Citation: Zhou Hongyan, Li Nana, Yang Jingya, Li Tianyuan, Li Zheng. Advance in Catalytic Asymmetric Conjugate Cyanation[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 502-511. doi: 10.6023/cjoc201510033 shu

Advance in Catalytic Asymmetric Conjugate Cyanation

Zhou Hongyan ^a,, ,
Li Nana ^b ,
Yang Jingya ^b,, ,
Li Tianyuan ^b ,
Li Zheng ^b

1.
a College of Science, Gansu Agricultural University, Lanzhou 730070;
2.
b College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Zhou Hongyan, Yang Jingya,
Received Date: 28 October 2015
Available Online: 25 November 2015
Fund Project: 国家自然科学基金(Nos. 21362034, 21462038) (Nos. 21362034, 21462038)高等学校博士学科点专项科研基金(No. 20136203120005) (No. 20136203120005)甘肃省高等学校科研(No. 2013B-003) (No. 2013B-003)甘肃农业大学科技创新基金(No. GAU-CX1115)资助项目. (No. GAU-CX1115)

As one of the most important methods to construct C—C bond in enantioselective manner and afford optically active β-cyano compounds, catalytic asymmetric conjugate cyanation reaction has attracted much attentions worldwide since the first report in 2003. Over the past decade, some important achievements have been made in the catalytic asymmetric conjugate cyanation of α,β-unsaturated imides, α,β-unsaturated N-acylpyrroles, α,β-unsaturated ketones, α,β-unsaturated esters, and nitroalkenes. The research progress in this field is reviewed from both metal catalysis and organocatalysis based on different Michael acceptors.
- asymmetric catalysis,
- cyanation,
- Michael addition,
- α,β-unsaturated compounds,
- transition metals,
- organocatalysis
1. [1]
  [1] For selected review, see:(a) Wang, W.; Liu, X.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2010, 4751. For representative examples, see:
2. [2]
  (b) Chen, F.-X.; Zhou, H.; Liu, X.; Qin, B.; Feng, X.; Zhang, G.; Jiang, Y. Chem. Eur. J. 2004, 10, 4790.
3. [3]
  (c) Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. J. Am. Chem. Soc. 2005, 127, 12224.
4. [4]
  (d) Shen, K.; Liu, X.; Li, Q.; Feng, X. Tetrahedron 2008, 64, 147.
5. [5]
  (e) Cao, J.-J.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2010, 49, 4976.
6. [6]
  [2] For selected review, see:(a) Liu, Y.-L.; Zhou, J. Synthesis 2015, 47, 1210.
7. [7]
  (b) Wang, J.; Liu, X.; Feng, X. Chem. Rev. 2011, 111, 6947. For representative examples, see:
8. [8]
  (c) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468.
9. [9]
  (d) Wang, J.; Wang, W.; Li, W.; Hu, X.; Shen, K.; Tan, C.; Liu, X.; Feng, X. Chem. Eur. J. 2009, 15, 11642.
10. [10]
  (e) Liu, Y.-L.; Zhou, F.; Cao, J.-J.; Ji, C.-B.; Ding, M.; Zhou, J. Org. Biomol. Chem. 2010, 8, 3847.
11. [11]
  (f) Liu, Y.-L.; Shi, T.-D.; Zhou, F.; Zhao, X.-L.; Wang, X.; Zhou, J. Org. Lett. 2011, 13, 3826.
12. [12]
  (g) Liu, Y.-L.; Zhou, J. Chem. Commun. 2013, 49, 4421.
13. [13]
  [3] Hegedus, L. S.; Cross, J. J. Org. Chem. 2004, 69, 8492.
14. [14]
  [4] Winkler, M.; Knall, A. C.; Kulterer, M. R.; Klempier, N. J. Org. Chem. 2007, 72, 7423.
15. [15]
  [5] Vázquez-Romero, A.; Rodríguez, J.; Lledó, A.; Verdaguer, X.; Riera, A. Org. Lett. 2008, 10, 4509.
16. [16]
  [6] Nicolaou, K. C.; Stepan, A. F.; Lister, T.; Li, A.; Montero, A.; Tria, G. S.; Turner, C. I.; Tang, Y.; Wang, J.; Denton, R. M.; Edmonds, D. J. J. Am. Chem. Soc. 2008, 130, 13110.
17. [17]
  [7] Rahman, S. M. A.; Ohno, H.; Maezaki, N.; Iwata, C.; Tanaka, T. Org. Lett. 2000, 2, 2893.
18. [18]
  [8] Rahman, S. M. A.; Ohno, H.; Yoshino, H.; Satoh, N.; Tsukaguchi, M.; Murakami, K.; Iwata, C.; Maezaki, N.; Tanaka, T. Tetrahedron 2001, 57, 127.
19. [19]
  [9] Mander, L. N.; Thomson, R. J. J. Org. Chem. 2005, 70, 1654.
20. [20]
  [10] Muratake, H.; Natsume, M. Tetrahedron 2006, 62, 7071.
21. [21]
  [11] Siwicka, A.; Cuperly, D.; Tedeschi, L.; Le Vézouët. R.; White, A. J. P.; Barrett, A. G. M. Tetrahedron 2007, 63, 5903.
22. [22]
  [12] Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
23. [23]
  [13] Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442.
24. [24]
  [14] Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 514.
25. [25]
  [15] Dahuron, N.; Langlois, N. Synlett 1996, 51.
26. [26]
  [16] Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J.-M. Synthesis 1996, 48.
27. [27]
  [17] Lassaletta, J. M.; Fernández, R.; MartínZamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
28. [28]
  [18] Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928.
29. [29]
  [19] Mazet, C.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1762.
30. [30]
  [20] Madhavan, N.; Weck, M. Adv. Synth. Catal. 2008, 350, 419.
31. [31]
  [21] Madhavan, N.; Takatani, T.; Sherrill, C. D.; Weck, M. Chem. Eur. J. 2009, 15, 1186.
32. [32]
  [22] Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. Tetrahedron 2007, 63, 5820.
33. [33]
  [23] Morita, M.; Drouin, L.; Motoki, R.; Kimura, Y.; Fujimori, I.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 138, 3858.
34. [34]
  [24] Tanaka, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 8862.
35. [35]
  [25] Sakaguchi, Y.; Kurono, N.; Yamauchi, K.; Ohkuma, T. Org. Lett. 2014, 16, 808.
36. [36]
  [26] Ohkuma, T.; Kurono, N. Synlett 2012, 23, 1865.
37. [37]
  [27] Tanaka, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 6072.
38. [38]
  [28] Yang, J.; Wang, Y.; Wu, S.; Chen, F.-X. Synlett 2009, 3365.
39. [39]
  [29] Yang, J.; Chen, F.-X. Chin. J. Chem. 2010, 28, 981.
40. [40]
  [30] Yang, J.; Shen, Y.; Chen, F.-X. Synthesis 2010, 1325.
41. [41]
  [31] Yang, J.; Wu, S.; Chen, F.-X. Synlett 2010, 2725.
42. [42]
  [32] Kurono, N.; Nii, N.; Sakaguchi, Y.; Uemura, M.; Ohkuma, T. Angew. Chem., Int. Ed. 2011, 50, 5541.
43. [43]
  [33] Wang, Y.-F.; Zeng, W.; Sohail, M.; Guo, J.; Wu, S.; Chen, F.-X. Eur. J. Org. Chem. 2013, 4624.
44. [44]
  [34] Zhang, J.; Liu, X.; Wang, R. Chem. Eur. J. 2014, 20, 4911.
45. [45]
  [35] Wang, J.; Li, W.; Liu, Y.; Chu, Y.; Lin, L.; Liu, X.; Feng, X. Org. Lett. 2010, 12, 1280.
46. [46]
  [36] Bernardi, L.; Fini, F.; Fochi, M.; Ricci, A. Synlett 2008, 1857.
47. [47]
  [37] Bernal, P.; Fernández, R.; Lassaletta, J. M. Chem. Eur. J. 2010, 16, 7714.
48. [48]
  [38] Lin, L.; Yin, W.; Fu, X.; Zhang, J.; Ma, X.; Wang, R. Org. Biomol. Chem. 2012, 10, 83.
49. [49]
  [39] North, M.; Watson, J. M. ChemCatChem 2013, 5, 2405.
50. [50]
  [40] Jakhar, A.; Sadhukhan, A.; Khan, N.-u. H.; Saravanan, S.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. ChemCatChem 2014, 6, 2656.
51. [51]
  [41] For selected reviews on asymmetric organocatalysis, see:(a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
52. [52]
  (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
53. [53]
  (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
54. [54]
  (d) List, B. Chem. Rev. 2007, 107, 5413.
55. [55]
  (e) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638.
56. [56]
  (f) MacMillan, D. W. C. Nature 2008, 455, 304.
57. [57]
  (g) Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178.
58. [58]
  (h) Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167.
59. [59]
  (i) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365.
60. [60]
  [42] For review, see: Alemán, J.; Cabrera, S. Chem. Soc. Rev. 2013, 42, 774.
61. [61]
  [43] For review, see:(a) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
62. [62]
  (b) Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222.
63. [63]
  (c) Jew, S.; Park, H. Chem. Commun. 2009, 7090.
64. [64]
  (d) Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534.
65. [65]
  [44] Provencher, B. A.; Bartelson, K. J.; Liu, Y.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2011, 50, 10565.
66. [66]
  [45] Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959.
67. [67]
  [46] Liu, Y.; Shirakawa, S.; Maruoka, K. Org. Lett. 2013, 15, 1230.
68. [68]
  [47](a) Li, Z.; Liu, C.; Zhang, Y.; Li, R.; Ma, B.; Yang, J. Synlett 2012, 23, 2567.
69. [69]
  (b) Li, Z.; Zhang, Y.; Wen, F.; Yin, J.; Zheng, H.; Li, H.; Yang, J. J. Chem. Res. 2013, 37, 601.
70. [70]
  (c) Li, Z.; Yin, J.; Li, T.; Wen, G.; Shen, X.; Yang, J. Tetrahedron 2014, 70, 5619.
71. [71]
  (d) Yang, J.; Zhan, B.; Ma, B.; Xiang, X.; Bao, Y.; Li, Z. Chin. J. Org. Chem. 2015, 35, 1286 (in Chinese). (杨靖亚, 占宝华, 马奔, 向现成, 保云芬, 李政, 有机化学, 2015, 35, 1286.)
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