Chinese Journal of Organic Chemistry >
Catalytic Asymmetric Synthesis of N—N Atropisomers
Received date: 2022-12-03
Revised date: 2023-01-05
Online published: 2023-01-18
Supported by
Natural Science Foundation of Henan Province(222300420084); Natural Science Foundation of Henan Province(222300420292); China Postdoctoral Science Foundation(2022M712862); Cultivating Fund Project of Zhengzhou University(JC22261005)
The N—N bond is widely found in natural products and bioactive compounds. The atropisomerism of N—N bond, however, has been dismissed for a long time due to the stereotype that N—N axis is unstable. The electronic barrier stemming from the repulsive interaction between the lone pairs on the two nitrogen atoms leads to a rotationally hindered axis, resulting in stable N—N atropisomers. Since the first report in 2021, the catalytic asymmetric synthesis of N—N atropisomers has been developed rapidly into an emerging area. These reactions include asymmetric N—H bond functionalization, asymmetric desymmetrization and atroposelective de novo construction of (hetero-)aromatic rings. The N—N axially chiral compounds are valuable molecules, in terms of their potential application in chiral ligand/catalysts design and biological activity evaluation. Herein, the state-of-the-art catalytic asymmetric synthesis of N—N atropisomers is summarized.
Key words： N—N bond; atropisomer; catalytic asymmetric synthesis
Tingyu Song , Ran Li , Lihua Huang , Shikun Jia , Guangjian Mei . Catalytic Asymmetric Synthesis of N—N Atropisomers[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 1977 -1990 . DOI: 10.6023/cjoc202212003
| [1] | Oki, M. Top. Stereochem. 1983, 14, 1. |
| [2] | (a) Cheng, J. K.; Xiang, S. H.; Tan, B. Acc. Chem. Res. 2022, 55, 2920. |
| [2] | (b) Cheng, J. K.; Xiang, S. H.; Li, S.; Ye, L.; Tan, B. Chem. Rev. 2021, 121, 4805. |
| [2] | (c) Wang, Y. B.; Tan, B. Acc. Chem. Res. 2018, 51, 534. |
| [3] | (a) Zhang, H. H.; Shi, F. Acc. Chem. Res. 2022, 55, 2562. |
| [3] | (b) Wu, S.; Xiang, S.-H.; Cheng, J. K.; Tan, B. Tetrahedron Chem. 2022, 1, 100009. |
| [3] | (c) Qin, W.; Liu, Y.; Yan, H. Acc. Chem. Res. 2022, 55, 2780. |
| [3] | (d) Bai, X.-F.; Cui, Y.-M.; Cao, J.; Xu, L.-W. Acc. Chem. Res. 2022, 55, 2545. |
| [3] | (e) Zhang, Z.-X.; Zhai, T.-Y.; Ye, L.-W. Chem. Catal. 2021, 1, 1378. |
| [3] | (f) Song, R.; Xie, Y.; Jin, Z.; Chi, Y. R. Angew. Chem., nt. Ed. 2021, 60, 26026. |
| [3] | (g) Liu, C. X.; Zhang, W. W.; Yin, S. Y.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2021, 143, 14025. |
| [3] | (h) Feng, J.; Gu, Z. SynOpen 2021, 5, 68. |
| [3] | (i) Da, B. C.; Xiang, S. H.; Li, S.; Tan, B. Chin. J. Chem. 2021, 39, 1787. |
| [4] | (a) Wu, Y.-J.; Liao, G.; Shi, B.-F. Green Synth. Catal. 2022, 3, 117. |
| [4] | (b) Rodriguez-Salamanca, P.; Fernandez, R.; Hornillos, V.; Lassaletta, J. M. Chem.-Eur. J. 2022, 28, e202104442. |
| [4] | (c) Mei, G.-J.; Koay, W. L.; Guan, C.-Y.; Lu, Y. Chem 2022, 8, 1855. |
| [4] | (d) Kitagawa, O. Acc. Chem. Res. 2021, 54, 719. |
| [4] | (e) Li, T. Z.; Liu, S. J.; Tan, W.; Shi, F. Chem.-Eur. J. 2020, 26, 15779. |
| [4] | (f) Kumarasamy, E.; Raghunathan, R.; Sibi, M. P.; Sivaguru, J. Chem. Rev. 2015, 115, 11239. |
| [5] | Verma, S. M.; Prasad, R. J. Org. Chem. 1973, 38, 1004. |
| [6] | Chang, C.; Adams, R. J. Am. Chem. Soc. 1931, 53, 2353. |
| [7] | (a) Reddy, P. S.; Bhavani, A. K. D. In Advances in Heterocyclic Chemistry, Vol. 114, Eds.: Scriven, E. F. V.; Ramsden, C. A., Academic Press, 2015, p. 271. |
| [7] | (b) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794. |
| [8] | (a) Zhang, Q.; Mándi, A.; Li, S.; Chen, Y.; Zhang, W.; Tian, X.; Zhang, H.; Li, H.; Zhang, W.; Zhang, S.; Ju, J.; Kurtán, T.; Zhang, C. Eur. J. Org. Chem. 2012, 2012, 5256. |
| [8] | (b) Xu, Z.; Baunach, M.; Ding, L.; Hertweck, C. Angew. Chem., nt. Ed. 2012, 51, 10293. |
| [9] | (a) Antognazza, P.; Benincori, T.; Mazzoli, S.; Sannicolo, F.; Pilati, T. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144, 405. |
| [9] | (b) Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T.; Zotti, G. J. Organomet. Chem. 1997, 529, 445. |
| [10] | (a) Kobayashi, T.; Ishiwari, F.; Fukushima, T.; Hanaya, K.; Sugai, T.; Higashibayashi, S. Eur. J. Org. Chem. 2021, 2021, 449. |
| [10] | (b) Rizzo, S.; Menta, S.; Faggi, C.; Pierini, M.; Cirilli, R. J. Chromatogr. A 2014, 1363, 128. |
| [10] | (c) Coogan, M. P.; Smart, E.; Hibbs, D. E. Chem. Commun. 1999, 1991. |
| [11] | Mei, G.-J.; Wong, J. J.; Zheng, W.; Nangia, A. A.; Houk, K. N.; Lu, Y. Chem 2021, 7, 2743. |
| [12] | Wang, X. M.; Zhang, P.; Xu, Q.; Guo, C. Q.; Zhang, D. B.; Lu, C. J.; Liu, R. R. J. Am. Chem. Soc. 2021, 143, 15005. |
| [13] | (a) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682. |
| [13] | (b) Terauchi, J.; Curran, D. P. Tetrahedron 2003, 14, 587. |
| [13] | (c) Liu, Y.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 125. |
| [13] | (d) Gao, Z.; Yan, C.-X.; Qian, J.; Yang, H.; Zhou, P.; Zhang, J.; Jiang, G. ACS Catal. 2021, 11, 6931. |
| [14] | (a) Li, S. L.; Yang, C.; Wu, Q.; Zheng, H. L.; Li, X.; Cheng, J. P. J. Am. Chem. Soc. 2018, 140, 12836. |
| [14] | (b) Lu, S.; Ng, S. V. H.; Lovato, K.; Ong, J. Y.; Poh, S. B.; Ng, X. Q.; Kurti, L.; Zhao, Y. Nat. Commun. 2019, 10, 3061. |
| [14] | (c) Yang, G.-H.; Zheng, H.; Li, X.; Cheng, J.-P. ACS Catal. 2020, 10, 2324. |
| [14] | (d) Zheng, G.; Li, X.; Cheng, J.-P. Org. Lett. 2021, 23, 3997. |
| [14] | (e) Xiao, X.; Lu, Y.-J.; Tian, H.-Y.; Zhou, H.-J.; Li, J.-W.; Yao, Y.-P.; Ke, M.-L.; Chen, F.-E. Org. Chem. Front. 2022, 9, 2830. |
| [15] | Merad, J.; Pons, J.-M.; Chuzel, O.; Bressy, C. Eur. J. Org. Chem. 2016, 2016, 5589. |
| [16] | (a) Li, D.; Wang, S.; Ge, S.; Dong, S.; Feng, X. Org. Lett. 2020, 22, 5331. |
| [16] | (b) Ong, J. Y.; Ng, X. Q.; Lu, S.; Zhao, Y. Org. Lett. 2020, 22, 6447. |
| [16] | (c) Munday, E. S.; Grove, M. A.; Feoktistova, T.; Brueckner, A. C.; Walden, D. M.; Young, C. M.; Slawin, A. M. Z.; Campbell, A. D.; Cheong, P. H.-Y.; Smith, A. D. Angew. Chem.,Int. Ed. 2020, 59, 7897. |
| [17] | Lin, W.; Zhao, Q.; Li, Y.; Pan, M.; Yang, C.; Yang, G.-H.; Li, X. Chem. Sci. 2022, 13, 141. |
| [18] | Shirakawa, S.; Maruoka, K. Angew. Chem.,Int. Ed. 2013, 52, 4312. |
| [19] | (a) Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916. |
| [19] | (b) Jolliffe, J. D.; Armstrong, R. J.; Smith, M. D. Nat. Chem. 2017, 9, 558. |
| [19] | (c) Wang, Y. B.; Wu, Q. H.; Zhou, Z. P.; Xiang, S. H.; Cui, Y.; Yu, P.; Tan, B. Angew. Chem.,Int. Ed. 2019, 58, 13443. |
| [20] | Pan, M.; Shao, Y.-B.; Zhao, Q.; Li, X. Org. Lett. 2022, 24, 374. |
| [21] | Portolani, C.; Centonze, G.; Luciani, S.; Pellegrini, A.; Righi, P.; Mazzanti, A.; Ciogli, A.; Sorato, A.; Bencivenni, G. Angew. Chem., nt. Ed. 2022, 61, e202209895. |
| [22] | (a) García-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313. |
| [22] | (b) Rendler, S.; Oestreich, M. Angew. Chem., nt. Ed. 2008, 47, 248. |
| [22] | (c) Díaz de Villegas, M. D.; Gálvez, J. A.; Etayo, P.; Badorrey, R.; López-Ram-de-Víu, P. Chem. Soc. Rev. 2011, 40, 5564. |
| [22] | (d) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330. |
| [23] | Zhang, L.; Xiang, S. H.; Wang, J. J.; Xiao, J.; Wang, J. Q.; Tan, B. Nat. Commun. 2019, 10, 566. |
| [24] | (a) Rousseaux, S.; Vrancken, E.; Campagne, J.-M. Angew. Chem., nt. Ed. 2012, 51, 10934. |
| [24] | (b) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. |
| [25] | (a) Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778. |
| [25] | (b) Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. J. Am. Chem. Soc. 2011, 133, 13782. |
| [25] | (c) Wu, H.; Wang, Q.; Zhu, J. Angew. Chem., nt. Ed. 2018, 57, 2721. |
| [26] | Xu, Q.; Zhang, H.; Ge, F.-B.; Wang, X.-M.; Zhang, P.; Lu, C.-J.; Liu, R.-R. Org. Lett. 2022, 24, 3138. |
| [27] | Zhang, L.; Zhang, J.; Ma, J.; Cheng, D. J.; Tan, B. J. Am. Chem. Soc. 2017, 139, 1714. |
| [28] | Kamikawa, K.; Arae, S.; Wu, W.-Y.; Nakamura, C.; Takahashi, T.; Ogasawara, M. Chem.-Eur. J. 2015, 21, 4954. |
| [29] | Zhang, H.-H.; Wang, C.-S.; Li, C.; Mei, G.-J.; Li, Y.; Shi, F. Angew. Chem., nt. Ed. 2017, 56, 116. |
| [30] | Hu, Y.-L.; Wang, Z.; Yang, H.; Chen, J.; Wu, Z.-B.; Lei, Y.; Zhou, L. Chem. Sci. 2019, 10, 6777. |
| [31] | Ma, C.; Jiang, F.; Sheng, F.-T.; Jiao, Y.; Mei, G.-J.; Shi, F. Angew. Chem., nt. Ed. 2019, 58, 3014. |
| [32] | Ma, C.; Sheng, F. T.; Wang, H. Q.; Deng, S.; Zhang, Y. C.; Jiao, Y.; Tan, W.; Shi, F. J. Am. Chem. Soc. 2020, 142, 15686. |
| [33] | Chen, K.-W.; Chen, Z.-H.; Yang, S.; Wu, S.-F.; Zhang, Y.-C.; Shi, F. Angew. Chem., nt. Ed. 2022, 61, e202116829. |
| [34] | Gao, Y.; Wang, L.-Y.; Zhang, T.; Yang, B.-M.; Zhao, Y. Angew. Chem., nt. Ed. 2022, 61, e202200371. |
| [35] | Zhang, P.; Xu, Q.; Wang, X.-M.; Feng, J.; Lu, C. J.; Li, Y.; Liu, R. R. Angew. Chem., nt. Ed. 2022, 61, e202212101. |
| [36] | Wang, Y. B.; Zheng, S. C.; Hu, Y. M.; Tan, B. Nat. Commun. 2017, 8, 15489. |
| [37] | Pu, L.-Y.; Zhang, Y.-J.; Liu, W.; Teng, F. Chem. Commun. 2022, 58, 13131. |
/
| 〈 |
|
〉 |
