Citation: Li Sha, Yang Wenhan, Luo Xian, Yao Changsheng. An Efficient N-Heterocyclic Carbene (NHC)-Catalyzed Synthesis of Polysubstituted Cyclopentene[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1404-1410. doi: 10.6023/cjoc201812035 shu

An Efficient N-Heterocyclic Carbene (NHC)-Catalyzed Synthesis of Polysubstituted Cyclopentene

Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Yao Changsheng, csyao@jsnu.edu.cn
Received Date: 19 December 2018
Revised Date: 9 January 2019
Available Online: 18 May 2019
Fund Project: the National Natural Science Foundation of China 21871113Project supported by the National Natural Science Foundation of China (Nos. 21871113, 21372101)the National Natural Science Foundation of China 21372101

Figures(5)

An one-pot, cascade assembly of polysubstituted cyclopentene was realized via the N-heterocyclic carbene (NHC)-catalyzed annulation of the in situ activated α, β-unsaturated carboxylic acid with 2-(2-oxo-2-arylethyl)malononitrile through the sequence of Michael addition, aldol condesation and decarboxylation. This method could serve as a new attractive strategy for the practical syntheses of multi-functionalized cyclopentene derivatives with broad substrate scope, readily availability of starting materials, mild reaction conditions, excellent yields and operational simplicity.
- N-heterocyclic carbene (NHC),
- α, β-unsaturated carboxylic acid,
- 2-(2-oxo-2-arylethyl)malononitrile,
- poly-substituted cyclopentene,
- cascade reaction
1. [1]
  (a) Mao, S.-C.; Guo, Y.-W. J. Nat. Prod. 2006, 69, 1209.
  (b) Yu, X.-Q.; He, W.-F.; Liu, D.-Q.; Feng, M.-T.; Fang, Y.; Wang, B.; Feng, L.-H.; Guo, Y.-W.; Mao, S.-C. Phytochemistry 2014, 103, 162.
  (c) Li, X.-L.; He, W.-F.; Li, J.; Lan, L.-F.; Li, X.-W.; Guo, Y.-W. J. Asian Nat. Prod. Res. 2015, 17, 1146.
  (d) Wang, Y.; Wei, D.; Wang, Y.; Zhang, W.; Tang, M. ACS Catal. 2016, 6, 279.
2. [2]
  (a) Zhang, Y.-M.; Tan, N.-H.; He, M.; Lu, Y.; Shang, S.-Q.; Zheng, Q.-T. Tetrahedron Lett. 2004, 45, 4319.
  (b) Ito, Y.; Takahashi, K.; Nagase, H.; Honda, T. Org. Lett. 2011, 13, 4640.
3. [3]
  (a) Jaroszewski, J. W.; Ramussen, A. B.; Rasmussen, H. B.; Olsen, C. E.; Joergensen, L. B. Phytochemistry 1996, 42, 649.
  (b) Andersen, L.; Adsersen, A.; Jaroszewski, J. W. Phytochemistry 1998, 47, 1049.
  (c) Bylov, T.; Franzyk, H.; Jaroszewski, J. W. Biochem. Syst. Ecol. 2004, 32, 695.
4. [4]
  Xie, J.; Shang, H.; Luo, L. CN 101851177, 2010.
5. [5]
  Aillard, P.; Gicquel, M.; Yavari, K.; Retailleau, P.; Voituriez, A.; Marinetti, A. Eur. J. Org. Chem. 2018, 2018, 5853. doi: 10.1002/ejoc.201800438
6. [6]
  Alishetty, S.; Shih, H. P.; Han, C. C. Org. Lett. 2018, 20, 2513. doi: 10.1021/acs.orglett.8b00510
7. [7]
  Clergue, S.; Rousseau, O.; Delaunay, T.; Dequirez, G.; Tran, T. V.; El Aakchioui, S.; Barozzino-Consiglio, G.; Robiette, R. Chem.-Eur. J. 2018, 24, 11417. doi: 10.1002/chem.v24.44
8. [8]
9. [9]
  (a) Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13, 4080.
  (b) Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494.
  (c) Lu, H.; Liu, J.-Y.; Li, C.-G.; Lin, J.-B.; Liang, Y.-M.; Xu, P.-F. Chem. Commun. 2015, 51, 4473.
10. [10]
  Xu, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2013, 15, 5028. doi: 10.1021/ol402358k
11. [11]
  Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592. doi: 10.1002/anie.201303247
12. [12]
  (a) Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176.
  (b) Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694.
  (c) Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2013, 135, 58.
13. [13]
  (a) Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134.
  (b) Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chem.-Eur. J. 2012, 18, 1914.
  (c) Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089.
  (d) Mondal, S.; Yetra, S. R.; Patra, A.; Kunte, S. S.; Gonnade, R. G.; Biju, A. T. Chem. Commun. 2014, 50, 14539.
  (e) Xie, Y.; Que, Y.; Li, T.; Zhu, L.; Yu, C.; Yao, C. Org. Biomol. Chem. 2015, 13, 1829.
  (f) Qiao, Y.; Wei, D.; Chang, J. J. Org. Chem. 2015, 80, 8619.
  (g) Wang, Y.; Wu, B.; Zheng, L.; Wei, D.; Tang, M. Org. Chem. Front. 2016, 3, 190.
  (h) Yu, C.; Shen, S.; Jiang, L.; Li, J.; Lu, Y.; Li, T.; Yao, C. Org. Biomol. Chem. 2017, 15, 9149.
14. [14]
  (a) Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810.
  (b) Zhu, Z.-Q.; Zheng, X.-L.; Jiang, N.-F.; Wan, X.; Xiao, J.-C. Chem. Commun. 2011, 47, 8670.
15. [15]
  Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696. doi: 10.1021/ar400239v
16. [16]
  Chen, X.-Y.; Gao, Z.-H.; Song, C.-Y.; Zhang, C.-L.; Wang, Z.-X.; Ye, S. Angew. Chem., Int. Ed. 2014, 53, 11611. doi: 10.1002/anie.201407469
17. [17]
  (a) Que, Y.; Li, T.; Yu, C.; Wang, X.-S.; Yao, C. J. Org. Chem. 2015, 80, 3289.
  (b) Que, Y.; Lu, Y.; Wang, W.; Wang, Y.; Wang, H.; Yu, C.; Li, T.; Wang, X.-S.; Shen, S.; Yao, C. Chem. Asian J. 2016, 11, 678.
18. [18]
  Que, Y.; Xie, Y.; Li, T.; Yu, C.; Tu, S.; Yao, C. Org. Lett. 2015, 17, 6234. doi: 10.1021/acs.orglett.5b03223
19. [19]
  Wang, Y.; Pan, J.; Dong, J.; Yu, C.; Li, T.; Wang, X.-S.; Shen, S.; Yao, C. J. Org. Chem. 2017, 82, 1790. doi: 10.1021/acs.joc.6b02444
20. [20]
  Hu, Y.; Pan, D.; Cong, L.; Yao, Y.; Yu, C.; Li, T.; Yao, C. ChemistrySelect 2018, 3, 1708. doi: 10.1002/slct.201702925
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