Citation: Guang Xu, Cuiju Zhu, Xiang Li, Kexin Zhu, Hao Xu. Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones[J]. Chinese Chemical Letters, ;2025, 36(4): 110114. doi: 10.1016/j.cclet.2024.110114 shu

Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones

Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan 430079, China

hao.xu@ccnu.edu.cn

Received Date: 12 February 2024
Revised Date: 3 June 2024
Accepted Date: 12 June 2024
Available Online: 13 June 2024

Figures(5)

An enantioselective catalytic method for the direct [4 + 1] annulation of yne–allylic acetates with pyrazolones has been realized by a copper-catalyzed remote strategy. A variety of enantioenriched spiropyrazolones are rapidly accessed in high yields with moderate to good enantiocontrol. The facile follow-up transformations highlight its potential utility in the synthesis of diverse spiropyrazolones building blocks.
- Asymmetric catalysis,
- Copper catalysis,
- Yne-allylic esters,
- Spiropyrazolones
1. [1]
  E. Amata, N.D. Bland, R.K. Campbell, M.P. Pollastri, Tetrahedron Lett. 56 (2015) 2832–2835. doi: 10.1016/j.tetlet.2015.04.061
2. [2]
  H. Zou, Z.L. Wang, Y. Cao, G. Huang, Chin. Chem. Lett. 29 (2018) 1355–1358. doi: 10.1016/j.cclet.2017.10.034
3. [3]
  W. Luo, B. Shao, J. Li, et al., Org. Chem. Front. 7 (2020) 1016–1021. doi: 10.1039/d0qo00140f
4. [4]
  S. Zhang, G. Xu, H. Yan, et al., Chin. Chem. Lett. 33 (2022) 5128–5131. doi: 10.1016/j.cclet.2022.04.006
5. [5]
  X. Han, W. Yao, T. Wang, et al., Angew. Chem. Int. Ed. 53 (2014) 5643–5647. doi: 10.1002/anie.201311214
6. [6]
  D. Hack, A.B. Dürr, K. Deckers, et al., Angew. Chem. Int. Ed. 55 (2016) 1797–1800. doi: 10.1002/anie.201510602
7. [7]
  L. Wang, S. Li, P. Chauhan, et al., Chem. Eur. J. 22 (2016) 5123–5127. doi: 10.1002/chem.201600515
8. [8]
  J. Zheng, S.B. Wang, C. Zheng, S.L. You, Angew. Chem. Int. Ed. 56 (2017) 4540–4544. doi: 10.1002/anie.201700021
9. [9]
  J.R. Chen, X.Q. Hu, L.Q. Lu, W.J. Xiao, Chem. Rev. 115 (2015) 5301–5365. doi: 10.1021/cr5006974
10. [10]
  C. Zhu, Y. Ding, L.W. Ye, Org. Biomol. Chem. 13 (2015) 2530–2536. doi: 10.1039/C4OB02556C
11. [11]
  B. Xiang, Y. Wang, C. Xiao, F. He, Y. Huang, Chin. Chem. Lett. 35 (2024) 108777. doi: 10.1016/j.cclet.2023.108777
12. [12]
  D.T. Ziegler, L. Riesgo, T. Ikeda, Y. Fujiwara, G.C. Fu, Angew. Chem. Int. Ed. 53 (2014) 13183–13187. doi: 10.1002/anie.201405854
13. [13]
  Q. Zhang, L. Yang, X. Tong, J. Am. Chem. Soc. 132 (2010) 2550–2551. doi: 10.1021/ja100432m
14. [14]
  S. Kramer, G.C. Fu, J. Am. Chem. Soc. 137 (2015) 3803–3806. doi: 10.1021/jacs.5b01944
15. [15]
  L. Li, P. Luo, Y. Deng, Z. Shao, Angew. Chem. Int. Ed. 58 (2019) 4710–4713. doi: 10.1002/anie.201901511
16. [16]
  X.N. Zhang, H.P. Deng, L. Huang, Y. Wei, M. Shi, Chem. Commun. 48 (2012) 8664–8666. doi: 10.1039/c2cc34619b
17. [17]
  X.N. Zhang, G.Q. Chen, X.Y. Tang, Y. Wei, M. Shi, Angew. Chem. Int. Ed. 53 (2014) 10768–10773. doi: 10.1002/anie.201406100
18. [18]
  Y.Y. Zhou, C. Uyeda, Science 363 (2019) 857–862. doi: 10.1126/science.aau0364
19. [19]
  M.J. Behlen, C. Uyeda, J. Am. Chem. Soc. 142 (2020) 17294–17300. doi: 10.1021/jacs.0c08262
20. [20]
  Z. Zhang, F. Xiao, H.M. Wu, X.Q. Dong, C.J. Wang, Org. Lett. 22 (2020) 569–574. doi: 10.1021/acs.orglett.9b04341
21. [21]
  Q.Y. Liao, C. Ma, Y.C. Wang, et al., Chin. Chem. Lett. 34 (2023) 108371. doi: 10.1016/j.cclet.2023.108371
22. [22]
  L. Zhang, J. Zhang, J. Ma, D.J. Cheng, B. Tan, J. Am. Chem. Soc. 139 (2017) 1714–1717. doi: 10.1021/jacs.6b09634
23. [23]
  K.W. Chen, Z.H. Chen, S. Yang, et al., Angew. Chem. Int. Ed. 61 (2022) e202116829. doi: 10.1002/anie.202116829
24. [24]
  Y. Gao, L.Y. Wang, T. Zhang, B.M. Yang, Y. Zhao, Angew. Chem. Int. Ed. 61 (2022) e202200371. doi: 10.1002/anie.202200371
25. [25]
  S. Matsumura, Y. Maeda, T. Nishimura, S. Uemura, J. Am. Chem. Soc. 125 (2003) 8862–8869. doi: 10.1021/ja035293l
26. [26]
  M. Shigeno, T. Yamamoto, M. Murakami, Chem. Eur. J. 15 (2009) 12929–12931. doi: 10.1002/chem.200902593
27. [27]
  N. Ishida, S. Sawano, Y. Masuda, M. Murakami, J. Am. Chem. Soc. 134 (2012) 17502–17504. doi: 10.1021/ja309013a
28. [28]
  N. Ishida, S. Sawano, M. Murakami, Nat. Commun. 5 (2014) 3111. doi: 10.1038/ncomms4111
29. [29]
  Y. Xia, Z. Liu, Z. Liu, et al., J. Am. Chem. Soc. 136 (2014) 3013–3015. doi: 10.1021/ja500118w
30. [30]
  A. Yada, S. Fujita, M. Murakami, J. Am. Chem. Soc. 136 (2014) 7217–7220. doi: 10.1021/ja502229c
31. [31]
  C. Zhang, X.H. Hu, Y.H. Wang, et al., J. Am. Chem. Soc. 134 (2012) 9585–9588. doi: 10.1021/ja303129s
32. [32]
  L. Shao, Y.H. Wang, D.Y. Zhang, J. Xu, X.P. Hu, Angew. Chem. Int. Ed. 55 (2016) 5014–5018. doi: 10.1002/anie.201510793
33. [33]
  X. Gao, R. Cheng, Y.L. Xiao, X.L. Wan, X. Zhang, Chem 5 (2019) 2987–2999. doi: 10.1016/j.chempr.2019.09.012
34. [34]
  R.Z. Li, D.Q. Liu, D. Niu, Nat. Catal. 3 (2020) 672–680. doi: 10.1038/s41929-020-0462-9
35. [35]
  L. Peng, Z. He, X. Xu, C. Guo, Angew. Chem. Int. Ed. 59 (2020) 14270–14274. doi: 10.1002/anie.202005019
36. [36]
  S.J. Li, J. Huang, J.Y. He, et al., RSC Adv. 10 (2020) 38478–38483. doi: 10.1039/d0ra07698h
37. [37]
  J. Huang, H.H. Kong, S.J. Li, et al., Chem. Commun. 57 (2021) 4674–4677. doi: 10.1039/d1cc00663k
38. [38]
  J.T. Xia, L. Li, X.P. Hu, ACS Catal. 11 (2021) 11843–11848. doi: 10.1021/acscatal.1c03421
39. [39]
  W. Guo, L. Zuo, M. Cui, B. Yan, S. Ni, J. Am. Chem. Soc. 143 (2021) 7629–7634. doi: 10.1021/jacs.1c03182
40. [40]
  Z. Li, D. Li, H. Xiang, et al., Chin. Chem. Lett. 33 (2022) 867–870. doi: 10.1016/j.cclet.2021.08.009
41. [41]
  X. Pu, Q.D. Dang, L. Yang, X. Zhang, D. Niu, Nat. Commun. 13 (2022) 2457. doi: 10.1038/s41467-022-29986-y
42. [42]
  H.D. Qian, Z.H. Li, S. Deng, et al., J. Am. Chem. Soc. 144 (2022) 15779–15785. doi: 10.1021/jacs.2c06560
43. [43]
  R.Q. Wang, C. Shen, X. Cheng, X.Q. Dong, C.J. Wang, Chem. Commun. 58 (2022) 8552–8555. doi: 10.1039/d2cc01695h
44. [44]
  T. Liu, S. Ni, W. Guo, Chem. Sci. 13 (2022) 6806–6812. doi: 10.1039/d2sc02318k
45. [45]
  W. Dong, Z. Zhao, C.Z. Gu, et al., J. Am. Chem. Soc. 145 (2023) 27539–27554. doi: 10.1021/jacs.3c09155
46. [46]
  G. Tian, M. Ji, F. Wu, et al., Org. Lett. 25 (2023) 4666–4671. doi: 10.1021/acs.orglett.3c01521
47. [47]
  C. Gui, Y. Peng, Y. Zhou, et al., ACS Catal. 13 (2023) 13735–13742. doi: 10.1021/acscatal.3c03814
48. [48]
  T. Wang, Y. You, Z.H. Wang, et al., Org. Lett. 25 (2023) 1274–1279. doi: 10.1021/acs.orglett.3c00075
49. [49]
  Z.Q. Geng, C. Zhao, H.D. Qian, et al., Org. Lett. 25 (2023) 4504–4509. doi: 10.1021/acs.orglett.3c01524
50. [50]
  Q. Cai, H. Rao, S.J. Li, et al., Chem 10 (2024) 265–282. doi: 10.1016/j.chempr.2023.09.006
51. [51]
  D.Y. Zhang, L. Shao, J. Xu, X.P. Hu, ACS Catal. 5 (2015) 5026–5030. doi: 10.1021/acscatal.5b01283
52. [52]
  T.R. Li, B.Y. Cheng, Y.N. Wang, et al., Angew. Chem. Int. Ed. 55 (2016) 12422–12426. doi: 10.1002/anie.201605900
53. [53]
  X. Lu, L. Ge, C. Cheng, et al., Chem. Eur. J. 23 (2017) 7689–7693. doi: 10.1002/chem.201701741
54. [54]
  H. Chen, X. Lu, X. Xia, et al., Org. Lett. 20 (2018) 1760–1763. doi: 10.1021/acs.orglett.8b00253
55. [55]
  Z.J. Zhang, L. Zhang, R.L. Geng, et al., Angew. Chem. Int. Ed. 58 (2019) 12190–12194. doi: 10.1002/anie.201907188
56. [56]
  B.C. Wang, T. Fan, F.Y. Xiong, et al., J. Am. Chem. Soc. 144 (2022) 19932–19941. doi: 10.1021/jacs.2c08090
57. [57]
  A. Jonek, S. Berger, E. Haak, Chem. Eur. J. 18 (2012) 15504–15511. doi: 10.1002/chem.201202414
58. [58]
  N. Thies, M. Gerlach, E. Haak, Eur. J. Org. Chem. 2013 (2013) 7354–7365. doi: 10.1002/ejoc.201300803
59. [59]
  N. Thies, E. Haak, Angew. Chem. Int. Ed. 54 (2015) 4097–4101. doi: 10.1002/anie.201412207
60. [60]
  S. Niu, Y. Luo, C. Xu, et al., ACS Catal. 12 (2022) 6840–6850. doi: 10.1021/acscatal.2c00911
61. [61]
  H.H. Kong, C. Zhu, S. Deng, et al., J. Am. Chem. Soc. 144 (2022) 21347–21355. doi: 10.1021/jacs.2c09572
62. [62]
  M.D. Li, Z.H. Wang, H. Zhu, et al., Angew. Chem. Int. Ed. 62 (2023) e202313911. doi: 10.1002/anie.202313911
63. [63]
  S.Y. Luo, G.Q. Lin; , Z.T. He, Org. Chem. Front. 11 (2024) 690–695. doi: 10.1039/d3qo01749d
64. [64]
  H.Y. Lu, Y.W. Chen, W.C. Zhao, et al., Nat. Synth. 2 (2023) 37–48.
65. [65]
  C. Xu, Y. Luo, S. Niu, et al., Green Synth. Catal. 5 (2024) 303–309. doi: 10.1016/j.gresc.2023.10.003
66. [66]
  H. Zhu, L. Xu, B. Zhu, et al., Org. Lett. 25 (2023) 9213–9218. doi: 10.1021/acs.orglett.3c03871
67. [67]
  Y.Z. Sun, Z.Y. Ren, Y.X. Yang, et al., Angew. Chem. Int. Ed. 62 (2023) e202314517. doi: 10.1002/anie.202314517
68. [68]
  D. Luo, S. Niu, F. Gong, et al., ACS Catal. 14 (2024) 2746–2757. doi: 10.1021/acscatal.3c06146
69. [69]
  H.D. Qian, X. Li, T. Yin, et al., Sci. China Chem. 67 (2024) 1175–1180. doi: 10.1007/s11426-023-1922-5
70. [70]
  J. Song, Z.J. Zhang, L.Z. Gong, Angew. Chem. Int. Ed. 56 (2017) 5212–5216. doi: 10.1002/anie.201700105
71. [71]
  J. Ren, C. Pi, Y. Wu, X. Cui, Org. Lett. 21 (2019) 4067–4071. doi: 10.1021/acs.orglett.9b01246
72. [72]
  Z.L. Li, G.C. Fang, Q.S. Gu, X.Y. Liu, Chem. Soc. Rev. 49 (2020) 32–48. doi: 10.1039/c9cs00681h
73. [73]
  X. Chang, Y. Yang, C. Shen, et al., J. Am. Chem. Soc. 143 (2021) 3519–3535. doi: 10.1021/jacs.0c12911
74. [74]
  Y.H. Wen, Z.J. Zhang, S. Li, J. Song, L.Z. Gong, Nat. Commun. 13 (2022) 1344. doi: 10.1038/s41467-022-29059-0
75. [75]
  Z. Zhang, P. Chen, G. Liu, Chem. Soc. Rev. 51 (2022) 1640–1658. doi: 10.1039/d1cs00727k
76. [76]
  Z. Yu, Z. Li, C. Yang, Q. Gu, X. Liu, Acta Chim. Sin. 81 (2023) 955–966. doi: 10.6023/a23040161
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