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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Corma, A. Chem. Rev. 1997, 97, 249
Moller, K.; Bein, T. Chem. Mater. 1998, 10, 2950.
Brunei, D. Micropor. Macropor. Mater. 1999, 27, 329.
Chiral Catalyst Immobilization and Recycling, De Vos, D. E.; Vankelecom, I. F. J.; Jacobs, P.A. Eds, Wiley-VCH: New York, 2000.
Baiker, A. J. Mol. Catal 1997, 175, 473.
Itsuno, S.; Frechet, J.M.J. J. Org. Chem, 1987, 52, 4140.
Zengpu, Z.; Hodge, P.; Stratford, P.W. React. Polymers 1991, 15, 71.
Soai, K.; Niwa, S.; Watanabe, M. J. J. Org. Chem. 1988, 53, 927.
De, B.B.; Lohray, B.B.; Sivaram, S.; Dhal, P. K. Tetrahedron: Asymmetry 1995, 6, 2105.
Minutolo, F.; Pini, D.; Petri, A.; Salvatori, P. Jet. Lett. 1996, 37, 3375.
Canali, L.; Cowan, E.; Deleuze, H.; Gibson, C.L.; Sherrington, D. C. Chem. Commun. 1998, 2561.
Breysse, E.; Pinel, C.; Lemaire, M. Tetrahedron: Asymmetry 1998, 9, 897.
Nagel, U.; Kinzel, E. J. Chem. Soc., Chem. Comm., 1986, 1098.
Pugin, B. J. Mol. Catal. A. 1996, 107, 273.
Collman, J. P.; Belmont, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1983, 105, 7288.
Battioni, P.; Lallier, J.-P.; Barloy, L.; Mansuy, D. J. Chem. Soc., Chem. Comm. 1989, 1149.
Martinez-Lorente, M. A.; Battioni, P.; Kleemiss, W.; Bartoli, J. F.; Mansuy, D. J. Mol. Catal. A 1996, 113, 343.
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.
Sorokin, A. B.; Tuel, A. New J. Chem. 1999, 23, 473.
Corma, A.; Iglesias, M.; del Pino, C.; Sanchez, F. J. Chem. Soc., Chem. Commun. 1991, 1253.
Sanchez, F. Iglesias, M; Corma, A.; del Pino, C. J. Mol. Catal. 1991, 70, 369.
Corma, A; Iglesias, M.; del Pino, C.; Sanchez, F. J. Organomet. Chem. 1992, 431, 233.
Corma, A.; Iglesias, M; Mohino, F.; Sanchez, F. J. Organomet. Chem. 1997, 544, 147.
Romanovsky, B.V. Proc. 8 th Congr. Catal. Verlag Chemie: Weinhein, 1984, 4, 657.
Herron, N.; Stucky, G. D.; Tolman, C. A. J. Chem. Soc., Chem. Comm. 1986, 1521.
Kimura, T.; Fukuoka, A.; Ichikawa, M. Catal. Lett. 1990, 4, 279.
Bowers, C.; Dutta, P. K. J. Catal 1990, 122, 271.
Parton, R. F.; Uytterhoeven, L.; Jacobs, P. A. Stud. Surf. Sci. Catal. 1991, 59, 395.
Knops-Gerrits, P. P.; De Vos, D., Thibault-Starzyk, F.; Jacobs, P. A. Nature, 1994, 369, 543.
Corma, A. Top. Catal. 1997, 4, 249.
Ying, J. Y.; Mehnert, C. P.; Wong, M. S., Angew. Chem. Chem. Int. Ed., 1999, 38, 56.
Tron On, D.; Desplantier-Giscard, D.; Danumah, C.; Kaliaguine, S. Appl. Catal. A 2001, 222, 299.
Sayari, A.; Hamoudi, S. Chem. Mater. 2001, 13, 3151.
Brunei, D.; Blanc, A. C.; Galarneau, A.; Fajula, F. Catal. Today 2002, 73, 139.
Kresge, C.T.; Leonowicz, M.E.; Roth, W. J.; Vartuli, J. C. Nature, 1992, 359, 710.
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.
Cauvel, A.; Brunei, D.; Di Renzo, F.; Fubini, B.; Garrone, E. Langmuir, 1997, 13, 2773.
Sutra, P.; Fajula, F.; Brunei, D.; Lentz, P.; Daelen, G.; Nagy, J. B. Colloid Surf. 1999, 158, 21.
Zhao, X. S.; Lu, G. Q. J. Phys. Chem. B 1998, 102, 1556.
Thomas, J. M. J. Mol. Catal. 1999, 146, 77.
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.
Thomas, J. M.; Mashmeyer, T.; Johnson, B. F. G.; Shephard, D. S. J. Mol. Catal. 1999, 141,139.
Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
Johnson, R. A.; Sharpless, K. B., in “Catalytic Asymmetric Synthesis” Ojima, I. Ed., VCH: New York, 1993.
Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S.Y.; Masumune, H.; Sharpless, K. B., J. Am. Chem. Soc., 1987, 109, 5765.
Canali, L.; Karjalainen, D. C.; Sherrington, D. C.; Horni, O. E. O., Chem. Commun. 1997, 123.
Karjalainen, D.C.; Horni, O.E.O.; Sherrington, D.C. Tetrahedron: Asymm. 1998, 9, 2019.
Farral, M. J.; Alexis, M.; Tracarten, M. New J. Chem. 1983, 7, 449.
Choudary, B. M.; Valli, V. L. K.; Prasad, A. D. D. J. Chem. Soc., Chem. Comm. 1990, 1186.
Ikeda, N.; Arai, L; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483.
Guo, H.; Shi, X.; Quiao, Z.; Hou, S.; Wang, M. Chem. Commun. 2002, 118.
Meunier, D; Piechaczyk. A.; de Mallmann, A.; Basset, J.-M. Angew. Chem. Int. Ed., 1999, 38, 3540.
Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.
Sabater, M.J.; Corma, A.; Domenech, A.; Fornés, V.; Garcia, H. Chem. Commun. 1997, 1285.
Ogunwumi, S.B.; Bein, T. Chem. Commun. 1997, 901.
Frunza, L.; Kosslick, H.; Landmesser, H.; Höft, E.; Fricke, R. J. Mol. Catal. 1997, 123, 179.
Piaggio, P.; McMorn, P.; Langham, C.; Bethel, D.; Buman-Page, P. C.; Hancock, F. E.; Hutchings, G. J. New J. Chem. 1998, 1167.
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.
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.
Kim, G.-J.; Shin, J.-H. Catal. Lett. 1999, 63, 83.
Corma, A.; Iglesias, M.; Obispo, J.R.; Sanchez, F. in Chiral Reactions in Heterogeneous Catalysis, Jannes, G.; Dubois, V. Eds., Plenum: New York, 1995.
Pini, D.; Mandoli, A.; Orlandi, S.; Salvadori, P. Tetrahedron: Asymm. 1999, 10, 3883.
Minutolo, F.; Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymm. 1996, 7, 2293.
Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Li, S.-G.; Li, L. S.; Che, C.-M. Chem. Commun. 1999, 1789.
Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. Chem. Commun. 1997, 67.
Kim, G.-J.; Shin, J.-H. Catal. Lett. 1999, 63, 205.
Kim, G.-J.; Shin, J.-H. Tet. Lett. 1999, 40, 6827.
Kim, G.-J.; Park, D.-W. Catal. Today 2000, 63, 537.
Baleizao, C.; Gigante, B.; Sabater, M.J.; Garcia, H.; Corma, A. App. Catal. A 2002, 228, 279.
Sutra, P.; Brunei, D. Chem. Commun. 1996, 2485.
Rao, Y. V. S.; DeVos, D. E., Bein, T.; Jacobs, P. A. Chem. Commun. 1997, 355.
De Vos, D. E.; De Wildeman, S.; Sels, B. F.; Grabet, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1033.
De Vos, D. E.; Sels, B. F.; Jacobs, P. A. Adv. Catal. 2001, 46, 1.
Bohm, C.; Kadereit, D.; Valacchi, M. Synlett, 1997, 687.
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.
Miki, K.; Sato, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2385.
Ogumi, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.
Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
Itsuno, S.; Frechet, J. M. J. J. Org. Chem. 1987, 52, 4140.
Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927.
Hodges, P;. Sung, D. W. L.; Stratford, P. W. J. Chem. Soc., Perkin Trans. 1, 1999, 2335.
Itsuno, S.; Sakurai, Y.; Ito, K.; Marumaya, T.; Nakahama, S.; Frechet, J. M. J. J. Org. Chem. 1990, 55, 304.
Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832.
Laspéras, M.; Bellocq, N.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1998, 9, 3053.
Bellocq, N.; Abramson, S.; Laspéras, M.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1999, 10, 3229.
Abramson, S.; Bellocq, N.; Laspéras, M. Top. Catal. 2000, 13, 339.
Bellocq, N.; Abramson, S.; Laspéras, M.; Brunei, D.; Moreau, P. Tetrahedron: Asymm. 1999, 10, 3229.
Bae, S. J.; Kim, S-W.; Hyeon T.; Kim, B. M. Chem. Commun. 2000, 31.
Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans 1, 1989, 109.
Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327.
Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233.
Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237.
Brunei, D.; Cauvel, A.; Di Renzo, F.; Fajula, F.; Fubini, B.; Onida, B.; Garrone, E. New J. Chem. 2000, 24, 807.
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.
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.
Lefevre, B.; Gobin, P. F.; Martin, T.; Galarneau, A.; Brunei, D. Materials Research Society 2002, April 1–5.
Abramson, S.; Laspéras, M.; Galarneau, A.; Desplantier-Giscard, D.; Brunei, D. Chem. Commun. 2000, 1773.
Heckel, A.; Seebach, D. Angew. Chem., Int. Engl. Ed. 2000, 39, 163.
Di Renzo, F.; Chiche, B.; Fajula, F.; Viale, S.; Garrone, E. Stud. Surf. Sci. Catal. 1996, 101, 851.
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.
Abramson, S.; Laspéras, M.; Brunei, D. Tetrahedron: Asymm. 2002, 13, 357.
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.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights 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