Metallomicellar supramolecular systems and their applications in catalytic reactions

Coordination Chemistry Reviews

Volumn 253, Issue 17-18, 2009, Pages 2166-2177

  Zhang, Ji ^a   Meng, Xiang Guang ^a   Zeng, Xian Cheng ^a   Yu, Xiao Qi ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Chiral catalysis; Enantioselectivity; Hydrolysis; Kinetic model; Metallomicellar catalysis

Indexed keywords

EID: 67649349597     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2008.11.019     Document Type: Review

References (123)

1. Taşcioǧlu S. Tetrahedron 52 (1996) 11113
2. Stein T.M., and Gellman S.H. J. Am. Chem. Soc. 114 (1992) 3943
3. Vriezema D.M., Aragonès M.C., Elemans J.A.A.W., Cornelissen J.J.L.M., Rowan A.E., and Nolte R.J.M. Chem. Rev. 105 (2005) 1445
4. Fendler J.H., and Fendler E.J. Catalysis in Micellar and Macromolecular Systems (1975), Academic Press, New York
5. Dugas H., and Penny C. Bioorganic Chemistry (1981), Springer-Varlay, New York
6. Fendler J.H. Membrane Mimetic Chemistry (1982), Wiley, New York
7. Fujita T., Inaba Y., Ogino K., and Tagaki W. Bull. Chem. Soc. Jpn. 61 (1988) 1661
8. Fornasier R., Scrimin P., Tecilla P., and Tonellato U. J. Am. Chem. Soc. 111 (1989) 224
9. Breslow R. Acc. Chem. Res. 28 (1995) 146
10. Hampl F., Liska F., Mancin F., Tecilla P., and Tonellato U. Langmuir 15 (1999) 405
11. Mancin F., Tecilla P., and Tonellato U. Langmuir 16 (2000) 227
12. Couderc S., and Toullec J. Langmuir 17 (2001) 3819
13. Tagaki W., Ogino K., Fujita T., Yoshida T., Nishi K., and Inaba Y. Bull. Chem. Soc. Jpn. 66 (1993) 140
14. Tagaki W., Ogino K., Tanaka O., Machiya K., Kashihara N., and Yoshida T. Bull. Chem. Soc. Jpn. 64 (1991) 74
15. Ogino K., Nishi K., Yamamoto H., Yoshida T., and Takagi W. Tetrahedron Lett. 31 (1990) 7023
16. Ogino K., Yoshida T., Yamamoto H., and Takagi W. Chem. Lett. (1992) 1197
17. Ogino K., Kashihara N., Ueda T., Isaka T., Yoshida T., and Tagaki W. Bull. Chem. Soc. Jpn. 65 (1992) 373
18. Ogino K., Inoue K., and Takagi W. Tetrahedron Lett. 33 (1992) 4194
19. Faiver V., Brembilla A., Roizard D., and Lochon P. Tetrahedron Lett. 32 (1991) 193
20. Ogino K., Yamamoto H., Yoshida T., and Tagaki W. J. Chem. Soc., Chem. Commun. (1995) 691
21. Fornasier R., Milani D., Scrimin P., and Tonellato U. Gazz. Chim. Ital. 116 (1986) 55
22. Scrimin P., Tecilla P., and Tonellato U. J. Org. Chem. 56 (1991) 161
23. Fornasier R., Milani D., Scrimin P., and Tonellato U. J. Chem. Soc., Perkin Trans. 2 (1986) 233
24. De Santi G., Scrimin P., and Tonellato U. Tetrahedron Lett. 31 (1990) 4791
25. Scrimin P., Tecilla P., and Tonellato U. J. Org. Chem. 59 (1994) 4194
26. Scrimin P., Tecilla P., and Tonellato U. J. Org. Chem. 59 (1994) 18
27. Weijnen J.G.J., Koudijs A., Schellekens G.A., and Engbersen J.F.J. J. Chem. Soc., Perkin Trans. 2 (1992) 829
28. Weijnen J.G.J., Koudijs A., and Engbersen J.F.J. J. Chem. Soc. Perkin Trans. 2 (1991) 1121
29. Kimura E., Hashimoto H., and Koike T. J. Am. Chem. Soc. 118 (1996) 10963
30. Griffiths P.C., Fallis I.A., Willock D.J., Paul A., Barrie C.L., Griffiths P.M., Williams G.M., King S.M., Heenan R.K., and Görgl R. Chem. Eur. J. 10 (2004) 2022
31. Polyzos A., Hughes A.B., and Christie J.R. Langmuir 23 (2007) 1872
32. Zana R. Adv. Colloid Interface Sci. 97 (2002) 205
33. Menger F.M., and Keiper J.S. Angew. Chem. Int. Ed. 39 (2000) 1906
34. Qiu L.-G., Jiang X., Gu L.-N., and Hu G. J. Mol. Cat. A: Chem. 277 (2007) 15
35. Cleij M.C., Drenth W., and Nolte R.J.M. Recl. Trav. Chim. Pays-Bas 111 (1992) 459
36. Ueoka R., Matsumoto Y., Moss R.A., Swarup S., Sugii A., Harada K., Kikuchi J., and Murakami Y. J. Am. Chem. Soc. 110 (1988) 1588
37. Matsumoto Y., and Ueoka R. J. Org. Chem. 55 (1990) 5797
38. Ihara Y., Asakawa S., Igata K., Matsumoto Y., and Ueoka R. J. Chem. Soc., Perkin Trans. 2 (1991) 543
39. Cleij M.C., Scrimin P., Tecilla P., and Tonellato U. Langmuir 12 (1996) 2956
40. Cleij M.C., Mancin F., Scrimin P., Tecilla P., and Tonellato U. Tetrahedron 53 (1997) 357
41. You J.-S., Yu X.-Q., Li X.-S., Yan Q.-S., and Xie R.-G. Tetrahedron Asym. 9 (1998) 1197
42. You J.-S., Yu X.-Q., Liu K., Tao L., Xiang Q.-X., and Xie R.-G. Tetrahedron Asym. 10 (1999) 243
43. You J.-S., Yu X.-Q., Su X.-Y., Wang T., Xiang Q.-X., Yang M., and Xie R.-G. J. Mol. Catal. A: Chem. 202 (2003) 17
44. Gellman S.H., Petter R., and Breslow R. J. Am. Chem. Soc. 108 (1986) 2388
45. Weijnen J.G.J., and Engbersen J.F.J. Recl. Trav. Chim. Pays-Bas 112 (1993) 351
46. Lim Y.Y., Tan E.H.L., and Gan L.H. J. Colloid Interface Sci. 157 (1993) 442
47. Bunton C.A., Scrimin P., and Tecilla P. J. Chem. Soc., Perkin Trans. 2 (1996) 419
48. Manger F.M., Gan L.H., Jonson E., and Durst D.H. J. Am. Chem. Soc. 109 (1987) 2800
49. Gutsche C.D., and Mei M.C. J. Am. Chem. Soc. 107 (1985) 7964
50. Zeng X.-C., Zhang Y.-Q., Yu X.-Q., and Tian A.-M. Langmuir 15 (1999) 1621
51. Jiang F.-B., Jiang B.-Y., Yu X.-Q., and Zeng X.-C. Langmuir 18 (2002) 6769
52. Menger F.M., and Portnoy C.E. J. Am. Chem. Soc. 89 (1967) 4698
53. Menger F.M. Pure Appl. Chem. 51 (1979) 999
54. Moroi Y. J. Phys. Chem. 84 (1980) 2186
55. Fanti M., Mancin F., Tecilla P., and Tonellato U. Langmuir 16 (2000) 10115
56. Hay R.W., Govan N., and Parchment K.E. Inorg. Chem. Commun. 1 (1998) 228
57. Qiu L.-G., Xie A.-J., and Shen Y.-H. J. Mol. Catal. A Chem. 244 (2006) 58
58. Maria P.D., Fontana A., Gasbarri C., and Siani G. Tetrahedron 61 (2005) 7176
59. Jiang W.-D., Xu B., Li J.-Z., Lin Q., Zeng X.-C., and Chen H. Int. J. Chem. Kinet. 39 (2007) 672
60. Jiang F.-B., Huang L.-Y., Meng X.-G., Du J., Yu X.-Q., Zhao Y.-F., and Zeng X.-C. J. Colloid Interface Sci. 303 (2006) 236
61. Jiang F.-B., Jiang B.-Y., Cao Y.-S., Meng X.-G., Yu X.-Q., and Zeng X.-C. Colloids Surf. A: Physicochem. Eng. Aspects 254 (2005) 91
62. Jiang F.-B., Du J., Yu X.-Q., Bao J.-K., and Zeng X.-C. J. Colloid Interface Sci. 273 (2004) 497
63. Du J., Jiang B.-Y., Kou X.-M., Zeng X.-C., and Xiang Q.-X. J. Colloid Interface Sci. 256 (2002) 428
64. Xiang Y., Jiang B.-Y., Zeng X.-C., and Xie J.-Q. J. Colloid Interface Sci. 247 (2002) 366
65. Cheng S.-Q., Zeng X.-C., Meng X.-G., and Yu X.-Q. J. Colloid Interface Sci. 224 (2000) 333
66. Lindström U.M. Chem. Rev. 102 (2002) 2751
67. Cordes E.H., and Dunlap R.B. Acc. Chem. Res. 2 (1969) 329
68. Oehme G., Paetzold E., and Selke R. J. Mol. Catal. 71 (1992) L1
69. Oehme G., Grassert I., Paetzold E., Fuhrmann H., Dwars T., Schmidt U., and Iovel I. Kinet. Catal. 44 (2003) 766
70. Grassert I., Paetzold E., and Oehme G. Tetrahedron 49 (1993) 6605
71. Oehme G., Grassert I., Paetzold E., Meisel R., Drexler K., and Fuhrmann H. Coord. Chem. Rev. 186 (1999) 585
72. Dwars T., Schmidt U., Fischer C., Grassert I., Kempe R., Fröhlich R., Drauz K.-H., and Oehme G. Angew. Chem. 110 (1998) 3033
73. Dwars T., Schmidt U., Fischer C., Grassert I., Kempe R., Fröhlich R., Drauz K.-H., and Oehme G. Angew. Chem. Int. Ed. Engl. 37 (1998) 2851
74. Yonehare K., Ohe K., and Uemura S. J. Org. Chem. 64 (1999) 9381
75. Selke R., Holz J., Riepe A., and Börner A. Chem. Eur. J. 4 (1998) 769
76. Ludwig M., Kadyrov R., Fiedler H., Haage K., and Selke R. Chem. Eur. J. 7 (2001) 3298
77. Grassert I., and Oehme G. J. Organomet. Chem. 621 (2001) 158
78. Li J., Zhang Y., Han D., Jia G., Gao J., Zhong L., and Li C. Green Chem. 10 (2008) 608
79. Machajewski T.D., and Wong C.-H. Angew. Chem. Int. Ed. 39 (2000) 1352
80. Kobayashi S., and Manabe K. Acc. Chem. Res. 35 (2002) 209
81. Kobayashi S., Wakabayashi T., Nagayama S., and Oyamada H. Tetrehedron Lett. 38 (1997) 4559
82. Kobayashi S., and Wakabayashi T. Tetrahedron Lett. 39 (1998) 5389
83. Manabe K., Mori Y., Wakabayashi T., Nagayama S., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 7202
84. Deleersnyder K., Shi D., Binnemans K., and Parac-Vogt T.N. J. Alloys Compd. 451 (2008) 418
85. Mori Y., Kakumoto K., Manabe K., and Kobayashi S. Tetrahedron Lett. 41 (2000) 3107
86. Manabe K., Aoyama N., and Kobayashi S. Adv. Synth. Catal. 343 (2001) 174
87. Biaggi C., Benaglia M., and Puglisi A. J. Organomet. Chem. 692 (2007) 5795
88. Aoyama N., Manabe K., and Kobayashi S. Chem. Lett. 33 (2004) 312
89. Tian H.-Y., Chen Y.-J., Wang D., Bu Y.-P., and Li C.-J. Tetrahedron Lett. 42 (2001) 1803
90. Mori Y., Manabe K., and Kobayashi S. Angew. Chem., Int. Ed. 40 (2001) 2816
91. Itoh J., Fuchibe K., and Akiyama T. Synthesis (2006) 4075
92. Breslow R., and Rideout D.C. J. Am. Chem. Soc. 102 (1980) 7816
93. Otto S., Engberts J.B.F.N., and Kwak J.C.T. J. Am. Chem. Soc. 120 (1998) 9517
94. van der Wel G.K., Wijnen J.W., and Engberts J.B.F.N. J. Org. Chem. 61 (1996) 9001
95. Wijnen J.W., and Engberts J.B.F.N. Liebigs Ann./Recl (1997) 1085
96. Manabe K., Mori Y., and Kobayashi S. Tetrahedron 55 (1999) 11203
97. Wijnen J.W., and Engberts J.B.F.N. J. Org. Chem. 62 (1997) 2039
98. Otto S., and Engberts J.B.F.N. Surf. Sci. Ser. 100 (2001) 247
99. Diego-Castro M.J., and Hailes H.C. Teterahedron Lett. 39 (1998) 2211
100. Rispens T., and Engberts J.B.F.N. Org. Lett. 3 (2001) 941
101. Boudou M., Ogawa C., and Kobayashi S. Adv. Synth. Catal. 348 (2006) 2585
102. Zhang L., and Wu J. Adv. Synth. Catal. 349 (2007) 1047
103. Ye Y., Ding Q., and Wu J. Tetrahedron 64 (2008) 1378
104. Fuji K., Morimoto T., Tsutsumi K., and Kakiuchi K. Angew. Chem. Int. Ed. 42 (2003) 2409
105. Goedheijt M.S., Hanson B.E., Reek J.N.H., Kamer P.C.J., and Van Leeuwen P.W.N.M. J. Am. Chem. Soc. 122 (2000) 1650
106. Dwars T., Paetzold E., and Oehme G. Angew. Chem. Int. Ed. 44 (2005) 7174
107. Seidel Y.E., Lindström R., Jusys Z., Cai J., Wiedwald U., Ziemann P., and Behm R.J. Langmuir 23 (2007) 5795
108. Veisz B., and Király Z. Langmuir 19 (2003) 4817
109. Danks M.J., Jervis H.B., Nowotny M., Zhou W., and Maschmeyer T.A. Catal. Lett. 82 (2002) 95
110. Kawasaki H., Uota M., Yoshimura T., Fujikawa D., Sakai G., Arakawa R., and Kijima T. Langmuir 23 (2007) 11540
111. Storrs R.W., Tropper F.D., Li H.Y., Song C.K., Kuniyoshi J.K., Sipkins D.A., Li K.C.P., and Bednarski M.D. J. Am. Chem. Soc. 117 (1995) 7301
112. Hashimoto S., and Thomas J.K. J. Phys. Chem. 89 (1985) 2771
113. Watanabe T., and Terabe S. J. Chromatogr. A 880 (2000) 295
114. Serrano J.M., and Silva M. Electrophoresis 28 (2007) 3242
115. Wang Y.-W., Li N.-B., and Luo H.-Q. Luminescence 23 (2008) 126
116. Lasovsky J., Hrbac J., Sichertova1 D., and Bednar P. Luminescence 22 (2007) 501
117. Ambade A.V., Savariar E.N., and Thayumanavan S. Mol. Pharm. 2 (2005) 264
118. Lavasanifar A., Samuel J., and Kwon G.S. J. Biomed. Mater. Res. 52 (2000) 831
119. Bromberg L., and Hatton T.A. Ind. Eng. Chem. Res. 44 (2005) 7991
120. Hafiz A.A. J. Surf. Detergent 8 (2005) 359
121. Hafiz A.A., El Awadi M.Y., Badawi A.M., and Mokhtar S.M. J. Surf. Detergents 8 (2005) 203
122. Martin M., Manea F., Fiammengo R., Prins L.J., Pasquato L., and Scrimin P. J. Am. Chem. Soc. 129 (2007) 6982
123. Riepe A., Beier H., and Gross H.J. FEBS Lett. 457 (1999) 193