS  Google Scholar 

  70. Sutra, P.; Brunei, D. Chem. Commun. 1996, 2485.

    Google Scholar 

  71. Rao, Y. V. S.; DeVos, D. E., Bein, T.; Jacobs, P. A. Chem. Commun. 1997, 355.

    Google Scholar 

  72. De Vos, D. E.; De Wildeman, S.; Sels, B. F.; Grabet, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1033.

    Google Scholar 

  73. De Vos, D. E.; Sels, B. F.; Jacobs, P. A. Adv. Catal. 2001, 46, 1.

    Article  Google Scholar 

  74. Bohm, C.; Kadereit, D.; Valacchi, M. Synlett, 1997, 687.

    Google Scholar 

  75. Riley, D. P.;.Henke, S. L.; Lennon, P. J.; Weiss, R. H.; Neumann, W.L.; Rivers, Jr., W. J.; Asto, K. W.; Sample, K. R.; Rahman, H.; Ling, C-S.; Shieh, J-J.; Busch, D. H.; Szulbinski, W. Inorg. Chem. 1996, 35, 5213.

    Article  CAS  Google Scholar 

  76. Miki, K.; Sato, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2385.

    Article  CAS  Google Scholar 

  77. Ogumi, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.

    Article  Google Scholar 

  78. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.

    Article  CAS  Google Scholar 

  79. Itsuno, S.; Frechet, J. M. J. J. Org. Chem. 1987, 52, 4140.

    Article  CAS  Google Scholar 

  80. Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927.

    Article  CAS  Google Scholar 

  81. Hodges, P;. Sung, D. W. L.; Stratford, P. W. J. Chem. Soc., Perkin Trans. 1, 1999, 2335.

    Google Scholar 

  82. Itsuno, S.; Sakurai, Y.; Ito, K.; Marumaya, T.; Nakahama, S.; Frechet, J. M. J. J. Org. Chem. 1990, 55, 304.

    Article  CAS  Google Scholar 

  83. Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832.

    Article  CAS  Google Scholar 

  84. Laspéras, M.; Bellocq, N.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1998, 9, 3053.

    Article  Google Scholar 

  85. Bellocq, N.; Abramson, S.; Laspéras, M.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1999, 10, 3229.

    Article  CAS  Google Scholar 

  86. Abramson, S.; Bellocq, N.; Laspéras, M. Top. Catal. 2000, 13, 339.

    Article  CAS  Google Scholar 

  87. Bellocq, N.; Abramson, S.; Laspéras, M.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1999, 10, 3229.

    Article  CAS  Google Scholar 

  88. Bae, S. J.; Kim, S-W.; Hyeon T.; Kim, B. M. Chem. Commun. 2000, 31.

    Google Scholar 

  89. Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans 1, 1989, 109.

    Google Scholar 

  90. Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327.

    Article  CAS  Google Scholar 

  91. Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233.

    Article  CAS  Google Scholar 

  92. Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237.

    Article  CAS  Google Scholar 

  93. Brunei, D.; Cauvel, A.; Di Renzo, F.; Fajula, F.; Fubini, B.; Onida, B.; Garrone, E. New J. Chem. 2000, 24, 807.

    Article  Google Scholar 

  94. Martin, T.; Galarneau, G.; Brunei, D.; Izard, V.; Hulea, V.; Blanc, A. C.; Abramson, S.; Di Renzo, F.; Fajula, F. Stud. Surf. Sci. Catal. 2001, 135, 2902.

    Google Scholar 

  95. Martin, T.; Brunei, D.; Galarneau, A.; Hulea, V.; Blanc, A.C; Abramson, S.; Di Renzo, F.; Fajula, F., Proc. Ind. Int. Conf. Silica Sci. Techn. Silica 2001, 108.

    Google Scholar 

  96. Lefevre, B.; Gobin, P. F.; Martin, T.; Galarneau, A.; Brunei, D. Materials Research Society 2002, April 1–5.

    Google Scholar 

  97. Abramson, S.; Laspéras, M.; Galarneau, A.; Desplantier-Giscard, D.; Brunei, D. Chem. Commun. 2000, 1773.

    Google Scholar 

  98. Heckel, A.; Seebach, D. Angew. Chem., Int. Engl. Ed. 2000, 39, 163.

    Article  CAS  Google Scholar 

  99. Di Renzo, F.; Chiche, B.; Fajula, F.; Viale, S.; Garrone, E. Stud. Surf. Sci. Catal. 1996, 101, 851.

    Article  Google Scholar 

  100. Noyori, R. in Architectural and Functional Molecular Engineering for Asymmetrie Catalysis, presented during the conference of Société Française de Chimie, F-Rennes, 2000, Sept 18–22.

    Google Scholar 

  101. Abramson, S.; Laspéras, M.; Brunei, D. Tetrahedron: Asymm. 2002, 13, 357.

    Article  CAS  Google Scholar 

  102. Martin, T.; Lefevre, B.; Brunei, D.; Galarneau, A.; Di Renzo, F.; Fajula, F.; Gobin, P. F.; Quinson, J. F.; Vigier, G. Chem. Commun. 2002, 24.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2005 Springer Science + Business Media, Inc.

About this chapter

Cite this chapter

Brunei, D., Laspéras, M. (2005). Design of Chiral Hybrid Organic-Inorganic Mesoporous Materials as Enantioselective Epoxidation and Alkylation Catalysts. In: Scott, S.L., Crudden, C.M., Jones, C.W. (eds) Nanostructured Catalysts. Nanostructure Science and Technology. Springer, Boston, MA. https://doi.org/10.1007/978-0-387-30641-4_6

Download citation

  • DOI: https://doi.org/10.1007/978-0-387-30641-4_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-47484-2

  • Online ISBN: 978-0-387-30641-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics