C—N轴手性化合物的不对称催化合成研究进展
收稿日期: 2023-08-13
修回日期: 2023-09-30
网络出版日期: 2023-10-30
基金资助
国家自然科学基金(22271065)
Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds
Received date: 2023-08-13
Revised date: 2023-09-30
Online published: 2023-10-30
Supported by
National Natural Science Foundation of China(22271065)
陈宛婷 , 钟雄威 , 邢佳乐 , 吴昌书 , 高杨 . C—N轴手性化合物的不对称催化合成研究进展[J]. 有机化学, 2024 , 44(2) : 349 -377 . DOI: 10.6023/cjoc202308012
Enantioenriched C—N axial chiral compounds are ubiquitous in many important field, such as natural products, chiral drugs and chiral ligands. Therefore, efficient construction of C—N axis chirality through asymmetric catalytic synthesis has attracted more and more attention and research interest. In this review, the recent progress in asymmetric synthesis of C—N axis chiral compounds has been discussed, mainly from three aspects: desymmetrization of prochiral molecules or kinetic resolution of racemates, atroposelective functionalization of C—N axis, and atroposelective C—N coupling reaction. The topic focuses on the evolution of asymmetric catalytic system and the key factors of chiral control. The existing problems and future development direction of this field are also discussed. This paper is a timely and systematic review and will stimulate more extensive research interest.
| [1] | (a) Cheng, J. K.; Xiang, S.-H.; Li, S.; Ye, L.; Tan, B. Chem. Rev. 2021, 121, 4805. |
| [1] | (b) Cheng, J. K.; Xiang, S.-H.; Tan, B. Acc. Chem. Res. 2022, 55, 2920. |
| [1] | (c) Da, B.; Xiang, S.; Li, S.; Tan, B. Chin. J. Chem. 2021, 39, 1787. |
| [1] | (d) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534. |
| [2] | (a) Kitagawa O. Acc. Chem. Res. 2021, 54, 719. |
| [2] | (b) Shi, B.-F.; Colobert, F. Chem. Catal. 2021, 1, 485. |
| [3] | Wu, Y.-J.; Liao, G.; Shi, B.-F. Green Synth. Catal. 2022, 3, 117. |
| [4] | (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131. |
| [4] | (b) Duan, W.-L.; Imazaki, Y.; Shintani, R.; Hayashi, T. Tetrahedro. 2007, 63, 8529. |
| [5] | Wang, J.; Chen, H.; Kong, L.; Wang, F.; Lan, Y.; Li, X. ACS Catal. 2021, 11, 9151. |
| [6] | Wang, J.; Li, X. Sci. China Chem. 2023, 66, 2046. |
| [7] | Sun, F.; Wang, T.; Cheng, G.-J.; Fang, X. ACS Catal. 2021, 11, 7578. |
| [8] | Gu, X.-W.; Sun, Y.-L.; Xie, J.-L.; Wang, X.-B.; Xu, Z.; Yin, G.-W.; Li, L.; Yang, K.-F.; Xu, L.-W. Nat. Commun. 2020, 11, 2904. |
| [9] | Liu, H.-C.; Tao, H.-Y.; Cong, H.; Wang, C.-J. J. Org. Chem. 2016, 81, 3752. |
| [10] | (a) Di Iorio, N.; Righi, P.; Mazzanti, A.; Mancinelli, M.; Ciogli, A.; Bencivenni, G. J. Am. Chem. Soc. 2014, 136, 10250. |
| [10] | (b) Eudier, F.; Righi, P.; Mazzanti, A.; Ciogli, A.; Bencivenni, G. Org. Lett. 2015, 17, 1728. |
| [10] | (c) Mondal, S.; Mukherjee, S. Org. Lett. 2022, 24, 8300. |
| [11] | (a) Di Iorio, N.; Champavert, F.; Erice, A.; Righi, P.; Mazzanti, A.; Bencivenni, G. Tetrahedro. 2016, 72, 5191. |
| [11] | (b) Di Iorio, N.; Soprani, L.; Crotti, S.; Marotta, E.; Mazzanti, A.; Righi, P.; Bencivenni, G. Synthesi. 2017, 49, 1519. |
| [12] | Zhang, J.; Zhang, Y.; Lin, L.; Yao, Q.; Liu, X.; Feng, X. Chem. Commun. 2015, 51, 10554. |
| [13] | (a) Zhuo, S.; Zhu, T.; Zhou, L.; Mou, C.; Chai, H.; Lu, Y.; Pan, L.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2019, 58, 1784. |
| [13] | (b) Barik, S.; Shee, S.; Das, S.; Gonnade, R. G.; Jindal, G.; Mukherjee, S.; Biju, A. T. Angew. Chem.. Int. Ed. 2021, 60, 12264. |
| [14] | Jin, J.; Huang, X.; Xu, J.; Li, T.; Peng, X.; Zhu, X.; Zhang, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2021, 23, 3991. |
| [15] | Zhang, J.-W.; Xu, J.-H.; Cheng, D.-J.; Shi, C.; Liu, X.-Y.; Tan, B. Nat. Commun. 2016, 7, 10677. |
| [16] | Zhang, L.-L.; Zhang, J.-W.; Xiang, S.-H.; Guo, Z.; Tan, B. Org. Lett. 2018, 20, 6022. |
| [17] | Zhang, L.; Xiang, S.-H.; Wang, J.; Xiao, J.; Wang, J.-Q.; Tan, B. Nat. Commun. 2019, 10, 566. |
| [18] | Dai, L.; Zhou, X.; Guo, J.; Dai, X.; Huang, Q.; Lu, Y. Nat. Commun. 2023, 14, 4813. |
| [19] | Hirai, M.; Terada, S.; Yoshida, H.; Ebine, K.; Hirata, T.; Kitagawa, O. Org. Lett. 2016, 18, 5700. |
| [20] | (a) Diener, M. E.; Metrano, A. J.; Kusano, S.; Miller, S. J. J. Am. Chem. Soc. 2015, 137, 12369. |
| [20] | (b) Crawford, J. M.; Stone, E. A.; Metrano, A. J.; Miller, S. J.; Sigman, M. S. J. Am. Chem. Soc. 2018, 140, 868. |
| [21] | Vaidya, S. D.; Toenjes, S. T.; Yamamoto, N.; Maddox, S. M.; Gustafson, J. L. J. Am. Chem. Soc. 2020, 142, 2198. |
| [22] | Kim, A.; Kim, A.; Park, S.; Kim, S.; Jo, H.; Ok, K. M.; Lee, S. K.; Song, J.; Kwon, Y. Angew. Chem.. Int. Ed. 2021, 60, 12279. |
| [23] | Bie, J.; Lang, M.; Wang, J. Org. Lett. 2018, 20, 5866. |
| [24] | (a) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682. |
| [24] | (b) Kitagawa, O.; Takahashi, M.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2003, 68, 9851. |
| [24] | (c) Liu, Y.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 125. |
| [24] | (d) Kikuchi, Y.; Nakamura, C.; Matsuoka, M.; Asami, R.; Kitagawa, O. J. Org. Chem. 2019, 84, 8112. |
| [24] | (e) Gao, Z.; Yan, C.-X.; Qian, J.; Yang, H.; Zhou, P.; Zhang, J.; Jiang, G. ACS Catal. 2021, 11, 6931. |
| [25] | Li, S.-L.; Yang, C.; Wu, Q.; Zheng, H.-L.; Li, X.; Cheng, J.-P. J. Am. Chem. Soc. 2018, 140, 12836. |
| [26] | Yang, G.-H.; Zheng, H.; Li, X.; Cheng, J.-P. ACS Catal. 2020, 10, 2324. |
| [27] | (a) Kitagawa, O.; Takahashi, M.; Yoshikawa, M.; Taguchi, T. J. Am. Chem. Soc. 2005, 127, 3676. |
| [27] | (b) Kitagawa, O.; Yoshikawa, M.; Tanabe, H.; Morita, T.; Takahashi, M.; Dobashi, Y.; Taguchi, T. J. Am. Chem. Soc. 2006, 128, 12923. |
| [27] | (c) Chen, L.-P.; Chen, J.-F.; Zhang, Y.-J.; He, X.-Y.; Han, Y.-F.; Xiao, Y.-T.; Lv, G.-F.; Lu, X.; Teng, F.; Sun, Q.; Li, J.-H. Org. Chem. Front. 2021, 8, 6067. |
| [28] | (a) Li, D.; Wang, S.; Ge, S.; Dong, S.; Feng, X. Org. Lett. 2020, 22, 5331. |
| [28] | (b) Ong, J.-Y.; Ng, X. Q.; Lu, S.; Zhao, Y. Org. Lett. 2020, 22, 6447. |
| [29] | Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916. |
| [30] | (a) Yao, Q.-J.; Xie, P.-P.; Wu, Y.-J.; Feng, Y.-L.; Teng, M.-Y.; Hong, X.; Shi, B.-F. J. Am. Chem. Soc. 2020, 142, 18266. |
| [30] | (b) Jia, Z.-S.; Wu, Y.-J.; Yao, Q.-J.; Xu, X.-T.; Zhang, K.; Shi, B.-F. Org. Lett. 2022, 24, 304. |
| [30] | (c) Wu, Y.-J.; Xie, P.-P.; Zhou, G.; Yao, Q.-J.; Hong, X.; Shi, B.-F. Chem. Sci. 2021, 12, 9391. |
| [31] | Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956. |
| [32] | (a) Zhang, J.; Xu, Q.; Wu, J.; Fan, J.; Xie, M. Org. Lett. 2019, 21, 6361. |
| [32] | (b) Dhawa, U.; Wdowik, T.; Hou, X.; Yuan, B.; Oliveira, J. C. A.; Ackermann, L. Chem. Sci. 2021, 12, 14182. |
| [33] | Wang, L.; Yuan, W.; Wang, Z.; Luo, J.; Zhou, T.; Shi, B. Chin. J. Chem. 2023, 41, 2788. |
| [34] | Mi, R.; Ding, Z.; Yu, S.; Crabtree, R. H.; Li, X. J. Am. Chem. Soc. 2023, 145, 8150. |
| [35] | (a) Takahashi, I.; Morita, F.; Kusagaya, S.; Fukaya, H.; Kitagawa, O. Tetrahedron: Asymmetry 2012, 23, 1657. |
| [35] | (b) Hirata, T.; Takahashi, I.; Suzuki, Y.; Yoshida, H.; Hasegawa, H.; Kitagawa, O. J. Org. Chem. 2016, 81, 318. |
| [35] | (c) Zhang, P.; Wang, X.; Xu, Q.; Guo, C.; Wang, P.; Lu, C.; Liu, R. Angew. Chem.. Int. Ed. 2021, 60, 21718. |
| [35] | (d) Zhang, P.; Guo, C.-Q.; Yao, W.; Lu, C.-J.; Li, Y.; Paton, R. S.; Liu, R.-R. ACS Catal. 2023, 13, 7680. |
| [36] | Fan, X.; Zhang, X.; Li, C.; Gu, Z. ACS Catal. 2019, 9, 2286. |
| [37] | Liu, Z.-S.; Xie, P.-P.; Hua, Y.; Wu, C.; Ma, Y.; Chen, J.; Cheng, H.-G.; Hong, X.; Zhou, Q. Che. 2021, 7, 1917. |
| [38] | (a) Ototake, N.; Morimoto, Y.; Mokuya, A.; Fukaya, H.; Shida, Y.; Kitagawa, O. Chem.-Eur. J. 2010, 16, 6752. |
| [38] | (b) Wang, Z.; Zhu, L.; Li, C.; Liu, B.; Hong, X.; Ye, L. Angew. Chem.. Int. Ed. 2022, 61, e202201436. |
| [39] | Liu, H.; Feng, W.; Kee, C. W.; Leow, D.; Loh, W.-T.; Tan, C.-H. Adv. Synth. Catal. 2010, 352, 3373. |
| [40] | Mishra, K.; Guyon, D.; San Martin, J.; Yan, Y. J. Am. Chem. Soc. 2023, 145, 17242. |
| [41] | Arunachalampillai, A.; Chandrappa, P.; Cherney, A.; Crockett, R.; Doerfler, J.; Johnson, G.; Kommuri, V. C.; Kyad, A.; McManus, J.; Murray, J.; Myren, T.; Fine Nathel, N.; Ndukwe, I.; Ortiz, A.; Reed, M.; Rui, H.; Silva Elipe, M. V.; Tedrow, J.; Wells, S.; Yacoob, S.; Yamamoto, K. Org. Lett. 2023, 25, 5856. |
| [42] | Sun, L.; Chen, H.; Liu, B.; Chang, J.; Kong, L.; Wang, F.; Lan, Y.; Li, X. Angew. Chem.. Int. Ed. 2021, 60, 8391. |
| [43] | Wang, P.; Wu, H.; Zhang, X.-P.; Huang, G.; Crabtree, R. H.; Li, X. J. Am. Chem. Soc. 2023, 145, 8417. |
| [44] | Wang, B.; Xu, G.; Huang, Z.; Wu, X.; Hong, X.; Yao, Q.; Shi, B. Angew. Chem.. Int. Ed. 2022, 61, e202208912. |
| [45] | Zhang, L.; Zhang, J.; Ma, J.; Cheng, D.-J.; Tan, B. J. Am. Chem. Soc. 2017, 139, 1714. |
| [46] | Wang, L.; Zhong, J.; Lin, X. Angew. Chem.. Int. Ed. 2019, 58, 15824. |
| [47] | (a) Kwon, Y.; Chinn, A. J.; Kim, B.; Miller, S. J. Angew. Chem.. Int. Ed. 2018, 57, 6251. |
| [47] | (b) Kwon, Y.; Li, J.; Reid, J. P.; Crawford, J. M.; Jacob, R.; Sigman, M. S.; Toste, F. D.; Miller, S. J. J. Am. Chem. Soc. 2019, 141, 6698. |
| [48] | Man, N.; Lou, Z.; Li, Y.; Yang, H.; Zhao, Y.; Fu, H. Org. Lett. 2020, 22, 6382. |
| [49] | Min, C.; Lin, Y.; Seidel, D. Angew. Chem.. Int. Ed. 2017, 56, 15353. |
| [50] | Wang, Y.-B.; Zheng, S.-C.; Hu, Y.-M.; Tan, B. Nat. Commu. 2017, 8, 15489. |
| [51] | Li, T.; Mou, C.; Qi, P.; Peng, X.; Jiang, S.; Hao, G.; Xue, W.; Yang, S.; Hao, L.; Chi, Y. R.; Jin, Z. Angew. Chem.. Int. Ed. 2021, 60, 9362. |
| [52] | Wang, L.; Li, S.; Blümel, M.; Philipps, A. R.; Wang, A.; Puttreddy, R.; Rissanen, K.; Enders, D. Angew. Chem.. Int. Ed. 2016, 55, 11110. |
| [53] | An, Q.; Xia, W.; Ding, W.; Liu, H.; Xiang, S.; Wang, Y.; Zhong, G.; Tan, B. Angew. Chem.. Int. Ed. 2021, 60, 24888. |
| [54] | Augé, M.; Feraldi-Xypolia, A.; Barbazanges, M.; Aubert, C.; Fensterbank, L.; Gandon, V.; Kolodziej, E.; Ollivier, C. Org. Lett. 2015, 17, 3754. |
| [55] | Li, H.; Yan, X.; Zhang, J.; Guo, W.; Jiang, J.; Wang, J. Angew. Chem.. Int. Ed. 2019, 58, 6732. |
| [56] | (a) Wang, F.; Jing, J.; Zhao, Y.; Zhu, X.; Zhang, X.; Zhao, L.; Hu, P.; Deng, W.; Li, X. Angew. Chem.. Int. Ed. 2021, 60, 16628. |
| [56] | (b) Wang, P.; Huang, Y.; Jing, J.; Wang, F.; Li, X. Org. Lett. 2022, 24, 2531. |
| [56] | (c) Zhu, X.; Mi, R.; Yin, J.; Wang, F.; Li, X. Chem. Sci. 2023, 14, 7999. |
| [57] | Zhou, L.; Li, Y.; Li, S.; Shi, Z.; Zhang, X.; Tung, C.-H.; Xu, Z. Chem. Sci. 2023, 14, 5182. |
| [58] | (a) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586. |
| [58] | (b) Oppenheimer, J.; Hsung, R. P.; Figueroa, R.; Johnson, W. L. Org. Lett. 2007, 9, 3969. |
| [58] | (c) Oppenheimer, J.; Johnson, W. L.; Figueroa, R.; Hayashi, R.; Hsung, R. P. Tetrahedro. 2009, 65, 5001. |
| [59] | Rae, J.; Frey, J.; Jerhaoui, S.; Choppin, S.; Wencel-Delord, J.; Colobert, F. ACS Catal. 2018, 8, 2805. |
| [60] | Frey, J.; Malekafzali, A.; Delso, I.; Choppin, S.; Colobert, F.; Wencel-Delord, J. Angew. Chem.. Int. Ed. 2020, 59, 8844. |
| [61] | (a) Sun, C.; Qi, X.; Min, X.-L.; Bai, X.-D.; Liu, P.; He, Y. Chem. Sci. 2020, 11, 10119. |
| [61] | (b) Zhang, X.; Gu, J.; Cui, W.; Ye, Z.; Yi, W.; Zhang, Q.; He, Y. Angew. Chem.. Int. Ed. 2022, 61, e202210456. |
| [61] | (c) Zou, J.; Yang, Y.; Gu, J.; Liu, F.; Ye, Z.; Yi, W.; He, Y. Angew. Chem.. Int. Ed. 2023, 62, e202310320. |
| [61] | (d) Wu, Y.-X.; Liu, Q.; Zhang, Q.; Ye, Z.; He, Y. Cell Rep. Phys. Sci. 2022, 3, 101005. |
| [61] | (e) Zhang, X.-L.; Qi, X.; Wu, Y.-X.; Liu, P.; He, Y. Cell Rep. Phys. Sci. 2021, 2, 100594. |
| [62] | (a) Brandes, S.; Bella, M.; Kj?rsgaard, A.; J?rgensen, K.A. Angew. Chem.. Int. Ed. 2006, 118, 1165. |
| [62] | (b) Bai, H.-Y.; Tan, F.-X.; Liu, T.-Q.; Zhu, G.-D.; Tian, J.-M.; Ding, T.-M.; Chen, Z.-M.; Zhang, S.-Y. Nat. Commun. 2019, 10, 3063. |
| [63] | Xia, W.; An, Q.; Xiang, S.; Li, S.; Wang, Y.; Tan, B. Angew. Chem.. Int. Ed. 2020, 59, 6775. |
| [64] | Qin, J.; Zhou, T.; Zhou, T.; Tang, L.; Zuo, H.; Yu, H.; Wu, G.; Wu, Y.; Liao, R.; Zhong, F. Angew. Chem.. Int. Ed. 2022, 61, e202205159. |
| [65] | Guo, C.; Lu, C.; Zhan, L.; Zhang, P.; Xu, Q.; Feng, J.; Liu, R. Angew. Chem.. Int. Ed. 2022, 61, e202212846. |
| [66] | (a) Ren, Q.; Cao, T.; He, C.; Yang, M.; Liu, H.; Wang, L. ACS Catal. 2021, 11, 6135. |
| [66] | (b) Niu, C.; Zhou, Y.; Chen, Q.; Zhu, Y.; Tang, S.; Yu, Z.-X.; Sun, J. Org. Lett. 2022, 24, 7428. |
/
| 〈 |
|
〉 |