亚胺的不对称催化氢化研究进展

doi:10.6023/cjoc201211036

摘要/Abstract

手性胺化合物是重要的有机合成中间体, 在农药、医药及精细化学品合成中有着广泛的应用, 而通过亚胺的不对称催化氢化是获得手性胺化合物最直接、最高效的方法之一. 近二十年来, 亚胺的不对称催化氢化取得了重大进展. 各种高活性、高立体选择性的手性配体和催化剂被设计并合成出来, 各种新的不对称催化方法和策略被发展并得到成功应用, 各种特殊及挑战性亚胺底物的氢化取得重要突破. 然而亚胺的不对称催化氢化反应依然存在着诸如反应活性低、底物范围窄、反应条件苛刻、催化剂不易回收等问题. 因此, 发展更加高效、高选择性、环境友好的不对称氢化方法, 是未来亚胺的不对称催化氢化发展的方向. 从亚胺的类型入手, 就环状和非环状的亚胺的不对称催化氢化反应的研究进展进行综述.

关键词: 亚胺, 不对称催化, 氢化, 手性配体

Chiral amines are important synthetic intermediates in the preparation of many physiologically active compounds. Catalytic asymmetric hydrogenation of prochiral imines represents one of the most direct and convenient route to chiral amines and their derivatives. During the past two decades, significant progress has been made in the asymmetric hydrogenation of imines. Many highly enantioselective chiral catalysts have been disclosed, some new methods and strategies have been developed, and some challenging imines substrates have been efficiently hydrogenated in high enantioselectivities. Despite these achievements, catalytic asymmetric hydrogenation of imines still have challenges of low reactivity, narrow substrate scope, harsh hydrogenation conditions and difficulty in catalyst reuse. Therefore, development of new catalyst system with high reactivity and enantioselectivity as well as environmental friendship in the asymmetric hydrogenation of imines is of great interest. This review presents a brief overview on the progress in catalytic asymmetric hydrogenation of cyclic and acyclic imines.

Key words: imines, asymmetric catalysis, hydrogenation, chiral ligand

引用此文

王东, 侯传金, 陈丽凤, 刘小宁, 安庆大, 胡向平. 亚胺的不对称催化氢化研究进展[J]. 有机化学, 2013, 33(07): 1355-1368.

Wang Dong, Hou Chuanjin, Chen Lifeng, Liu Xiaoning, An Qingda, Hu Xiangping. Progress on the Catalytic Asymmetric Hydrogenation of Imines[J]. Chin. J. Org. Chem., 2013, 33(07): 1355-1368.

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参考文献

[1] Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications, Wiley-VCH, Weinheim, 2010.
[2] (a) Blaser, H.-U.; Spinder, F. In Comprehensive Asymmetric Catalysis, Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, Berlin, 1999, p. 248. (b) Spinder, F.; Blaser, H.-U. In The Handbook of Homogeneous Hydrogenation, Eds.: de Vries, J. G.; Elsevier, C. J., Wiley-VCH, Weinheim, 2007, p. 1193. (c) Claver, C.; Femández, E. In Morden Reduction Methods, Eds.: Andersson, P. G.; Munslow, I. J., Wiley-VCH, Weinheim, 2008, p. 237.
[3] Levi, A.; Modena, G.; Scorrano, G. J. Chem. Soc., Chem. Commun. 1975, 6.
[4] (a) Bakos, J.; Heil, B.; Lecomte, L.; Sinou, D. In 5th IUPAC Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS-V), Florence, Italy, 1989, pp. 1～36. (b) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sino, D. J. Chem. Soc., Chem. Commun. 1991, 1684.
[5] (a) Blaser, H.-U.; Buser, H.-P.; Loers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Spindler, F.; Wagmann, A. Chimia 1999, 53, 275. (b) Blaser, H.-U.; Malan, C.; Pugin, B.; Spinder, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
[6] Willoughbly, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562.
[7] Schbider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. M.; Kruger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
[8] Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425.
[9] (a) He, Y.-M.; Fan, Q.-H. Org. Biomol. Chem. 2010, 8, 2497. (b) Wang, C.; Villa-Marcos, B.; Xiao, J. Chem. Commun. 2011, 47, 9773.
[10] (a) Liu, P.; Jiang, H. Chin. J. Org. Chem. 2004, 24, 1317 (in Chinese). (刘鹏, 江焕峰, 有机化学, 2004, 24, 1317.) (b) Zhang, J.; Yang, D.; Long, Y. Chin. J. Org. Chem. 2009, 29, 835 (in Chinese). (张俊芳, 杨定乔, 龙玉华, 有机化学, 2009, 29, 835.) (c) Fleury-Bregeot, N.; de la Fuente, V.; Castillon, S.; Claver, C. ChemCatChem 2010, 2, 1346. (d) Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753. (e) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713. (f) Xie, J.; Zhou, Q. Acta. Chim. Sinica 2012, 70, 1427 (in Chinese). (谢建华, 周其林, 化学学报, 2012, 70, 1427.)
[11] (a) Noyori, R.; Hashigughi, S. Acc. Chem. Res. 1997, 30, 97. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045. (c) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226. (d) You, S.-L. Chem. Asian J. 2007, 2, 820. (e) Wang, C.; Wu, X.; Xiao, J. Chem. Asian J. 2008, 3, 1750. (f) Wang, Z.; Jiang, Z. Asian J. Chem. 2010, 22, 4141.
[12] (a) Carpentier, J.-F.; Bette, V. Curr. Org. Chem. 2002, 6, 913. (b) Riant, O.; Mostefa?, N.; Courmarcel, J. Synthesis 2004, 2943. (c) Díez-González, S.; Nolan, S. P. Org. Prep. Proced. Int. 2007, 39, 523. (d) Arena, C. G. Mini-Rev. Org. Chem. 2009, 6, 159.
[13] (a) Baeza, A; Pfaltz, A. Chem. Eur. J. 2010, 16, 4003. (b) Franzke, A.; Voss, F.; Pfaltz, A. Tetrahedron 2011, 67, 4358.
[14] Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc. 1999, 121, 6421.
[15] Solinas, M.; Pfaltz, A.; Cozzi, P. G.; Leitner, W. J. Am. Chem. Soc. 2004, 126, 16142.
[16] Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402.
[17] Cozzi, P. G.; Menges, F.; Kaise, S. Synlett 2003, 833.
[18] Blanc, C.; Agbossou-Niedercorn, F.; Nowogrocki, G. Tetrahedron: Asymmetry 2004, 15, 2159.
[19] (a) Trifonova, A.; Diesen, J. S.; Chapman, C. J.; Andersson, P. G. Org. Lett. 2004, 6, 3825. (b) Trifonova, A.; Diesen, J. S.; Andersson, P. G. Chem. Eur. J. 2006, 12, 2318.
[20] Zhu, S.-F.; Xie, J.-B.; Zhang, Y.-Z.; Li, S.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 12886.
[21] (a) Han, Z.; Wang, Z.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2009, 48, 5345. (b) Liu, Y.; Wang, Z.; Ding, K. Acta. Chim. Sinica 2012, 70, 1464-1470 (in Chinese). (刘龑, 王正, 丁奎岭, 化学学报, 2012, 70, 1464.)
[22] Réthoré, C.; Riobé, F.; Fourmigué, M.; Avarvari, N.; Suisse, I.; Agbossou-Niedercorn, F. Tetrahedron: Asymmetry 2007, 18, 1877.
[23] Yao, D.; Tian, F.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 505 (in Chinese). (姚冬梅, 田丰涛, 张万斌, 有机化学, 2011, 31, 505.)
[24] Moessner, C.; Bolm, C. Angew. Chem. Int. Ed. 2005, 44, 7564.
[25] Cheemala, M. N.; Knochel, P. Org. Lett. 2007, 9, 3089.
[26] Kutlescha, K.; Irrgang, T.; Kempe, R. Adv. Synth. Catal. 2010, 352, 3126.
[27] Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
[28] Dervisi, A.; Carcedo, C.; Ooi, L. Adv. Synth. Catal. 2006, 348, 175.
[29] Vargas, S.; Rubio, M.; Suárez, A.; Pizzano, A. Tetrahedron Lett. 2005, 46, 2049.
[30] Vargas, S.; Rubio, M.; Suárez, A.; del Río, D.; Álvarez, E.; Pizzano, A. Organometallics 2006, 25, 961.
[31] Zhou, X.-Y.; Bao, M.; Zhou, Y.-G. Adv. Synth. Catal. 2011, 353, 84.
[32] Guiu, E.; Muñoz, B.; Castillón, S.; Claver, C. Adv. Synth. Catal. 2003, 345, 169.
[33] Guiu, E.; Aghmiz, M.; Díaz, Y.; Claver, C.; Meseguer, B.; Militzer, C.; Castillón, S. Eur. J. Org. Chem. 2006, 627.
[34] (a) Li, G.; Liang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 5830. (b) Kang, Q.; Zhao, Z.-A.; You, S.-L. Adv. Synth. Catal. 2007, 349, 1657. (c) Kang, Q.; Zhao, Z.-A.; You, S.-L. Org. Lett. 2008, 10, 2031.
[35] Abe, H.; Amii, H.; Uneyama, K. Org. Lett. 2001, 3, 313.
[36] Chang, G.; Yang, Q.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 6360.
[37] Chen, M.-W.; Duan, Y.; Chen, Q.-A.; Wang, D.-S.; Yu, C.-B.; Zhou, Y.-G. Org. Lett. 2010, 12, 5075.
[38] (a) Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 17. (b) Pugin, B.; Landert, H.; Spindler, F.; Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 974. (c) Dorta, R.; Broggini, D.; Stoop, R.; Rüegger, H.; Spindler, F.; Togni, A. Chem. Eur. J. 2004, 10, 267. (d) Dorta, R.; Broggini, D.; Kissner, R.; Togni, A. Chem. Eur. J. 2004, 10, 4546. (e) Blaser, H.-U.; Pugin, B.; Spindler, F.; Thommen, M. Acc. Chem. Res. 2007, 40, 1240.
[39] (a) Chan, Y. N. C.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400. (b) Sablong, R.; Osborn, J. A. Tetrahedron: Asymmetry 1996, 7, 3059. (c) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. M.; Kruger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887. (d) Blaser, H.-U.; Buser, H.-P.; Hausel, R.; Jalett, H.-P.; Spindler, F. J. Organomet. Chem. 2001, 621, 34.
[40] Hou, C.-J.; Wang, Y.-H.; Zheng, Z.; Xu, J.; Hu, X.-P. Org. Lett. 2012, 14, 3554.
[41] Imamoto, T.; Iwadate, N.; Yoshida, K. Org. Lett. 2006, 8, 2289.
[42] Li, W.; Hou, G.; Chang, M.; Zhang, X. Adv. Synth. Catal. 2009, 351, 3123.
[43] (a) Kitamura, M.; Noyori, R. In Ruthenium in Organic Synthesis, Ed.: Murahashi, S.-I., Wiley-VCH, Weinheim, 2004, Chapter 2. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
[44] Arai, N.; Utsumi, N.; Matsumoto, Y.; Murata, K.; Tsutsumi, K.; Ohkuma, T. Adv. Synth. Catal. 2012, 354, 2089.
[45] Mršić, N.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Am. Chem. Soc. 2009, 131, 8358.
[46] Lyubimov, S. E.; Rastorguev, E. A.; Petrovskii, P. V.; Kelbysheva, E. S.; Loim, N. M.; Davankov, V. A. Tetrahedron Lett. 2011, 52, 1395.
[47] Li, C.; Wang, C.; Villa-Marcos, B.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 14450.
[48] Zhou, S.; Fleischer, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 5120.
[49] Werkmeister, S.; Fleischer, S.; Junge, K.; Beller, M. Chem. Asian J. 2012, 7, 2562.
[50] Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475.
[51] Ghattas, G.; Chen, D.; Pan, F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026.
[52] Lensink, C.; de Vries, J. G. Tetrahedron: Asymmetry 1992, 3, 235.
[53] Margalef-Català, R.; Claver, C.; Salagre, P.; Fernández, E. Tetrahedron: Asymmetry 2000, 11, 1469.
[54] Jiang, X.-B.; Minnaard, A. J.; Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de Vries, J. G. Org. Lett. 2003, 5, 1503.
[55] Reetz, M. T.; Bondarev, O. Angew. Chem., Int. Ed. 2007, 46, 4523.
[56] Ringwald, M.; Stürmer, R.; Bringzinger, H. H. J. Am. Chem. Soc. 1999, 111, 1524.
[57] Shirai, S.; Nara, H.; Kayaki, Y.; Ikariya, T. Organometallics 2009, 28, 802.
[58] (a) Chen, F.; Wang, T.; He, Y.; Ding, Z.; Li, Z.; Xu, L.; Fan, Q.-H. Chem. Eur. J. 2011, 17, 1109. (b) Chen, F.; Ding, Z.; He, Y.; Qin, J.; Wang, T.; Fan, Q.-H. Tetrahedron 2012, 68, 5248.
[59] Burk, M.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
[60] Charette, A. B.; Giroux, A. Tetrahedron Lett. 1996, 37, 6669.
[61] Yang, Q.; Shang, G.; Gao, W.; Deng, J.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 3832.
[62] Wang, Y.-Q.; Zhou, Y.-G. Synlett 2006, 1189.
[63] Yu, Z.; Jin, W.; Jiang, Q. Angew. Chem., Int. Ed. 2012, 51, 6060.
[64] Hou, G.; Gosselin, F.; Li, W.; Mcwillams, J. C.; Sun, Y.; Weisel, M.; O'shea, P. D.; Chen, C.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882.
[65] Hou, G.; Tao, R.; Sun, Y.; Zhang, X.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124.
[66] (a) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Chin. J. Org. Chem. 2006, 25, 634 (in Chinese). (卢胜梅, 韩秀文, 周永贵, 有机化学, 2006, 25, 634.) (b) Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357. (c) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
[67] (a) Willoughby, C. A.; Buchwald, S. L. J. Org. Chem. 1993, 58, 7627. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703.
[68] Chang, M.; Li, W.; Hou, G.; Zhang, X. Adv. Synth. Catal. 2010, 352, 3121.
[69] Chen, F.; Ding, Z.; Qin, J.; Wang, T.; He, Y.; Fan, Q.-H. Org. Lett. 2011, 13, 4348.
[70] Morimoto, T.; Nakajima, N.; Achiwa, K. Synlett 1995, 748.
[71] Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415.
[72] Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 2661.
[73] Li, C.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 13208.
[74] Xie, J.-H.; Yan, P.-C.; Zhang, Q.-Q.; Yuan, K.-X.; Zhou, Q.-L. ACS Catal. 2012, 2, 561.
[75] Chang, M.; Li, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 10679.
[76] Berhal, F.; Wu, Z.; Zhang, Z.; Ayad, T.; Ratovelomanana-Vidal, V. Org. Lett. 2012, 14, 3308.
[77] (a) Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432. (b) Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442.
[78] Gao, K.; Yu, C.-B.; Wang, D.-S.; Zhou, Y.-G. Adv. Synth. Catal. 2012, 354, 483.
[79] Hu, J.; Wang, D.; Zheng, Z.; Hu, X. Chin. J. Chem. 2012, 30, 2664.
[80] Gao, K.; Wu, B.; Yu, C.-B.; Chen, Q.-A.; Ye, Z.-S.; Zhou, Y.-G. Org. Lett. 2012, 14, 3890.
[81] Gao, K.; Yu, C.-B.; Li, W.; Zhou, Y.-G.; Zhang, X. Chem. Commun. 2011, 47, 7845.
[82] Ding, Z.-Y.; Chen, F.; Qin, J.; He, Y.-M.; Fan, Q.-H. Angew. Chem., Int. Ed. 2012, 51, 5706.
[83] Wang, Y.-Q.; Lu, S.-M.; Zhou, Y.-G. J. Org. Chem. 2007, 72, 3729.
[84] Yu, C.-B.; Wang, D.-W.; Zhou, Y.-G. J. Org. Chem. 2009, 74, 5633.
[85] Wang, Y.-Q.; Yu, C.-B.; Wang, D.-W.; Wang, X.-B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071.
[86] Chen, F.; Li, Z.; He, Y.; Fan, Q. Chin. J. Chem. 2010, 28, 1529.