Advances of Immobilization of Catalysts for Cyclopropanation

Abstract

Recent advances of immobilization of catalysts for cyclopropanation are reviewed in this paper. The catalysts including achiral andchiral complexes comprise Schiff base copper, chrial ruthenium porphyrin, rhodium pyrrolidone-carboxylate, metal pyrrolidine, metal bis(oxazoline), and chrial disulfoamide. The application of ionic liquid and FBS strategy in this area is alsodiscussed.

Key words: cyclopropanation, immobilization, ligand, ionic liquid, FBS strategy

Cite this article

BIAN, Qing-Hua, QIAO, Zhen, HOU, Shi-Cong, WANG, Xian, WANG, Min. Advances of Immobilization of Catalysts for Cyclopropanation[J]. Chinese Journal of Organic Chemistry, 2004, 24(7): 831-841.

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1 Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
2 Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
3 Tomlin, C. D. S. The Pesticide Manual, 11th ed., The British Crop Protection Council, Surrey, 1997, p. 1056.
4 Aratani, T. Pure Appl. Chem. 1985, 57, 1839.
5 Liu, X.; Liu, Y.; Li, X. H.; Xiang, S.; Zhang, Y. L.; Ying, P. L.; Wei, Z. B.; Li, C. Appl. Catal. A: Gen. 2003, 239, 279.
6 (a) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
(b) Singh, V. K.; DattaGupta, A.; Sekar, G. Synthesis 1997, 137.
(c) Xu, M.-H.; Lin, G.-Q. Chin. J. Org. Chem. 2000, 20(4), 475 (in Chinese).
(徐明华, 林国强, 有机化学, 2000, 20(4), 475.)
(d) Yao, X.-Q.; Chen, H.-L.; Zheng, Z. Progress Chem. 2000, 12(3), 282 (in Chinese).
(姚小泉, 陈惠麟, 郑卓, 化学进展, 2000, 12(3), 282.)
(e) Xu, Y.; You, T.-B.; Wang, Z.-Y. Chem. Reag. 1999, 21(6), 347 (in Chinese).
(许毓, 尤田耙, 王忠义, 化学试剂, 1999, 21(6), 347.)
(f) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98,911.
(g) Tye, H. J. Chem. Soc., Perkin Trans. 1 2000,275.
7 Redlich, M.; Mahmood, S. J.; Mayer, M. F.; Hossain M. M.Synth. Commun. 2000, 30, 1401.
8 Díaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.;Pérez,P. J. Organmetallics 2000, 19, 285.
9 Díaz-Requejo, M. M ; Pérez, P. J. J. Organomet. Chem. 2001, 617～618, 110.
10 Kantam, M. L.; Haritha, Y.; Reddy, N. M.; Choudary, B. M.; Figueras, F. Catal. Lett. 2002, 83, 187.
11 Leadbeater, N. E.; Scott, K. A.; Scott, L. J. J. Org. Chem.2000, 65, 3231.
12 Bergbreiter, D. E.; Morvant, M.; Chen, B. Tetrahedron Lett.1991, 32, 2731.
13 Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans.1999, 2133.
14 Yang, F.; Zhang, Y.-M.; Qiu, W.-W.; Tang, J.; He, M.-Y. Chin. J. Chem. 2002, 20, 114.
15 Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
16 Endres, A.; Maas, G. Tetrahedron Lett. 1999, 40, 6365.
17 Endres, A.; Maas, G. Tetrahedron 2002, 58, 3999.
18 Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
19 Sun, W.; Xia, C.-G.; Wang, A.-Q. Acta Chim. Sinica 2002, 60(1), 162 (in Chinese).
(孙伟, 夏春谷, 王爱勤, 化学学报, 2002, 60(1), 162.)
20 Sun, W.; Xia, C.-G.; Wang, A.-Q. New J. Chem. 2002, 26, 755.
21 Wang, H.-W.; Sun, W.; Xia, C.-G.; Xu, L.-W.; Li, F.-W. Chin. J. Mol. Catal. 2003, 17(1), 1 (in Chinese).
(王红旺, 孙伟, 夏春谷, 徐利文, 李福伟, 分子催化, 2003, 17(1), 1.)
22 Wang, H.-W.; Sun, W.; Xia, C.-G. J. Mol. Catal. A: Chem.2003, 206, 199.
23 Franeukron M.; Berkessed, A. Tetrahedron Lett. 1997, 38, 7175.
24 Zhang, J.-L.; Liu, Y.- L.; Che, C.-M. Chem. Commun. 2002, 2906.
25 Zhang, J.-L.; Che, C.-M. Org. Lett. 2002, 4, 1911.
26 Doyle, M. P.; Brandes, B. D.; Kazala, A. P.; Pieters, R. J.; Jarstfer, M. B.; Watkins, L. M.; Eagle, C. T. Tetrahedron Lett. 1990, 31, 6613.
27 Doyle, M. P.; Eismont, M. Y.; Bergbreiter, D. E.; Gray, H. N. J. Org. Chem. 1992, 57, 6103.
28 Doyle, M. P.; Timmons, D. J.; Tumonis, J. S.; Gau, H. M.; Blossey, E. C. Organometallics 2002, 21, 1747.
29 Doyle, M. P.; Zhou, Q. L.; Simonsen, S. H.; Lynch, V. Synlett 1996, 697.
30 Doyle, M. P.; Yan, M. Org. Lett. 2003, 5, 561.
31 Carmona, A.; Corma, A.; Iglesias, M.; José, A. S.; Sánchez, F.J. Organomet. Chem. 1995, 492, 11.
32 Alcón, M. J.; Corma, A.; Iglesias, M.; Sánchez, F. J. Mol.Catal. A: Chem. 1999, 144, 337.
33 Alcón, M. J.; Corma, A.; Iglesias, M.; Sánchez, F. J. Organomet. Chem. 2002, 655, 134.
34 Nagashima, T.; Davies, M. L. Org. Lett. 2002, 4, 1989.
35 Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. 1998, 37, 510.
36 Denmark, S.; Christenson, B.; Coe, D.; Connor, S. O. Tetrahedron Lett. 1995, 36, 2215.
37 Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett.1990, 31, 6005.
38 Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
39 Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
40 Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S. B.; Itoh, K.J. Am. Chem. Soc. 1994, 116, 2223.
41 Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verdugo,E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, J.A. Org. Lett. 2002, 4, 3927.
42 Iwasa, S.; Tsushima, S.; Nishiyama, K.; Tsuchiya, Y.; Takezawa, F.; Nishiyama, H. Tetrahedron:Asymmetry 2003, 14,855.
43 Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
44 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.
45 Fraile, J. M.; García, J. I.; Mayoral, J. A.; Tarnai, T. Tetranhedron: Asymmetry 1997, 8, 2089.
46 Fraile, J. M.; García, J. I.; Mayoral, J. A.; Tarnai, T. Tetranhedron: Asymmetry 1998, 9, 3997.
47 Alonso, P. J.; Fraile, J. M.; García, J.; García, J. I.; Martínez, J. I.; Mayoral, J. A.; Sánchez, M. C. Langmuir 2000,16, 5607.
48 Fernández, A. I.; Fraile, J. M.; García, J. I.; Herrerías, C.I.; Mayoral, J. A.; Salvatella, L. Catal. Commun. 2001, 2, 165.
49 Fraile, J. M.; García, J. I.; Mayoral, J. A.; Tarnai, T.; Harmer, M. A. J. Catal. 1999, 186, 214.
50 Fernández, M. J.; Fraile, J. M.; García, J. I.; Mayoral, J. A.; Burguete, M. I.; García- Verdugo, E.; Luis, S. V.; Harmer, M. A. Top. Catal. 2000, 13, 303.
51 Clarke, R. J.; Shannon, I. J. Chem. Commun. 2001,1936.
52 Burguete, M. I.; Fraile, J. M.; García, J. I.; García-Verdugo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, J. A. J. Org. Chem. 2001, 66, 8893.
53 Mandoli, A.; Orlandi, S.; Pini, D.; Salvadori, P. Chem. Commun. 2003, 2466.
54 Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo,M. J. Org. Chem. 2001, 66, 3160.
55 Burguete, M. I.; Fraile, J. M.; García, J. I.; García-Verdugo, E.; Luis, S. V.; Mayoral, J. A. Org. Lett. 2000, 2, 3905.
56 Burguete, M. I.; Díez-Barra, E.; Fraile, J. M.; García, J. I.; García-Verdugo E., González, R.; Herrerías, C. I.; Luis, S. V.; Mayoral J. A. Bioorg. Med. Chem. Lett. 2002, 12, 1821.
57 Díez-Barra, E.; Fraile, J. M.; García, J. I.; García-Verdugo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral J. A.; Sánchez-Verdú, P.;Tolosa, J. Tetrahedron: Asymmetry 2003, 14, 773.
58 Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, J. A.; Carrié, D.; Vaultier, M. Tetrahedron: Asymmetry 2001, 12, 1891.

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