N—N单键阻转异构体的催化不对称合成

doi:10.6023/cjoc202212003

摘要/Abstract

N—N单键广泛存在于天然产物和生物活性化合物中. 然而, 由于N—N轴不稳定的刻板印象, N—N单键的阻转异构现象长期以来被忽视. 事实上, N—N单键两端氮原子上的孤对之间存在排斥相互作用, 即电子能垒. 该电子能垒会导致N—N单键的旋转受阻, 从而产生稳定的N—N阻转异构体. 自2021年首次被报道以来, 催化不对称合成N—N阻转异构体迅速发展成为一个新兴领域. 这些反应包括不对称的N—H键功能化、不对称的去对称化和(杂)芳香烃环的阻转异构选择性从头构建. 综述了N—N单键阻转异构体催化不对称合成的最新进展.

关键词: N—N单键, 阻转异构体, 催化不对称合成

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

引用此文

宋亭谕, 李冉, 黄利华, 贾世琨, 梅光建. N—N单键阻转异构体的催化不对称合成[J]. 有机化学, 2023, 43(6): 1977-1990.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 15

Figure 1. C—C, C—X and N—N atropisomers

Scheme 1. Representative molecules bearing an N—N axis and resolution strategy

Scheme 2. Catalytic asymmetric strategies for N—N atropisomers

Scheme 3. Catalytic asymmetric N-allylic alkylation

Scheme 4. Catalytic asymmetric N-acylation

Scheme 5. Catalytic asymmetric N-alkylation

Scheme 6. Sequential catalysis protocol of α-amination and N-alkylation

Scheme 7. Desymmetrization via enantioselective Friedel-Crafts alkylation

Scheme 8. Plausible catalytic cycle

Scheme 9. Desymmetrization via enantioselective C-H arylation

Scheme 10. Atroposelective de novo construction of the pyrrole ring by Shi/Zhang and coworkers

Scheme 11. Plausible mechanism

Scheme 12. Atroposelective de novo construction of the pyrrole ring by Zhao/Yang and coworkers

Scheme 13. Atroposelective de novo construction of the indole ring

Scheme 14. Atroposelective de novo construction of the dual quinazolinone rings

参考文献 37

[1]	Oki, M. Top. Stereochem. 1983, 14, 1.
[2]	(a) Cheng, J. K.; Xiang, S. H.; Tan, B. Acc. Chem. Res. 2022, 55, 2920. doi: 10.1021/acs.accounts.2c00509
	(b) Cheng, J. K.; Xiang, S. H.; Li, S.; Ye, L.; Tan, B. Chem. Rev. 2021, 121, 4805. doi: 10.1021/acs.chemrev.0c01306
	(c) Wang, Y. B.; Tan, B. Acc. Chem. Res. 2018, 51, 534. doi: 10.1021/acs.accounts.7b00602
[3]	(a) Zhang, H. H.; Shi, F. Acc. Chem. Res. 2022, 55, 2562. doi: 10.1021/acs.accounts.2c00465
	(b) Wu, S.; Xiang, S.-H.; Cheng, J. K.; Tan, B. Tetrahedron Chem. 2022, 1, 100009. doi: 10.1016/j.tchem.2022.100009
	(c) Qin, W.; Liu, Y.; Yan, H. Acc. Chem. Res. 2022, 55, 2780. doi: 10.1021/acs.accounts.2c00486
	(d) Bai, X.-F.; Cui, Y.-M.; Cao, J.; Xu, L.-W. Acc. Chem. Res. 2022, 55, 2545. doi: 10.1021/acs.accounts.2c00417
	(e) Zhang, Z.-X.; Zhai, T.-Y.; Ye, L.-W. Chem. Catal. 2021, 1, 1378.
	(f) Song, R.; Xie, Y.; Jin, Z.; Chi, Y. R. Angew. Chem., nt. Ed. 2021, 60, 26026.
	(g) Liu, C. X.; Zhang, W. W.; Yin, S. Y.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2021, 143, 14025. doi: 10.1021/jacs.1c07635
	(h) Feng, J.; Gu, Z. SynOpen 2021, 5, 68. doi: 10.1055/s-0040-1706028
	(i) Da, B. C.; Xiang, S. H.; Li, S.; Tan, B. Chin. J. Chem. 2021, 39, 1787. doi: 10.1002/cjoc.v39.7
[4]	(a) Wu, Y.-J.; Liao, G.; Shi, B.-F. Green Synth. Catal. 2022, 3, 117. pmid: 26414162
	(b) Rodriguez-Salamanca, P.; Fernandez, R.; Hornillos, V.; Lassaletta, J. M. Chem.-Eur. J. 2022, 28, e202104442. pmid: 26414162
	(c) Mei, G.-J.; Koay, W. L.; Guan, C.-Y.; Lu, Y. Chem 2022, 8, 1855. doi: 10.1016/j.chempr.2022.04.011 pmid: 26414162
	(d) Kitagawa, O. Acc. Chem. Res. 2021, 54, 719. doi: 10.1021/acs.accounts.0c00767 pmid: 26414162
	(e) Li, T. Z.; Liu, S. J.; Tan, W.; Shi, F. Chem.-Eur. J. 2020, 26, 15779. doi: 10.1002/chem.v26.68 pmid: 26414162
	(f) Kumarasamy, E.; Raghunathan, R.; Sibi, M. P.; Sivaguru, J. Chem. Rev. 2015, 115, 11239. doi: 10.1021/acs.chemrev.5b00136 pmid: 26414162
[5]	Verma, S. M.; Prasad, R. J. Org. Chem. 1973, 38, 1004. doi: 10.1021/jo00945a031
[6]	Chang, C.; Adams, R. J. Am. Chem. Soc. 1931, 53, 2353. doi: 10.1021/ja01357a049
[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.
	(b) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794. doi: 10.1021/np400124n
[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. doi: 10.1002/ejoc.201200599
	(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.
	(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. doi: 10.1016/S0022-328X(96)06682-X
[10]	(a) Kobayashi, T.; Ishiwari, F.; Fukushima, T.; Hanaya, K.; Sugai, T.; Higashibayashi, S. Eur. J. Org. Chem. 2021, 2021, 449. doi: 10.1002/ejoc.v2021.3
	(b) Rizzo, S.; Menta, S.; Faggi, C.; Pierini, M.; Cirilli, R. J. Chromatogr. A 2014, 1363, 128. doi: 10.1016/j.chroma.2014.08.060
	(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. doi: 10.1016/j.chempr.2021.07.013
[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. doi: 10.1021/jacs.1c07741
[13]	(a) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682. pmid: 12444660
	(b) Terauchi, J.; Curran, D. P. Tetrahedron 2003, 14, 587. pmid: 12444660
	(c) Liu, Y.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 125. doi: 10.1039/C4OB01087F pmid: 12444660
	(d) Gao, Z.; Yan, C.-X.; Qian, J.; Yang, H.; Zhou, P.; Zhang, J.; Jiang, G. ACS Catal. 2021, 11, 6931. doi: 10.1021/acscatal.1c01345 pmid: 12444660
[14]	(a) Li, S. L.; Yang, C.; Wu, Q.; Zheng, H. L.; Li, X.; Cheng, J. P. J. Am. Chem. Soc. 2018, 140, 12836. doi: 10.1021/jacs.8b06014
	(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. doi: 10.1038/s41467-019-10940-4
	(c) Yang, G.-H.; Zheng, H.; Li, X.; Cheng, J.-P. ACS Catal. 2020, 10, 2324. doi: 10.1021/acscatal.9b05443
	(d) Zheng, G.; Li, X.; Cheng, J.-P. Org. Lett. 2021, 23, 3997. doi: 10.1021/acs.orglett.1c01201
	(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. doi: 10.1039/D2QO00219A
[15]	Merad, J.; Pons, J.-M.; Chuzel, O.; Bressy, C. Eur. J. Org. Chem. 2016, 2016, 5589. doi: 10.1002/ejoc.201600399
[16]	(a) Li, D.; Wang, S.; Ge, S.; Dong, S.; Feng, X. Org. Lett. 2020, 22, 5331. doi: 10.1021/acs.orglett.0c01581
	(b) Ong, J. Y.; Ng, X. Q.; Lu, S.; Zhao, Y. Org. Lett. 2020, 22, 6447. doi: 10.1021/acs.orglett.0c02266
	(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. doi: 10.1002/anie.v59.20
[17]	Lin, W.; Zhao, Q.; Li, Y.; Pan, M.; Yang, C.; Yang, G.-H.; Li, X. Chem. Sci. 2022, 13, 141. doi: 10.1039/D1SC05360D
[18]	Shirakawa, S.; Maruoka, K. Angew. Chem.,Int. Ed. 2013, 52, 4312. doi: 10.1002/anie.201206835
[19]	(a) Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916. doi: 10.1021/ja211069f pmid: 28537599
	(b) Jolliffe, J. D.; Armstrong, R. J.; Smith, M. D. Nat. Chem. 2017, 9, 558. doi: 10.1038/nchem.2710 pmid: 28537599
	(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. doi: 10.1002/anie.v58.38 pmid: 28537599
[20]	Pan, M.; Shao, Y.-B.; Zhao, Q.; Li, X. Org. Lett. 2022, 24, 374. doi: 10.1021/acs.orglett.1c04028
[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. pmid: 21731960
	(b) Rendler, S.; Oestreich, M. Angew. Chem., nt. Ed. 2008, 47, 248. pmid: 21731960
	(c) Díaz de Villegas, M. D.; Gálvez, J. A.; Etayo, P.; Badorrey, R.; López-Ram-de-Víu, P. Chem. Soc. Rev. 2011, 40, 5564. doi: 10.1039/c1cs15120g pmid: 21731960
	(d) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330. doi: 10.1021/acs.chemrev.6b00094 pmid: 21731960
[23]	Zhang, L.; Xiang, S. H.; Wang, J. J.; Xiao, J.; Wang, J. Q.; Tan, B. Nat. Commun. 2019, 10, 566. doi: 10.1038/s41467-019-08447-z pmid: 30718716
[24]	(a) Rousseaux, S.; Vrancken, E.; Campagne, J.-M. Angew. Chem., nt. Ed. 2012, 51, 10934. pmid: 26861673
	(b) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. doi: 10.1021/acs.chemrev.5b00547 pmid: 26861673
[25]	(a) Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778. doi: 10.1021/ja206047h pmid: 21848265
	(b) Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. J. Am. Chem. Soc. 2011, 133, 13782. doi: 10.1021/ja206050b pmid: 21848265
	(c) Wu, H.; Wang, Q.; Zhu, J. Angew. Chem., nt. Ed. 2018, 57, 2721. pmid: 21848265
[26]	Xu, Q.; Zhang, H.; Ge, F.-B.; Wang, X.-M.; Zhang, P.; Lu, C.-J.; Liu, R.-R. Org. Lett. 2022, 24, 3138. doi: 10.1021/acs.orglett.2c00812
[27]	Zhang, L.; Zhang, J.; Ma, J.; Cheng, D. J.; Tan, B. J. Am. Chem. Soc. 2017, 139, 1714. doi: 10.1021/jacs.6b09634 pmid: 28106384
[28]	Kamikawa, K.; Arae, S.; Wu, W.-Y.; Nakamura, C.; Takahashi, T.; Ogasawara, M. Chem.-Eur. J. 2015, 21, 4954. doi: 10.1002/chem.201500226 pmid: 25676145
[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. doi: 10.1039/C9SC00810A
[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. doi: 10.1021/jacs.0c00208
[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. doi: 10.1038/ncomms15489
[37]	Pu, L.-Y.; Zhang, Y.-J.; Liu, W.; Teng, F. Chem. Commun. 2022, 58, 13131. doi: 10.1039/D2CC05172A