综述与进展

路易斯碱有机小分子催化亚胺的不对称还原研究进展

  • 葛新 ,
  • 陈新志 ,
  • 钱超
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  • a 江南大学化学与材料工程学院无锡 214122;
    b 浙江大学生物质化工教育部重点实验室杭州 310027

收稿日期: 2015-12-21

  修回日期: 2016-01-26

  网络出版日期: 2016-02-02

基金资助

国家自然科学基金(Nos.21376213,21476194)、浙江省科技厅公益性技术应用研究计划项目(Nos.2014C31123,2015C31038)、江南大学自主科研计划(No.JUSRP115A05)资助项目.

Progress on the Lewis-Basic Organocatalytic Asymmetric Reduction of Imines

  • Ge Xin ,
  • Chen Xinzhi ,
  • Qian Chao
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  • aSchool of Chemical and Material Engineering, Jiangnan University, Wuxi 214122;
    b Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027

Received date: 2015-12-21

  Revised date: 2016-01-26

  Online published: 2016-02-02

Supported by

Project supported by the Natural Science Foundation of China (Nos. 21376213, 21476194), Zhejiang Provincial Public Technology Research of China (Nos. 2014C31123, 2015C31038) and the Fundamental Research Funds for the Central Universities (No. JUSRP115A05).

摘要

近年来, 路易斯碱有机小分子催化的亚胺不对称还原反应, 因氢源廉价和后处理简单等优点而受到关注. 分别介绍了甲酰胺类、吡啶酰胺类、亚磺酰胺类、非酰胺类以及负载型路易斯碱有机小分子催化剂在亚胺不对称还原中的应用, 并且对催化剂的结构特点、催化活性及催化机理等方面展开了论述.

本文引用格式

葛新 , 陈新志 , 钱超 . 路易斯碱有机小分子催化亚胺的不对称还原研究进展[J]. 有机化学, 2016 , 36(6) : 1208 -1217 . DOI: 10.6023/cjoc201512029

Abstract

Recently, the asymmetric reduction of imines catalyzed by Lewis-basic organocatalyst has been received much attention as the cheap hydrogen source and the simple post treatment. Based on the different functional groups of organocatalysts, this paper introduced formamide, pyridine amide, sulfonamide, supported and other Lewis basic organocatalysts. The structural characteristics, catalytic activity and mechanism of the Lewis-basic organocatalysts were summarized.

参考文献

[1] Lin, G. Q.; Li, Y. M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis, Wiley, New York, 2001.
[2] Blaser, H. U. Chem Commun. 2003, 293.
[3] Langlois, N.; Dang, T.; Kagan, H. B. Tetrahedron Lett. 1973, 4865.
[4] Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem.Soc.-Chem. Commun. 1991, 1684.
[5] Wang, D.; Hou, C. J.; Chen, L. F.; Liu, X. N.; An, Q. D.; Hu, X. P. Chin. J. Org. Chem .2013, 33, 1355 (in Chinese). (王东, 侯传金, 陈丽凤, 刘小宁, 安庆大, 胡向平, 有机化学, 2013, 33, 1355.)
[6] Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562.
[7] Schnider, P.; Koch, G.; Pretot, R.; Wang, G. Z.; Bohnen, F. M.; Kruger, C.; Pfaltz, A. Chem-Eur J. 1997, 3, 887.
[8] Xiao, D. M.; Zhang, X. M. Angew. Chem., Int. Ed. 2001, 40, 3425.
[9] Wang, C.; Villa-Marcos, B.; Xiao, J. L. Chem. Commun. 2011, 47, 9773.
[10] Blaser, H. U.; Buser, H. P.; Coers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Spindler, F.; Wegmann, A. Chimia 1999, 53, 275.
[11] Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
[12] List, B. J. Am. Chem. Soc. 2000, 122, 9336.
[13] List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
[14] List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
[15] Mitsumori, S.; Zhang, H.; Cheong, P. H. Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 1040.
[16] List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
[17] Iwasaki, F.; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett. 2001, 42, 2525.
[18] Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int Ed. 2005, 44, 7424.
[19] Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751.
[20] Rueping, M.; Antonchick, A. R.; Theissmann, T. Angew Chem., Int. Ed. 2006, 45, 3683.
[21] Rueping, M.; Theissmann, T.; Antonchick, A. P. Synlett 2006, 1071.
[22] Malkov, A. V.; Mariani, A.; MacDougall, K. N.; Kocovsky, P. Org. Lett. 2004, 6, 2253.
[23] Wang, Z. Y.; Wei, S. Y.; Wang, C.; Sun, J. Tetrahedron: Asymmetry 2007, 18, 705.
[24] Wang, Z. Y.; Wang, C.; Zhou, L.; Sun, J. Org. Biomol. Chem. 2013, 11, 787.
[25] Wang, Z. Y.; Cheng, M.; Wu, P. C.; Wei, S. Y.; Sun, J. Org. Lett. 2006, 8, 3045.
[26] Wang, Z. Y.; Ye, X. X.; Wei, S. Y.; Wu, P. C.; Zhang, A. J.; Sun, J. Org. Lett. 2006, 8, 999.
[27] Zhou, L.; Wang, Z. Y.; Wei, S. Y.; Sun, J. Chem. Commun. 2007, 2977.
[28] Zhang, Z. G.; Rooshenas, P.; Hausmann, H.; Schreiner, P. R. Synthesis-Stuttgart 2009, 1531.
[29] Kanemitsu, T.; Umehara, A.; Haneji, R.; Nagata, K.; Itoh, T. Tetrahedron 2012, 68, 3893.
[30] Malkov, A. V.; Stoncius, S.; MacDougall, K. N.; Mariani, A.; McGeoch, G. D.; Kocovsky, P. Tetrahedron 2006, 62, 264.
[31] Malkov, A. V.; Vrankova, K.; Sigerson, R. C.; Stoncius, S.; Kocovsky, P. Tetrahedron 2009, 65, 9481.
[32] Malkov, A. V.; Vrankova, K.; Stoncius, S.; Kocovsky, P. J. Org. Chem. 2009, 74, 5839.
[33] Malkov, A. V.; Stoncius, S.; Kocovsky, P. Angew. Chem., Int Ed. 2007, 46, 3722.
[34] Malkov, A. V.; Stoncius, S.; Vrankova, K.; Arndt, M.; Kocovsky, P. Chem. Eur. J. 2008, 14, 8082.
[35] Xiao, Y.-C.; Wang, C.; Yao, Y.; Sun, J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2011, 50, 10661.
[36] Onomura, O.; Kouchi, Y.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 2006, 47, 3751.
[37] Zheng, H.-J.; Chen, W.-B.; Wu, Z.-J.; Deng, J.-G.; Lin, W.-Q.; Yuan, W.-C.; Zhang, X.-M. Chem-Eur J. 2008, 14, 9864.
[38] Xue, Z.-Y.; Jiang, Y.; Yuan, W.-C.; Zhang, X.-M. Eur. J. Org. Chem. 2010, 616.
[39] Chen, X.; Zheng, Y.; Shu, C.; Yuan, W.; Liu, B.; Zhang, X. J. Org. Chem. 2011, 76, 9109.
[40] Gautier, F. M.; Jones, S.; Martin, S. J. Org. Biomol. Chem. 2009, 7, 229.
[41] Jones, S.; Li, X. F. Tetrahedron 2012, 68, 5522.
[42] Zheng, H.; Deng, J.; Lin, W.; Zhang, X. Tetrahedron Lett. 2007, 48, 7934.
[43] Xue, Z.-Y.; Jiang, Y.; Peng, X.-Z.; Yuan, W.-C.; Zhang, X.-M. Adv. Synth. Catal. 2010, 352, 2132.
[44] Jiang, Y.; Chen, X.; Zheng, Y.; Xue, Z.; Shu, C.; Yuan, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 7304.
[45] Guizzetti, S.; Benaglia, M.; Bonsignore, M.; Raimondi, L. Org. Biomol. Chem. 2011, 9, 739.
[46] Pei, D.; Wang, Z.; Wei, S.; Zhang, Y.; Sun, J. Org. Lett. 2006, 8, 5913.
[47] Pei, D.; Zhang, Y.; Wei, S. Y.; Wang, M.; Sun, J. Adv. Synth. Catal. 2008, 350, 619.
[48] Wang, C.; Wu, X.; Zhou, L.; Sun, J. Chem. Eur. J. 2008, 14, 8789.
[49] Wu, X. J.; Li, Y.; Wang, C.; Zhou, L.; Lu, X. X.; Sun, J. A. Chem. Eur. J. 2011, 17, 2846.
[50] Malkov, A. V.; Liddon, A.; Ramirez-Lopez, P.; Bendova, L.; Haigh, D.; Kocovsky, P. Angew Chem., Int. Edit .2006, 45, 1432.
[51] Song, S. S.; Zhou, H. Y.; Li, X. N.; Wang, L. H.; Li, Y. Q.; Wang, J. X. Chin. J. Org. Chem. 2014, 34, 706 (in Chinese). (宋沙沙, 周宏勇, 李小娜, 王丽华, 李云庆, 王家喜, 有机化学, 2014, 34, 706.)
[52] Ge, X.; Qian, C.; Chen, Y. B.; Chen, X. Z. Tetrahedron: Asymmetry 2014, 25, 596.
[53] Malkov, A. V.; Figlus, M.; Stoncius, S.; Kocovsky, P. J. Org. Chem. 2007, 72, 1315.
[54] Malkov, A. V.; Figlus, M.; Kocovsky, P. J. Org. Chem. 2008, 73, 3985.
[55] Malkov, A. V.; Figlus, M.; Cooke, G.; Caldwell, S. T.; Rabani, G.; Prestly, M. R.; Kocovsky, P. Org. Biomol. Chem. 2009, 7, 1878.
[56] Malkov, A. V.; Figlus, M.; Prestly, M. R.; Rabani, G.; Cooke, G.; Kocovsky, P. Chem. Eur. J. 2009, 15, 9651.
[57] Ge, X.; Qian, C.; Chen, X. Z. Tetrahedron: Asymmetry 2014, 25, 1450.
[58] Yuan, D. Z.; Huang, B. Chin. J. Org. Chem. 2012, 32, 1368 (in Chinese). (袁定重, 黄斌, 有机化学, 2012, 32, 1368.)
[59] Ge, X.; Qian, C.; Ye, X. M.; Chen, X. Z. RSC Adv. 2015, 5, 65402.

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