Chinese Journal of Organic Chemistry >
Research Progress in the Ring-Opening Reactions of Aziridines by Carbon Nucleophiles
Received date: 2017-02-23
Revised date: 2017-05-03
Online published: 2017-06-02
Supported by
Project supported by the Natural Science Foundation of Shanxi Province (Nos.201601D011028,20130110094).
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.
Key words： aziridines; ring-opening reactions; carbon nucleophiles
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
[1] Feng, J. J.; Zhang, J. L. ACS catal. 2016, 6, 6651.
[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). (王清宇, 常宏宏, 魏文龙, 刘强, 高文超, 李彦威, 李兴, 有机化学, 2016, 36, 939.)
[3] Cardoso, L. A.; Pinhoe Melo, M. V. D. T. Eur. J. Org. Chem. 2012, 33, 6479.
[4] Subrahmanyam, G.; Adhya, A. J. Sci. Ind. Res. Indian 1974, 33, 308.
[5] Ha, H. J.; Jung, J. H.; Lee, W. K. Asian J. Org. Chem. 2014, 3, 1020.
[6] Luginina, J.; Turks, M. Chem. Heterocycl. Compd. 2016, 10, 773.
[7] Pineschi, M. Synlett 2014, 1817.
[8] Turks, M.; Posevins, D. Eur. J. Org. Chem. 2016, 2016, 1760.
[9] Benjamin, L.; Richard, G.; Markus, L.; Riccardo, M. M. Angew. Chem., Int. Ed. 2014, 53, 7063.
[10] Hammond, B. G.; Xu, B.; Mashuta, S. M.; Okoromoba, E. O. Chem. Commun. 2016, 52, 13353.
[11] Wang, R.; Jiang, X. X.; Liu, X.; Li, D. Chem.-Eur. J. 2016, 22, 17141.
[12] Murty, M. S. R.; Yadav, J. S. Tetrahedron Lett. 2005, 46, 6385.
[13] Feng, X. M.; Lin, L. L.; Liu, X. H.; Li, J. Chem. Commun. 2014, 50, 6672.
[14] Li, Y. W.; Su, J. J.; Chang, H. H.; Li, X.; Wei, W. L. Chem. Ind. 2011, 39, 12(in Chinese). (李彦威, 苏继娟, 常宏宏, 李兴, 魏文龙, 广州化工, 2011, 39, 12.)
[15] Schneider, C. Angew. Chem., Int. Ed. 2009, 48, 2082.
[16] Hu, X. E. Tetrahedron 2004, 60, 2701.
[17] McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
[18] Ding, C. H.; Dai, L. X.; Hou, X. L. Synlett 2004, 1691.
[19] Ding, C. H.; Dai, L. X.; Hou, X. L. Tetrahedron 2005, 61, 9586.
[20] Bertolini, F.; Woodward, S.; Crotti, S.; Pineschi, M. Tetrahedron Lett. 2009, 50, 4515.
[21] Wu, J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2000, 65, 1344.
[22] Mita, T.; Fujimori, I.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
[23] Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509.
[24] Fujimori, I.; Mita, T.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438.
[25] Minakata, S.; Hotta, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2006, 71, 7471.
[26] Matsukawa, S.; Tsukamoto, K. Org. Biomol. Chem. 2009, 7, 3792.
[27] Wu, B.; Gallucci, C. J.; Parquette, R. J.; RajanBabu, V. T. Angew. Chem., Int. Ed. 2009, 48, 1126.
[28] Wu, B.; Gallucci, C. J.; Parquette, R. J.; RajanBabu, V. T. Chem. Sci. 2014, 5, 1102.
[29] Matsukawa, S.; Harada, T.; Yasuda, S. Org. Biomol. Chem. 2012, 10, 4886.
[30] Schneider, M. R.; Mann, A.; Taddei, M. Tetrahedron Lett. 1996, 37, 8493.
[31] Yadav, J. S.; Reddy, S. V. B.; Nagaiah, K. Tetrahedron Lett. 2001, 42, 8067.
[32] Bergmeier, C. S.; Katz, J. S.; Donoghue, J. P.; Reed, D. D. Tetrahedron Lett. 2004, 45, 5011.
[33] Bera, M.; Roy, S. Tetrahedron Lett. 2007, 48, 7144.
[34] Sun, X. Y.; Sun, W.; Fan, R. H.; Wu, J. Adv. Synth. Catal. 2007, 349, 2151.
[35] Wang, Z. Y.; Sun, X. Y.; Wu, J. Tetrahedron 2008, 64, 5013.
[36] Michaelis, J. D.; Dineen, A. T. Tetrahedron Lett. 2009, 50, 1920.
[37] Wu, Y. C.; Zhu, J. P. Org. Lett. 2009, 11, 5558.
[38] Bera, M.; Roy, S. J. Org. Chem. 2010, 75, 4402.
[39] Yoon, D. H.; Lee, K. W.; Kim, Y.; Ha, H. J. Org. Lett. 2012, 14, 429.
[40] Nielsen, K. D.; Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2013, 135, 13605.
[41] Ghorai, K. M.; Tiwari, P. D.; Jain, N. J. Org. Chem. 2013, 78, 7121.
[42] Duda, L. M.; Michael, E. F. J. Am. Chem. Soc. 2013, 135, 18347.
[43] Li, X. W.; Yu, S. J.; Wan, B. S.; Yu, X. Z. Angew. Chem., Int. Ed. 2013, 52, 2577.
[44] Gao, K.; Paira, R.; Yoshikai, N. Adv. Synth. Catal. 2014, 356, 1486.
[45] Takeda, Y.; Ikeda, Y.; Kuroda, A.; Minakata, S. J. Am. Chem. Soc. 2014, 136, 8544.
[46] Chaudhari, P.; Bari, S. Synth. Commun. 2015, 45, 391.
[47] Farr, N. R.; Alabaster, J. R.; Johnson, A. S.; Grabowski, J. J. E. Tetrahedron:Asymmetry 2003, 14, 3503.
[48] Kaiser, M. H.; Lo, F. W.; Beller, M. Tse, K. M. Org. Lett. 2006, 8, 5761.
[49] Tirotta, I.; Fifer, L. N.; Hutton, A. C. Tetrahedron Lett. 2013, 54, 618.
[50] Yang, D. X.; Wang, L. Q.; Han, F. X.; Wang, R. Chem.-Eur. J. 2014, 20, 16478.
[51] Hirotaki, K.; Yamada, Y.; Hanamoto, T. Asian J. Org. Chem. 2014, 3, 285.
[52] Liu, H.; Zheng, C.; You, S. L. J. Org. Chem. 2014, 79, 1047.
[53] Noji, T.; Okano, K.; Tokuyama, H. Tetrahedron 2015, 71, 3833.
[54] Ghosal, C. N.; Santra, S.; Das, S.; Majee, A. Green Chem. 2016, 18, 565.
[55] Kidd, J.; Maiden, K.; Morgan, B. J. Tetrahedron 2016, 72, 3802.
[56] Ge, C.; Liu, R. R.; Gao, J. R.; Jia, Y. X. Org. Lett. 2016, 18, 3122.
[57] Rossi, E.; Abbiati, G.; Dell'Acqua, M.; Negrato, M.; Paganoni, A.; Pirovano, V. Org. Biomol. Chem. 2016, 14, 6095.
[58] Yin, J. X.; Hyland, J. T. C. Asian J. Org. Chem. 2016, 5, 1368.
[59] Yang, D. X.; Wang, L. Q.; Han, F. X.; Wang, R. Angew. Chem., Int. Ed. 2015, 54, 2185.
[60] Yadav, J. S.; Reddy, S. V. B.; Nagaiah, K. Tetrahedron Lett. 2002, 43, 1565.
[61] Yadav, D. S. L.; Rai, K. V.; Singh, S.; Singh, P. Tetrahedron Lett. 2010, 51, 1657.
[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.
[63] Chen, D. D.; Ding, C. H.; Hou, X. L.; Dai, L. X. Chem. J. Chin. Univ. 2011, 32, 694(in Chinese). (陈冬冬, 丁昌华, 侯雪龙, 戴立信, 高等学校化学学报, 2011, 32, 694.)
[64] D'hooghe, M.; Kerkaert, I.; Rottiers, M.; Kimpe, D. N. Tetrahedron 2004, 60, 3637.
[65] Blyumin, V. E.; Gallon, J. H.; Yudin, K. A. Org. Lett. 2007, 9, 4677.
[66] Ghorai, K. M.; Nanaji, Y.; Yadav, K. A. Org. Lett. 2011, 13, 4256.
[67] Xu, Y. J.; Lin, L. Q.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2011, 133, 5791.
[68] Li, X.; Su, J. J.; Chang, H. H. Wei, W. L. J. Mol. Catal. A:Chem. 2012, 363~364, 446.
[69] Xu, Y. J.; Shibasaki, M.; Matsunaga, S. J. Am. Chem. Soc. 2014, 136, 9190.
[70] Wang, G.; Franke, J.; Krische, J. M. J. Am. Chem. Soc. 2015, 137, 7915.
[71] Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, A.; Mimura, N.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Pekin Trans. 11995, 1359.
[72] Hudlicky, T.; Tian, X. R.; Konisberger, K.; Maurya, R. Fan, B. J. Am. Chem. Soc. 1996, 118, 10752.
[73] Penkett, C. S.; Simpson, I. D. Tetrahedron Lett. 2001, 42, 1179.
[74] Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2012, 134, 9541.
[75] Jensen, L. K.; Standley, A. E.; Jamison, F. T. J. Am. Chem. Soc. 2014, 136, 11145.
[76] Huang, C. Y.; Doyle, G. A. J. Am. Chem. Soc. 2015, 137, 5638.
[77] Moss, A. T.; Fenwick, R. D.; Dixon, J. D. J. Am. Chem. Soc. 2008, 130, 10076.
[78] Moss, A. T.; Alba, A.; Dixon, J. D. Chem. Commun. 2008, 21, 2474.
[79] Ohmatsu, K.; Ando, Y.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 18706.
[80] Moss, A. T.; Barber, M. D.; Dixon, J. D. Chem.-Eur. J. 2013, 19, 3071.
[81] Li, D.; Wang, L. Q.; Yang, D. X.; Zhang, B. Z.; Wang, R. ACS Catal. 2015, 5, 7432.
[82] Wang, L. Q.; Yang, D. X.; Li, D.; Wang, R. Org. Lett. 2015, 17, 3004.
[83] Wang, L. Q.; Li, D.; Su, W.; Wang, R. Chem. Asian J. 2016, 11, 691.
/
| 〈 |
|
〉 |
