Chinese Journal of Organic Chemistry >
Organic Reactions Catalyzed by Cyclodextrin and Its Derivatives
Received date: 2014-09-02
Revised date: 2014-10-19
Online published: 2014-11-05
Supported by
Project supported by the Eastern Scholar, Shanghai Pujiang Program, the Key Subject of Shanghai Municipal Education Commission (No. J50704), and the National Natural Science Foundation of China (Nos. 21102088, 21174081).
Cyclodextrin (CD) and its derivatives catalyzed organic reactions, including asymmetric reactions, show mild conditions with good yield. This review is an overview of recent advances of CD catalyzed reactions, which is organized in the order of the following reaction types: the modified cyclodextrin catalyzed organic reaction, cyclodextrin catalyzed organic reaction of metal ion present, cyclodextrin catalyzed organic reaction without metal ion, and cyclodextrin catalyzed organic reactions in application of asymmetric synthesis and photochemical reactions.
Hong Shibin , Liu Mengyan , Zhang Wei , Deng Wei . Organic Reactions Catalyzed by Cyclodextrin and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(2) : 325 -336 . DOI: 10.6023/cjoc201409001
[1] (a) Yebeutchou, R. M.; Dalcanale, E. J. Am. Chem. Soc. 2009, 131, 2452.
(b) Liu, L.; Guo, Q.-X. J. Inclusion Phenom. Macrocyclic Chem. 2002, 42, 1.
(c) Cheng, P.-F.; Jiao, S.-Y.; Xu, K.-X.; Wang, C.-J. Chin. J. Org. Chem. 2013, 33, 280 (in Chinese). (程鹏飞, 焦书燕, 徐括喜, 王超杰, 有机化学, 2013, 33, 280.)
(d) Zong, Q.-S.; Wu, J.-Y. Chin. J. Org. Chem. 2013, 33, 568 (in Chinese). (宗乾收, 吴建一, 有机化学, 2013, 33, 568.)
(e) Liu, B.-Y.; Jin, Y.-X.; Yu, S.-S.; Qu, F.-Y.; Tan, G.-H. Chin. J. Org. Chem. 2013, 33, 1950 (in Chinese). (粱波颖, 金英学, 于沙沙, 曲凤玉, 谭广慧, 有机化学, 2013, 33, 1950.)
(f) Liu, H.; Huang, Z.-G.; Wen, K.; Jiang, B. Chin. J. Org. Chem. 2014, 34, 316 (in Chinese). (刘华, 黄祚刚, 文珂, 姜标, 有机化学, 2014, 34, 316.)
[2] (a) Kaliappan, R.; Kaanumalle, L. S.; Ramamurthy, V. Chem. Commun. 2005, 4056.
(b) Kaliappan, R.; Ling, Y.; Kaifer, A. E.; Ramamurthy, V. Langmuir 2009, 25, 8982.
[3] (a) Klöck, C.; Dsouza, R. N.; Nau, W. M. Org. Lett. 2009, 11, 2595.
(b) Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938.
(c) Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574.
(d) Yang, C.; Ke, C.; Liang, W.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. J. Am. Chem. Soc. 2011, 133, 13786.
(e) Yi, J.-M.; Xiao, X.; Zhang, Y.-Q.; Xue, S.-F.; Tan, Z.; Zhang, J.-X. Acta Chim. Sinica 2014, 72, 158 (in Chinese). (易君明, 肖欣, 张云黔, 薛赛凤, 陶朱, 张建新, 化学学报, 2014, 72, 158.)
[4] (a) Yuan, Z.; Chen, J.; Zeng, Y.; Li, Y.-Y.; Han, Y.; Li, Y. Org. Biomol. Chem. 2011, 9, 6256.
(b) Yuan, Z.; Zheng, S.; Zeng, Y.; Chen, J.; Han, Y.; Li, Y.; Li, Y. New J. Chem. 2010, 34, 718.
[5] (a) Han, C.; Xu, Z.; Diao, C.-H.; Chen, X.; Liu, J.; Gou, M.-J.; Fan, J. Acta Chim. Sinica 2013, 71, 439 (in Chinese). (韩聪, 徐喆, 刁春华, 陈鑫, 刘靖, 郭敏杰, 樊志, 化学学报, 2013, 71, 439.)
(b) Kong, R.; Shi, D.-J.; Liu, R.-J.; Wu, C.; Ni, P.-H.; Chen, M.-Q. Acta Chim. Sinica 2013, 71, 1540 (in Chinese). (孔蕊, 施冬健, 刘蓉瑾, 吴超, 倪沛红, 陈明清, 化学学报, 2013, 71, 1540.)
(c) Yao, J.-B.; Xu, M.-Y.; Yan, Z.-Q.; Wu, W.-H.; Yang, C. Chin. J. Org. Chem. 2014, 34, 26 (in Chinese). (姚家斌, 徐梦瑜, 严志强, 伍晚花, 杨成, 有机化学, 2014, 34, 26.)
(d) Shen, H.-M.; Wu, H.-K.; Ji, H.-B.; Shi, H.-X. Chin. J. Org. Chem. 2014, 34, 630. (in Chinese) (沈海民, 武宏科, 纪红兵, 史鸿鑫, 有机化学, 2014, 34, 630.)
(e) Shen, H.-M.; Wu, H.-K.; Ji, H.-B.; Shi, H.-X. Chin. J. Org. Chem. 2014, 34, 1549 (in Chinese). (沈海民, 纪红兵, 武宏科, 史鸿鑫, 有机化学, 2014, 34, 1549.)
[6] Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977.
[7] Breslow, R.; Canary, J. W.; Varney, M.; Waddell, S. T.; Yang, D. J. Am. Chem. Soc. 1990, 112, 5212.
[8] Liu, Y.; Zhao, Y.-L.; Chen, Y.; Liang, P.; Li, L. Tetrahedron Lett. 2005, 46, 2507.
[9] (a) Sridhar, R.; Srinivas, B.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D.; Rao, K. R. Can. J. Chem. 2009, 87, 1704.
(b) Kumar, V. P.; Sridhar, R.; Srinivas, B.; Narender, M.; Rao, K. R. Can. J. Chem. 2008, 86, 907.
(c) Srinivas, B.; Kumar, V. P.; Sridhar, R.; Surendra, K.; Nageswar, Y. V. D.; Rao, K. R. J. Mol. Catal. A: Chem. 2007, 261, 1.
(d) Sridhar, R.; Srinivas, B.; Kumar, V. P.; Narender, M.; Rao, K. R. Adv. Synth. Catal. 2007, 349, 1873.
(e) Reddy, M. S.; Narender, M.; Nageswar, Y. V. D.; Rao, K. R. Synth. Commun. 2007, 37, 1983.
(f) Kumar, V. P.; Narender, M.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Synth. Commun. 2007, 37, 4331.
(g) Surendra, K.; Krishnaveni, N. S.; Sridhar, R.; Rao, K. R. Tetrahedron Lett. 2006, 47, 2125.
(h) Surendra, K.; Krishnaveni, N. S.; Rao, K. R. Tetrahedron Lett. 2006, 47, 2133.
(i) Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Adv. Synth. Catal. 2006, 348, 696.
(j) Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Chem. Commun. 2005, 669.
[10] (a) Ramesh, K.; Karnakar, K.; Satish, G.; Anil Kumar, B. S. P.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 6936.
(b) Madhav, B.; Narayana Murthy, S.; Anil Kumar, B. S. P.; Ramesh, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 3835.
(c) Ramesh, K.; Narayana Murthy, S.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 4734.
(d) Ramesh, K.; Karnakar, K.; Satish, G.; Nageswar, Y. V. D. Chin. Chem. Lett. 2012, 23, 1331.
[11] Kumar, A.; Tripathi, V. D.; Kumar, P. Green Chem. 2011, 13, 51.
[12] Shin, J. A.; Lim, Y. G.; Lee, K. H. J. Org. Chem. 2012, 77, 4117.
[13] Ji, H.-B.; Shi, D.-P.; Shao, M.; Li, Z.; Wang, L.-F. Tetrahedron Lett. 2005, 46, 2517.
[14] Patil, D. R.; Wagh, Y. B.; Ingole, P. G.; Singh, K.; Dalal, D. S. New J. Chem. 2013, 37, 3261.
[15] Liberto, N. A.; de Paiva Silva, S.; de Fátima, Â.; Fernandes, S. A. Tetrahedron 2013, 69, 8245.
[16] Breslow, R.; Duggan, P. J.; Light, J. P. J. Am. Chem. Soc. 1992, 114, 3982.
[17] Maksimov, A. L.; Sakharov, D. A.; Filippova, T. Y.; Zhuchkova, A. Y.; Karakhanov, E. A. Ind. Eng. Chem. Res. 2005, 44, 8644.
[18] (a) Hapiot, F.; Bricout, H.; Tilloy, S.; Monflier, E. Eur. J. Inorg. Chem. 2012, 2012, 1571.
(b) Al-Maksoud, W.; Menuel, S.; Jahjah, M.; Monflier, E.; Pinel, C.; Djakovitch, L. Appl. Catal., A 2014, 469, 250.
(c) Six, N.; Guerriero, A.; Landy, D.; Peruzzini, M.; Gonsalvi, L.; Hapiot, F.; Monflier, E. Catal. Sci. Technol. 2011, 1, 1347.
(d) Leger, B.; Menuel, S.; Landy, D.; Blach, J. F.; Monflier, E.; Ponchel, A. Chem. Commun. 2010, 46, 7382.
[19] Guitet, M.; Marcelo, F.; de Beaumais, S. A.; Zhang, Y.; Jiménez-Barbero, J.; Tilloy, S.; Monflier, E.; Ménand, M.; Sollogoub, M. Eur. J. Org. Chem. 2013, 2013, 3691.
[20] Herbois, R.; Noel, S.; Leger, B.; Bai, L.; Roucoux, A.; Monflier, E.; Ponchel, A. Chem. Commun. 2012, 48, 3451.
[21] Tran, D. N.; Legrand, F. X.; Menuel, S.; Bricout, H.; Tilloy, S.; Monflier, E. Chem. Commun. 2012, 48, 753.
[22] Suresh, P.; Pitchumani, K. J. Org. Chem. 2008, 73, 9121.
[23] Azath, I. A.; Suresh, P.; Pitchumani, K. New J. Chem. 2012, 36, 2334.
[24] (a) Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Eur. J. Org. Chem. 2011, 2011, 6656.
(b) Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Org. Biomol. Chem. 2012, 10, 4543.
(c) Kaboudin, B.; Mostafalu, R.; Yokomatsu, T. Green Chem. 2013, 15, 2266.
[25] (a) Jouffroy, M.; Gramage-Doria, R.; Armspach, D.; Sémeril, D.; Oberhauser, W.; Matt, D.; Toupet, L. Angew. Chem., Int. Ed. 2014, 53, 3937.
(b) Jouffroy, M.; Sémeril, D.; Armspach, D.; Matt, D. Eur. J. Org. Chem. 2013, 2013, 6069.
(c) Gramage-Doria, R.; Armspach, D.; Matt, D.; Toupet, L. Dalton Trans 2012, 41, 8786.
[26] Hong S.; Liu M.; Yuan S.; Wang Z.; Shi L.; Deng W. J. Inclusion Phenom. Macrocyclic Chem. 2014, 80, 443.
[27] (a) Zhou, Y.; Pedersen, C. M.; Bols, M. Tetrahedron Lett. 2013, 54, 2458.
(b) Zhou, Y.; Lindbäck, E.; Marinescu, L. G.; Pedersen, C. M.; Bols, M. Eur. J. Org. Chem. 2012, 2012, 4063.
(c) Lindbäck, E.; Zhou, Y.; Pedersen, C. M.; Bols, M. Tetrahedron Lett. 2012, 53, 5023.
[28] (a) Chen, H.; Ji, H. Supramol. Chem. 2014, 1.
(b) Yang, Z.; Ji, H. ACS Sustainable Chem. Eng. 2013, 1, 1172.
(c) Yang, Z.; Zeng, H.; Zhou, X.; Ji, H. Tetrahedron 2012, 68, 5912.
(d) Shen, H.-M.; Ji, H.-B. Tetrahedron Lett. 2012, 53, 3541.
(e) Long, Q.; Ji, H.; Lu, S. Comput. Theor. Chem. 2011, 963, 200.
[29] Azath, I. A.; Puthiaraj, P.; Pitchumani, K. ACS Sustainable Chem. Eng. 2012, 1, 174.
[30] Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2010, 51, 3312.
[31] Hu, S.; Li, J.; Xiang, J.; Pan, J.; Luo, S.; Cheng, J.-P. J. Am. Chem. Soc. 2010, 132, 7216.
[32] Shen, H.-M.; Ji, H.-B. Tetrahedron 2013, 69, 8360.
[33] Guitet, M.; Zhang, P.; Marcelo, F.; Tugny, C.; Jimenez-Barbero, J.; Buriez, O.; Amatore, C.; Mouries-Mansuy, V.; Goddard, J. P.; Fensterbank, L.; Zhang, Y.; Roland, S.; Menand, M.; Sollogoub, M. Angew. Chem., Int. Ed. 2013, 52, 7213.
[34] Kanagaraj, K.; Suresh, P.; Pitchumani, K. Org. Lett. 2010, 12, 4070.
[35] Kanagaraj, K.; Pitchumani, K. J. Org. Chem. 2013, 78, 744.
[36] (a) Herrmann, W.; Wehrle, S.; Wenz, G. Chem. Commun. 1997, 1709.
(b) Rao, K. S. S. P.; Hubig, S. M.; Moorthy, J. N.; Kochi, J. K. J. Org. Chem. 1999, 64, 8098.
(c) Utsuki, T.; Hirayama, F.; Uekama, K. J. Chem. Soc., Perkin Trans. 2 1993, 109.
[37] Brinker, U. H.; Walla, P.; Krois, D.; Arion, V. B. Eur. J. Org. Chem. 2011, 2011, 1249.
[38] Marconi, G.; Mezzina, E.; Manet, I.; Manoli, F.; Zambelli, B.; Monti, S. Photochem. Photobiol. Sci. 2011, 10, 48.
[39] Ikeda, H.; Nihei, T.; Ueno, A. J. Org. Chem. 2005, 70, 1237.
[40] (a) Yang, C.; Wang, Q.; Yamauchi, M.; Yao, J.; Zhou, D.; Nishijima, M.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. Photochem. Photobiol. Sci. 2014, 13, 190.
(b) Fukuhara, G.; Umehara, H.; Higashino, S.; Nishijima, M.; Yang, C.; Mori, T.; Wada, T.; Inoue, Y. Photochem. Photobiol. Sci. 2014, 13, 162.
(c) Liang, W.; Yang, C.; Nishijima, M.; Fukuhara, G.; Mori, T.; Mele, A.; Castiglione, F.; Caldera, F.; Trotta, F.; Inoue, Y. Beilstein J. Org. Chem. 2012, 8, 1305.
(d) Wang, Q.; Yang, C.; Ke, C.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. Chem. Commun. 2011, 47, 6849.
[41] Yang, C.; Ke, C.; Liang, W.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. J. Am. Chem. Soc. 2011, 133, 13786.
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