Chinese Journal of Organic Chemistry >
Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine
Received date: 2022-08-19
Revised date: 2022-10-11
Online published: 2022-10-14
Supported by
National Natural Science Foundation of China(22171147); National Natural Science Foundation of China(21871148); National Natural Science Foundation of China(21672109)
Chiral aza-heterocycles are important molecular skeletons of organic chemistry, which are extensively found in pharmaceuticals, pesticides and biologically active natural products. As a significant organic chemistry research filed, the development of efficient novel synthetic methods of them has been a challenge. Among these strategies for the synthesis of aza-heterocycles compounds, chiral phosphine organocatalysis provides a practical and powerful platform. The recent progress in synthesis of chiral nitrogen heterocycles catalyzed by chiral phosphine is summarized, and the development of this field is also prospected.
Hongxia Ren , Mengmeng Ma , You Huang . Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3129 -3142 . DOI: 10.6023/cjoc202208024
| [1] | Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. |
| [2] | Das, P.; Delost, M. D.; Qureshi, M. H.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2019, 62, 4265. |
| [3] | Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. |
| [4] | Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. |
| [5] | Ye, L.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. |
| [6] | Fan, Y.; Kwon, O. Chem. Commun. 2013, 49, 11588. |
| [7] | Xie, P.; Huang, Y. Eur. J. Org. Chem. 2013, 2013, 6213. |
| [8] | Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578. |
| [9] | Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049. |
| [10] | Ni, H.; Chan, W. L.; Lu, Y. Chem. Rev. 2018, 118, 9344. |
| [11] | Li, E.; Huang, Y. Chem. Commun. 2020, 56, 680. |
| [12] | Chen, S.; Salo, E.; Wheeler, K.; Kerrigan, N. Org. Lett. 2012, 14, 1784. |
| [13] | Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. |
| [14] | Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. |
| [15] | Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141. |
| [16] | Scherer, A.; Gladysz, J. A. Tetrahedron Lett. 2006, 47, 6335. |
| [17] | Fleury-Bregeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron Lett. 2007, 63, 11920. |
| [18] | Pinto, N.; Fleury-Brégeot, N.; Marinetti, A. Eur. J. Org. Chem. 2009, 2009, 146. |
| [19] | Fang, Y.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660. |
| [20] | Takizawa, S.; Inoue, N.; Hirata, S.; Sasai, H. Angew. Chem., Int. Ed. 2010, 49, 9725. |
| [21] | Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510. |
| [22] | Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767. |
| [23] | Yu, Z.; Jin, Z.; Duan, M.; Bai, R.; Lu, Y.; Lan, Y. J. Org. Chem. 2018, 83, 9729. |
| [24] | Cai, L.; Zhang, K.; Kwon, O. J. Am. Chem. Soc. 2016, 138, 3298. |
| [25] | Lundgren, R. J.; Wilsily, A.; Marion, N.; Ma, C.; Chung, Y. K.; Fu, G. C. Angew. Chem., Int. Ed. 2013, 52, 2525. |
| [26] | Wang, Y. Q.; Zhang, Y.; Dong, H.; Zhang, J.; Zhao, J. Eur. J. Org. Chem. 2013, 2013, 3764. |
| [27] | Yu, H.; Zhang, L.; Yang, Z.; Li, Z.; Zhao, Y.; Xiao, Y.; Guo, H. J. Org. Chem. 2013, 78, 8427. |
| [28] | Henry, C.; Xu, Q.; Fan, Y.; Martin, T.; Belding, L.; Dudding, T.; Kwon, O. J. Am. Chem. Soc. 2014, 136, 11890. |
| [29] | Kramer, S.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 3803. |
| [30] | Lee, S.; Fujiwara, Y.; Nishiguchi, A.; Kalek, M.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 4587. |
| [31] | Han, X.; Chan, W.-L.; Yao, W.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2016, 55, 6492. |
| [32] | Sankar, M.; Garcia-Castro, M.; Golz, C.; Strohmann, C.; Kumar, K. RSC Adv. 2016, 6, 56537. |
| [33] | Sankar, M.; Garcia-Castro, M.; Golz, C.; Strohmann, C.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 9709. |
| [34] | Li, E.; Jin, H.; Jia, P.; Dong, X.; Huang, Y. Angew. Chem., Int. Ed. 2016, 55, 11591. |
| [35] | Jin, H.; Zhang, Q.; Li, E.; Jia, P.; Li, N.; Huang, Y. Org. Biomol. Chem. 2017, 15, 7097. |
| [36] | Xing, J.; Lei, Y.; Gao, Y. N.; Shi, M. Org. Lett. 2017, 19, 2382. |
| [37] | Ni, C.; Chen, J.; Zhang, Y.; Hou, Y.; Wang, D.; Tong, X.; Zhu, S. F.; Zhou, Q. Org. Lett. 2017, 19, 3668. |
| [38] | Li, H.; Luo, J.; Li, B.; Yi, X.; He, Z. Org. Lett. 2017, 19, 5637. |
| [39] | Kitagaki, S.; Nakamura, K.; Kawabata, C.; Ishikawa, A.; Takenaga, N.; Yoshida, K. Org. Biomol. Chem. 2018, 16, 1770. |
| [40] | Cheng, Y.; Han, Y.; Li, P. Org. Lett. 2017, 19, 4774. |
| [41] | Cong, T.; Wang, H.; Li, X.; Wu, H.; Zhang, J. Chem. Commun. 2019, 55, 9176. |
| [42] | Wang, C.; Chen, Y.; Li, J.; Zhou, L.; Wang, B.; Xiao, Y.; Guo, H. Org. Lett. 2019, 21, 7519. |
| [43] | Manzano, R.; Romaniega, A.; Prieto, L.; Díaz, E.; Reyes, E.; Uria, U.; Carrillo, L.; Vicario, J. L. Org. Lett. 2020, 22, 4721. |
| [44] | Dai, Z.; Jin, Z. J.; Su, W.; Zeng, W.; Liu, Z.; Chen, M.; Zhou, Q. Org. Lett. 2020, 22, 7008. |
| [45] | Zhou, L.; Zhang, X.; Wang, Q.; Liu, M.; Wang, W.; Wu, Y.; Chen, L.; Guo, H. Org. Lett. 2021, 23, 9173. |
| [46] | Zhu, X.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716. |
| [47] | Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234. |
| [48] | Xiao, H.; Chai, Z.; Wang, H.; Wang, X.; Cao, D.; Liu, W.; Lu, Y.; Yang, Y.; Zhao, G. Chem.-Eur. J. 2011, 17, 10562. |
| [49] | Cowen, B.; Miller, S. J. Am. Chem. Soc. 2007, 129, 10988. |
| [50] | Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726. |
| [51] | Shi, Z.; Tong, Q.; Leong, W.; Zhong, G. Chem.-Eur. J. 2012, 18, 9802. |
| [52] | Shi, Z.; Yu, P.; Loh, T.; Zhong, G. Angew. Chem., Int. Ed. 2012, 51, 7825. |
| [53] | Jin, Z.; Yang, R.; Tiwari, B.; Ganguly, R.; Chi, Y. Org. Lett. 2012, 14, 3226. |
| [54] | Zhang, X.; Chen, G.; Dong, X.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2013, 355, 3351. |
| [55] | Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Suzuki, M.; Sasai, H. Asian J. Org. Chem. 2014, 3, 412. |
| [56] | Yu, H.; Zhang, L.; Li, Z.; Liu, H.; Wang, B.; Xiao, Y.; Guo, H. Tetrahedron 2014, 70, 340. |
| [57] | Zhang, L.; Liu, H.; Qiao, G.; Hou, Z.; Liu, Y.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2015, 137, 4316. |
| [58] | Zhou, L.; Yuan, C.; Zhang, C.; Zhang, L.; Gao, Z.; Wang, C.; Liu, H.; Wu, Y.; Guo, H. Adv. Synth. Catal. 2017, 359, 2316. |
| [59] | Wang, Z.; Xu, H.; Su, Q.; Hu, P.; Shao, P.; He, Y.; Lu, Y. Org. Lett. 2017, 19, 3111. |
| [60] | Zhang, X.; Gan, K.; Liu, X.; Deng, Y.; Wang, F.; Yu, K.; Zhang, J.; Fan, C. Org. Lett. 2017, 19, 3207. |
| [61] | Zhang, Q.; Jin, H.; Feng, J.; Zhu, Y.; Jia, P.; Wu, C.; Huang, Y. Org. Lett. 2019, 21, 1407. |
| [62] | Wang, X.; Lu, M.; Su, Q.; Zhou, M.; Addepalli, Y.; Yao, W.; Wang, Z.; Lu, Y. Chem.-Asian J. 2019, 14, 3409. |
| [63] | Yuan, C.; Zhou, L.; Xia, M.; Sun, Z.; Wang, D.; Guo, H. Org. Lett. 2016, 18, 5644. |
| [64] | Ni, H.; Tang, X.; Zheng, W.; Yao, W.; Ullah, N.; Lu, Y. Angew. Chem., Int. Ed. 2017, 56, 14222. |
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