Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2700-2721.DOI: 10.6023/cjoc202403004 Previous Articles Next Articles
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宣良明a, 赵伟a, 范润东a, 严琼姣a,*(), 汪伟a,*(), 陈芬儿a,b,*()
收稿日期:
2024-03-03
修回日期:
2024-03-29
发布日期:
2024-05-10
通讯作者:
严琼姣, 汪伟, 陈芬儿
基金资助:
Liangming Xuana, Wei Zhaoa, Rundong Fana, Qiongjiao Yana(), Wei Wanga(), Fen'er Chena,b()
Received:
2024-03-03
Revised:
2024-03-29
Published:
2024-05-10
Contact:
Qiongjiao Yan, Wei Wang, Fen'er Chen
Supported by:
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Liangming Xuan, Wei Zhao, Rundong Fan, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances of the Catalysis Systems in the α-C(sp3)—H Functionalization of Glycine Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2700-2721.
[1] |
(a) Albericio, F.; Kruger, H. G. Future Med. Chem. 2012, 4, 1527.
doi: 10.4155/fmc.12.94 pmid: 27589349 |
(b) Xiao, H.; Chatterjee, A.; Choi, S.-H.; Bajjuri, K. M.; Sinha, S. C.; Schultz, P. G. Angew. Chem., Int. Ed. 2013, 52, 14080.
doi: 10.1002/anie.201308137 pmid: 27589349 |
|
(c) Lang, K.; Chin, J. W. Chem. Rev. 2014, 114, 4764.
pmid: 27589349 |
|
(d) Blaskovich, M. A. T. J. Med. Chem. 2016, 59, 10807.
doi: 10.1021/acs.jmedchem.6b00319 pmid: 27589349 |
|
(e) Rémond, E.; Martin, C.; Martinez, J.; Cavelier, F. Chem. Rev. 2016, 116, 11654.
pmid: 27589349 |
|
(f) Mei, P.; Zhang, Y.; Feng, X. Acta Chim. Sinica 2020, 78, 1041 (in Chinese).
doi: 10.6023/A20060256 pmid: 27589349 |
|
(梅佩, 张媛媛, 冯霄, 化学学报, 2020, 78, 1041.)
doi: 10.6023/A20060256 pmid: 27589349 |
|
(g) Zhou, Y.; Chen, H.; Lei, P.; Gui, C.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Chin. Chem. Lett. 2022, 33, 4850.
pmid: 27589349 |
|
(h) Gui, C.; Peng, Y.; Zhou, Y.; Zheng, Y.; Wang, H.; Yan, Q.; Zhou, H.; Wang, W.; Chen, F. ACS Catal. 2023, 13, 13735.
pmid: 27589349 |
|
[2] |
(a) Chaloner, P. A. J. Organomet. Chem. 1987, 337, 431.
pmid: 32926032 |
(b) Higham, J. I.; Bull, J. A. Org. Biomol. Chem. 2020, 18, 7291.
doi: 10.1039/d0ob01587c pmid: 32926032 |
|
[3] |
(a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
|
(b) Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8.
|
|
(c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
|
|
[4] |
(a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
pmid: 12914490 |
(b) Bayer, A.; Kazmaier, U. J. Org. Chem. 2014, 79, 8491.
pmid: 12914490 |
|
[5] |
(a) Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429.
doi: 10.1002/anie.201105123 pmid: 21915984 |
(b) Zhu, Z.-Q.; Xiao, L.-J.; Xie, Z.-B.; Le, Z.-G. Chin. J. Org. Chem. 2019, 39, 2345 (in Chinese).
pmid: 21915984 |
|
(祝志强, 肖利金, 谢宗波, 乐长高, 有机化学, 2019, 39, 2345.)
doi: 10.6023/cjoc201903006 pmid: 21915984 |
|
(c) Deshpande, N.; Satani, P.; Bharodiya, A.; Naveen, T. Asian J. Org. Chem. 2022, 11, e202200532.
pmid: 21915984 |
|
(d) Wang, C.; Qi, R.; Wang, R.; Xu, Z. Acc. Chem. Res. 2023, 56, 2110.
pmid: 21915984 |
|
(e) Xu, G.-Q.; Wang, W. D.; Xu, P.-F. J. Am. Chem. Soc. 2024, 146, 1209.
pmid: 21915984 |
|
[6] |
(a) Godula, K.; Sames, D. Science 2006, 312, 67.
pmid: 16601184 |
(b) Bergman, R. G. Nature 2007, 446, 391.
pmid: 16601184 |
|
[7] |
(a) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
pmid: 27701109 |
(b) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
pmid: 27701109 |
|
(c) Salvador, T. K.; Arnett, C. H.; Kundu, S.; Sapiezynski, N. G.; Bertke, J. A.; Raghibi Boroujeni, M.; Warren, T. H. J. Am. Chem. Soc. 2016, 138, 16580.
doi: 10.1021/jacs.6b09057 pmid: 27701109 |
|
(d) Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl, S. S.; Liu, G. Science 2016, 353, 1014.
pmid: 27701109 |
|
(e) Li, J.; Zhang, Z.; Wu, L.; Zhang, W.; Chen, P.; Lin, Z.; Liu, G. Nature 2019, 574, 516.
pmid: 27701109 |
|
[8] |
(a) Jain, P.; Verma, P.; Xia, G.; Yu, J.-Q. Nat. Chem. 2017, 9, 140.
|
(b) Saint-Denis, T. G.; Zhu, R.-Y.; Chen, G.; Wu, Q.-F.; Yu, J.-Q. Science 2018, 359, eaao4798.
|
|
[9] |
San Segundo, M.; Guerrero, I.; Correa, A. Org. Lett. 2017, 19, 5288.
doi: 10.1021/acs.orglett.7b02567 pmid: 28937777 |
[10] |
Jiang, W.; Wang, Y.; Niu, P.; Quan, Z.; Su, Y.; Huo, C. Org. Lett. 2018, 20, 4649.
doi: 10.1021/acs.orglett.8b01941 pmid: 30033734 |
[11] |
Wu, R.; Li, J.; Wang, Y.; Quan, Z.; Su, Y.; Huo, C. Adv. Synth. Catal. 2019, 361, 3436.
|
[12] |
(a) Zhu, Z.-Q.; Xiao, L.-J.; Guo, D.; Chen, X.; Ji, J.-J.; Zhu, X.; Xie, Z.-B.; Le, Z.-G. J. Org. Chem. 2019, 84, 435.
|
(b) Liu, S.; Zhu, Z.-Q.; Hu, Z.-Y.; Tang, J.; Yuan, E. Org. Biomol. Chem. 2021, 19, 1616.
|
|
[13] |
Liang, J.; Fu, Y.; Bao, X.; Ou, L.; Sang, T.; Yuan, Y.; Huo, C. Chem. Commun. 2021, 57, 3014.
|
[14] |
Lu, D.; Cui, J.; Yang, S.; Gong, Y. ACS Catal. 2021, 11, 4288.
|
[15] |
Yu, F.; Yang, S.; Xie, Z.; Lu, D.; Gong, Y. Org. Chem. Front. 2023, 10, 382.
|
[16] |
Song, S.; Cheng, X.; Cheng, S.; Lin, Y.-M.; Gong, L. Chem.-Eur. J. 2023, 29, e202203404.
|
[17] |
Li, Y.; Lu, D.; Gong, Y. Org. Chem. Front. 2023, 10, 2301.
|
[18] |
Sang, T.; Liang, J.; Huang, S.; Guo, G.; Yang, J.; Bao, X.; Huo, C. J. Org. Chem. 2023, 88, 10232.
|
[19] |
Xiang, H.; Ye, Y. ACS Catal. 2024, 14, 522.
|
[20] |
(a) Li, H.; Chen, H.; Zhou, Y.; Huang, J.; Yi, J.; Zhao, H.; Wang, W.; Jing, L. Chem. Asian J. 2020, 15, 555.
|
(b) Zhou, T.; Chen, H.; Liu, Y.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. J. Org. Chem. 2022, 87, 15582.
|
|
(c) Xuan, L.; Du, R.; Lei, P.; Zhao, W.; Tan, L.; Ni, C.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Green Chem. 2022, 24, 9475.
|
|
(d) Lei, P.; Chen, Q.; Chen, H.; Zhou, Y.; Jin, L.; Wang, W.; Chen, F. Chin. J. Org. Chem. 2023, 43, 254 (in Chinese).
|
|
(雷盼盼, 陈沁琳, 陈航, 周洋, 敬林海, 汪伟, 陈芬儿, 有机化学, 2023, 43, 254.)
doi: 10.6023/cjoc202206057 |
|
(e) Zhao, W.; Xuan, L.; Liu, Y.; Yin, J.; Wang, H.; Yan, Q.; Wang, W.; Huang, J.; Chen, F. New J. Chem. 2023, 47, 10744.
|
|
(f) Chen, H.; Zhou, Y.; Lei, P.; Wang, H.; Yan, Q.; Properzi, R.; Wang, W.; Jing, L.; Chen, F. Green Synth. Catal. 2023, 4, 350.
|
|
(g) Liu, Y.; Zhou, T.; Xuan, L.; Lin, Y.; Li, F.; Wang, H.; Lyu, J.; Yan, Q.; Zhou, H.; Wang, W.; Chen, F. Org. Lett. 2023, 25, 8693.
|
|
(h) Chen, B.; Chen, Q.; Liu, Y.; Chen, J.; Zhou, X.; Wang, H.; Yan, Q.; Wang, W.; Cai, Z.; Chen, F. Org. Lett. 2023, 25, 9124.
|
|
(i) Lei, P.; Chen, B.; Zhang, T.; Chen, Q.; Xuan, L.; Wang, H.; Yan, Q.; Wang, W.; Zeng, J.; Chen, F. Org. Chem. Front. 2024, 11, 458.
|
|
(j) Zhou, T.; Zeng, J.; Liu, Y.; Chen, H.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Green Chem. 2024, 26, 1375.
|
|
[21] |
Wang, C.; Guo, M.; Qi, R.; Shang, Q.; Liu, Q.; Wang, S.; Zhao, L.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2018, 57, 15841.
|
[22] |
Xu, Y.; Xu, Z.-J.; Liu, Z.-P.; Lou, H. Org. Chem. Front. 2019, 6, 3902.
|
[23] |
Wang, C.; Qi, R.; Xue, H.; Shen, Y.; Chang, M.; Chen, Y.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2020, 59, 7461.
|
[24] |
Xue, H.; Guo, M.; Wang, C.; Shen, Y.; Qi, R.; Wu, Y.; Xu, Z.; Chang, M. Org. Chem. Front. 2020, 7, 2426.
|
[25] |
Wang, C.; Yu, Y.; Liu, W.-L.; Duan, W.-L. Org. Lett. 2019, 21, 9147.
|
[26] |
Wang, J.; Su, Y.; Quan, Z.; Li, J.; Yang, J.; Yuan, Y.; Huo, C. Chem. Commun. 2021, 57, 1959.
|
[27] |
Zhu, Z.-Q.; Liu, S.; Hu, Z.-Y.; Xie, Z.-B.; Tang, J.; Le, Z.-G. Adv. Synth. Catal. 2021, 363, 2568.
|
[28] |
Zhang, Y.; Jiang, W.; Bao, X.; Qiu, Y.; Yuan, Y.; Yang, C.; Huo, C. Chin. J. Chem. 2021, 39, 3238.
|
[29] |
Wang, J.; Ye, Y.; Sang, T.; Zhou, C.; Bao, X.; Yuan, Y.; Huo, C. Org. Lett. 2022, 24, 7577.
|
[30] |
Yang, S.; Hu, H.; Li, J.-H.; Chen, M. ACS Catal. 2023, 13, 15652.
|
[31] |
He, Y.; Yan, B.; Tao, H.; Zhang, Y.; Li, Y. Org. Biomol. Chem. 2018, 16, 3816.
|
[32] |
Zhang, Y.; Yang, X.; Zhou, H.; Li, S.; Zhu, Y.; Li, Y. Org. Chem. Front. 2018, 5, 2120.
|
[33] |
Zhou, H.; Yang, X.; Li, S.; Zhu, Y.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2018, 16, 6728.
|
[34] |
Natarajan, P.; Chuskit, D.; Priya, Green Chem. 2019, 21, 4406.
|
[35] |
Wang, J.; Li, L.; Guo, Y.; Li, S.; Wang, S.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2020, 18, 8179.
|
[36] |
Xin, H.; Yuan, Z.-H.; Yang, M.; Wang, M.-H.; Duan, X.-H.; Guo, L.-N. Green Chem. 2021, 23, 9549.
|
[37] |
Gao, Y.; Liu, J.; Wei, C.; Li, Y.; Zhang, K.; Song, L.; Cai, L. Nat. Commun. 2022, 13, 7450.
|
[38] |
Yuan, Z.-H.; Xin, H.; Zhang, L.; Gao, P.; Yang, X.; Duan, X.-H.; Guo, L.-N. Green Chem. 2023, 25, 6733.
|
[39] |
Zhu, Z.-Q.; Hu, J.-Y.; Xie, Z.-B.; Le, Z.-G. Chem. Commun. 2024, 60, 106.
|
[40] |
Wang, G.-Z.; Liu, D.-G.; Liu, M.-T.; Fu, Y. Green Chem. 2021, 23, 5082.
|
[41] |
Li, H.; Huang, S.; Wang, Y.; Huo, C. Org. Lett. 2018, 20, 92.
|
[42] |
Wei, Y.; Wang, J.; Wang, Y.; Yao, X.; Yang, C.; Huo, C. Org. Biomol. Chem. 2018, 16, 4985.
|
[43] |
Huang, S.; Bao, X.; Fu, Y.; Zhang, Y.; Quan, Z.; Huo, C. Asian J. Org. Chem. 2020, 9, 925.
|
[44] |
Tian, H.; Xu, W.; Liu, Y.; Wang, Q. Org. Lett. 2020, 22, 5005.
doi: 10.1021/acs.orglett.0c01574 pmid: 32610920 |
[45] |
Che, C.; Li, Y.-N.; Cheng, X.; Lu, Y.-N.; Wang, C.-J. Angew. Chem., Int. Ed. 2021, 60, 4698.
|
[46] |
Che, C.; Lu, Y.-N.; Wang, C.-J. J. Am. Chem. Soc. 2023, 145, 2779.
|
[47] |
Qi, R.; Wang, C.; Huo, Y.; Chai, H.; Wang, H.; Ma, Z.; Liu, L.; Wang, R.; Xu, Z. J. Am. Chem. Soc. 2021, 143, 12777.
|
[48] |
Qi, R.; Wang, C.; Ma, Z.; Wang, H.; Chen, Q.; Liu, L.; Pan, D.; Ren, X.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2022, 61, e202200822.
|
[49] |
Qi, R.; Chen, Q.; Liu, L.; Ma, Z.; Pan, D.; Wang, H.; Li, Z.; Wang, C.; Xu, Z. Nat. Commun. 2023, 14, 3295.
|
[50] |
Ding, Y.-N.; Li, N.; Huang, Y.-C.; An, Y.; Liang, Y.-M. Org. Lett. 2022, 24, 4519.
|
[51] |
Wang, W.; Xuan, L.; Chen, Q.; Fan, R.; Zhao, F.; Dong, J.; Wang, H.; Yan, Q.; Zhou, H.; Chen, F. J. Am. Chem. Soc. 2024, 146, 6307.
|
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[3] | Luwen Zhang, Wei He. Research Progress in C(sp3)—H Functionalization Reaction via Molecular Iodine-Catalyzed Oxidation [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1359-1395. |
[4] | Zhu Zhiqiang, Xiao Lijin, Xie Zongbo, Le Zhanggao. Recent Advances in the α-C(sp3)-H Bond Functionalization of Glycine Derivatives [J]. Chin. J. Org. Chem., 2019, 39(9): 2345-2364. |
[5] | Zhao Liang, Zhou Shengbin, Tong Junhua, Wang Jiang, Liu Hong. Asymmetric Synthesis of 3, 5-Disubstituted Prolines [J]. Chin. J. Org. Chem., 2018, 38(6): 1437-1446. |
[6] | Si Yanyan, Guo Ye, Li Haiyan, Sun Haoyuan, Fang Gemin. Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides [J]. Chin. J. Org. Chem., 2014, 34(3): 450-460. |
[7] | Zhu Hualing, Ban Litong, Shi Jun, Chen Chen, Wei Zhen. Synthesis, Structure and Biological Activities of New 1-Phenyl-3-methyl-4-acyl-2-pyrzolin-5-one Derivatives Modified with Glycylglycine Methyl Ester [J]. Chin. J. Org. Chem., 2013, 33(12): 2631-2636. |
[8] | Chen Jinquan, Kang Tairan, Liu Jinglin, He Long, Liu Quanzhong. Phase Transfer Catalyzed Enantioselective and Diastereoselective Conjugate Additions of Glycinate Imine to Unsaturated Imines Formed in situ from Sulfonylindoles [J]. Chin. J. Org. Chem., 2013, 33(07): 1483-1489. |
[9] | Hui Ailing, Wu Zeyu, Yuan Yuan, Zhou An, Pan Jian. Progress in Synthesis and Antagonistic Activities towards PAFR and GlyR of Ginkgolide Derivatives and Analogs [J]. Chin. J. Org. Chem., 2013, 33(06): 1263-1272. |
[10] | Lu Jinrong, Ju Yong. Organogels Based on Natural Products [J]. Chin. J. Org. Chem., 2013, 33(03): 469-482. |
[11] | Jin Yingxue, Wang Jiachang, Yue Qunfeng, Qu Fengyu, Wei Shuquan, Tan Guanghui. Photoinduced Single Electron Transfer Cyclization Reaction of N-(Amidosilane terminated polybenzylglycine peptide chain)-2,3-naphthalimide [J]. Chin. J. Org. Chem., 2012, 32(07): 1290-1295. |
[12] | Pan Chengxue, Wang Zhongchang, Su Guifa, Zong Xi, Xue Wenbin, Qin Jiangke. Synthesis, Structure and Properties of Ferrocene-Peptide Conjugates CH3O-Fc-NH-ΔPhe-COPh [J]. Chin. J. Org. Chem., 2012, 32(04): 742-746. |
[13] | LIAO Ben-Ren, AN Guo-Cheng, ZHU Jun-Ru, YANG Fan, TANG Jie. Crystallization-Induced Dynamic Kinetic Resolution of Phenylglycine Amide [J]. Chin. J. Org. Chem., 2011, 31(9): 1495-1498. |
[14] | Zhou, Jiadong; Cao, Fei*; Zhang, Xiaolong; Yang, Ying; Ying, Hanjie; Wei, Ping. A Novel Method for the Synthesis of Glutathione Based on a Co-protection Strategy [J]. Chin. J. Org. Chem., 2009, 29(08): 1272-1277. |
[15] |
Li, Yingjun* ; Liu, Jun; Xu, Yongting; Jin, Kun; Sun, Shuqin; Ding, Wangang; Liu, Lijun . Synthesis and Characterization of N,N-Disubstituted Glycine Tetraacetyl Glucosyl Esters [J]. Chin. J. Org. Chem., 2009, 29(02): 302-306. |
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