Application of Cyclodextrin Derivatives in Metal-Catalyzed Organic Synthesis

doi:10.6023/cjoc1110243

Abstract

The application of cyclodextrin (α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin) derivatives in metal-catalyzed organic synthesis has been reviewed, especially as ligands of metal ion, stabilizers of metal nanoparticles and inverse phase transfer catalysts in oxidation, hydrolysis, reduction, coupling reactions and so on. The cyclodextrin derivatives employed as ligands of metal ion are used most widely in which the formation of inclusion complexes between the cyclodextrin unit and substrate narrows the distance between the substrate and the metal ion, and fixes the reaction site of the substrate. Thus, the reaction rate can be increased obviously, and the regioselectivity and enantioselectivity can be enhanced remarkably.

Key words: cyclodextrin derivatives, metal-catalysis, organic synthesis

Cite this article

Shen Haimin, Ji Hongbing. Application of Cyclodextrin Derivatives in Metal-Catalyzed Organic Synthesis[J]. Chin. J. Org. Chem., 2012, 32(06): 975-985.

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References

[1] Sallas, F.; Darcy, R. Eur. J. Org. Chem. 2008, 957.

[2] Ji, H. B.; Huang, L. Q.; Shi, D. P.; Zhou, X. T. Chin. J. Org. Chem.2008, 28, 2072 (in Chinese).(纪红兵, 黄丽泉, 石东坡, 周贤太, 有机化学, 2008, 28, 2072.)

[3] Engeldinger, E.; Armspach, D.; Matt, D. Chem. Rev. 2003, 103,4147.

[4] Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev.1998, 98, 1977.

[5] An, W.; Zhang, H. C.; Sun, T.; Li, X. J.; Hao, A. Y. Chin. J. Org.Chem. 2011, 31, 275 (in Chinese).(安伟, 张华承, 孙涛, 李祥军, 郝爱友, 有机化学, 2011, 31,275.)

[6] Breslow, R. Acc. Chem. Res. 1995, 28, 146.

[7] Bjerre, J.; Rousseau, C.; Marinescu, L.; Bols, M. Appl. Microbiol.Biotechnol. 2008, 81, 1.

[8] Hu, S. S.; Li, J. Y.; Xiang, J. F.; Pan, J.; Luo, S. Z.; Cheng, J. P. J.Am. Chem. Soc. 2010, 132, 7216.

[9] Shen, H. M.; Ji, H. B. Chin. J. Org. Chem. 2011, 31, 791 (inChinese).(沈海民, 纪红兵, 有机化学, 2011, 31, 791.)

[10] Yang, C.; Mori, T.; Wada, T.; Inoue, Y. New J. Chem. 2007, 31,697.

[11] Ikeda, H.; Nihei, T.; Ueno, A. J. Inclusion Phenom. MacrocylicChem. 2004, 50, 63.

[12] Breslow, R.; Steven, D. D. Chem. Rev. 1998, 98, 1997.

[13] Bellia, F.; La Mendola, D.; Pedone, C.; Rizzarelli, E.; Saviano, M.;Vecchio, G. Chem. Soc. Rev. 2009, 38, 2756.

[14] Woggon, W. D. Curr. Org. Chem. 2010, 14, 1362.

[15] Bricout, H.; Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, E.Sustainability 2009, 1, 924.

[16] Denicourt-Nowicki, A.; Roucoux, A. Curr. Org. Chem. 2010, 14,1266.

[17] Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, E. C. R. Chim. 2011,14, 135.

[18] Hapiot, F.; Leclercq, L.; Azaroual, N.; Fourmentin, S.; Tilloy, S.;Monflier, E. Curr. Org. Synth. 2008, 5, 162.

[19] Bricout, H.; Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, E. Curr.Org. Chem. 2010, 14, 1296.

[20] Ji, H. B. Eur. J. Org. Chem. 2003, 3659.

[21] Ji, H. B.; Shi, D. P.; Shao, M.; Li, Z.; Wang, L. F. Tetrahedron Lett.2005, 46, 2517.

[22] Chen, H. Y.; Ji, H. B. AIChE J. 2010, 56, 466.

[23] Ji, H. B.; Chen, H. Y.; Zhou, X. T.; Wang, L. F. Tetrahedron 2010,66, 9888.

[24] Ji, H. B.; Huang, L. Q.; Shen, H. M.; Zhou, X. T. Chem. Eng. J.2011, 167, 349.

[25] Breslow, R.; Zhang, X.; Xu, R.; Maletic, M.; Merger, R. J. Am.Chem. Soc. 1996, 118, 11678.

[26] Karakhanov, E.; Maximov, A.; Kirillov, A. J. Mol. Catal. A: Chem.2000, 157, 25.

[27] French, R. R.; Holzer, P.; Leuenberger, M. G.; Woggon, W. D.Angew. Chem., Int. Ed. 2000, 39, 1267.

[28] French, R. R.; Holzer, P.; Leuenberger, M.; Nold, M. C.; Woggon,W. D. J. Inorg. Biochem. 2002, 88, 295.

[29] Breslow, R.; Zhang, X.; Huang, Y. J. Am. Chem. Soc. 1997, 119,4535.

[30] Yang, J.; Breslow, R. Angew. Chem., Int. Ed. 2000, 39, 2692.

[31] Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. J.Org. Chem. 2002, 67, 5057.

[32] Breslow, R.; Yan, J. M.; Belvedere, S. Tetrahedron Lett. 2002, 43,363.

[33] Breslow, R.; Yang, J.; Yan, J. M. Tetrahedron 2002, 58, 653.

[34] Bonchio, M.; Carofiglio, T.; Di Furia, F.; Fornasier, R. J. Org.Chem. 1995, 60, 5986.

[35] Sakuraba, H.; Maekawa, H. J. Inclusion Phenom. MacrocyclicChem. 2006, 54, 41.

[36] Bonchio, M.; Carofiglio, T.; Carraro, M.; Fornasier, R.; Tonellato,U. Org. Lett. 2002, 4, 4635.

[37] Kano, K.; Kitagishi, H.; Dagallier, C.; Kodera, M.; Matsuo, T.;Hayashi, T.; Hisaeda, Y.; Hirota, S. Inorg. Chem. 2006, 45, 4448.

[38] Dong, S. D.; Breslow, R. Tetrahedron Lett. 1998, 39, 9343.

[39] Kim, D. H.; Lee, S. S. Bioorg. Med. Chem. 2000, 8, 647.

[40] Barr, L.; Easton, C. J.; Lee, K.; Lincoln, S. F.; Simpson, J. S.Tetrahedron Lett. 2002, 43, 7797.

[41] Li, X. Q.; Liang, K.; Wang, C. Y.; Bai, X. L.; Xu, J. Y.; Shen, J. C.;Liu, J. Q. J. Mol. Catal. A: Chem. 2008, 295, 47.

[42] Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1992, 114, 5882.

[43] Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.

[44] Zhang, B.; Breslow, R. J. Am. Chem. Soc. 1997, 119, 1676.

[45] Jeon, W. B.; Bae, K. H.; Byun, S. M. J. Inorg. Biochem. 1998, 71,163.

[46] Sallas, F.; Marsura, A.; Petot, V.; Pinter, I.; Kovacs, J.; Jicsinszky,L. Helv. Chim. Acta 1998, 81, 632.

[47] Yan, J. M.; Breslow, R. Tetrahedron Lett. 2000, 41, 2059.

[48] Luo, M. M.; Xie, R. G.; Xia, P. F.; Tao, L.; Yuan, D. Q.; Zhao, H.M. J. Phys. Org. Chem. 2001, 14, 515.

[49] Zhou, Y. H.; Zhao, M.; Mao, Z. W.; Ji, L. N. Chem.-Eur. J. 2008,14, 7193.

[50] Zhou, Y. H.; Zhao, M.; Li, J. H.; Mao, Z. W.; Ji, L. N. J. Mol.Catal. A: Chem. 2008, 293, 59.

[51] Zhou, Y. H.; Zhao, M.; Sun, H. Z.; Mao, Z. W.; Ji, L. N. J. Mol.Catal. A: Chem. 2009, 308, 61.

[52] Tang, S. P.; Zhou, Y. H.; Chen, H. Y.; Zhao, C. Y.; Mao, Z. W.; Ji,L. N. Chem.-Asian J. 2009, 4, 1354.

[53] Tang, S. P.; Chen, S.; Wu, G. F.; Chen, H. Y.; Mao, Z. W.; Ji, L. N.Inorg. Chem. Commun. 2011, 14, 184.

[54] Zhao, M.; Wang, H. L.; Zhang, L.; Zhao, C. Y.; Ji, L. N.; Mao, Z.W. Chem. Commun. 2011, 47, 7344.

[55] Nakajima, H.; Sakabe, Y.; Ikeda, H.; Ueno, A. Bioorg. Med. Chem.Lett. 2004, 14, 1783.

[56] Reetz, M. T.; Waldvogel, S. R. Angew. Chem., Int. Ed. 1997, 36,865.

[57] Wong, Y. T.; Yang, C.; Ying, K. C.; Jia, G. C. Organometallics2002, 21, 1782.

[58] Schlatter, A.; Kundu, M. K.; Woggon, W. D. Angew. Chem., Int.Ed. 2004, 43, 6731.

[59] Schlatter, A.; Woggon, W. D. Adv. Synth. Catal. 2008, 350, 995.

[60] Yuan, D. Q.; Lu, J. Z.; Atsumi, M.; Izuka, A.; Kai, M.; Fujita, K.Chem. Commun. 2002, 730.

[61] Yuan, D. Q.; Lu, J.; Atsumi, M.; Yan, J. M.; Kai, M.; Fujita, K.Org. Biomol. Chem. 2007, 5, 2932.

[62] Suresh, P.; Pitchumani, K. J. Org. Chem. 2008, 73, 9121.

[63] Alvarez, J.; Liu, J.; Roman, E.; Kaifer, A. E. Chem. Commun. 2000,1151.

[64] Liu, J.; Alvarez, J.; Ong, W.; Roman, E.; Kaifer, A. E. Langmuir2001, 17, 6762.

[65] Denicourt-Nowicki, A.; Zhang, Y.; Leger, B.; Rolland, J. P.;Bricout, H.; Monflier, E.; Roucoux, A. Chem. Commun. 2006, 296.

[66] Denicourt-Nowicki, A.; Ponchel, A.; Monflier, E.; Roucoux, A.Dalton Trans. 2007, 5714.

[67] Denicourt-Nowicki, A.; Roucoux, A.; Wyrwalski, F.; Kania, N.;Monflier, E.; Ponchel, A. Chem.-Eur. J. 2008, 14, 8090.

[68] Hubert, C.; Denicourt-Nowicki, A.; Roucoux, A.; Landy, D.; Leger,B.; Crowyn, G.; Monflier, E. Chem. Commun. 2009, 1228.

[69] Wyrwalski, F.; Leger, B.; Lancelot, C.; Roucoux, A.; Monflier, E.;Ponchel, A. Appl. Catal., A 2011, 391, 334.

[70] Strimbu, L.; Liu, J.; Kaifer, A. E. Langmuir 2003, 19, 483.

[71] Cassez, A.; Ponchel, A.; Hapiot, F.; Monflier, E. Org. Lett. 2006, 8,4823.

[72] Cassez, A.; Kania, N.; Hapiot, F.; Fourmentin, S.; Monflier, E.;Ponchel, A. Catal. Commun. 2008, 9, 1346.

[73] Senra, J. D.; Malta, L. F. B.; de Souza, A. L. F.; Medeiros, M. E.;Aguiar, L. C. S.; Antunes, O. A. C. Tetrahedron Lett. 2007, 48,8153.

[74] Senra, J. D.; Malta, L. F. B.; Souza, A. L. F.; Aguiar, L. C. S.;Antunes, O. A. C. Adv. Synth. Catal. 2008, 350, 2551.

[75] Senra, J. D.; Malta, L. F. B.; da Costa, M. E. H. M.; Michel, R. C.;Aguiar, L. C. S.; Simas, A. B. C.; Antunes, O. A. C. Adv. Synth.Catal. 2009, 351, 2411.

[76] Tachikawa, T.; Tojo, S.; Fujitsuka, M.; Majima, T. Chem.-Eur. J.2006, 12, 7585.

[77] Matta, R.; Hanna, K.; Kone, T.; Chiron, S. Chem. Eng. J. 2008,144, 453.

[78] Li, X. Q.; Qi, Z. H.; Liang, K.; Bai, X. L.; Xu, J. Y.; Liu, J. Q.;Shen, J. C. Catal. Lett. 2008, 124, 413.

[79] Monflier, E.; Tilloy, S.; Castanet, Y.; Mortreux, A. TetrahedronLett. 1998, 39, 2959.

[80] Tilloy, S.; Bricout, H.; Monflier, E. Green Chem. 2002, 4, 188.

[81] Kirschner, D.; Jaramillo, M.; Green, T.; Hapiot, F.; Leclercq, L.;Bricout, H.; Monflier, E. J. Mol. Catal. A: Chem. 2008, 286, 11.

[82] Legrand, F. X.; Sauthier, M.; Flahaut, C.; Hachani, J.; Elfakir, C.;Fourmentin, S.; Tilloy, S.; Monflier, E. J. Mol. Catal. A: Chem.2009, 303, 72.

[83] Dabbawala, A. A.; Parmar, J. N.; Jasra, R. V.; Bajaj, H. C.;Monflier, E. Catal. Commun. 2009, 10, 1808.

[84] Badi, N.; Guegan, P.; Legrand, F.-X.; Leclercq, L.; Tilloy, S.;Monflier, E. J. Mol. Catal. A: Chem. 2010, 318, 8.

[85] Monflier, E.; Tilloy, S.; Blouet, E.; Barbaux, Y.; Mortreux, A. J.Mol. Catal. A: Chem. 1996, 109, 27.

[86] Tilloy, S.; Bertoux, F.; Mortreux, A.; Monflier, E. Catal. Today1999, 48, 245.

[87] Cabou, J.; Bricout, H.; Hapiot, F.; Monflier, E. Catal. Commun.2004, 5, 265.

[88] Blach, P.; Landy, D.; Fourmentin, S.; Surpateanu, G.; Bricout, H.;Ponchel, A.; Hapiot, F.; Monflier, E. Adv. Synth. Catal. 2005, 347,1301.

[89] Hapiot, F.; Lyskawa, J.; Bricout, H.; Tilloy, S.; Monflier, E. Adv.Synth. Catal. 2004, 346, 83.

[90] Leclercq, L.; Sauthier, M.; Castanet, Y.; Mortreux, A.; Bricout, H.;Monflier, E. Adv. Synth. Catal. 2005, 347, 55.

[91] Leclercq, L.; Bricout, H.; Tilloy, S.; Monflier, E. J. ColloidInterface Sci. 2007, 307, 481.

[92] Monflier, E.; Bricout, H.; Hapiot, F.; Tilloy, S.; Aghmiz, A.;Masdeu-Bulto, A. M. Adv. Synth. Catal. 2004, 346, 425.

[93] Canipelle, M.; Tilloy, S.; Ponchel, A.; Bricout, H.; Monflier, E. J.Inclusion Phenom. Macrocyclic Chem. 2005, 51, 79.

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