Citation: Chu Xu, Chang Honghong, Gao Wenchao, Wei Wenlong, Li Xing. Research Progress in the Ring-Opening Reactions of Aziridines by Carbon Nucleophiles[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2569-2589. doi: 10.6023/cjoc201702033 shu

Research Progress in the Ring-Opening Reactions of Aziridines by Carbon Nucleophiles

College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Corresponding author: Wei Wenlong, Li Xing, lixing@tyut.edu.cn
Received Date: 23 February 2017
Revised Date: 3 May 2017
Available Online: 2 October 2017
Fund Project: the Natural Science Foundation of Shanxi Province 201601D011028the Natural Science Foundation of Shanxi Province 20130110094Project supported by the Natural Science Foundation of Shanxi Province (Nos. 201601D011028, 20130110094)

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The recent progress in ring-opening reactions of aziridines by various carbon nucleophiles, such as alkynes, nitriles, arenes, heteroarenes, active methylene compounds, organometallic reagents and so on, is reviewed. Moreover, the prospects of future development are also discussed.
- aziridines,
- ring-opening reactions,
- carbon nucleophiles
1. [1]
  Feng, J. J.; Zhang, J. L. ACS catal. 2016, 6, 6651. doi: 10.1021/acscatal.6b02072
2. [2]
  Wang, Q. Y.; Chang, H. H.; Wei, W. L.; Liu, Q.; Gao, W. C.; Li, Y. W.; Li, X. Chin. J. Org. Chem. 2016, 36, 939(in Chinese).
3. [3]
  Cardoso, L. A.; Pinhoe Melo, M. V. D. T. Eur. J. Org. Chem. 2012, 33, 6479.
4. [4]
  Subrahmanyam, G.; Adhya, A. J. Sci. Ind. Res. Indian 1974, 33, 308.
5. [5]
  Ha, H. J.; Jung, J. H.; Lee, W. K. Asian J. Org. Chem. 2014, 3, 1020. doi: 10.1002/ajoc.v3.10
6. [6]
  Luginina, J.; Turks, M. Chem. Heterocycl. Compd. 2016, 10, 773.
7. [7]
  Pineschi, M. Synlett 2014, 1817.
8. [8]
  Turks, M.; Posevins, D. Eur. J. Org. Chem. 2016, 2016, 1760. doi: 10.1002/ejoc.v2016.9
9. [9]
  Benjamin, L.; Richard, G.; Markus, L.; Riccardo, M. M. Angew. Chem., Int. Ed. 2014, 53, 7063. doi: 10.1002/anie.201400169
10. [10]
  Hammond, B. G.; Xu, B.; Mashuta, S. M.; Okoromoba, E. O. Chem. Commun. 2016, 52, 13353. doi: 10.1039/C6CC07855A
11. [11]
  Wang, R.; Jiang, X. X.; Liu, X.; Li, D. Chem.-Eur. J. 2016, 22, 17141. doi: 10.1002/chem.201603898
12. [12]
  Murty, M. S. R.; Yadav, J. S. Tetrahedron Lett. 2005, 46, 6385. doi: 10.1016/j.tetlet.2005.06.165
13. [13]
  Feng, X. M.; Lin, L. L.; Liu, X. H.; Li, J. Chem. Commun. 2014, 50, 6672. doi: 10.1039/c4cc02206h
14. [14]
  Li, Y. W.; Su, J. J.; Chang, H. H.; Li, X.; Wei, W. L. Chem. Ind. 2011, 39, 12(in Chinese). doi: 10.3969/j.issn.1001-9677.2011.05.005
15. [15]
  Schneider, C. Angew. Chem., Int. Ed. 2009, 48, 2082. doi: 10.1002/anie.v48:12
16. [16]
  Hu, X. E. Tetrahedron 2004, 60, 2701. doi: 10.1016/j.tet.2004.01.042
17. [17]
  McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
18. [18]
  Ding, C. H.; Dai, L. X.; Hou, X. L. Synlett 2004, 1691.
19. [19]
  Ding, C. H.; Dai, L. X.; Hou, X. L. Tetrahedron 2005, 61, 9586. doi: 10.1016/j.tet.2005.07.076
20. [20]
  Bertolini, F.; Woodward, S.; Crotti, S.; Pineschi, M. Tetrahedron Lett. 2009, 50, 4515. doi: 10.1016/j.tetlet.2009.05.081
21. [21]
  Wu, J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2000, 65, 1344. doi: 10.1021/jo9913816
22. [22]
  Mita, T.; Fujimori, I.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252. doi: 10.1021/ja053486y
23. [23]
  Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509. doi: 10.1021/ol051186f
24. [24]
  Fujimori, I.; Mita, T.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438. doi: 10.1021/ja067003h
25. [25]
  Minakata, S.; Hotta, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2006, 71, 7471. doi: 10.1021/jo061239m
26. [26]
  Matsukawa, S.; Tsukamoto, K. Org. Biomol. Chem. 2009, 7, 3792. doi: 10.1039/b908322g
27. [27]
  Wu, B.; Gallucci, C. J.; Parquette, R. J.; RajanBabu, V. T. Angew. Chem., Int. Ed. 2009, 48, 1126. doi: 10.1002/anie.v48:6
28. [28]
  Wu, B.; Gallucci, C. J.; Parquette, R. J.; RajanBabu, V. T. Chem. Sci. 2014, 5, 1102. doi: 10.1039/C3SC52929K
29. [29]
  Matsukawa, S.; Harada, T.; Yasuda, S. Org. Biomol. Chem. 2012, 10, 4886. doi: 10.1039/c2ob25435b
30. [30]
  Schneider, M. R.; Mann, A.; Taddei, M. Tetrahedron Lett. 1996, 37, 8493. doi: 10.1016/0040-4039(96)01975-2
31. [31]
  Yadav, J. S.; Reddy, S. V. B.; Nagaiah, K. Tetrahedron Lett. 2001, 42, 8067. doi: 10.1016/S0040-4039(01)01699-9
32. [32]
  Bergmeier, C. S.; Katz, J. S.; Donoghue, J. P.; Reed, D. D. Tetrahedron Lett. 2004, 45, 5011. doi: 10.1016/j.tetlet.2004.05.009
33. [33]
  Bera, M.; Roy, S. Tetrahedron Lett. 2007, 48, 7144. doi: 10.1016/j.tetlet.2007.07.200
34. [34]
  Sun, X. Y.; Sun, W.; Fan, R. H.; Wu, J. Adv. Synth. Catal. 2007, 349, 2151. doi: 10.1002/(ISSN)1615-4169
35. [35]
  Wang, Z. Y.; Sun, X. Y.; Wu, J. Tetrahedron 2008, 64, 5013. doi: 10.1016/j.tet.2008.03.081
36. [36]
  Michaelis, J. D.; Dineen, A. T. Tetrahedron Lett. 2009, 50, 1920. doi: 10.1016/j.tetlet.2009.02.047
37. [37]
  Wu, Y. C.; Zhu, J. P. Org. Lett. 2009, 11, 5558. doi: 10.1021/ol9024919
38. [38]
  Bera, M.; Roy, S. J. Org. Chem. 2010, 75, 4402. doi: 10.1021/jo100260k
39. [39]
  Yoon, D. H.; Lee, K. W.; Kim, Y.; Ha, H. J. Org. Lett. 2012, 14, 429. doi: 10.1021/ol202683k
40. [40]
  Nielsen, K. D.; Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2013, 135, 13605. doi: 10.1021/ja4076716
41. [41]
  Ghorai, K. M.; Tiwari, P. D.; Jain, N. J. Org. Chem. 2013, 78, 7121. doi: 10.1021/jo401028j
42. [42]
  Duda, L. M.; Michael, E. F. J. Am. Chem. Soc. 2013, 135, 18347. doi: 10.1021/ja410686v
43. [43]
  Li, X. W.; Yu, S. J.; Wan, B. S.; Yu, X. Z. Angew. Chem., Int. Ed. 2013, 52, 2577. doi: 10.1002/anie.v52.9
44. [44]
  Gao, K.; Paira, R.; Yoshikai, N. Adv. Synth. Catal. 2014, 356, 1486. doi: 10.1002/adsc.v356.7
45. [45]
  Takeda, Y.; Ikeda, Y.; Kuroda, A.; Minakata, S. J. Am. Chem. Soc. 2014, 136, 8544. doi: 10.1021/ja5039616
46. [46]
  Chaudhari, P.; Bari, S. Synth. Commun. 2015, 45, 391. doi: 10.1080/00397911.2014.965328
47. [47]
  Farr, N. R.; Alabaster, J. R.; Johnson, A. S.; Grabowski, J. J. E. Tetrahedron:Asymmetry 2003, 14, 3503. doi: 10.1016/j.tetasy.2003.08.038
48. [48]
  Kaiser, M. H.; Lo, F. W.; Beller, M. Tse, K. M. Org. Lett. 2006, 8, 5761. doi: 10.1021/ol062338p
49. [49]
  Tirotta, I.; Fifer, L. N.; Hutton, A. C. Tetrahedron Lett. 2013, 54, 618. doi: 10.1016/j.tetlet.2012.11.139
50. [50]
  Yang, D. X.; Wang, L. Q.; Han, F. X.; Wang, R. Chem.-Eur. J. 2014, 20, 16478. doi: 10.1002/chem.201404354
51. [51]
  Hirotaki, K.; Yamada, Y.; Hanamoto, T. Asian J. Org. Chem. 2014, 3, 285. doi: 10.1002/ajoc.v3.3
52. [52]
  Liu, H.; Zheng, C.; You, S. L. J. Org. Chem. 2014, 79, 1047. doi: 10.1021/jo402511b
53. [53]
  Noji, T.; Okano, K.; Tokuyama, H. Tetrahedron 2015, 71, 3833. doi: 10.1016/j.tet.2015.04.015
54. [54]
  Ghosal, C. N.; Santra, S.; Das, S.; Majee, A. Green Chem. 2016, 18, 565. doi: 10.1039/C5GC01323B
55. [55]
  Kidd, J.; Maiden, K.; Morgan, B. J. Tetrahedron 2016, 72, 3802. doi: 10.1016/j.tet.2016.03.031
56. [56]
  Ge, C.; Liu, R. R.; Gao, J. R.; Jia, Y. X. Org. Lett. 2016, 18, 3122. doi: 10.1021/acs.orglett.6b01317
57. [57]
  Rossi, E.; Abbiati, G.; Dell'Acqua, M.; Negrato, M.; Paganoni, A.; Pirovano, V. Org. Biomol. Chem. 2016, 14, 6095. doi: 10.1039/C6OB00672H
58. [58]
  Yin, J. X.; Hyland, J. T. C. Asian J. Org. Chem. 2016, 5, 1368. doi: 10.1002/ajoc.v5.11
59. [59]
  Yang, D. X.; Wang, L. Q.; Han, F. X.; Wang, R. Angew. Chem., Int. Ed. 2015, 54, 2185. doi: 10.1002/anie.201410257
60. [60]
  Yadav, J. S.; Reddy, S. V. B.; Nagaiah, K. Tetrahedron Lett. 2002, 43, 1565. doi: 10.1016/S0040-4039(02)00015-1
61. [61]
  Yadav, D. S. L.; Rai, K. V.; Singh, S.; Singh, P. Tetrahedron Lett. 2010, 51, 1657. doi: 10.1016/j.tetlet.2010.01.058
62. [62]
  Li, D.; Wang, Y. J.; Wang, L. Q.; Wang, J.; Wang, P. X.; Wang, K. Z.; Lin, L.; Liu, D. S.; Jiang, X. X.; Yang, D. X. Chem. Commun. 2016, 52, 9640. doi: 10.1039/C6CC02877B
63. [63]
  Chen, D. D.; Ding, C. H.; Hou, X. L.; Dai, L. X. Chem. J. Chin. Univ. 2011, 32, 694(in Chinese).
64. [64]
  D'hooghe, M.; Kerkaert, I.; Rottiers, M.; Kimpe, D. N. Tetrahedron 2004, 60, 3637. doi: 10.1016/j.tet.2004.02.059
65. [65]
  Blyumin, V. E.; Gallon, J. H.; Yudin, K. A. Org. Lett. 2007, 9, 4677. doi: 10.1021/ol7015302
66. [66]
  Ghorai, K. M.; Nanaji, Y.; Yadav, K. A. Org. Lett. 2011, 13, 4256. doi: 10.1021/ol2016077
67. [67]
  Xu, Y. J.; Lin, L. Q.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2011, 133, 5791. doi: 10.1021/ja201492x
68. [68]
  Li, X.; Su, J. J.; Chang, H. H. Wei, W. L. J. Mol. Catal. A:Chem. 2012, 363~364, 446.
69. [69]
  Xu, Y. J.; Shibasaki, M.; Matsunaga, S. J. Am. Chem. Soc. 2014, 136, 9190. doi: 10.1021/ja5039165
70. [70]
  Wang, G.; Franke, J.; Krische, J. M. J. Am. Chem. Soc. 2015, 137, 7915. doi: 10.1021/jacs.5b04404
71. [71]
  Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, A.; Mimura, N.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Pekin Trans. 1 1995, 1359.
72. [72]
  Hudlicky, T.; Tian, X. R.; Konisberger, K.; Maurya, R. Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. doi: 10.1021/ja960596j
73. [73]
  Penkett, C. S.; Simpson, I. D. Tetrahedron Lett. 2001, 42, 1179. doi: 10.1016/S0040-4039(00)02202-4
74. [74]
  Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2012, 134, 9541. doi: 10.1021/ja3013825
75. [75]
  Jensen, L. K.; Standley, A. E.; Jamison, F. T. J. Am. Chem. Soc. 2014, 136, 11145. doi: 10.1021/ja505823s
76. [76]
  Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2015, 137, 5638. doi: 10.1021/jacs.5b02503
77. [77]
  Moss, A. T.; Fenwick, R. D.; Dixon, J. D. J. Am. Chem. Soc. 2008, 130, 10076. doi: 10.1021/ja8036965
78. [78]
  Moss, A. T.; Alba, A.; Dixon, J. D. Chem. Commun. 2008, 21, 2474.
79. [79]
  Ohmatsu, K.; Ando, Y.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 18706. doi: 10.1021/ja411647x
80. [80]
  Moss, A. T.; Barber, M. D.; Dixon, J. D. Chem.-Eur. J. 2013, 19, 3071. doi: 10.1002/chem.201203825
81. [81]
  Li, D.; Wang, L. Q.; Yang, D. X.; Zhang, B. Z.; Wang, R. ACS Catal. 2015, 5, 7432. doi: 10.1021/acscatal.5b02177
82. [82]
  Wang, L. Q.; Yang, D. X.; Li, D.; Wang, R. Org. Lett. 2015, 17, 3004. doi: 10.1021/acs.orglett.5b01291
83. [83]
  Wang, L. Q.; Li, D.; Su, W.; Wang, R. Chem. Asian J. 2016, 11, 691. doi: 10.1002/asia.201501369
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