Citation: Zou Xuejie, Liu Yangzi, Shang Shaojing, Yang Wulin, Deng Weiping. Diastereoselective synthesis of functionalized tetrahydro-γ-carbolines via a [3 + 3] cycloaddition of 2, 2'-diester aziridines with β-(indol-2-yl)-α, β-unsaturated ketones[J]. Chinese Chemical Letters, ;2020, 31(5): 1293-1296. doi: 10.1016/j.cclet.2019.09.002 shu

Diastereoselective synthesis of functionalized tetrahydro-γ-carbolines via a [3 + 3] cycloaddition of 2, 2'-diester aziridines with β-(indol-2-yl)-α, β-unsaturated ketones

Shanghai Key Laboratory of New Drug Design and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

yangwl@ecust.edu.cn

weiping_deng@ecust.edu.cn

Received Date: 30 July 2019
Revised Date: 24 August 2019
Accepted Date: 2 September 2019
Available Online: 4 September 2019

Figures(3)

A Sc(OTf)₃-catalyzed [3 + 3] cycloaddition of 2, 2'-diester aziridines with β-(indol-2-yl)-α, β-unsaturated ketones was developed, affording polysubstituted tetrahydro-γ-carbolines in single diastereoisomers in good to excellent yields.
- Aziridine,
- Tetrahydro-γ-carboline,
- [3+3] cycloaddition,
- Sc(OTf)₃,
- Diastereoselectivity
1. [1]
  J. Dai, W. Dan, Y. Zhang, J. Wang, Eur. J. Med. Chem. 157(2018) 447-461.
2. [2]
  Y. Lee, R.S. Klausen, E.N. Jacobsen, Org. Lett. 13(2011) 5564-4467. doi: 10.1021/ol202300t
3. [3]
  D. Sole, M.L. Bennasar, I. Jimenez, Org. Biomol. Chem. 9(2011) 4535-4544.
4. [4]
  H.G. Cheng, C.B. Chen, F. Tan, et al., Eur. J. Org. Chem. 2010(2010) 4976-4980. doi: 10.1002/ejoc.201000853
5. [5]
  X.X. Sun, H.H. Zhang, G.H. Li, et al., Chem. -Eur. J. 22(2016) 17526-17532.
6. [6]
  R.P. Hsung, A.V. Kurdyumov, N. Sydorenko, Eur. J. Org. Chem. (2005) 23-44. doi: 10.1002/chin.200516251
7. [7]
  X. Xu, M.P. Doyle, Acc. Chem. Res. 47(2014) 1396-1405. doi: 10.1021/ar5000055
8. [8]
  F. Shi, R.Y. Zhu, W. Dai, et al., Chem. -Eur. J. 20(2014) 2597-2604.
9. [9]
  X.X. Sun, C. Li, Y.Y. He, et al., Adv. Synth. Catal. 359(2017) 2660-2670.
10. [10]
  W. Dai, H. Lu, X. Li, et al., Chem. Eur. J. 20(2014) 11382-11389. doi: 10.1002/chem.201402485
11. [11]
  Z.Q. Zhu, L. Yu, M. Sun, et al., Adv. Synth. Catal. 36(2018) 3109-3116.
12. [12]
  W.L. Yang, C.Y. Li, W.J. Qin, et al., ACS Catal. 6(2016) 5685-5690.
13. [13]
  X. Zheng, W.L. Yang, Y.Z. Liu, et al., Adv. Synth. Catal. 360(2018) 2843-2853. doi: 10.1002/adsc.201800553
14. [14]
  Y.Z. Liu, S.J. Shang, J.Y. Zhu, et al., Adv. Synth. Catal. 360(2018) 2191-2203.
15. [15]
  X. Wu, J. Zhang, Synthesis 44(2012) 2147-2154. doi: 10.1055/s-0031-1290816
16. [16]
  P.D. Pohlaus, R.K. Bowman, J.S. Johnson, J. Am. Chem. Soc. 126(2004) 2294-2295. doi: 10.1021/ja0397963
17. [17]
  L. Li, X. Wu, J. Zhang, Chem. Commun. 47(2011) 5049-5051. doi: 10.1039/c1cc10926j
18. [18]
  X. Wu, L. Li, J. Zhang, Chem. Commun. 47(2011) 7824-7826. doi: 10.1039/c1cc12189h
19. [19]
  L. Li, J. Zhang, Org. Lett. 13(2011) 5940-5943. doi: 10.1021/ol202603e
20. [20]
  Z. Jiang, J. Wang, P. Lu, Y.G. Wang, Tetrahedron 67(2011) 9609-9617. doi: 10.1016/j.tet.2011.09.085
21. [21]
  R.A. Craig II, N.R. O'Connor, A.F. Goldberg, B.M. Stoltz, Eur. J. Chem. 20(2014) 4806-4813. doi: 10.1002/chem.201303699
22. [22]
  H. Liu, C. Zheng, S.L. You, Chin. J. Chem. 32(2014) 709-714. doi: 10.1002/cjoc.201400178
23. [23]
  T. Soeta, Y. Miyamoto, S. Fujinami, Y. Ukaji, Tetrahedron 70(2014) 6623-6629. doi: 10.1016/j.tet.2014.06.118
24. [24]
  A. Ghosh, A.K. Pandey, P. Banerjee, J. Org. Chem. 80(2015) 7235-7242. doi: 10.1021/acs.joc.5b00705
25. [25]
  B. Wang, M. Liang, J. Tang, et al., Org. Lett. 18(2016) 4614-4617. doi: 10.1021/acs.orglett.6b02253
26. [26]
  M. Liang, S. Zhang, J. Jia, et al., Org. Lett. 19(2017) 2526-2529. doi: 10.1021/acs.orglett.7b00804
27. [27]
  Y. Liao, B. Zhou, Y. Xia, et al., ACS Catal. 7(2017) 3934-3939.
28. [28]
  Y. Zhan, T. Liu, J. Ren, Z. Wang, Chem. -Eur. J. 23(2017) 17862-17866.
29. [29]
  M. Alajarin, D. Banon, A. Egea, et al., Org. Chem. Front. 5(2018) 2020-2029. doi: 10.1039/C8QO00255J
30. [30]
  Y. Xu, F. Chang, W. Cao, et al., ACS Catal. 8(2018) 10261-10266.
31. [31]
  R.K. Varshnaya, P. Banerjee, Org. Biomol. Chem. 15(2017) 5182-5190. doi: 10.1039/c7ob00941k
32. [32]
  S.G. Lee, S. Sin, S. Kim, S.G. Kim, Tetrahedron Lett. 59(2018) 1480-1483. doi: 10.1016/j.tetlet.2018.03.004
33. [33]
  S.G. Lee, S.G. Kim, Tetrahedron 74(2018) 3671-3678. doi: 10.1016/j.tet.2018.12.006
34. [34]
  R. Talukdar, D.P. Tiwari, A. Saha, M.K. Ghorai, Org. Lett. 16(2014) 3954-3957.
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