氮杂环卡宾催化实现的动力学拆分近期研究进展
收稿日期: 2023-08-25
修回日期: 2023-09-30
网络出版日期: 2023-10-26
基金资助
国家自然科学基金(22071242); 国家自然科学基金(21871260); 中国科学院战略重点研究方案(XDB20000000); 福建省自然科学基金(2021J01522)
Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update
Received date: 2023-08-25
Revised date: 2023-09-30
Online published: 2023-10-26
Supported by
National Natural Science Foundation of China(22071242); National Natural Science Foundation of China(21871260); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000); Fujian Provincial Natural Science Foundation(2021J01522)
杨爽 , 房新强 . 氮杂环卡宾催化实现的动力学拆分近期研究进展[J]. 有机化学, 2024 , 44(2) : 448 -480 . DOI: 10.6023/cjoc202308023
Kinetic resolution is one of the most commonly used methods allowing access to enantioenriched compounds. The last two decades have seen the rapid development of kinetic resolutions enabled by N-heterocyclic carbene catalysis, and part of the achievements have been summarized in our previous review paper published in 2017. Since then, a series of new advances have been realized, and this review will provide an update of this field covering reports from mid-2017 to 2023.
| [1] | (a) Kagan, H. B.; Fiaud, J. C.In Kinetic Resolution, Topics in Stereochemistry, Eds.: Eliel, E. L.; Wilen, S. H., Wiley, New York, 1988, pp. 249-330. |
| [1] | (b) Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers. Racemates, and Resolutions, Wiley, New York, 1981. |
| [2] | (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249. |
| [2] | (b) Kagan H. B. Tetrahedro. 2001, 57, 2449. |
| [2] | (c) Faber K. Chem.-Eur. J. 2001, 7, 5004. |
| [2] | (d) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5. |
| [2] | (e) Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407. |
| [2] | (f) Vedejs, E.; Jure, M. Angew. Chem.. Int. Ed. 2005, 44, 3974. |
| [2] | (g) Pellissier H. Adv. Synth. Catal. 2011, 353, 1613. |
| [2] | (h) Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471. |
| [2] | (i) Pellissier H. In Separation of Enantiomers: Synthetic Methods, 1st ed, Ed.: Todd, M., Wiley-VCH, Weinheim, 2014, pp. 75-122. |
| [2] | (j) Ma, G.; Sibi, M. P. Chem.-Eur. J. 2015, 21, 11644. |
| [2] | (k) Petersen K. S. Asian J. Org. Chem. 2016, 5, 308. |
| [2] | (l) Gurubrahamam, R.; Cheng, Y.-S.; Huang, W.-Y.; Chen, K. ChemCatChe. 2016, 8, 86. |
| [2] | (m) Kreituss, I.; Bode, J. W. Acc. Chem. Res. 2016, 49, 2807. |
| [2] | (n) Yang, H.; Zheng, W.-H. Tetrahedron Lett. 2018, 59, 583. |
| [2] | (o) Pellissier H. Tetrahedro. 2018, 74, 3459. |
| [2] | (o) Harwood, L. A.; Wong, L. L.; Robertson, J. Angew. Chem.. Int. Ed. 2021, 60, 4434. |
| [2] | (q) Chen, Y.; Liu, W.; Yang, X. Chin. J. Org. Chem. 2022, 42, 679 (in Chinese). |
| [2] | (陈运荣, 刘炜, 杨晓瑜, 有机化学. 2022, 42, 679.) |
| [2] | (p) Ding, B.; Xue, Q.; Jia, S.; Cheng, H.-G.; Zhou, Q. Synthesi. 2022, 54, 1721. |
| [2] | (s) Peng, T.; Li, S.; Yang, D.; Wang, L. Org. Chem. Front. 2023, 10, 3401. |
| [2] | (t) Li, H.; Yin, L. Chin. J. Org. Chem. 2022, 42, 3183 (in Chinese). |
| [2] | (李晖, 殷亮, 有机化学. 2022, 42, 3183.) |
| [2] | (u) Liu, H.; Shen, C.; Chang, X.; Wang, C. Chin. J. Org. Chem. 2022, 42, 3322. (in Chinese). |
| [2] | (刘华超, 沈冲, 常鑫, 王春江, 有机化学. 2022, 42, 3322.) |
| [2] | (v) Liu, W.; Wang, D.; Zhang, D.; Yang, X. Synlet. 2022, 33, 1788. |
| [3] | (a) Ward R. S. Tetrahedron: Asymmetr. 1995, 6, 1475. |
| [3] | (b) Pellissier H. Tetrahedro. 2003, 59, 8291. |
| [3] | (c) Pellissier H. Tetrahedro. 2008, 64, 1563. |
| [3] | (d) Pellissier H. Chirality from Dynamic Kinetic Resolution. Royal Society of Chemistry, Cambridge, 2011. |
| [3] | (e) Pellissier H. Tetrahedro. 2011, 67, 3769. |
| [3] | (f) Pellissier H. Adv. Synth. Catal. 2011, 353, 659. |
| [3] | (g) Nakano, K.; Kitamura, M. In Separation of Enantiomers: Synthetic Methods, 1st ed, Ed.: Todd, M., Wiley-VCH, Weinheim, 2014, p. 161. |
| [3] | (h) Pellissier H. Tetrahedro. 2016, 72, 3133. |
| [3] | (i) Li, P.; Hu, X.; Dong, X.-Q.; Zhang, X. Molecule. 2016, 21, 1327. |
| [3] | (j) Liu, W.; Yang, X. Asian J. Org. Chem. 2021, 10, 692. |
| [3] | (k) Pellissier H. Eur. J. Org. Chem. 2022, e202101561. |
| [4] | Millera, L. C.; Sarpong, R. Chem. Soc. Rev. 2011, 40, 4550. |
| [5] | (a) Zeitler K. Angew. Chem.. Int. Ed. 2005, 44, 7506. |
| [5] | (b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606. |
| [5] | (c) Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336. |
| [5] | (d) Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem.. Int. Ed. 2012, 51, 11686. |
| [5] | (e) Douglas, J.; Churchill, G.; Smith, A. D. Synthesi. 2012, 44, 2295. |
| [5] | (f) Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53. |
| [5] | (g) Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906. |
| [5] | (h) De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.- Eur. J. 2013, 19, 4664. |
| [5] | (i) Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696. |
| [5] | (j) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Natur. 2014, 510, 485. |
| [5] | (k) Chauhan, P.; Enders, D. Angew. Chem.. Int. Ed. 2014, 53, 1485. |
| [5] | (l) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307. |
| [5] | (m) Wang, M. H.; Scheidt, K. A. Angew. Chem.. Int. Ed. 2016, 55, 14912 |
| [5] | (n) Chen, X.-Y.; Liu, Q.; Chauhan, P.; Enders, D. Angew. Chem.. Int. Ed. 2018, 57, 3862. |
| [5] | (o) Wang, J.; Zhao, C.; Wang, J. ACS Catal. 2021, 11, 12520. |
| [5] | (p) Song, R.; Xie, Y.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2021, 60, 2. |
| [5] | (q) Li, Q.-Z.; Zeng, R.; Han, B.; Li, J.-L. Chem.-Eur. J. 2021, 27, 3238. |
| [5] | (r) Song, R.; Jin, Z.; Chi, Y. R. Chem. Sci. 2021, 12, 5037. |
| [5] | (s) Marzo L. Eur. J. Org. Chem. 2021, 4603. |
| [5] | (t) Zhang, B.; Yang, G.; Guo, D.; Wang, J. Org. Chem. Front. 2022, 9, 5016. |
| [5] | (u) Sharma, D.; Chatterjee, R.; Dhayalan, V.; Dandela, R. Synthesi. 2022, 54, 4129. |
| [5] | (v) Liu, Y.; Wang, Y.; Wu, X.; Chi, Y. R. Chem. Rec. 2023, 23, e202200219. |
| [5] | (w) Yang, X.; Zhang, Y.; Li, T.; Jin, Z. Adv. Synth. Catal. 2023, 365, 1756. |
| [5] | (x) Nie, G.; Li, T. Asian J. Org. Chem. 2023, 12, e202200680. |
| [5] | (y) Li, Q.-Z.; Kou, X.-X.; Qi, T.; Li, J.-L. ChemCatChe. 2023, 15, e202201320. |
| [5] | (z) De Risi, C.; Brandolese, A.; Di Carmine, G.; Ragno, D.; Massi, A.; Bortolini, O. Chem.-Eur. J. 2023, 29, e202202467. |
| [6] | (a) Yang, S.; Fang, X. Curr. Org. Synth. 2017, 14, 654. |
| [6] | (b) Wang, Z.; Pan, D.; Li, T.; Jin, Z. Chem. Asian J. 2018, 13, 2149. |
| [6] | (c) Chen, S.; Shi, Y.-H.; Wang, M. Chem. Asian J. 2018, 13, 2184. |
| [6] | (d) Risi, C. D.; Bortolini, O.; Di Carmine, G.; Ragno, D.; Massi, A. Synthesi. 2019, 51, 1871. |
| [7] | Dong, S.; Frings, M.; Zhang, D.; Guo, Q.; Daniliuc, C. G.; Cheng, H.; Bolm, C. Chem.-Eur. J. 2017, 23, 13888. |
| [8] | Liu, B.; Yan, J.; Huang, R.; Wang, W.; Jin, Z.; Zanoni, G.; Zheng, P.; Yang, S.; Chi, Y. R. Org. Lett. 2018, 20, 3447. |
| [9] | Bie, J.; Lang, M.; Wang, J. Org. Lett. 2018, 20, 5866. |
| [10] | Zhao, C.; Wang, J. Adv. Synth. Catal. 2019, 361, 1668. |
| [11] | Lu, S.; Poh, S. B.; Rong, Z.-Q.; Zhao, Y. Org. Lett. 2019, 21, 6169. |
| [12] | Yang, G.; Guo, D.; Meng, D.; Wang, J. Nat. Commun. 2019, 10, 3062. |
| [13] | Yuan, H.; Du, Y.; Liu, F.; Guo, L.; Sun, Q.; Feng, L.; Gao, H. Chem. Commun. 2020, 56, 8226. |
| [14] | Liu, Y.; Majhi, P. K.; Song, R.; Mou, C.; Hao, L.; Chai, H.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2020, 59, 3859. |
| [15] | Gao, Y.-Y.; Zhang, C.-L.; Dai, L.; Han, Y.-F.; Ye, S. Org. Lett. 2021, 23, 1361. |
| [16] | (a) Chen, X.; Fong, J. Z. M.; Xu, J.; Mou, C.; Lu, Y.; Yang, S.; Song, B.-A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7212. |
| [16] | (b) Liu, B.; Song, R.; Xu, J.; Majhi, P. K.; Yang, X.; Yang, S.; Jin, Z.; Chi, Y. R. Org. Lett. 2020, 22, 3335. |
| [17] | Brandolese, A.; Ragno, D.; Leonardi, C.; Di Carmine, G.; Bortolini, O.; De Risi, C.; Massi, A. Eur. J. Org. Chem. 2020, 16, 2439. |
| [18] | Porey, A.; Mondal, B. D.; Guin, J. Angew. Chem.. Int. Ed. 2021, 60, 8786-8791. |
| [19] | Yang, X.; Majhi, P. K.; Chai, H.; Liu, B.; Sun, J.; Liu, T.; Liu, Y.; Zhou, L.; Xu, J.; Liu, J.; Wang, D.; Zhao, Y.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2021, 60, 159. |
| [20] | Guo, D.; Peng, Q.; Zhang, B.; Wang, J. Org. Lett. 2021, 23, 7765. |
| [21] | Liu, J.; Zhou, M.; Deng, R.; Zheng, P.; Chi, Y. R. Nat. Commun. 2022, 13, 4793. |
| [22] | Wang, Y.; Yamauchi, A.; Hashimoto, K.; Fujiwara, T.; Inokuma, T.; Mitani, Y.; Ute, K.; Kuwano, S.; Yamaoka, Y.; Takasu, K.; Yamada, K.-I. ACS Catal. 2022, 12, 6100. |
| [23] | Yamada, K.-I.; Yamauchi, A.; Fujiwara, T.; Hashimoto, K.; Wang, Y.; Kuwano, S.; Inokuma, T. Asian J. Org. Chem. 2022, 11, e202200452. |
| [24] | Zhu, P.; Li, W.; Lan, J.; Zhu, T. Nat. Commun. 2023, 13, 3827. |
| [25] | Zhang, G.; Xu, W.; Liu, J.; Das, D. K.; Yang, S.; Perveen, S.; Zhang, H.; Li, X.; Fang, X. Chem. Commun. 2017, 53, 13336. |
| [26] | Chen, X.-Y.; Li, S.; Liu, Q.; Kumar, M.; Peuronen, A.; Rissanen, K.; Enders, D. Chem.-Eur. J. 2018, 24, 9735. |
| [27] | Chen, K.-Q.; Gao, Z.-H.; Ye, S. Angew. Chem.. Int. Ed. 2019, 58, 1183. |
| [28] | (a) Cano, R.; Zakarian, A.; McGlacken, G. P. Angew. Chem.. Int. Ed. 2017, 56, 9278. |
| [28] | (b) Janey J. M. Angew. Chem.. Int. Ed. 2005, 44, 4292. |
| [28] | (c) Smith, A. M. R.; Hii, K. K. M. Chem. Rev. 2011, 111, 1637. |
| [29] | Liu, J.; Vasamsetty, L.; Anwar, M.; Yang, S.; Xu, W.; Liu, J.; Nagaraju, S.; Fang, X. ACS Catal. 2020, 10, 2882. |
| [30] | Vasamsetty, L.; Kong, X.; Meng, M.; Yang, S.; Xu, W.; Reddy, P. S.; Fang, X. Chem. Asian J. 2018, 13, 3838. |
| [31] | Zhao, Z.; Yang, S.; Lan, S.; Liu, J.; Liu, S.; Fang, X. Adv. Synth. Catal. 2019, 361, 3943. |
| [32] | Zehra, S. T.; Zhang, G.; Yang, S.; Fang X. Org. Biomol. Chem. 2019, 17, 2169. |
| [33] | Xu, W.; Li, Y.; Liu, R.; Yang, S.; Liu, J.; Fang, X. Org. Chem. Front. 2019, 6, 290. |
| [34] | Perveen, S.; Yang, S.; Meng, M.; Xu, W.; Zhang, G.; Fang, X. Commun. Chem. 2019, 2, 8. |
| [35] | Lv, Y.; Luo, G.; Liu, Q.; Jin, Z.; Zhang, X.; Chi, Y. R. Nat. Commun. 2022. 13, 36. |
| [36] | Mondal, S.; Mukherjee, S.; Das, T. K.; Gonnade, R.; Biju, A. T. ACS Catal. 2017, 7, 3995. |
| [37] | Lv, J.; Xu, J.; Pan, X.; Jin, Z.; Chi, Y. R. Sci. China Chem. 2021, 64, 985. |
| [38] | Wang, M. H.; Barsoum, D.; Schwamb, C. B.; Cohen, D. T.; Goess, B. C.; Riedrich, M.; Chan, A.; Maki, B. E.; Mishra, R. K.; Scheidt, K. A. J. Org. Chem. 2017, 82, 4689. |
| [39] | Bhattacharya, A.; mani Shukla, P.; Kaushika, L. K.; Maji, B. Org. Chem. Front. 2019, 6, 3523. |
| [40] | Zhang, Z.-J.; Wen, Y.-H.; Song, J.; Gong, L.-Z. Angew. Chem.. Int. Ed. 2021, 60, 3268. |
| [41] | (a) Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472. |
| [41] | (b) Chen, X.-Y.; Ye, S. Org. Biomol. Chem. 2013, 11, 7991. |
| [42] | Scott, L.; Nakano, Y.; Zhang, C.; Lupton, D. W. Angew. Chem.. Int. Ed. 2018, 57, 10299. |
/
| 〈 |
|
〉 |