Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1789-1803.DOI: 10.6023/cjoc202011005 Previous Articles Next Articles
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孙忠文1,*(), 张聪聪1, 陈丽君1, 谢惠定1, 柳波1, 刘丹丹1,*()
收稿日期:
2020-11-04
修回日期:
2020-12-10
发布日期:
2020-12-31
通讯作者:
孙忠文, 刘丹丹
基金资助:
Zhongwen Sun1,*(), Congcong Zhang1, Lijun Chen1, Huiding Xie1, Bo Liu1, Dandan Liu1,*()
Received:
2020-11-04
Revised:
2020-12-10
Published:
2020-12-31
Contact:
Zhongwen Sun, Dandan Liu
About author:
Supported by:
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Zhongwen Sun, Congcong Zhang, Lijun Chen, Huiding Xie, Bo Liu, Dandan Liu. Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1789-1803.
[1] |
(a) Furuya, T.; Kamlet, A. S.; Ritter, T. Natrue 2011, 473, 470.
doi: 10.1038/nature10108 |
(b) Merino, F.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
doi: 10.1039/C4CS00025K |
|
(c) Usachev, B. I. J. Fluorine Chem. 2015, 175, 36.
doi: 10.1016/j.jfluchem.2015.02.009 |
|
(d) Huang, S.-C.; Schlinquer, C.; Poisson, T.; Pannecoucke, X.; Charette, A. B.; Jubault, P. Chem.-Eur. J. 2018, 24, 10339.
doi: 10.1002/chem.201802685 |
|
(d) He, X.-H.; Ji, Y.-L.; Peng, C.; Han, B. Adv. Synth. Catal. 2019, 361, 1923.
doi: 10.1002/adsc.v361.9 |
|
[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.
pmid: 15115411 |
(b) Jlalia, I.; Lensen, N.; Chaume, G.; Dzhambazova, E.; Astasidi, L.; Hadjiolova, R.; Bocheva, A.; Brigaud, T. Eur. J. Med. Chem. 2013, 62, 122.
doi: 10.1016/j.ejmech.2012.12.041 pmid: 15115411 |
|
(c) Liu, Y.; Chen, J.-L.; Wang, G.-H.; Sun, P.; Huang, H.; Qing, F.-L. Tetrahedron Lett. 2013, 54, 5541.
doi: 10.1016/j.tetlet.2013.08.027 pmid: 15115411 |
|
(d) Guillaume, M.; Benoit, C.; Sebastien, C.; Philippe, G.; Pierre, B. J.; Daniele, B. D. J. Med. Chem. 2004, 47, 2694.
pmid: 15115411 |
|
(e) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
doi: 10.1021/cr100166a pmid: 15115411 |
|
[3] |
(a) Timperley, C.M. Waters, M. J. Fluorine Chem. 2005, 126, 1144.
doi: 10.1016/j.jfluchem.2005.04.016 |
(b) Morandi, B.; Carreira, C. M. Angew. Chem., Int. Ed. 2010, 49, 119.
|
|
(c) Morandi, B.; Mariampillai, B.; Carreira, C. M. Angew. Chem., Int. Ed. 2011, 50, 1101.
|
|
(d) Li, F.; Nie, J.; Dun, L.; Zheng, Y.; Ma, J.-A. Angew. Chem., Int. Ed. 2013, 52, 6255.
doi: 10.1002/anie.201301870 |
|
(e) Molander, G. A.; Ryu, D. Angew. Chem., Int. Ed. 2014, 53, 14181.
doi: 10.1002/anie.v53.51 |
|
(f) Brusoe, A.T; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8460.
doi: 10.1021/jacs.5b02512 |
|
(g) Li, S.; Cao, W.-J.; Ma, J.-A. Synlett 2017, 28, 673.
doi: 10.1055/s-0036-1588363 |
|
(h) Kotozaki, M.; Chanthamath, S.; Fujii, T.; Shibatomi, K.; Iwasa, S. Chem. Commun. 2018, 54, 5110.
doi: 10.1039/C8CC02286K |
|
(i) Zhang, X.-W.; Hu, W.-L.; Chen, S.; Hu, X.-G. Org. Lett. 2018, 20, 860.
doi: 10.1021/acs.orglett.7b04028 |
|
(j) Gui, H.-Z.; Wei, Y.; Shi, M. Chem.-Asian J. 2020, 15, 1225.
doi: 10.1002/asia.v15.8 |
|
[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.
doi: 10.1039/C4CC10216A |
[5] |
Zhi, Y.; Zhao, K.; Liu, Q.; Wang, A.; Enders, D. Chem. Commun. 2016, 52, 14011.
doi: 10.1039/C6CC08352H |
[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.
doi: 10.1021/acs.joc.6b02949 |
[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.
doi: 10.1002/adsc.201500416 |
[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.
doi: 10.1021/acs.orglett.8b01730 |
[9] |
Gao, X.-Y.; Yan, R.-J.; Xiao, B.-X.; Du, W.; Albrecht, L.; Chen, Y.-C. Org. Lett. 2019, 21, 9628.
doi: 10.1021/acs.orglett.9b03794 |
[10] |
Zhou, C.-C.; Han, Y.-Y.; Zeng, C.-K.; Zhang, T.-Y.; Ye, J.-X. Chin. Chem. Lett. 2020, 31, 377.
doi: 10.1016/j.cclet.2019.07.052 |
[11] |
Choudhury, A.R; Mukherjee, S. Chem. Soc. Rev. 2020, 49, 6755.
doi: 10.1039/c9cs00346k pmid: 32785345 |
[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.
doi: 10.1039/C6CC06367E |
[13] |
(a) Song, Y.-X.; Du, D.-M. J. Org. Chem. 2018, 83, 9278.
doi: 10.1021/acs.joc.8b01245 |
(b) Lin, Y.; Song, Y.-X.; Du, D.-M. Adv. Synth. Catal. 2019, 361, 1064.
doi: 10.1002/adsc.201801608 |
|
(c) An, T.-L.; Du, D.-M. ChemistrySelect 2019, 4, 11302.
doi: 10.1002/slct.v4.38 |
|
[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.
doi: 10.1039/C9QO00241C |
(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.
doi: 10.1039/c9ob00720b |
|
[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.
doi: 10.1039/C9QO00452A |
[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.
doi: 10.1002/adsc.v362.7 |
[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.
doi: 10.1002/anie.v54.45 |
(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.
doi: 10.1021/acs.orglett.6b00873 |
|
(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.
doi: 10.1021/acs.joc.7b00733 |
|
(d) Yang, Q.-Q.; Xiao, W.; Du, W.; Qin, Q.-Y.; Chen, Y.-C. Chem. Commun. 2018, 54, 1129.
doi: 10.1039/C7CC09221K |
|
(e) Wang, C.-Y.; Wang, Z.-Y.; Yang, J.; Shi, S.-H.; Hui, X.-P. Org. Lett. 2020, 22, 4440.
doi: 10.1021/acs.orglett.0c01447 |
|
[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.
doi: 10.1039/C6QO00723F |
(b) Zhi, Y.; Zhao, K.; Essen, C. V.; Rissanen, K.; Enders, D. Synlett 2017, 28, 2876.
doi: 10.1055/s-0036-1589070 |
|
(c) Zhao, B.-L.; Du, D.-M. Adv. Synth. Catal. 2019, 361, 3412.
doi: 10.1002/adsc.v361.14 |
|
(d) Li, Yang, Hua, Y.-Z.; Lu, H.-J.; Liu, L.-T.; Wan, M.-C. Org. Lett. 2020, 22, 2527.
doi: 10.1021/acs.orglett.0c00283 |
|
[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.
doi: 10.1055/s-0037-1612089 |
[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.
doi: 10.1021/acs.orglett.5b03566 |
[21] |
Shi, L.-M.; Sun, X.-S.; Chen, C.; Wang, Z.-F.; Tao, H.-Y.; Wang, C.-J. Org. Lett. 2019, 21, 4842.
doi: 10.1021/acs.orglett.9b01738 |
[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.
doi: 10.1021/acs.orglett.0c01578 |
[24] |
(a) Zhu, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 4500.
doi: 10.1021/ja501560x |
(b) Liu, J.; Cao, C.-G.; Sun, H.-B.; Zhang, X.; Niu, D.-W. J. Am. Chem. Soc. 2016, 138, 13103.
doi: 10.1021/jacs.6b05288 |
|
[25] |
(a) Wang, Y.-W.; Deng, L.-F.; Zhang, X.; Niu, D.-W. Org. Lett. 2019, 21, 6951.
doi: 10.1021/acs.orglett.9b02550 |
(b) Shen, C.; Wang, R.-Q.; Wei, L.; Wang, Z.-F.; Tao, H.-Y.; Wang, C.-J. Org. Lett. 2019, 21, 6940.
doi: 10.1021/acs.orglett.9b02543 |
|
[26] |
Wang, W.; Xiong, Q.; Gong, L.; Wang, Y.-W.; Liu, J.; Lan, Y.; Zhang, X. Org. Lett. 2020, 22, 5479.
doi: 10.1021/acs.orglett.0c01836 |
[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.
doi: 10.1002/adsc.201600688 |
[28] |
Liu, Q.; Zhao, K.; Zhi, Y.; Raabe, G.; Enders, D. Org. Chem. Front. 2017, 4, 1416.
doi: 10.1039/C7QO00161D |
[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.
doi: 10.1039/C9OB00325H |
[30] |
Zhu, W.-Y.; Su, Q.; Lin, N.; Chen, Q.; Zhang, Z.-W.; Weng, J.; Lu, G. Org. Chem. Front. 2020, 7, 3452.
doi: 10.1039/D0QO00990C |
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