Chiral synthesis on catalysts immobilized in microporous and mesoporous materials

Catalysis Reviews - Science and Engineering

Volumn 46, Issue 3-4, 2004, Pages 419-492

  Li, Can ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Asymmetric Aldol reaction; Asymmetric Diels Alder reaction; Asymmetric epoxidation; Asymmetric hydrogenation; C C bond formation; Chemical grafting; Chiral catalysis; Confinement; Enantioselectivity; Encapsulating; Heterogeneous asymmetric catalysis; Inorganic organic hybrid; Intercalation; Mesoporous; Microporous; Pore effect; Porous materials; Surface effect; Transition state

Indexed keywords

ENCAPSULATION; GRAFTING (CHEMICAL); HYDROGENATION; INTERCALATION COMPOUNDS; MESOPOROUS MATERIALS; MICROPOROUS MATERIALS; PORE SIZE; SYNTHESIS (CHEMICAL);

ASYMMETRIC ALDOL REACTION; ASYMMETRIC DIELS-ALDER REACTION; ASYMMETRIC EPOXIDATION; CHIRAL CATALYSIS; CONFINEMENT EFFECT; ENANTIOSELECTIVITY; HETEROGENOUS ASYMMETRIC CATALYSIS; INORGANIC-ORGANIC HYBRID; PORE EFFECT; TRANSITION STATE;

CATALYSTS;

EID: 9744268958     PISSN: 01614940     EISSN: None     Source Type: Journal    
DOI: 10.1081/CR-200036734     Document Type: Review

References (158)

1. Stinson, S.C. Chem. Eng. News 2001, 79, 79.
2. Rouhi, A.M. Chem. Eng. News 2003, 81, 45.
3. Rouhi, A.M. Chem. Eng. News 2004, 82, 47.
4. Davis, M.E. Nature 2002, 417, 813.
5. Trong On, D.; Desplantier-Giscard, D.; Danumah, C.; Kaliaguine, S. Appl. Catal. A: Chem. 2003, 253, 545.
6. Thomas, J.M.; Maschmeyer, T.; Johnson, B.F.G.; Shephard, D.S. J. Mol. Catal. A: Chem. 1999, 141, 139.
7. McMorn, P.; Hutchings, G. J. Chem. Soc. Rev. 2004, 33, 108.
8. Song, C.E.; Lee, S. Chem. Rev. 2002, 102, 3495.
9. Bianchini, C.; Barbaro, P. Top. Catal. 2002, 19, 17.
10. Meunier, D.; Piechaczyk, A.; Mallmann, A.; Basset, J.-M. Angew. Chem. Int. Ed. 1999, 38, 3540.
11. Heckel, A.; Seebach, D. Helv. Chim. Acta. 2002, 85, 913.
12. Bigi, F.; Franca, B.; Moroni, L.; Maggi, R.; Sartori, G. J. Chem. Soc. Chem. Commun. 2002, 716.
13. Zhou, X.; Yu, X.; Huang, J.; Li, S.; Li, L.; Che, C. Chem. Commun. 1999, 1789.
14. Kim, G.-J.; Shin, J.-H. Tetrahedron Lett. 1999, 40, 6827.
15. Choudary, B.M.; Kantam, M.L.; Bharathi, B.; Sreekanth, P.; Figueras, F. J. Mol. Catal. A: Chem. 2000, 159, 417.
16. Kim, G-J.; Park, D-W. Catal. Today 2000, 63, 537.
17. Park, D.W.; Choi, S.D.; Choi, S-J.; Lee, C-Y.; Kim, G-J. Catal. Lett. 2002, 78, 145.
18. Kim, G.-J.; Shin, J.-H. Catal. Lett. 1999, 63, 205.
19. Kim, J.-H.; Kim, G.-J. Catal. Lett. 2004, 92, 123.
20. Xiang, S.; Zhang, Y.; Xin, Q.; Li, C. Chem. Commun. 2002, 2696.
21. Choudary, B.M.; Chowdari, N.S.; Kantam, M.L.; Santhi, P.L. Catal. Lett. 2001, 76, 213.
22. Baleizao, C.; Gigante, B.; Sabater, M.J.; Garcia, H.; Corma, A. Appl. Catal. A, 2002, 228, 279.
23. Annis, D.A.; Jacobsen, E.N. J. Am. Chem. Soc. 1999, 121, 4147.
24. Baleizao, C.; Gigante, B.; Garcia, H.; Corma, A. J. Catal. 2003, 215, 207.
25. Baleizao, C.; Gigante, B.; Garcia, H.; Corma, A. J. Catal. 2004, 221, 77.
26. Pini, D.; Mandoli, A.; Orlanddi, S.; Salvadori, P. Tetrahedron: Asymmetry 1999, 10, 3883.
27. Baleizao, C.; Gigante, B.; Das, D.; Alvaro, M.; Garcia, H.; Corma, A. Chem. Commun. 2003, 1860.
28. Vankelecom, I.F.J.; Jacobs, P.A. In Chiral Catalyst Immobilization and Recycling; De Vos, D.E., Ivo, F., Vankelecom, J., Jacobs, P.A., Eds.; Wiley-VCH, 36.
29. Ogunwumi, S.B.; Bein, T. Chem. Commun. 1997, 901.
30. Sabatier, M.J.; Corma, A.; Domenech, A.; Fornes, V.; Garcia, H. Chem. Commun. 1997, 1285.
31. Schulz-Ekloff, G.; Ernst, S. In Preparation of Solid Catalysts; Ertl, G., Knozinger, H., Eds.; Wiley-VCH, 405.
32. Horvath, I.T. In Encyclopedia of Catalysis; Wiley-Interscience, Vol. 4, 178.
33. Zsigmond, Á.; Bogár, K.; Notheisz, F. J. Catal. 2003, 213 103.
34. Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145.
35. Jamis, J.; Anderson, J.R.; Dickson, R.S.; Campi, E.M.; Jackson, W.R.J. Organomet. Chem. 2001, 627, 37.
36. Vankelecom, I.F.J.; Tas, D.; Parton, R.F.; Van de Vyver, V.; Jacobs, P.A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1346.
37. Wolfson, A.; Janssens, S.; Vankelcom, I.; Geresh, S.; Gottlieb, M.; Herkowitz, M. Chem. Commun. 2002, 388.
38. Sakka, S.; Kamiya, K.J. Non-Cryst. Solids 1980, 42, 403.
39. Brinker, C.J.; Scherer, G.W. Sol-Gel Science: the Physics and Chemistry of Sol-Gel Processing; Academic Press: San Diego, 1990.
40. Loy, D.A.; Shea, K.J. Chem. Rev. 1995, 95, 1431.
41. Baney, R.H.; Itoh, M.; Sakakibara, A.; Suzuki, T. Chem. Rev. 1995, 95, 1409.
42. Corriu, R.J.P. Angew. Chem. Int. Ed. 2000, 39, 1376.
43. Adima, A.; Moreau, J.J.E.; Wong Chi Man, M. J. Mater. Chem. 1997, 7, 2331.
44. Adima, A.; Moreau, J.J.E.; Wong Chi Man, M. Chirality 2000, 12 411.
45. Moreau, J.J.E.; Vellutini, L.; Wong Chi Man, M.; Bied, C. J. Am. Chem. Soc. 2001, 123, 1509.
46. Brethon, A.; Moreau, J.J.E.; Wong Chi Man, M. Tetrahedron: Asymmetry 2004, 15, 495.
47. Hesemann, P.; Moreau, J.J.E. Tetrahedron: Asymmetry 2000, 11 2183.
48. Hesemann, P.; Moreau, J.J.E. C.R. Chimie 2003, 6, 199.
49. Bied, C.; Gauthier, D.; Moreau, J.J.E.; Wong Chi Man, M. J. Sol-Gel Sci. Tech. 2001, 20, 313.
50. Inagaki, S.; Guan, S.; Fukushima, Y.; Ohsuna, T.; Terasaki, O. J. Am. Chem. Soc. 1999, 121, 9611.
51. Melde, B.J.; Holland, B.T.; Blanford, C.F.; Stein, A. Chem. Mater. 1999, 11, 3302.
52. Asefa, T.; Maclachlan, M.J.; Coombs, N.; Ozin, G.A. Nature 1999, 402, 867.
53. Baleizão, C.; Gigante, B.; Das, D.; Alvaro, M.; Garcia, H.; Corma, A. J. Catal. 2004, 223, 106.
54. Chin, J.; Lee, S.S.; Lee, K.J.; Park, S.; Kim, D.H. Nature 1999, 401, 254.
55. Rivera, J.M.; Martin, T.; Rebek, J., Jr. Science 1998, 279, 1021.
56. Mallouk, T.E.; Gavin, J.A. Acc. Chem. Res. 1998, 31, 209.
57. Treacy, M.M.; Newsam, J.M. Nature 1988, 332, 249.
58. Gardner, G.B.; Venkataraman, D.; Moore, J.S.; Lee, S. Nature 1995, 374, 792.
59. Abrahams, B.F.; Hoskins, B.F.; Michail, D.M.; Robson, R. Nature 1994 369, 727.
60. Chui, S.S.-Y.; Lo, S.M.-F.; Charmant, I.P.H.; Orpen, A.G.; Williams. I.D.A. Science 1999, 283, 1148.
61. Xiong, R.; You, X.; Abrahams, B.F.; Xue, Z.; Che, C. Angew. Chem. Int. Ed. 2001, 40, 4422.
62. Seo, J.S.; Whang, D.; Lee, H.; Jun, S.I.; Oh, J.; Jeon, Y.J.; Kim, K. Nature 2000, 404, 982.
63. Evans, O.R.; Ngo, H.L.; Lin, W. J. Am. Chem. Soc. 2001, 123, 10395.
64. Hu, A.; Ngo, H.L.; Lin, W. J. Am. Chem. Soc. 2003, 125, 11490.
65. Crocker, M.; Herold, R.H.M.; Buglass, J.G.; Companje, P. J. Catal. 1993, 141, 700.
66. Cao, G.; Garcia, M.E.; Alcala, M.; Burgess, L.F.; Mallouk, T.E. J. Am. Chem. Soc. 1992, 114, 7574.
67. Sento, T.; Shimazu, S.; Ichikuni, N.; Uematsu, T. J. Mol. Catal. A. 1999, 137, 263.
68. Kureshy, R.I.; Khan, N.H.; Abdi, S.H.R.; Ahmad, I.; Singh, S.; Jasra, R.V.J. Catal. 2004, 221, 234.
69. Mazzei, M.; Marconi, W.; Riocci, M. J. Mol. Catal. A. 1980, 9 381.
70. Shimazu, S.; Ro, K.; Sento, T.; Ichikuni, N.; Uematsu, T. J. Mol. Catal. A. 1996, 107, 297.
71. Margalef-Català, R.; Claver, C.; Salagre, P.; Fernández, E. Tetrahedron: Asymmetry 2000, 11, 1469.
72. Fraile, J.M.; García, J.I.; Massam, J.; Mayoral, J.A. J. Mol. Catal. A. 1998, 136, 47.
73. Fraile, J.M.; García, J.I.; Mayoral, J.A.; Tarnai, T.; Harmer, M.A. J. Catal. 1999, 186, 214.
74. Fraile, J.M.; García, J.I.; Harmer, M.A.; Herrerías, C.I.; Mayoral, J.A.; Reiser, O.; Werner, H. J. Mater. Chem. 2002, 12 3290.
75. Fraile, J.M.; García, J.I.; Harmer, M.A.; Herrerías, C.I.; Mayoral, J.A .J. Mol. Catal. A. 2001, 165, 211.
76. Segarra, A.M.; Guirado, F.; Claver, C.; Fernández, E. Tetrahedron: Asymmetry 2003, 14, 1611.
77. Sels, B.F.; Vos, D.E.D.; Jacobs, P.A. Catal. Rev. 2001, 43, 443.
78. Bhattacharjee, S.; Anderson, J.A. Chem. Comm. 2004, 554.
79. Bhattacharjee, S.; Anderson, J.A. Catal. Lett. 2004, 95, 119.
80. Choudary, B.M.; Kavita, B.; Chowdari, N.S.; Sreedhar, B.; Kantam, M.L. Catal. Lett. 2002, 78, 373.
81. Selke, R.; Capka, M. J. Mol. Catal. 1990, 63, 319.
82. Feast, S.; Bethell, D.; Pate, P.C.B.; King, F.; Rochester, C.H.; Siddiqui, M.R.H.; Willock, D.J.; Huchings, G.J.J. Chem. Soc. Chem. Commun. 1995, 2499.
83. Piaggio, P.; McMorn, D.; Murphy, P.; Bethell, D.; Bullman Page, P.C.; Hancock, F.E.; Sly, C.; Kerton, O.J.; Hutchings, G.J. J. Chem. Soc. Perkin 2000, 2, 2008.
84. Tailor, S.; Gullick, J.; McMorn, P.; Bethell, D.; Bullman Page, P.C.; Hancock, F.E.; King, F.; Hutchings, G.J. J. Chem. Soc. Perkin 2001 2, 1714.
85. Wan, Y.; McMorn, P.; Hancock, F.E.; Hutchings, G.J. Catal. Lett. 2003 91, 145.
86. Caplan, N.A.; Hancock, F.E.; Bulman, P.P.C.; Hutchings, G.J. Angew. Chem. Int. Ed. 2004, 43, 1685.
87. Traa, Y.; Murphy, D.M.; Farley, R.D.; Hutchings, G. J. Phys. Chem. Chem. Phys. 2001, 3, 1073.
88. Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765.
89. Shum, W.P.; Cannarsa, M.J. In Chirality in Industry II; Collins, A.N., Shedrake, G.N., Crosby, J., Eds.; John Wiley & Sons: New York, 1996; 363.
90. Choudary, B.M.; Valli, V.L.K.; Prasad, A.D. J. Chem. Soc. Chem. Commun. 1990, 1186.
91. Baiker, A.; Blaser, H.U. In Handbook of Heterogeneous Catalysis; Ertl, G., Knözinger, H., Weitkamp, J., Eds.; VCH: Weinheim, 1997; Vol. 5, 2432.
92. Xiang, S.; Zhang, Y.L.; Xin, Q.; Li, C. Angew Chem. Int. Ed. Engl. 2002, 41 (5), 821-824.
93. Herron, N. Inorg. Chem. 1986, 25, 4714.
94. Gigante, B.; Corma, A.; Garcia, H.; Sabater, M.J. Catal. Lett. 2000 68, 113.
95. Varkey, S.P.; Ratnasamy, P. J. Mol. Catal. A. 1998, 135, 295.
96. Schuster, C.; Mollmann, E.; Tompos, A.; Hölderich, W.F. Catal. Lett. 2001, 74, 69.
97. Dioos, B.M.L.; Jacobs, P.A. Tetrahedron Lett. 2003, 44, 8815.
98. Piaggio, P.; McMorn, P.; Langham, C.; Bathell, D.; Page, P.C.B.; Hancock, F.E.; Hutchings, G.J. New. J. Chem. 1998, 1167.
99. Piaggio, P.; Langham, C.; McMorn, P.; Bathell, D.; Page, P.C.B.; Hancock, F.E.; Sly, C.; Hutchings, G.J. J. Chem. Soc., Perkin Trans. 2000, 2, 143.
100. Kim, G-J.; Kim, S-H. Catal. Lett. 1999, 57, 139.
101. Kim, G.J.; Shin, J.H. Catal. Lett. 1999, 63, 83.
102. Frunza, L.; Kosslick, H.; Landmesser, H.; Hoft, E.; Fricke, R. J. Mol. Catal. A. 1997, 123, 179.
103. Xiang, S.; Zhang, Y.; Xin, Q.; Li, C. Chin. J. Catal. 2002, 23 393.
104. Karandikar, P.; Dhanya, K.C.; Deshpande, S.; Chandwadkar, A.J.; Sivasanker, S.; Agashe, M. Catal. Commun. 2004, 5, 69.
105. Silva, A.R.; Vital, J.; Figueiredo, J.L.; Freire, C.; Castro, B.D. New J. Chem. 2003, 27, 1511.
106. Silva, A.R.; Figueiredo, J.L.; Freire, C.; Castro, B. Microporous Mesoporous Mater. 2004, 68, 83.
107. Choi, S.-D.; Kim, G.-J. Catal. Lett. 2004, 92, 35.
108. Blaser, H.U.; Pugin, B. Chiral Reactions in Heterogeneous Catalysis Plenum: New York, 1995; 33.
109. Sherrington, D.C. Catal. Today 2000, 57, 87.
110. Raynor, S.A.; Thomas, J.M.; Raja, R.; Johnson, B.F.G.; Bell, R.G.; Mantle, M.D. Chem. Commun. 2000, 1925.
111. Jones, M.D.; Raja, R.; Thomas, J.M.; Johnson, B.F.G.; Lewis, D.W.; Rouzaud, J.; Harris, K.D.M. Angew. Chem. Int. Ed. 2003, 42, 4326.
112. Raja, R.; Thomas, J.M.; Jones, M.D.; Johnson, B.F.G.; Vaughan, D.E.W. J. Am. Chem. Soc. 2003, 125, 14982.
113. Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
114. Hu, A.; Ngo, H.L.; Lin, W. Angew. Chem. Int. Ed. 2003, 42, 6000.
115. Liu, P.; Gu, P.; Wang, F.; Tu, Y. Organic Letters 2004, 6, 169.
116. Osawa, T.; Harada, T.; Tai, A. Catal. Today 1997, 37, 465.
117. Osawa, T.; Harada, T.; Tai, A. Abstracts for the Seventh International Symposium on Relations Between Homogeneous and Heterogeneous Catalysis. Tokyo, 1992; 230.
118. Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473.
119. Blaser, H.U.; Jalett, H.P.; Muller, M.; Studer, M. Catal. Today 1997 37, 441.
120. Baiker, A. J. Mol. Catal. A: Chem. 2000, 163, 205 and refs cited therein.
121. Blaser, H.U.; Jalett, H.P.; Lottenbach, W.; Studer, M. J. Am. Chem. Soc. 2000, 122, 12675.
122. Studer, M.; Blaser, H.U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45.
123. Balazsika, K.; Toroka, B.; Szakonyic, G.; Bartok, M. Appl. Catal. A: General 1999, 182, 53.
124. Mastalir, Á.; Szöllösi, G.; Király, Z.; Rá zga, Z. Appl. Clay Sci., 2002, 22, 9.
125. Hall, T.J.; Halder, J.E.; Hutchings, G.J.; Jenkins, R.L.; Johnston, P.; McMorn, P.; Wells, P.B.; Wells, R.P.K. Top. Catal. 2000, 11 /12 351.
126. Böhmer, U.; Franke, F.; Morgenschweis, K.; Bieber, T.; Reschetilowski, W. Catal. Today 2000, 60, 167.
127. Síýpos, É.; Fogassy, G.; Tungler, A.; Samant, P.V.; Figueiredo, J.L. J. Mol. Catal. A: Chem. 2004, 212, 245.
128. Síýpos, É.; Tungler, A.; Bitter, I. React. Kinet. Catal. Lett. 2003, 79, 101.
129. Soai, K.; Watanabe, M.; Yammoto, A. J. Org. Chem. 1990, 55, 4832.
130. Lasperas, M.; Bellocq, N.; Brunel, D.; Moreau, P. Tetrahedron: Asymmetry 1998, 9, 3053.
131. Bellocq, N.; Abramson, S.; Lasperas, M.; Brunel, D.; Moreau, P. Tetrahedron: Asymmetry 1999, 10, 3229.
132. Abramson, S.; Lasperas, M.; Galamear, A.; Desplantier-Giscard, D.; Brun, D. Chem. Commun. 2000, 1773.
133. Bae, S.J.; Kim, S.W.; Hyeon, T.; Kim, B. Chem. Commun. 2000, 31.
134. Heckel, A.; Seebach, D. Angew. Chem. Int. Ed. 2000, 39, 163.
135. Corma, A.; Iborra, S.; Roddriguez, I.; Iglesias, M.; Sanchez, F. Catal. Lett. 2002, 82, 237.
136. Corma, A.; Iglesias, M.; Martin, M.V.; Rubio, J.; Sanchez, F. Tetrahedron: Asymmetry 1992, 3, 845.
137. Beadham, I.; Dhar, D.; Chandrasekaran, S. Proc. Indian Acad. Sci. (Chem. Sci.), 2003, 115, 365.
138. Rechavi, D.; Lemaire, M. Org. Lett. 2001, 3, 2493.
139. Evans, D.A.; Burgey, C.S.; Paras, N.A.; Vojkovsky, T.; Tregaly, S.W. J. Am. Chem. Soc. 1998, 120, 5824.
140. Corma, A.; Garcia, H.; Moussaif, A.; Sabater, M.J.; Zzniber, R.; Redouane, A. Chem. Commun. 2002, 1058.
141. Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051.
142. Shibahara, F.; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 125, 8555.
143. Coronado, J.M.; Coloma, F.; Anderson, J.A. J. Mol. Catal. A: Chem. 2000, 154, 143.
144. Li, C.; et al. unpublished results.
145. Köckritz, A.; Bischoff, S.; Morawsky, V.; Prüße, U.; Vodop, K-D. J. Mol. Catal. A. 2002, 180, 231.
146. Fuerte, A.; Iglesias, M.; Sánchez, F. J. Organometallic Chem. 1999 588, 186.
147. Fan, Q.-H.; Li, Y.-M.; Chan, S.C. Chem. Rev. 2002, 102, 3385.
148. North, M. Synlett 1993, 11, 807.
149. Belekon, Y.N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617.
150. Belekon, Y.N.; Green, B.; Ikonnikov, N.S.; North, M.; Parsons, T.; Tararov, V.I. Tetrahedron 2001, 57, 771.
151. Baleizao, C.; Gigante, B.; Garcia, H.; Corma, A. J. Catal. 2003, 215, 199.
152. Hultman, H.M.; de Lang, M.; Nowotny, M.; Arends, I.W.C.E.; Hanefeld, U.; Sheldon, R.A.; Maschmeyer, T. J. Catal. 2003, 217, 264.
153. Hultman, H.M.; de Lang, M.; Arends, I.W.C.E.; Hanefeld, U.; Sheldon, R.A.; Maschmeyer, T. J. Catal. 2003, 217, 275.
154. Corma, A.; Iglesias, M.; del Pino, C.; Sanchez, F. J. Organomet. Chem. 1992, 431, 233.
155. Raja, R.; Thomas, J.M. J. Mol. Catal. A: Chem. 2002, 181, 3.
156. Blackmond, D.G. Cattech 1998, 3, 17.
157. Zhang, H.; Li, C. unpublished results.
158. Ishihara, K.; Yamamoto, H. Cattech 1997, 1, 51.