基于甘氨酸衍生物α-C(sp3)—H官能团化的催化体系研究进展
收稿日期: 2024-03-03
修回日期: 2024-03-29
网络出版日期: 2024-05-11
基金资助
湖北省重点研发计划(2023BCB055); 湖北省教育厅科研计划(Q20211503)
Recent Advances of the Catalysis Systems in the α-C(sp3)—H Functionalization of Glycine Derivatives
Received date: 2024-03-03
Revised date: 2024-03-29
Online published: 2024-05-11
Supported by
Key Research and Development Program of Hubei Province(2023BCB055); Scientific Research Project of Education Department of Hubei Province(Q20211503)
α-氨基酸是组成蛋白质的基本结构单元, 应用范围非常广泛, 它不仅能用于许多生物活性分子的合成、药物化学和材料工业中, 还可作为有机催化剂或配体用于各类化合物的不对称合成中. 甘氨酸作为最普遍且具有潜手性的α-氨基酸, 在有机合成领域是一类非常重要的合成砌块, 利用甘氨酸衍生物或多肽的α-C(sp3)—H官能团化, 高效构建结构多样性的非天然α-氨基酸或多肽引起了越来越多科研工作者的关注. 对近五年来甘氨酸衍生物α-C(sp3)—H官能团化领域所取得的研究进展进行了综述, 根据不同类型的催化体系进行了分类讨论, 并对该领域所面临的挑战和机遇进行了展望和探讨.
关键词: α-氨基酸; 催化体系; C(sp3)—H官能团化; 甘氨酸; 多肽
宣良明 , 赵伟 , 范润东 , 严琼姣 , 汪伟 , 陈芬儿 . 基于甘氨酸衍生物α-C(sp3)—H官能团化的催化体系研究进展[J]. 有机化学, 2024 , 44(9) : 2700 -2721 . DOI: 10.6023/cjoc202403004
α-Amino acids are essential components of proteins, which are not only widely used in biologically active compound syntheses, medicinal chemistry, and the materials industry, but also are useful as organic catalysts or ligands for asymmetric synthesis. Glycines are the most fundamental and sole achiral α-amino acids, and are particularly useful building blocks in organic synthesis. Direct α-C(sp3)—H functionalization of glycine derivatives or peptides to construct unnatural α-amino acids or peptides has attracted tremendous attention of many scholars in recent decades. The research progress of the α-C(sp3)—H functionalization of glycine derivatives is reviewed during the past five years. The catalysis systems are systematically discussed, and the challenges and opportunities of this field are included.
Key words: a-amino acids; catalysis systems; C(sp3)—H functionalization; glycine; peptides
| [1] | (a) Albericio, F.; Kruger, H. G. Future Med. Chem. 2012, 4, 1527. |
| [1] | (b) Xiao, H.; Chatterjee, A.; Choi, S.-H.; Bajjuri, K. M.; Sinha, S. C.; Schultz, P. G. Angew. Chem., Int. Ed. 2013, 52, 14080. |
| [1] | (c) Lang, K.; Chin, J. W. Chem. Rev. 2014, 114, 4764. |
| [1] | (d) Blaskovich, M. A. T. J. Med. Chem. 2016, 59, 10807. |
| [1] | (e) Rémond, E.; Martin, C.; Martinez, J.; Cavelier, F. Chem. Rev. 2016, 116, 11654. |
| [1] | (f) Mei, P.; Zhang, Y.; Feng, X. Acta Chim. Sinica 2020, 78, 1041 (in Chinese). |
| [1] | (梅佩, 张媛媛, 冯霄, 化学学报, 2020, 78, 1041.) |
| [1] | (g) Zhou, Y.; Chen, H.; Lei, P.; Gui, C.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Chin. Chem. Lett. 2022, 33, 4850. |
| [1] | (h) Gui, C.; Peng, Y.; Zhou, Y.; Zheng, Y.; Wang, H.; Yan, Q.; Zhou, H.; Wang, W.; Chen, F. ACS Catal. 2023, 13, 13735. |
| [2] | (a) Chaloner, P. A. J. Organomet. Chem. 1987, 337, 431. |
| [2] | (b) Higham, J. I.; Bull, J. A. Org. Biomol. Chem. 2020, 18, 7291. |
| [3] | (a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27. |
| [3] | (b) Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8. |
| [3] | (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. |
| [4] | (b) Bayer, A.; Kazmaier, U. J. Org. Chem. 2014, 79, 8491. |
| [5] | (a) Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429. |
| [5] | (b) Zhu, Z.-Q.; Xiao, L.-J.; Xie, Z.-B.; Le, Z.-G. Chin. J. Org. Chem. 2019, 39, 2345 (in Chinese). |
| [5] | (祝志强, 肖利金, 谢宗波, 乐长高, 有机化学, 2019, 39, 2345.) |
| [5] | (c) Deshpande, N.; Satani, P.; Bharodiya, A.; Naveen, T. Asian J. Org. Chem. 2022, 11, e202200532. |
| [5] | (d) Wang, C.; Qi, R.; Wang, R.; Xu, Z. Acc. Chem. Res. 2023, 56, 2110. |
| [5] | (e) Xu, G.-Q.; Wang, W. D.; Xu, P.-F. J. Am. Chem. Soc. 2024, 146, 1209. |
| [6] | (a) Godula, K.; Sames, D. Science 2006, 312, 67. |
| [6] | (b) Bergman, R. G. Nature 2007, 446, 391. |
| [7] | (a) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. |
| [7] | (b) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780. |
| [7] | (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. |
| [7] | (d) Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl, S. S.; Liu, G. Science 2016, 353, 1014. |
| [7] | (e) Li, J.; Zhang, Z.; Wu, L.; Zhang, W.; Chen, P.; Lin, Z.; Liu, G. Nature 2019, 574, 516. |
| [8] | (a) Jain, P.; Verma, P.; Xia, G.; Yu, J.-Q. Nat. Chem. 2017, 9, 140. |
| [8] | (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. |
| [10] | Jiang, W.; Wang, Y.; Niu, P.; Quan, Z.; Su, Y.; Huo, C. Org. Lett. 2018, 20, 4649. |
| [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. |
| [12] | (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. |
| [20] | (b) Zhou, T.; Chen, H.; Liu, Y.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. J. Org. Chem. 2022, 87, 15582. |
| [20] | (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. |
| [20] | (d) Lei, P.; Chen, Q.; Chen, H.; Zhou, Y.; Jin, L.; Wang, W.; Chen, F. Chin. J. Org. Chem. 2023, 43, 254 (in Chinese). |
| [20] | (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.) |
| [20] | (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. |
| [20] | (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. |
| [20] | (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. |
| [20] | (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. |
| [20] | (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. |
| [20] | (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. |
| [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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