Citation: Manman Song, Jing Zhao, Er-Qing Li. Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates[J]. Chinese Chemical Letters, ;2022, 33(5): 2372-2382. doi: 10.1016/j.cclet.2021.11.044 shu

Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates

Manman Song ^a ,
Jing Zhao ^b ,
Er-Qing Li ^{a, *,}

a.
College of Chemistry, Green Catalysis Center, Zhengzhou University, Zhengzhou 450001, China
b.
Xuchang Environmental Monitoring Center, Xuchang 461000, China

lierqing@zzu.edu.cn

Received Date: 17 September 2021
Revised Date: 8 November 2021
Accepted Date: 15 November 2021
Available Online: 19 November 2021

Figures(34)

Lewis base-catalyzed annulations of allenoates have been one of the most powerful synthetic strategies for the synthesis of various valuable cycles, especially in the preparation of biologically active natural products and pharmaceuticals. Generally, the effective Lewis bases mainly include tertiary phosphine, NHC and tertiary amine catalysts, among those catalysis, tertiary amine Lewis bases have proven to be effective catalysts for a range of synthetic transformations. In the past decades, tremendous progress involving tertiary amines-promoted cycloaddition of allenoates has been made in the chemoselective construction of valuable motifs. This review describes a comprehensive and updated summary of tertiary amine Lewis base-promoted annulation reactions of allenoates. Diverse reactivities, chemoselectivties and detailed reaction mechanisms will be highlighted in this review.
- Lewis base,
- Tertiary amine,
- Annualtion,
- Allenoates,
- Olefin
1. [1]
  S. Kobayashi, K.A. Jørgensen, Cycloaddition Reactions in Organic Synthesis, Wiley, 2001.
2. [2]
  M. Lautens, W. Klute, W. Tam, Chem. Rev. 96 (1996) 49-92. doi: 10.1021/cr950016l
3. [3]
  M.M. Rauhut, H. Currier, Chem. Abstr. 58 (1963) 66109.
4. [4]
  A.B. Baylis, M.E.D. Hillman, Chem. Abstr. 77 (1972) 34174.
5. [5]
  C. Zhang, X. Lu, J. Org. Chem. 60 (1995) 2906-2908. doi: 10.1021/jo00114a048
6. [6]
  C. Xie, A.J. Smaligo, X.R. Song, O. Kwon, ACS Cent. Sci. 7 (2021) 536-558. doi: 10.1021/acscentsci.0c01493
7. [7]
  P. Xie, Y. Huang, Eur. J. Org. Chem. (2013) 6213-6226.
8. [8]
  E.Q. Li, Y. Huang, Chem. Commun. 56 (2020) 680-694. doi: 10.1039/C9CC08241G
9. [9]
  H. Guo, Y. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev. 118 (2018) 10049-10293. doi: 10.1021/acs.chemrev.8b00081
10. [10]
  Y. Wei, M. Shi, Chem. Asian J. 9 (2014) 2720-2734. doi: 10.1002/asia.201402109
11. [11]
  L.W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 37 (2008) 1140-1152. doi: 10.1039/b717758e
12. [12]
  X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 34 (2001) 535-544. doi: 10.1021/ar000253x
13. [13]
  L. Dai, S. Ye, Chin. Chem. Lett. 32 (2021) 660-667. doi: 10.1016/j.cclet.2020.08.027
14. [14]
  D.M. Flanigan, F. Romanov-Michailidis, N.A. White, T. Rovis, Chem. Rev. 115 (2015) 9307-9387. doi: 10.1021/acs.chemrev.5b00060
15. [15]
  M.N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 510 (2014) 485-496. doi: 10.1038/nature13384
16. [16]
  D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 107 (2007) 5606-5655. doi: 10.1021/cr068372z
17. [17]
  Q. Deng, F. Mu, Y. Qiao, D. Wei, Org. Biomol. Chem. 18 (2020) 6781-6800. doi: 10.1039/D0OB01378A
18. [18]
  S. Tsuboi, S. Takatsuka, M. Utaka, Chem. Lett. 17 (1988) 2003-2004. doi: 10.1246/cl.1988.2003
19. [19]
  Y.L. Shi, M. Shi, Org. Lett. 7 (2005) 3057-3060. doi: 10.1021/ol051044l
20. [20]
  G.L. Zhao, Y.L. Shi, M. Shi, Org. Lett. 7 (2005) 4527-4530. doi: 10.1021/ol051920v
21. [21]
  X.Y. Chen, M.W. Wen, S. Ye, Z.X. Wang, Org. Lett. 13 (2011) 1138-1141. doi: 10.1021/ol103165y
22. [22]
  X.C. Zhang, S.H. Cao, Y. Wei, M. Shi, Org. Lett. 13 (2011) 1142-1145. doi: 10.1021/ol1031798
23. [23]
  Y. Wang, Z.H. Yu, H.F. Zheng, D.Q. Shi, Org. Biomol. Chem. 10 (2012) 7739-7746. doi: 10.1039/c2ob26300a
24. [24]
  X.S. Meng, S. Jiang, X.Y. Xu, et al., RSC Adv. 6 (2016) 66630-66633. doi: 10.1039/C6RA15117E
25. [25]
  J. Mu, X. Xie, S. Xiong, et al., Chin. Chem. Lett. 32 (2021) 1897-1901. doi: 10.1016/j.cclet.2021.01.033
26. [26]
  K.K. Wang, W. Du, J. Zhu, Y.C. Chen, Chin. Chem. Lett. 32 (2021) 512-516.
27. [27]
  J.W.H. Li, J.C. Vederas, Science 32 (2009) 161-165.
28. [28]
  A.L. Harvey, Drug Discovery Today 13 (2008) 894-901. doi: 10.1016/j.drudis.2008.07.004
29. [29]
  Y. Liu, Y. Du, A. Yu, H. Mu, X. Meng, Org. Biomol. Chem. 14 (2016) 1226-1230. doi: 10.1039/C5OB02383A
30. [30]
  Y. Liu, Y. Du, A. Yu, D. Qin, X. Meng, Tetrahedron 71 (2015) 7706-7716. doi: 10.1016/j.tet.2015.07.057
31. [31]
  A.L.S. Kumari, K.C.K. Swamy, J. Org. Chem. 80 (2015) 4084-4096. doi: 10.1021/acs.joc.5b00415
32. [32]
  H. Jin, E. Li, Y. Huang, Org. Chem. Front. 4 (2017) 2216-2220. doi: 10.1039/C7QO00596B
33. [33]
  Q. Liu, S.J. Li, X. Li, L.B. Qu, D. Wei, ChemistrySelect 3 (2018) 10553-10558. doi: 10.1002/slct.201802267
34. [34]
  Y. Xiao, X.Y. Zhang, J.M. Zhao, Y. Qiao, J. Phys. Org. Chem. 32 (2019) 3914. doi: 10.1002/poc.3914
35. [35]
  Y. Wang, M. Song, E.Q. Li, Z. Duan, Org. Chem. Front. 8 (2021) 3366-3371. doi: 10.1039/D1QO00330E
36. [36]
  K. Li, Z. Gan, E.Q. Li, Z. Duan, Org. Lett. 23 (2021) 3094-3099. doi: 10.1021/acs.orglett.1c00780
37. [37]
  Y. Wang, S. Jia, E.Q. Li, Z. Duan J. Org. Chem. 84 (2019) 15323-15330. doi: 10.1021/acs.joc.9b02349
38. [38]
  Q.Z. Xi, Z.J. Gan, E.Q. Li, Z. Duan, Eur. J. Org. Chem. (2018) 4917-4925.
39. [39]
  J. Jia, A. Yu, X. Liu, X. Meng, Chin. J. Org. Chem. 39 (2019) 2175-2182. doi: 10.6023/cjoc201904082
40. [40]
  J. Feng, Y. Chen, W. Qin, Y. Huang, Org. Lett. 22 (2020) 433-437. doi: 10.1021/acs.orglett.9b04176
41. [41]
  J. Feng, Y. Huang, ACS Catal. 10 (2020) 3541-3547. doi: 10.1021/acscatal.0c00588
42. [42]
  X. Meng, Y. Huang, H. Zhao, et al., Org. Lett. 11 (2009) 991-994. doi: 10.1021/ol802917d
43. [43]
  Y. Gu, F. Li, P. Hu, D. Liao, X. Tong, Org. Lett. 17 (2015) 1106-1109. doi: 10.1021/acs.orglett.5b00359
44. [44]
  S.K. Arupula, A.A. Qureshi, K.C.K. Swamy, J. Org. Chem. 85 (2020) 4130-4144. doi: 10.1021/acs.joc.9b03281
45. [45]
  A.S. Kumar, S. Chauhan, K.C.K. Swamy, Org. Lett. 23 (2021) 1123-1129. doi: 10.1021/acs.orglett.1c00076
46. [46]
  X.L. Huang, L. He, P.L. Shao, S. Ye, Angew. Chem. Int. Ed. 48 (2009) 192-195. doi: 10.1002/anie.200804487
47. [47]
  A. Chan, K. Scheidt, J. Am. Chem. Soc. 130 (2008) 2740-2741. doi: 10.1021/ja711130p
48. [48]
  Q. Zhang, L.G. Meng, J. Zhang, L. Wang, Org. Lett. 17 (2015) 3272-3275. doi: 10.1021/acs.orglett.5b01237
49. [49]
  M. Chang, C. Wu, J. Zheng, Y. Huang, Chem. Asian J. 11 (2016) 1512-1517. doi: 10.1002/asia.201600102
50. [50]
  C. Cheng, X. Sun, Z. Wu, et al., Org. Biomol. Chem. 17 (2019) 3232-3238. doi: 10.1039/C9OB00179D
51. [51]
  W. Luo, B. Shao, J. Li, et al., Tetrahedron Lett. 60 (2019) 151206. doi: 10.1016/j.tetlet.2019.151206
52. [52]
  G.L. Zhao, J.W. Huang, M. Shi, Org. Lett. 5 (2003) 4737-4739. doi: 10.1021/ol0359416
53. [53]
  T. Wang, X.Y. Chen, S. Ye, Tetrahedron Lett. 52 (2011) 5488-5490. doi: 10.1016/j.tetlet.2011.08.057
54. [54]
  P. Selig, A. Turočkina, W. Raven, Chem. Commun. 49 (2013) 2930-2932. doi: 10.1039/c3cc40855h
55. [55]
  M. Rommel, T. Fukuzumi, J.W. Bode, J. Am. Chem. Soc. 130 (2008) 17266-17267. doi: 10.1021/ja807937m
56. [56]
  X.F. Xiong, H. Zhang, J. Peng, Y.C. Chen, Chem. Eur. J. 17 (2011) 2358-2360. doi: 10.1002/chem.201002592
57. [57]
  X.Y. Chen, R.C. Lin, S. Ye, Chem. Commun. 48 (2012) 1317-1319. doi: 10.1039/C2CC16055B
58. [58]
  S. Xu, J. Chen, J. Shang, et al., Tetrahedron Lett. 56 (2015) 6456-6459. doi: 10.1016/j.tetlet.2015.09.151
59. [59]
  G. Rainoldi, M. Faltracco, L.L. Presti, A. Silvani, G. Lesma, Chem. Commun. 52 (2016) 11575-11578. doi: 10.1039/C6CC05838H
60. [60]
  T. Liu, C. He, F. Wang, et al., Synthesis 53 (2021) 518-526. doi: 10.1055/s-0040-1707292
61. [61]
  X.F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 125 (2003) 4716-4717. doi: 10.1021/ja0344009
62. [62]
  C. Li, Q. Zhang, X. Tong, Chem. Commun. 46 (2010) 7828-7830. doi: 10.1039/c0cc01966f
63. [63]
  D. Kaiser, I. Klose, R. Oost, J. Neuhaus, N. Maulide, Chem. Rev. 119 (2019) 8701-8780. doi: 10.1021/acs.chemrev.9b00111
64. [64]
  Q. Deng, X. Meng, Chem. Asian J. 15 (2020) 2838-2853. doi: 10.1002/asia.202000550
65. [65]
  K. Li, J. Hu, H. Liu, X. Tong, Chem. Commun. 48 (2012) 2900-2902. doi: 10.1039/c2cc30242j
66. [66]
  Y. Choe, P.H. Lee, Org. Lett. 11 (2009) 1445-1448. doi: 10.1021/ol9001703
67. [67]
  C. Ni, Y. Zhang, Y. Hou, X. Tong, Chem. Commun. 53 (2017) 2567-2570. doi: 10.1039/C6CC09788J
68. [68]
  M. Li, Z.M. Zhou, L.R. Wen, Z.X. Qiu, J. Org. Chem. 76 (2011) 3054-3063. doi: 10.1021/jo102167g
69. [69]
  Y. Liu, Q. Zhang, Y. Du, et al., RSC Adv. 4 (2014) 52629-52632. doi: 10.1039/C4RA09249J
70. [70]
  Y.T. Tian, F.G. Zhang, J.A. Ma, Tetrahedron 81 (2021) 131922. doi: 10.1016/j.tet.2021.131922
71. [71]
  W. Sun, F. Jiang, H. Liu, et al., Chin. Chem. Lett. 30 (2019) 363-366. doi: 10.1016/j.cclet.2018.04.024
72. [72]
  X. Shang, K. Liu, Z. Zhang, et al., Org. Biomol. Chem. 16 (2018) 895-898. doi: 10.1039/C7OB03040A
73. [73]
  Y. Zhu, Y. Huang, Org. Lett. 22 (2020) 6750-6755. doi: 10.1021/acs.orglett.0c02164
74. [74]
  Z.B. Zhang, Y. Yang, Z.X. Yu, J.B. Xia, ACS Catal. 10 (2020) 5419-5429. doi: 10.1021/acscatal.0c01000
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