Citation: Xu Shuanghua, Chen Jun, Chen Jiarong, Xiao Wenjing. Recent Progress in Applications of Cinchona Alkaloids and Their Derivatives in Asymmetric Catalysis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3493-3516. doi: 10.6023/cjoc202007004 shu

Recent Progress in Applications of Cinchona Alkaloids and Their Derivatives in Asymmetric Catalysis

College of Chemistry, Central China Normal University, Wuhan 43007

Corresponding author: Chen Jiarong, chenjiarong@mail.ccnu.edu.cn Xiao Wenjing, wxiao@mail.ccnu.edu.cn
Received Date: 1 July 2020
Revised Date: 1 August 2020
Available Online: 11 August 2020
Fund Project: National Natural Science Foundation of China 91956201National Natural Science Foundation of China 21820102003Project supported by the National Natural Science Foundation of China (Nos. 21820102003, 91956201)

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Cinchona alkaloids widely exist in nature, which have attracted extensive interest of researchers because of their readily availability, biological activity, unique structural properties, and easy modification. With the development of asymmetric synthetic chemistry, cinchona alkaloids and their derivatives have been used as a privileged class of chiral catalysts or ligands in many catalytic asymmetric reactions. In particular, a variety of cinchona alkaloid-derived chiral catalysts and ligands have been developed and applied by organic chemists in catalytic asymmetric synthesis in rencent years. The recent progress made in this field over the past few years is summarized. Moreover, the related reaction mechanisms and future development prospects are also discussed.
- cinchona alkaloids,
- organic catalysts,
- chiral ligands,
- asymmetric synthesis,
- asymmetric catalysis
1. [1]
  Yang, F.; Hanon, S.; Lam, P.; Schweitzer, P. Am. J. Med. 2009, 122, 317. doi: 10.1016/j.amjmed.2008.11.019
2. [2]
  Haas, L. F. J. Neurol., Neurosurg. Psychiatry 1994, 57, 1333. doi: 10.1136/jnnp.57.11.1333
3. [3]
  Rabe, P.; Ackerman, E.; Schneider, W. Chem. Ber. 1907, 40, 3655. doi: 10.1002/cber.190704003157
4. [4]
  Woodward, R. B.; Doering, W. E. J. Am. Chem. Soc. 1945, 67, 860. doi: 10.1021/ja01221a051
5. [5]
  Carter, O. L.; McPhail, A. T.; Sim, G. A. J. Chem. Soc. A 1967, 365.
6. [6]
  Stork, G.; Niu, D.; Fujimoto, R. A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239. doi: 10.1021/ja004325r
7. [7]
  Yeboah, E. O.; Yeboah, S.; Singh, G. Tetrahedron 2011, 67, 1725. doi: 10.1016/j.tet.2010.12.050
8. [8]
  Boratyński, P. J.; Błajet, M. Z; Skarżewsk, J. Textbook of The Alkaloids:Chemistry and Biology, Elsevier, Poland, 2019, p. 29.
9. [9]
  List, B. Angew. Chem., Int. Ed. 2010, 49, 1730. doi: 10.1002/anie.200906900
10. [10]
  MacMillan, D. W. C. Nature 2008, 455, 304. doi: 10.1038/nature07367
11. [11]
  (a) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961.
  (b) Tian, S. K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
  (c) Singh, G.; Yeboah, E. Rep. Org. Chem. 2016, 6, 47.
12. [12]
  Shi, L. M.; Dong, W. W.; Tao, H. Y.; Dong, X. Q.; Wang, C. J. Org. Lett. 2017, 19, 4532. doi: 10.1021/acs.orglett.7b02107
13. [13]
  Shao, Y. D.; He, X. Y.; Han, D. D.; Yang, X. R.; Yao, H. B.; Cheng, D. J. Asian J. Org. Chem. 2019, 8, 2023. doi: 10.1002/ajoc.201900504
14. [14]
  Mukhopadhyay, S.; Pan, S. C. Eur. J. Org. Chem. 2019, 2639.
15. [15]
  Nakamura, S.; Hayama, D.; Miura, M.; Hatanaka, T.; Funahashi, Y. Org. Lett. 2018, 20, 856. doi: 10.1021/acs.orglett.7b04022
16. [16]
  Takata, S.; Endo, Y.; Ullah, M. S.; Itsuno, S. RSC Adv. 2016, 6, 72300. doi: 10.1039/C6RA14535C
17. [17]
  Endo, Y.; Takata, S.; Kumpuga, B. T.; Itsuno, S. ChemistrySelect 2017, 2, 10107. doi: 10.1002/slct.201702010
18. [18]
  Reddy, R. R.; Gudup, S. S.; Ghora, P. Angew. Chem. Int. Ed. 2016, 55, 15115. doi: 10.1002/anie.201607039
19. [19]
  Mondal, K.; Pan, S. C. J. Org. Chem. 2018, 83, 5301. doi: 10.1021/acs.joc.8b00436
20. [20]
  Wu, Y. C.; Jhong, Y.; Lin, H. J.; Swain, S. P.; Tsaia, H. H. G.; Hou, D. R. Adv. Synth. Catal. 2019, 361, 4966. doi: 10.1002/adsc.201900997
21. [21]
  Jiang, H. Y.; Li, Q.; Qi, Q. J.; Yang, C. X.; Zhang, D. Chin. J. Org. Chem. 2018, 38, 825(in Chinese).
22. [22]
  Zhu, W.-R.; Liu, K.; Huang, W.-H.; Huang, W.-J.; Chen, Q.; Weng, J.; Lin, N.; Lu, G. Org. Lett. 2020, 22, 5014. doi: 10.1021/acs.orglett.0c01578
23. [23]
  Zi, Y.; Lange, M.; Schultz, C.; Vilotijevic, I. Angew. Chem. Int. Ed. 2019, 58, 10727. doi: 10.1002/anie.201903392
24. [24]
  Breman, A. C.; Heijden, G. V. D.; Maarseveen, J. H. V.; Ingemann, S.; Hiemstra, H. Chem. Eur. J. 2016, 22, 14247. doi: 10.1002/chem.201601917
25. [25]
  Kumpuga, B. T.; Itsuno, S. Asian J. Org. Chem. 2019, 8, 251. doi: 10.1002/ajoc.201800740
26. [26]
  Tichá, I. C.; Hybelbauerová, S.; Jindřich, J. J. Org. Chem. 2019, 15, 830.
27. [27]
  Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. doi: 10.1021/cr00032a009
28. [28]
  Yang, F.; Zhao, D. B.; Lan, J. B.; Xi, P. H.; Yang, L.; Xiang, S. H.; You, J. S. Angew. Chem. Int. Ed. 2008, 47, 5646. doi: 10.1002/anie.200801766
29. [29]
  Wang, J.; Wang, W. T.; Li, W.; Hu, X. L.; Shen, K.; Tan, C, ; Liu, X. H.; Feng, X. M. Chem. Eur. J. 2009, 15, 11642. doi: 10.1002/chem.200900936
30. [30]
  Su, Z. S.; Li, W. Y.; Wang, J.; Hu, C. W.; Feng, X. M. Chem. Eur. J. 2013, 19, 1637. doi: 10.1002/chem.201202237
31. [31]
  Wang, W. T.; Shen, K.; Hu, X. L.; Wang, J.; Liu, X. H.; Feng, X. M. Synlett 2009, 1655.
32. [32]
  Wang, J.; Li, W.; Liu, Y. L.; Chu, Y. Y.; Lin, L. L.; Liu, X. H.; Feng, X. M. Org. Lett. 2010, 12, 1280. doi: 10.1021/ol100169r
33. [33]
  Shi, J.; Wang, M.; He, L.; Zheng, K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Commun. 2009, 31, 4711.
34. [34]
  Richter, C.; Ranganath, K. V. S.; Glorius, F. Adv. Synth. Catal. 2012, 354, 377. doi: 10.1002/adsc.201100669
35. [35]
  Hartikka, A.; Modin, S. A.; Arvidsson, P. G. Org. Biomol. Chem. 2003, 1, 2522. doi: 10.1039/b304060g
36. [36]
  He, W.; Liu, P.; Zhang, B. L.; Sun, X. L.; Zhang, S. Y. Appl. Organomet. Chem. 2006, 20, 328. doi: 10.1002/aoc.1055
37. [37]
  Hayashi, M.; Shiomi, N.; Funahashi, Y.; Nakamura, S. J. Am. Chem. Soc. 2012, 134, 19366. doi: 10.1021/ja309963w
38. [38]
  Hayashi, M.; Iwanaga, M.; Shiomi, N.; Nakane, D.; Masuda, H.; Nakamura, S. Angew. Chem. Int. Ed. 2014, 53, 8411. doi: 10.1002/anie.201404629
39. [39]
  Yamaji, R.; Iwanaga, M.; Nakamura, S. Chem. Commun. 2016, 52, 7462. doi: 10.1039/C6CC02911F
40. [40]
  Shen, B.; Huang, H. Y.; Bian, G. L.; Zong, H.; Song, L. Chirality 2013, 25, 561. doi: 10.1002/chir.22171
41. [41]
  Liu, M.; Ma, S. J.; Tian, Z. Q.; Wu, H.; Wu, L. L.; Xu, X. F.; Huang, Y. D.; Wang, Y. M. Tetrahedron:Asymmetry 2013, 24, 736. doi: 10.1016/j.tetasy.2013.05.009
42. [42]
  Li, X. T.; Gu, Q. S.; Dong, X. Y.; Meng, X.; Liu, X. Y. Angew. Chem. Int. Ed. 2018, 57, 7668. doi: 10.1002/anie.201804315
43. [43]
  Li, X. T.; Lv, L.; Wang, T.; Zhang, X. H.; Cheng, G. J.; Liu, X. Y. Chem 2020, 6, 1692. doi: 10.1016/j.chempr.2020.03.024
44. [44]
  Tian, Q. Q.; Liu, Y. L.; Wang, X. Y.; Wang, X.; He, W. Eur. J. Org. Chem. 2019, 24, 3850.
45. [45]
  Zielińska, B. M.; Skarżewski, J. Tetrahedron:Asymmetry 2009, 20, 1992. doi: 10.1016/j.tetasy.2009.07.020
46. [46]
  Wei, Y.; Yao, L.; Zhang, B. L.; He, W.; Zhang, S. Y. Tetrahedron 2011, 67, 8552. doi: 10.1016/j.tet.2011.08.076
47. [47]
  Wang, Q. F.; He, W.; Liu, X. Y.; Chen, H.; Qin, X. Y.; Zhang, S. Y. Tetrahedron:Asymmetry 2008, 19, 2447. doi: 10.1016/j.tetasy.2008.10.030
48. [48]
  Sladojevich, F.; Trabocchi, A.; Guarna, A.; Dixon, D. J. J. Am. Chem. Soc. 2011, 133, 1710. doi: 10.1021/ja110534g
49. [49]
  Campa, R.; Dixon, D. J. Angew. Chem. Int. Ed. 2015, 54, 4895. doi: 10.1002/anie.201411852
50. [50]
  Ortin, I.; Dixon, D. J. Angew. Chem. Int. Ed. 2014, 53, 3462. doi: 10.1002/anie.201309719
51. [51]
  Campa, R.; Yamagata, A. D. G.; Ortin, I, Franchino, A.; Thompson, A. L.; Odell, B.; Dixon, D. J. Chem. Commun. 2016, 52, 10632. doi: 10.1039/C6CC04132A
52. [52]
  Manzano, R.; Rubén; Datta, S.; Paton, R.; Dixon, D. J. Angew. Chem. Int. Ed. 2017, 56, 5834. doi: 10.1002/anie.201612048
53. [53]
  Zheng, S. C.; Wang, Q.; Zhu, J. P. Angew. Chem. Int. Ed. 2019, 58, 1494. doi: 10.1002/anie.201812654
54. [54]
  Casarotto, V.; Li, Z. T.; Boucau, J.; Lin, Y. M. Tetrahedron. Lett. 2007, 48, 5561. doi: 10.1016/j.tetlet.2007.05.130
55. [55]
  Yao, L.; Wei, Y.; Wang, P. G.; He, W.; Zhang, S. Y. Tetrahedron 2012, 68, 9119. doi: 10.1016/j.tet.2012.08.029
56. [56]
  Dong, X. Y.; Zhang, Y. F.; Ma, C. L, ; Gu, Q. S.; Wang, F. L.; Li, Z. L.; Jiang, S. P.; Liu, X. Y. Nat. Chem. 2019, 11, 1158. doi: 10.1038/s41557-019-0346-2
57. [57]
  Xia, H. D.; Li, Z. L.; Gu, Q. S.; Dong, X. Y.; Fang, J. H.; Du, X. Y.; Wang, L. L.; Liu, X. Y. Angew. Chem. Int. Ed. 2020, 59, 16926. doi: 10.1002/anie.202006317
58. [58]
  Zhang, Z. H.; Dong, X. Y.; Du, X. Y.; Gu, Q. S.; Li, Z. L.; Liu, X. Y. Nat. Commun. 2019, 10, 5689. doi: 10.1038/s41467-019-13705-1
59. [59]
  Dong, X.-Y.; Cheng, J.-T.; Zhang, Y.-F.; Li, Z.-L.; Zhan, T.-Y.; Chen, J.-J.; Wang, F.-L.; Yang, N.-Y.; Ye, L.; Gu, Q.-S.; Liu, X.-Y. J. Am. Chem. Soc. 2020, 142, 9501. doi: 10.1021/jacs.0c03130
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