Citation: Xu Ronghua, Yang He, Tang Wenjun. Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1409-1422. doi: 10.6023/cjoc202003015 shu

Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands

Xu Ronghua ^a ,
Yang He ^c,, ,
Tang Wenjun ^a,b,d,,

a.
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210
b.
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032
c.
Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, Guangdong 518055
d.
School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Corresponding author: Yang He, yanghe@sioc.ac.cn Tang Wenjun, tangwenjun@sioc.ac.cn
Received Date: 6 March 2020
Revised Date: 6 April 2020
Available Online: 17 April 2020
Fund Project: the National Natural Science Foundation of China 21432007the National Natural Science Foundation of China 21725205the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000Project supported by the National Natural Science Foundation of China (Nos. 21725205, 21432007, 21572246), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000) and the K. C. Wong Education Foundationthe National Natural Science Foundation of China 21572246

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Development of efficient and practical asymmetric catalytic reactions plays a pivotal role for the concise syntheses of chiral drugs. Chiral ligands and catalysts are crucial for the selectivity and reactivity of the catalytic reactions. In this account, the design and development of a series of P-chiral mono- and bis-phosphorus ligands were summarized based on a benzooxaphosphane backbone and their applications in the synthesis of chiral drugs. Beside their P-chirality, these ligands are structurally rigid, sterically bulky, and electron-rich, providing good physical properties and tunabilities. Facilitated by these chiral ligands, a series of efficient and practical reactions including asymmetric hydrogenation, asymmetric cross-coupling, asymmetric cyclization, and asymmetric nucleophilic additions have been developed. The excellent conversions, yields, regioselectivities, enantioselectivities, and broad substrate scope have enabled concise and efficient syntheses of a series of chiral drugs.
- chiral phosphorus ligands,
- transition metal catalysis,
- asymmetric synthesis,
- enantioselectivity,
- chiral drugs
1. [1]
  Lin, G. Q.; Wang, M. X. Chiral Synthesis and Chiral Drugs, Chemical Industry Press, Beijing, 2008, pp. 1~4 (in Chinese).
2. [2]
  Lin, G. Q.; Sun, X. W.; Chen, Y. Q.; Li, Y. M.; Chen, X. Z. Chiral Synthesis-Asymmetric Reactions and Their Applications, Science Press, Beijing, 2013, pp. 36~38 (in Chinese).
3. [3]
  Tang, W; Zhang, X. Chem. Rev. 2003, 103, 3029. doi: 10.1021/cr020049i
4. [4]
  Tang, W. In Proceedings of the 11th National Conference on Natural Organic Chemistry of the Chinese Chemical Society, Volume 1, Shanghai, 2019, p. 71 (in Chinese).
5. [5]
  (a) Xu, G.; Senanayake, C. H; Tang, W. Acc. Chem. Res. 2019, 52, 1601.
  (b) Wu, T.; Xu, G.; Tang, W. Aldrichim. Acta 2020, 53, 27.
  (c) Tang, W.; Li, K. Strem Chem. 2019, XXXI, 1.
6. [6]
  Liu, G.; Liu, X.; Cai, Z.; Jiao, G.; Xu, G.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 42359.
7. [7]
  Li, C.; Wan, F; Chen, Y.; Peng, H.; Tang, W.; Yu, S.; McWilliams, H. C.; Mustakis, J.; Samp, L.; Maguire, R. J. Angew. Chem., Int. Ed. 2019, 58, 13573. doi: 10.1002/anie.201908089
8. [8]
  Daniella M. S.; Yuka K.; Alejandro V.; Michael W.; Massimo G.; John J. O. Nat. Rev. Drug Discovery 2017, 16, 843. doi: 10.1038/nrd.2017.201
9. [9]
  Patil, Y. S.; Bonde, N. L.; Kekan, A. S.; Sathe, D. G.; Das, A. Org. Process Res. Dev. 2014, 18, 1714. doi: 10.1021/op500274j
10. [10]
  Zhu, J.; Huang, L.; Dong, W.; Li, N.; Yu, X.; Deng, W.; Tang, W. Angew. Chem., Int. Ed. 2019, 58, 16119. doi: 10.1002/anie.201910008
11. [11]
  Rottmann, M.; McNamara, C.; Yeung, B. K. S. Science 2010, 329, 1175. doi: 10.1126/science.1193225
12. [12]
  Huang, L.; Zhu, J.; Jiao, G.; Wang, Z.; Yu, X.; Deng, W.; Tang W. Angew. Chem., Int. Ed. 2016, 55, 4527. doi: 10.1002/anie.201600979
13. [13]
  Dhillon, S.; Scott, L. J.; Plosker, G. L. CNS Drugs 2006, 20, 763. doi: 10.2165/00023210-200620090-00010
14. [14]
  Yang, H.; Tang, W. Chem. Rec. 2020, 20, 23. doi: 10.1002/tcr.201900003
15. [15]
  Cao, Z.; Du, K.; Liu, J. H.; Tang, W. Tetrahedron 2016, 72, 1782. doi: 10.1016/j.tet.2016.02.043
16. [16]
  Li, B.; Li, T.; Aliyu, M. A.; Li, Z.; Tang, W. Angew. Chem., Int. Ed. 2019, 58, 11355. doi: 10.1002/anie.201905174
17. [17]
  Dodou, K.; Anderson, R. J.; Lough, W. J.; Small, D. A. P.; Shelley, M. D.; Groundwater, P. W. Bioorg. Med. Chem. 2005, 13, 4228. doi: 10.1016/j.bmc.2005.04.026
18. [18]
19. [19]
  Yang, H.; Sun, J.; Gu, W.; Tang, W. J. Am. Chem. Soc. 2020, 142, 8036. doi: 10.1021/jacs.0c02686
20. [20]
  Lu, Y.; Dong, C.; Huang, J.; Zhou, H.; Wang, W. Future Med. Chem. 2017, 9, 1243. doi: 10.4155/fmc-2017-0046
21. [21]
  Fandrick, K. R.; Li, W.; Zhang, Y.; Tang, W.; Gao, J.; Rodriguez, S.; Patel, N. D.; Reeves, D. C.; Wu, J.-P.; Sanyal, S.; Gonnella, N.; Qu, B.; Haddad, N.; Lorenz, J. C.; Sidhu, K.; Wang, J.; Ma, S.; Grinberg, N.; Lee, H.; Tsantrizos, Y.; Poupart, M.-A.; Busacca, C. A.; Yee, N. K.; Lu, B. Z.; Senanayake, C. H. Angew. Chem., Int. Ed. 2015, 54, 7144. doi: 10.1002/anie.201501575
22. [22]
  Haddad, N.; Mangunuru, H. P. R.; Fandrick, K. R.; Qu, B.; Sieber, J. D.; Rodriguez, S.; Desrosiers, J. N.; Patel, N. D.; Lee, H.; Kurouski, D.; Grinberg, N.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Adv. Synth. Catal. 2016, 358, 3522. doi: 10.1002/adsc.201600889
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