SIOC English
有机化学
高级检索

有机化学 >

2014 , Vol. 34 >Issue 8: 1509 - 1522

DOI: https://doi.org/10.6023/cjoc201402029

综述与进展

双功能手性硫脲催化的不对称Michael加成反应研究进展

  • 侯学会 ,
  • 马志伟 ,
  • 王建玲 ,
  • 刘宏民
展开
  • a 河南牧业经济学院质检系 郑州 450011;
    b 郑州大学化学与分子工程学院 郑州 450001;
    c 郑州大学药学院 郑州 450001

收稿日期: 2014-02-24

  修回日期: 2014-03-12

  网络出版日期: 2014-04-28

基金资助

河南省教育厅科学技术研究重点（Nos.14A150052，12A150026）、郑州市科技攻关计划（No.121PPTGG509-2）资助项目.

收起

Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas

  • Hou Xuehui ,
  • Ma Zhiwei ,
  • Wang Jianling ,
  • Liu Hongmin
Expand
  • a Department of Quality Detection and Management, Henan University of Animal Husbandry and Economy, Zhengzhou 450011;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
    c School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001

Received date: 2014-02-24

  Revised date: 2014-03-12

  Online published: 2014-04-28

Supported by

Project supported by the Science and Technology Research Projects of Education Department of Henan Province (Nos. 14A150052, 12A150026), the Scientific Research Plan of Zhenzhou City (No. 121PPTGG509-2).

Fold

摘要

手性有机小分子催化是近年来不对称催化领域的一个热门研究课题. 其具有反应条件温和、环境友好等优点，符合绿色化学的要求. 手性氨基-硫脲类催化剂，特别是双功能的手性硫脲，已经在众多的不对称反应中表现出了优秀的催化性能. 主要综述了双功能手性硫脲在不对称Michael加成反应中的应用，并对其前景及发展趋势作了展望.

关键词： 有机催化; 双功能; 手性硫脲; Michael加成

本文引用格式

侯学会 , 马志伟 , 王建玲 , 刘宏民 . 双功能手性硫脲催化的不对称Michael加成反应研究进展[J]. 有机化学, 2014 , 34(8) : 1509 -1522 . DOI: 10.6023/cjoc201402029

Abstract

Asymmetric organocatalysis has been a frontier in the field of asymmetric catalysis. The comparable advantages, including mild reaction conditions, environment benign, and so on, render the organocatalytic reaction to possess some features of green chemistry. Chiral amino-thiourea organocatalyst, especially chiral bifunctional thiourea, has been shown excellent catalytic performance in a variety of asymmetric reactions. This review provides an overview of applications of chiral bifunctional thiourea in asymmetry Michael addition reaction, and the prospect and development are depicted finally.

Key words： organocatalysis; bifunctional; chiral thiourea; Michael addition

参考文献

[1] List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
[2] Serdyuk, O. V.; Heckel, C. M.; Tsogoeva, S. B. Org. Biomol. Chem. 2013, 11, 7051.
[3] Tsakos, M.; Kokotos, C. G. Tetrahedron 2013, 69, 10199.
[4] Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
[5] Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
[6] Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481.
[7] Connon, S. J. Chem. Commun. 2008, 2499.
[8] Yeboah, E. M. O.; Yeboah, S. O.; Singh, G. S. Tetrahedron 2011, 67, 1725.
[9] Xi, Y.; Shi, X. Chem. Commun. 2013, 49, 8583.
[10] Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4713.
[11] Peng, F.-Z.; Shao, Z.-H.; Fan, B.-M.; Song, H.; Li, G.-P.; Zhang, H.-B. J. Org. Chem. 2008, 73, 5202.
[12] Pu, X.; Li, P.; Peng, F.; Li, X.; Zhang, H.; Shao, Z. Eur. J. Org. Chem. 2009, 4622.
[13] Jiang, X.; Zhang, Y.; Liu, X.; Zhang, G.; Lai, L.; Wu, L.; Zhang, J.; Wang, R. J. Org. Chem. 2009, 74, 5562.
[14] Shi, X.-M.; Dong, W.-P.; Zhu, L.-P.; Jiang, X.-X.; Wang, R. Adv. Synth. Catal. 2013, 355, 3119.
[15] Ma, Z.-W.; Liu, Y.-X.; Huo, L.-J.; Gao, X.; Tao, J.-C. Tetrahedron: Asymmetry 2012, 23, 443.
[16] Rahman, A. U.; Basha, A. Indole Alkaloids, Harwood Academic Publishers, Amsterdam, 1997.
[17] Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2003, 2209.
[18] Bui, T.; Syed, S.; Barbas, C. F. J. Am. Chem. Soc. 2009, 131, 8758.
[19] Li, X.; Xi, Z.; Luo, S.; Cheng, J.-P. Adv. Synth. Catal. 2010, 352, 1097.
[20] Li, X.; Hu, S.; Xi, Z.; Zhang, L.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2010, 75, 8697.
[21] Li, X.; Xue, X.-S.; Liu, C.; Wang, B.; Tan, B.-X.; Jin, J.-L.; Zhang, Y.-Y.; Dong, N.; Cheng, J.-P. Org. Biomol. Chem. 2012, 10, 413.
[22] Ma, Z.-W.; Wu, Y.; Sun, B.; Du, H.-L.; Shi, W.-M.; Tao, J.-C. Tetrahedron: Asymmetry 2013, 24, 7.
[23] Pettersen, D.; Piana, F.; Bernardi, L.; Fini, F.; Fochi, M.; Sgarzani, V.; Ricci, A. Tetrahedron Lett. 2007, 48, 7805.
[24] Tressaud, A.; Haufe, G. Fluorine and Health-Molecular Imaging, Biomedical Materials and Pharmaceuticals, Elsevier, Amsterdam, 2008.
[25] Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, New York, 2009.
[26] Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2010, 111, 455.
[27] Dong, X.-Q.; Fang, X.; Wang, C.-J. Org. Lett. 2011, 13, 4426.
[28] Dong, X.-Q.; Fang, X.; Tao, H.-Y.; Zhou, X.; Wang, C.-J. Adv. Synth. Catal. 2012, 354, 1141.
[29] Fang, X.; Li, J.; Wang, C.-J. Org. Lett. 2013, 15, 3448.
[30] Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 2006, 29.
[31] Alcaine, A.; Marques-Lopez, E.; Merino, P.; Tejero, T.; Herrera, R. P. Org. Biomol. Chem. 2011, 9, 2777.
[32] Nodes, W. J.; Nutt, D. R.; Chippindale, A. M.; Cobb, A. J. A. J. Am. Chem. Soc. 2009, 131, 16016.
[33] Schweizer, E. E.; Meeder-Nycz, O. Chromenes, Chromansses and Chromones, Wiley-Interscience, New York, 1977.
[34] Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595.
[35] Jia, Z.-X.; Luo, Y.-C.; Wang, Y.; Chen, L.; Xu, P.-F.; Wang, B. Chem. Eur. J. 2012, 18, 12958.
[36] Jia, Z.-X.; Luo, Y.-C.; Xu, P.-F. Org. Lett. 2011, 13, 832.
[37] Jia, Z.-X.; Luo, Y.-C.; Cheng, X.-N.; Xu, P.-F.; Gu, Y.-C. J. Org. Chem. 2013, 78, 6488.
[38] Wang, X.-F.; Hua, Q.-L.; Cheng, Y.; An, X.-L.; Yang, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 8379.
[39] Wang, X.-F.; An, J.; Zhang, X.-X.; Tan, F.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2011, 13, 808.
[40] Meadows, D. C.; Gervay-Hague, J. Med. Res. Rev. 2006, 26, 793.
[41] Alba, A.-N. R.; Companyo, X.; Rios, R. Chem. Soc. Rev. 39, 2018.
[42] Liu, T.-Y.; Long, J.; Li, B.-J.; Jiang, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2006, 4, 2097.
[43] Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794.
[44] Cao, C.-L.; Ye, M.-C.; Sun, X.-L.; Tang, Y. Org. Lett. 2006, 8, 2901.
[45] Shen, Z.; Zhang, Y.; Jiao, C.; Li, B.; Ding, J.; Zhang, Y. Chirality 2007, 19, 307.
[46] Cao, Y.-J.; Lu, H.-H.; Lai, Y.-Y.; Lu, L.-Q.; Xiao, W.-J. Synthesis 2006, 3795, 3800.
[47] Cao, Y.-J.; Lai, Y.-Y.; Wang, X.; Li, Y.-J.; Xiao, W.-J. Tetrahedron Lett. 2007, 48, 21.
[48] Ban, S.-R.; Zhu, X.-X.; Zhang, Z.-P.; Xie, H.-Y.; Li, Q.-S. Eur. J. Org. Chem. 2013, 2013, 2977.
[49] Lu, A.; Gao, P.; Wu, Y.; Wang, Y.; Tang, C. Org. Biomol. Chem. 2009, 7, 3141.
[50] Chen, J.-R.; Cao, Y.-J.; Zou, Y.-Q.; Tan, F.; Fu, L.; Zhu, X.-Y.; Xiao, W.-J. Org. Biomol. Chem. 2010, 8, 1275.
[51] Wang, Q.-W.; Peng, L.; Fu, J.-Y.; Huang, Q.-C.; Wang, L.-X.; Xu, X.-Y. ARKIVOC 2010, ii, 340.
[52] Bai, J.-F.; Xu, X.-Y.; Huang, Q.-C.; Peng, L.; Wang, L.-X. Tetrahedron Lett. 2010, 51, 2803.
[53] Kokotos, C. G.; Limnios, D.; Triggidou, D.; Trifonidou, M.; Kokotos, G. Org. Biomol. Chem. 2011, 9, 3386.
[54] Tsakos, M.; Trifonidou, M.; Kokotos, C. G. Tetrahedron 2012, 68, 8630.
[55] Meninno, S.; Croce, G.; Lattanzi, A. Org. Lett. 2013, 15, 3436.
[56] Tsogoeva, S. B.; Wei, S. Chem. Commun. 2006, 1451.
[57] Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Adv. Synth. Catal. 2006, 348, 826.
[58] Wei, S.; Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Catal. Today 2007, 121, 151.
[59] Liu, K.; Cui, H.-F.; Nie, J.; Dong, K.-Y.; Li, X.-J.; Ma, J.-A. Org. Lett. 2007, 9, 923.
[60] Jiang, X.; Zhang, Y.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.
[61] Uehara, H.; Barbas, C. F. Angew. Chem., Int. Ed. 2009, 48, 9848.
[62] Ma, H.; Liu, K.; Zhang, F.-G.; Zhu, C.-L.; Nie, J.; Ma, J.-A. J. Org. Chem. 2010, 75, 1402.
[63] Chen, J.-R.; Zou, Y.-Q.; Fu, L.; Ren, F.; Tan, F.; Xiao, W.-J. Tetrahedron 2010, 66, 5367.
[64] Ma, Z.-W.; Liu, Y.-X.; Zhang, W.-J.; Tao, Y.; Zhu, Y.; Tao, J.-C.; Tang, M.-S. Eur. J. Org. Chem. 2011, 6747.
[65] Retini, M.; Bergonzini, G.; Melchiorre, P. Chem. Commun. 2012, 48, 3336.
[66] Li, P.; Wang, Y.; Liang, X.; Ye, J. Chem. Commun. 2008, 3302.
[67] Li, P.; Wen, S.; Yu, F.; Liu, Q.; Li, W.; Wang, Y.; Liang, X.; Ye, J. Org. Lett. 2009, 11, 753.
[68] Dudziński, K.; Pakulska, A. M.; Kwiatkowski, P. Org. Lett. 2012, 14, 4222.
[69] Moritaka, M.; Miyamae, N.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2012, 2554.
[70] Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem. Eur. J. 2009, 15, 7846.
[71] Xue, F.; Liu, L.; Zhang, S.; Duan, W.; Wang, W. Chem. Eur. J. 2010, 16, 7979.
[72] Ma, Z.-W.; Liu, Y.-X.; Li, P.-L.; Ren, H.; Zhu, Y.; Tao, J.-C. Tetrahedron: Asymmetry 2011, 22, 1740.
[73] Mei, R.-Q.; Xu, X.-Y.; Li, Y.-C.; Fu, J.-Y.; Huang, Q.-C.; Wang, L.-X. Tetrahedron Lett. 2011, 52, 1566.
[74] Zhou, Y.; Li, X.; Li, W.; Wu, C.; Liang, X.; Ye, J. Synlett 2010, 2357.
[75] Wu, H.; Tian, Z.; Zhang, L.; Huang, Y.; Wang, Y. Adv. Synth. Catal. 2012, 354, 2977.
[76] Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058.
[77] Wen, S.; Li, P.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 4806.
[78] Lu, A.; Hu, K.; Wang, Y.; Song, H.; Zhou, Z.; Fang, J.; Tang, C. J. Org. Chem. 2012, 77, 6208.
[79] Wu, H.; Zhang, L.-L.; Tian, Z.-Q.; Huang, Y.-D.; Wang, Y.-M. Chem. Eur. J. 2013, 19, 1747.
Options
文章导航

/

〈 〉