综述与进展

三氟乙基酮亚胺参与的催化不对称反应研究进展

  • 孙忠文 ,
  • 张聪聪 ,
  • 陈丽君 ,
  • 谢惠定 ,
  • 柳波 ,
  • 刘丹丹
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  • 1 昆明医科大学药学院 云南省天然药物药理重点实验室 昆明 650500

收稿日期: 2020-11-04

  修回日期: 2020-12-10

  网络出版日期: 2020-12-31

基金资助

国家自然科学基金(21907044); 云南省基础研究计划项目(2019FB124); 云南省科技厅-昆明医科大学应用基础研究联合专项基金项目(2017FE468(-138)); 云南省教育厅科学研究基金(2016ZZX089); 西南林业大学西南地区林业生物质高效利用国家林和草原局重点实验室开放基金(2019-KF18); 西南林业大学西南地区林业生物质高效利用国家林和草原局重点实验室开放基金(2020-KF06)

Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines

  • Zhongwen Sun ,
  • Congcong Zhang ,
  • Lijun Chen ,
  • Huiding Xie ,
  • Bo Liu ,
  • Dandan Liu
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  • 1 School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500
* Corresponding authors. E-mail: ;

Received date: 2020-11-04

  Revised date: 2020-12-10

  Online published: 2020-12-31

Supported by

National Natural Science Foundation of China(21907044); Yunnan Fundamental Research Projects(2019FB124); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(2017FE468(-138)); Yunnan Provincial Department of Education Science Research Fund Project(2016ZZX089); Open Fund of Key Laboratory of State Forestry and Grassland Adminstration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, Southwest Forestry University(2019-KF18); Open Fund of Key Laboratory of State Forestry and Grassland Adminstration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, Southwest Forestry University(2020-KF06)

摘要

氟原子或含氟基团在材料科学、药物化学等领域的生物活性分子中广泛存在. 三氟乙基酮亚胺同时存在高活性亲电和亲核中心, 是良好的1,3-偶极子. 因其在催化不对称构建含有三氟甲基立体中心的反应中具有极高的研究价值而备受关注. 以三氟乙基酮亚胺的底物和反应类型为主线, 综述了近五年三氟乙基酮亚胺参与的催化不对称反应研究进展, 同时对该领域的未来发展进行了展望.

本文引用格式

孙忠文 , 张聪聪 , 陈丽君 , 谢惠定 , 柳波 , 刘丹丹 . 三氟乙基酮亚胺参与的催化不对称反应研究进展[J]. 有机化学, 2021 , 41(5) : 1789 -1803 . DOI: 10.6023/cjoc202011005

Abstract

The fluorine atoms or fluorine-containing groups are widely found in biologically molecules in the fields of materials science, pharmaceutical chemistry, etc. The properties of trifluoroethylketimines provide both electrophilic and nucleophilic centers, and become an excellent 1,3-dipole, which possessed high research value in catalytic asymmetric reactions of construction of trifluoromethyl stereocenters. Based on the substrates and reaction types of trifluoroethylketimine, the research progress of catalytic asymmetric reactions involving trifluoroethylketimine in recent five years is reviewed, and the future development of this field is prospected.

参考文献

[1]
(a) Furuya, T.; Kamlet, A. S.; Ritter, T. Natrue 2011, 473, 470.
[1]
(b) Merino, F.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
[1]
(c) Usachev, B. I. J. Fluorine Chem. 2015, 175, 36.
[1]
(d) Huang, S.-C.; Schlinquer, C.; Poisson, T.; Pannecoucke, X.; Charette, A. B.; Jubault, P. Chem.-Eur. J. 2018, 24, 10339.
[1]
(d) He, X.-H.; Ji, Y.-L.; Peng, C.; Han, B. Adv. Synth. Catal. 2019, 361, 1923.
[2]
(a) Corbett, J. W.; Ko, S. S.; Rodgers, J. D.; Gearhart, L. A.; Magnus, N. A.; Bacheler, L. T.; Diamond, S.; Jeffrey, S.; Klabe, R. M.; Cordova, B. C.; Garber, S.; Logue, K.; Trainor, G. L.; Anderson, P. S.; Erickson-Viitanen, S. K. J. Med. Chem. 2000, 43, 2019.
[2]
(b) Jlalia, I.; Lensen, N.; Chaume, G.; Dzhambazova, E.; Astasidi, L.; Hadjiolova, R.; Bocheva, A.; Brigaud, T. Eur. J. Med. Chem. 2013, 62, 122.
[2]
(c) Liu, Y.; Chen, J.-L.; Wang, G.-H.; Sun, P.; Huang, H.; Qing, F.-L. Tetrahedron Lett. 2013, 54, 5541.
[2]
(d) Guillaume, M.; Benoit, C.; Sebastien, C.; Philippe, G.; Pierre, B. J.; Daniele, B. D. J. Med. Chem. 2004, 47, 2694.
[2]
(e) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
[3]
(a) Timperley, C.M. Waters, M. J. Fluorine Chem. 2005, 126, 1144.
[3]
(b) Morandi, B.; Carreira, C. M. Angew. Chem., Int. Ed. 2010, 49, 119.
[3]
(c) Morandi, B.; Mariampillai, B.; Carreira, C. M. Angew. Chem., Int. Ed. 2011, 50, 1101.
[3]
(d) Li, F.; Nie, J.; Dun, L.; Zheng, Y.; Ma, J.-A. Angew. Chem., Int. Ed. 2013, 52, 6255.
[3]
(e) Molander, G. A.; Ryu, D. Angew. Chem., Int. Ed. 2014, 53, 14181.
[3]
(f) Brusoe, A.T; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8460.
[3]
(g) Li, S.; Cao, W.-J.; Ma, J.-A. Synlett 2017, 28, 673.
[3]
(h) Kotozaki, M.; Chanthamath, S.; Fujii, T.; Shibatomi, K.; Iwasa, S. Chem. Commun. 2018, 54, 5110.
[3]
(i) Zhang, X.-W.; Hu, W.-L.; Chen, S.; Hu, X.-G. Org. Lett. 2018, 20, 860.
[3]
(j) Gui, H.-Z.; Wei, Y.; Shi, M. Chem.-Asian J. 2020, 15, 1225.
[4]
Ma, M.-X.; Zhu, Y.-Y.; Sun, Q.-T.; Li, X.-Y.; Su, J.-H.; Zhao, L.; Zhap, Y.-Y.; Qiu, S.; Yan, W.-J.; Wang, K.-R.; Wang, R. Chem. Commun. 2015, 51, 8789.
[5]
Zhi, Y.; Zhao, K.; Liu, Q.; Wang, A.; Enders, D. Chem. Commun. 2016, 52, 14011.
[6]
Dong, Z.-H.; Zhu, Y.-Y.; Li, B.-Y.; Wang, C.; Yan, W.-J.; Wang, K.-R.; Wang, R. J. Org. Chem. 2017, 82, 3482.
[7]
Sun, Q.-T.; Li, X.-Y.; Su, J.-H.; Zhao, L.; Ma, M.-X.; Zhu, Y.-Y.; Zhao, Y.-Y.; Zhu, R.-R.; Yan, W.-J.; Wang, K.-R.; Wang, R. Adv. Synth. Catal. 2015, 357, 3187.
[8]
You, Y.; Lu, W.-Y.; Wang, Z.-H.; Chen, Y.-Z.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2018, 20, 4453.
[9]
Gao, X.-Y.; Yan, R.-J.; Xiao, B.-X.; Du, W.; Albrecht, L.; Chen, Y.-C. Org. Lett. 2019, 21, 9628.
[10]
Zhou, C.-C.; Han, Y.-Y.; Zeng, C.-K.; Zhang, T.-Y.; Ye, J.-X. Chin. Chem. Lett. 2020, 31, 377.
[11]
Choudhury, A.R; Mukherjee, S. Chem. Soc. Rev. 2020, 49, 6755.
[12]
Wang, Z.-H.; Wu, Z.-J.; Yue, D.-F.; Hu, W.-F.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. Chem. Commun. 2016, 52, 11708.
[13]
(a) Song, Y.-X.; Du, D.-M. J. Org. Chem. 2018, 83, 9278.
[13]
(b) Lin, Y.; Song, Y.-X.; Du, D.-M. Adv. Synth. Catal. 2019, 361, 1064.
[13]
(c) An, T.-L.; Du, D.-M. ChemistrySelect 2019, 4, 11302.
[14]
(a) Li, B.-Y.; Gao, F.-Y.; Feng, X.; Sun, M.-M.; Guo, Y.-F.; Wen, D.-W.; Deng, Y.-B.; Huang, J.-Q.; Wang, K.-R.; Yan, W.-J. Org. Chem. Front. 2019, 6, 1567.
[14]
(b) Wang, C.; Wen, D.-W.; Chen, H.; Deng, Y.-B.; Liu, X.-T.; Liu, X.; Wang, L.; Gao, F.-Y.; Guo, Y.-F.; Sun, M.-M.; Wang, K.-R.; Yan, W.-J. Org. Biomol. Chem. 2019, 17, 5514.
[15]
Zhao, X.-Y.; Xiong, J.-L.; An, J.-K.; Yu, J.-C.; Zhu, L.-P.; Feng, X.; Jiang, X.-X. Org. Chem. Front. 2019, 6, 1989.
[16]
Liu, X.; Lu, D.-M.; Wu, J.-H.; Tan, J.-P.; Jiang, C.-H.; Gao, G.-W.; Wang, T.-L. Adv. Synth. Catal. 2020, 362, 1490.
[17]
(a) Sun, Q.-S.; Zhu, H.; Chen, Y.-J.; Yang, X.-D.; Sun, X.-W.; Lin, G.-Q. Angew. Chem., Int. Ed. 2015, 54, 13253.
[17]
(b) Zhu, L.-Y.; Chen, Q.-L.; Shen, D.; Zhang, W.-H.; Shen, C.; Zeng, X.-F.; Zhong, G.-F. Org. Lett. 2016, 18, 2387.
[17]
(c) Ren, J.-W.; Wang, J.; Xiao, J.-A.; Li, J.; Xiang, H.-Y.; Chen, X.-Q.; Yang, H. J. Org. Chem. 2017, 82, 6441.
[17]
(d) Yang, Q.-Q.; Xiao, W.; Du, W.; Qin, Q.-Y.; Chen, Y.-C. Chem. Commun. 2018, 54, 1129.
[17]
(e) Wang, C.-Y.; Wang, Z.-Y.; Yang, J.; Shi, S.-H.; Hui, X.-P. Org. Lett. 2020, 22, 4440.
[18]
(a) Huang, W.-J.; Chen, Q.; Lin, N.; Long, X.-W.; Pan, W.-G.; Xiong, Y.-S.; Weng, J.; Lu, G. Org. Chem. Front. 2017, 4, 472.
[18]
(b) Zhi, Y.; Zhao, K.; Essen, C. V.; Rissanen, K.; Enders, D. Synlett 2017, 28, 2876.
[18]
(c) Zhao, B.-L.; Du, D.-M. Adv. Synth. Catal. 2019, 361, 3412.
[18]
(d) Li, Yang, Hua, Y.-Z.; Lu, H.-J.; Liu, L.-T.; Wan, M.-C. Org. Lett. 2020, 22, 2527.
[19]
Zhu, W.-R.; Zhang, Z.-W.; Huang, W.-H.; Lin, N.; Chen, K.-B.; Wang, B.-C.; Weng, J.; Lu, G. Synthesis 2019, 51, 1969.
[20]
Li, X.-Y.; Sun, J.-H.; Liu, Z. -R.-J.; Zhu, Y.-Y.; Dong, Z.-H.; Qiu, S.; Wang, J.-Y.; Lin, L.; Shen, Z.-Q.; Yan, W.-J.; Wang, K.-R.; Wang, R. Org. Lett. 2016, 18, 956.
[21]
Shi, L.-M.; Sun, X.-S.; Chen, C.; Wang, Z.-F.; Tao, H.-Y.; Wang, C.-J. Org. Lett. 2019, 21, 4842.
[22]
Onywagusi, C. I.; Shao, X.-X.; Malcolmson, S. J. Org. Lett. 2020, 22, 681.
[23]
Zhu, W.-R.; Liu, K.; Weng, J.; Huang, W.-H.; Huang, W.-J.; Chen, Q.; Lin, N.; Lu, G. Org. Lett. 2020, 22, 5014.
[24]
(a) Zhu, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 4500.
[24]
(b) Liu, J.; Cao, C.-G.; Sun, H.-B.; Zhang, X.; Niu, D.-W. J. Am. Chem. Soc. 2016, 138, 13103.
[25]
(a) Wang, Y.-W.; Deng, L.-F.; Zhang, X.; Niu, D.-W. Org. Lett. 2019, 21, 6951.
[25]
(b) Shen, C.; Wang, R.-Q.; Wei, L.; Wang, Z.-F.; Tao, H.-Y.; Wang, C.-J. Org. Lett. 2019, 21, 6940.
[26]
Wang, W.; Xiong, Q.; Gong, L.; Wang, Y.-W.; Liu, J.; Lan, Y.; Zhang, X. Org. Lett. 2020, 22, 5479.
[27]
Sun, J.-H.; Ma, Z.-L.; Li, X.-Y.; Li, L.; Shen, Z.-Q.; Yang, P.-J.; Li, Y.; Wang, H.-L.; Yan, W.-J.; Wang, K.-R.; Wang, R. Adv. Synth. Catal. 2016, 358, 3777.
[28]
Liu, Q.; Zhao, K.; Zhi, Y.; Raabe, G.; Enders, D. Org. Chem. Front. 2017, 4, 1416.
[29]
Li, B.-Y.; Liu, J.-K.; Gao, F. Y.; Sun, M.-M.; Guo, Y.-F.; Zhou, Y.; Wen, D.-W.; Deng, Y.-B.; Chen, H.; Wang, K.-R.; Yan, W.-J. Org. Biomol. Chem. 2019, 17, 2892.
[30]
Zhu, W.-Y.; Su, Q.; Lin, N.; Chen, Q.; Zhang, Z.-W.; Weng, J.; Lu, G. Org. Chem. Front. 2020, 7, 3452.
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