Citation: Ding Chen-Hao, Dong Jian-Lian, Yu Li-Si-Han, Xie Jian-Wu. Organocatalytic Domino Michael/cyclization for the synthesis of highly substituted 4, 5-dihydrothiophenes[J]. Chinese Chemical Letters, ;2018, 29(3): 517-520. doi: 10.1016/j.cclet.2017.08.048 shu

Organocatalytic Domino Michael/cyclization for the synthesis of highly substituted 4, 5-dihydrothiophenes

Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, China

Corresponding author: Xie Jian-Wu, xiejw@zjnu.cn
Received Date: 28 April 2017
Revised Date: 1 August 2017
Accepted Date: 24 August 2017
Available Online: 30 March 2017

Figures(4)

Based on an umpolung strategy, a series of novel full substituted, optically active dihydrothiophenes, which contain several functional groups, such as amine, ester and oxime groups, were obtained via an efficient organocatalytic asymmetric a formal thio[3 + 2]-cyclization of acyclic thioamides with (E)-α-nitrostyrenes.
- Dihydrothiophenes,
- Organocatalysis,
- 1, 3-Dicarbonyl compounds,
- Thioamides,
- Nitrostyrenes
1. [1]
  (a) E. Campaigne, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford U. K., 1984, pp. 863-934;
  (b) S. Gronowitz, A. B. Hornfeldt, Thiophenes, Elsevier, Oxford U. K., 2004;
  (c) G. C. Nandi, S. Samai, M. S. Singh, J. Org. Chem. 76(2011) 8009-8014;
  (d) W. You, X. Yan, Q. Liao, C. Xi, Org. Lett. 12(2010) 3930-3933.
2. [2]
  P.S. Wei, M.X. Wang, D.C. Xu, J.W. Xie, J. Org. Chem. 81(2016) 1216-1222. doi: 10.1021/acs.joc.5b02369
3. [3]
  V.A. Tsygankova, Y.B. Blume, Biopolim. Kletka 13(1997) 484-492.
4. [4]
  (a) G. Hallas, A. D. Towns, Dyes Pigments 33(1997) 319-336;
  (b) M. K. R. Fischer, S. Wenger, M. Wang, et al., Chem. Mater 22(2010) 1836-1845.
5. [5]
  (a) C. B. Nielsen, J. M. Fraser, B. C. Schroeder, et al., Org. Lett. 13(2011) 2414-2417;
  (b) J. Wang, K. Liu, Y. Y. Liu, et al., Org. Lett. 11(2009) 2563-2566;
  (c) C. Qiao, K. Q. Ling, E. M. Shepard, D. M. Dooley, L. M. Sayre, J. Am. Chem. Soc. 128(2006) 6206-6219.
6. [6]
  (a) J. Zempleni, S. S. K. Wijeratne, Y. I. Hassan, Bio. Factors 35(2009) 36-46;
  (b) S. Benetti, C. D. Risi, G. P. Pollini, V. Zanirato, Chem. Rev. 112(2012) 2129-2163;
  (c) K. Haraguchi, H. Shimada, H. Tanaka, et al., J. Med Chem. 51(2008) 1885-1893.
7. [7]
  E. Hauptman, R. Shapiro, W. Marshall, Organometallics 17(1998) 4976-4982. doi: 10.1021/om980540t
8. [8]
  (a) E. M. McGarrigle, E. L. Myers, O. Illa, et al., Chem. Rev. 107(2007) 5841-5883;
  (b) N. Furukawa, Y. Sugihara, H. Fujihara, J. Org. Chem. 54(1989) 4222-4224;
  (c) A. H. Li, L. X. Dai, X. L. Hou, Y. Z. Huang, F. W. Li, J. Org. Chem. 61(1996) 489-493;
  (d) K. Julienne, P. Metzner, J. Org. Chem. 63(1998) 4532-4534;
  (e) J. Zanardi, C. Leriverend, D. Aubert, K. Julienne, P. Metzner, J. Org. Chem. 66(2001) 5620-5623;
  (f) J. Zanardi, D. Lamazure, S. Miniere, V. Reboul, P. Metzner, J. Org. Chem. 67(2002) 9083-9086;
  (g) M. T. Huang, H. Y. Wu, R. J. Chein, Chem. Commun. 50(2014) 1101-1103.
9. [9]
  (a) L. P. Garrod, Br. Med. J. 1(1960) 527-529;
  (b) C. J. Schofield, J. E. Baldwin, M. F. Byford, et al., Curr. Opin. Struct. Biol. 7(1997) 857-864;
  (c) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. Baran, Angew Chem. Int. Ed. 39(2000) 44-122.
10. [10]
  (a) M. Yoshikawa, T. Murakami, H. Shimada, et al., Tetrahedron Lett. 38(1997) 8367-8370;
  (b) M. Yoshikawa, T. Murakami, K. Yashiro, H. Matsuda, Chem. Pharm. Bull. 46(1998) 1339-1340;
  (c) H. Matsuda, T. Murakami, K. Yashiro, J. Yamahara, M. Yoshikawa, Chem. Pharm. Bull. 47(1999) 1725-1729.
11. [11]
  (a) J. Zempleni, S. S. K. Wijeratne, Y. I. Hassan, Bio. Factors 35(2009) 36-46;
  (b) S. Benetti, C. D. Risi, G. P. Pollini, V. Zanirato, Chem. Rev. 112(2012) 2129-2163.
12. [12]
  (a) S. Benetti, C. D. Risi, G. P. Pollini, V. Zanirato, Chem. Rev. 112(2012) 2129-2163;
  (b) A. M. Ponce, L. E. Overman, J. Am. Chem. Soc. 122(2000) 8672-8676;
  (c) D. Desmaele, S. Delarue-Cochin, C. Cave, J. Angelo, G. Morgant, Org. Lett. 6(2004) 2421-2424;
  (d) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 128(2006) 14986-14991;
  (e) H. Li, L. Zu, H. Xie, J. Wang, W. Wang, Org. Lett. 9(2007) 1833-1835;
  (f) C. Yu, Y. Zhang, A. Song, Y. Ji, W. Wang, Chem. Eur. J. 17(2011) 770-774;
  (g) J. Tang, D. Q. Xu, A. B. Xia, et al., Adv. Synth. Catal. 352(2010) 2121-2126.
13. [13]
  (a) X. M. Zeng, C. Y. Meng, J. X. Bao, et al., J. Org Chem. 80(2015) 11521-11528;
  (b) X. M. Zeng, J. W. Xie, J. Org. Chem. 81(2016) 3553-3559.
14. [14]
  (a) J. W. Xie, M. L. Xu, R. Z. Zhang, J. Y. Pan, W. D. Zhu, Adv. Synth. Catal. 356(2014) 395-400;
  (b) R. Z. Zhang, C. Y. Meng, J. W. Xie, M. L. Xu, W. D. Zhu, Eur. J. Org. Chem. 15(2014) 3104-3107;
  (c) Y. R. Zhang, J. W. Xie, X. J. Huang, W. D. Zhu, Org. Biomol. Chem. 10(2012) 6554-6561;
  (d) L. P. Fan, P. Li, X. S. Li, et al., J. Org Chem. 75(2010) 8716-8719.
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