Chinese Journal of Organic Chemistry >
[3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives
Received date: 2021-03-11
Revised date: 2021-04-11
Online published: 2021-05-08
Supported by
National Natural Science Foundation of China(21772010)
[3,3] σ shift is one of classic reactions in organic chemistry. Since its discovery, the reactions have been expanding to different types and widely used in the fields of organic and pharmaceutical synthesis. Because the N—O bond strength of hydroxylamine derivatives is weak and easy to break, their [3,3] σ shift can be carried out under mild conditions to afford complex molecules containing hydroxyl and amino groups. In recent years, more and more attention has been paid to these reactions. The [3,3] σ shift rearrangements of hydroxylamine derivatives, including N-aryl-O-alkenylhydroxylamines, N,O-diaryl hydroxylamines, N,O-dialkenyloxyamines, N-alkenyl-O-arylhydroxyamines, and N-alkyl-O-acylhydroxyamines are reviewed, and a new prospect for the [3,3] σ shifts of hydroxylamine derivatives and their future development are put forward.
Key words： [3,3] σ shift; hydroxylamine; rearrangement; nucleophilic reaction; N—O bond
Guangyu Zhang , Jiaxi Xu . [3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3002 -3014 . DOI: 10.6023/cjoc202103022
| [1] | Sweeney, J. B. Chem. Soc. Rev. 2009, 38, 1027. |
| [2] | Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Chem. Soc. Rev. 2009, 38, 3133. |
| [3] | Martín Castro, A. M. Chem. Rev. 2004, 104, 2939. |
| [4] | Tejedor, D.; Mendez-Abt, G.; Cotos, L.; Garcia-Tellado, F. Chem. Soc. Rev. 2013, 42, 458. |
| [5] | Cope, A. C.; Hardy, E. M. J. Am. Chem. Soc. 1940, 62, 441. |
| [6] | Malinowski, J. T.; Malow, E. J.; Johnson, J. S. Chem. Commun. 2012, 48, 7568. |
| [7] | Chen, B.; Mapp, A. K. J. Am. Chem. Soc. 2004, 126, 5364. |
| [8] | Yanagi, T.; Otsuka, S.; Kasuga, Y.; Fujimoto, K.; Murakami, K.; Nogi, K.; Yorimitsu, H.; Osuka, A. J. Am. Chem. Soc. 2016, 138, 14582. |
| [9] | Huang, X.; Maulide, N. J. Am. Chem. Soc. 2011, 133, 8510. |
| [10] | Kaldre, D.; Maryasin, B.; Kaiser, D.; Gajsek, O.; Gonzalez, L.; Maulide, N. Angew. Chem., Int. Ed. 2017, 56, 2212. |
| [11] | Boekelheide, V.; Linn, W. J. Am. Chem. Soc. 1954, 76, 1286. |
| [12] | Lagiakos, H. R.; Aguilar, M.-I.; Perlmutter, P. J. Org. Chem. 2009, 74, 8001. |
| [13] | Figueira, V. B.; Esqué, A. G.; Varala, R.; González-Bello, C.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett. 2010, 51, 2029. |
| [14] | Yang, Z. H.; Hou, S. L.; He, W.; Cheng, B. X.; Jiao, P.; Xu, J. X. Tetrahedron 2016, 72, 2186. |
| [15] | Hou, S. L.; Li, X. Y.; Xu, J. X. Org. Biomol. Chem. 2014, 12, 4952. |
| [16] | Xu, J. X. Curr. Org. Synth. 2017, 14, 511. |
| [17] | Shang, L.; Chang, Y. H.; Luo, F.; He, J. N.; Huang, X.; Zhang, L.; Kong, L. C.; Li, K. X.; Peng, B. J. Am. Chem. Soc. 2017, 139, 4211. |
| [18] | Liu, G. Y.; Hou, S. L.; Xu, J. X. Org. Biomol. Chem. 2019, 17, 10088. |
| [19] | Chen, M. Y.; Liang, Y. C.; Dong, T. T.; Liang, W. J.; Liu, Y. P.; Zhang, Y. G.; Huang, X.; Kong, L. C.; Wang, J. X.; Peng, B. Angew. Chem., Int. Ed. 2021, 60, 2339. |
| [20] | Sousa, E. S. F. C.; Van, N. T.; Wengryniuk, S. E. J. Am. Chem. Soc. 2020, 142, 64. |
| [21] | Hori, M.; Guo, J. D.; Yanagi, T.; Nogi, K.; Sasamori, T.; Yorimitsu, H. Angew. Chem., Int. Ed. 2018, 57, 4663. |
| [22] | Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 30, 2129. |
| [23] | Bosco, M.; Dalpozzo, R.; Bartoli, G.; Palmieri, G.; Petrini, M. J. Chem. Soc., Perkin Trans. 2 1991, 657. |
| [24] | Bartoli, G.; Dalpozzo, R.; Nardi, M. Chem. Soc. Rev. 2014, 43, 4728. |
| [25] | Yuan, H. R.; Guo, L. R.; Liu, F. T.; Miao, Z. C.; Feng, L.; Gao, H. Y. ACS Catal. 2019, 9, 3906. |
| [26] | Lovato, K.; Bhakta, U.; Ng, Y. P.; Kürti, L. Org. Biomol. Chem. 2020, 18, 3281. |
| [27] | Chan, D. M.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933. |
| [28] | Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295. |
| [29] | Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. |
| [30] | Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360. |
| [31] | Vallavoju, N.; Selvakumar, S.; Jockusch, S.; Sibi, M. P.; Sivaguru, J. Angew. Chem., Int. Ed. 2014, 53, 5604. |
| [32] | Bianchi, L.; Dell'Erba, C.; Maccagno, M.; Mugnoli, A.; Novi, M.; Petrillo, G.; Severi, E.; Tavani, C. Eur. J. Org. Chem. 2004, 2004, 3566. |
| [33] | Gao, H.; Ess, D. H.; Yousufuddin, M.; Kurti, L. J. Am. Chem. Soc. 2013, 135, 7086. |
| [34] | Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2007, 120, 215. |
| [35] | Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157. |
| [36] | Guo, L.; Liu, F.; Wang, L.; Yuan, H.; Feng, L.; Kurti, L.; Gao, H. Org. Lett. 2019, 21, 2894. |
| [37] | Forkosh, H.; Vershinin, V.; Reiss, H.; Pappo, D. Org. Lett. 2018, 20, 2459. |
| [38] | Patel, D. C.; Breitbach, Z. S.; Woods, R. M.; Lim, Y.; Wang, A.; Foss, F. W., Jr.; Armstrong, D. W. J. Org. Chem. 2016, 81, 1295. |
| [39] | Yuan, H.; Du, Y.; Liu, F.; Guo, L.; Sun, Q.; Feng, L.; Gao, H. Chem. Commun. 2020, 56, 8226. |
| [40] | Zhang, J. W.; Qi, L. W.; Li, S. Y.; Xiang, S.-H.; Tan, B. Chin. J. Chem. 2020, 38, 1503. |
| [41] | Guo, L. R.; Liu, F. T.; Wang, L. Y.; Yuan, H. R.; Feng, L.; Lu, H. F.; Gao, H. Y. Org. Chem. Front. 2020, 9, 1077. |
| [42] | Wang, M.; Liu, Y.; Wang, L. Y.; Lu, H.F; Feng, L.; Gao, H. Y. Adv. Synth. Catal. 2021, 363, 1733. |
| [43] | Shirakawa, S.; Wu, X.; Maruoka, K. Angew. Chem., Int. Ed. 2013, 52, 14200. |
| [44] | Lu, S.; Ng, S. V. H.; Lovato, K.; Ong, J. Y.; Poh, S. B.; Ng, X. Q.; Kurti, L.; Zhao, Y. Nat. Commun. 2019, 10, 3061. |
| [45] | Lu, S.; Poh, S. B.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 11041. |
| [46] | Yang, G.; Guo, D.; Meng, D.; Wang, J. Nat. Commun. 2019, 10, 3062. |
| [47] | Lu, S.; Poh, S. B.; Rong, Z. Q.; Zhao, Y. Org. Lett. 2019, 21, 6169. |
| [48] | Vallavoju, N.; Selvakumar, S.; Jockusch, S.; Prabhakaran, M. T.; Sibi, M. P.; Sivaguru, J. Adv. Synth. Catal. 2014, 356, 2763. |
| [49] | He, R. D.; Li, C. L.; Pan, Q. Q.; Guo, P.; Liu, X. Y.; Shu, X. Z. J. Am. Chem. Soc. 2019, 141, 12481. |
| [50] | Son, J.; Reidl, T. W.; Kim, K. H.; Wink, D. J.; Anderson, L. L. Angew. Chem., Int. Ed. 2018, 57, 6597. |
| [51] | Chellat, M. F.; Riedl, R. Angew. Chem., Int. Ed. 2017, 56, 13184. |
| [52] | Alshreimi, A. S.; Zhang, G.; Reidl, T. W.; Pena, R. L.; Koto, N. G.; Islam, S. M.; Wink, D. J.; Anderson, L. L. Angew. Chem., Int. Ed. 2020, 59, 15244. |
| [53] | Xu, J. X. Univ. Chem. 2006, 21(4), 40. (in Chinese) |
| [53] | (许家喜, 大学化学, 2006, 21(4), 40.) |
| [54] | Singh, G. S.; Desta, Z. Y. Chem Rev. 2012, 112, 6104. |
| [55] | Chan, S. T.; Pearce, A. N.; Januario, A. H.; Page, M. J.; Kaiser, M.; McLaughlin, R. J.; Harper, J. L.; Webb, V. L.; Barker, D.; Copp, B. R. J. Org. Chem. 2011, 76, 9151. |
| [56] | Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748. |
| [57] | Ochiai, E. J. Org. Chem. 1953, 18, 534. |
| [58] | (a) House, H. O.; Richey, F. A. J. Org. Chem. 1969, 34, 1430. |
| [58] | (b) Beshara, C. S.; Hall, A.; Jenkins, R. L.; Jones, T. C.; Parry, R. T.; Thomas, S. P.; Tomkinson, N. C. Chem. Commun. 2005, 1478. |
| [59] | Kokuev, A. O.; Antonova, Y. A.; Dorokhov, V. S.; Golovanov, I. S.; Nelyubina, Y. V.; Tabolin, A. A.; Sukhorukov, A. Y.; Ioffe, S. L. J. Org. Chem. 2018, 83, 11057. |
| [60] | Marenich, A. V.; Jerome, S. V.; Cramer, C. J.; Truhlar, D. G. J. Chem. Theory Comput. 2012, 8, 527. |
| [61] | Breuning, M.; Ha?user, T.; Tanzer, E.-M. Org. Lett. 2009, 11, 4032. |
| [62] | Adam, W.; Boland, W.; Hartmann-Schreier, J.; Humpf, H.-U.; Lazarus, M.; Saffert, A.; Saha-Möller, C. R.; Schreier, P. J. Am. Chem. Soc. 1998, 120, 11044. |
| [63] | Adam, W.; Lazarus, M.; Saha-Mǒller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1996, 7, 2287. |
| [64] | Takeda, N.; Arisawa, N.; Miyamoto, M.; Kobori, Y.; Shinada, T.; Miyata, O.; Ueda, M. Org. Chem. Front. 2019, 6, 3721. |
| [65] | Verbrugghen, T.; Cos, P.; Maes, L.; Van Calenbergh, S. J. Med. Chem. 2010, 53, 5342. |
| [66] | Pradere, U.; Garnier-Amblard, E. C.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2014, 114, 9154. |
| [67] | Hecker, S. J.; Erion, M. D. J. Med. Chem. 2008, 51, 2328. |
| [68] | Yang, Y.; Qu, C.; Chen, X.; Sun, K.; Qu, L.; Bi, W.; Hu, H.; Li, R.; Jing, C.; Wei, D.; Wei, S.; Sun, Y.; Liu, H.; Zhao, Y. Org. Lett. 2017, 19, 5864. |
| [69] | Ramirez, F.; Marecek, J. F. Synthesis 1985, 449. |
| [70] | Koser, G. F.; Lodaya, J. S.; Ray, D. G.; Kokil, P. B. J. Am. Chem. Soc. 1988, 110, 2987. |
| [71] | Khan, S.; Battula, S.; Ahmed, Q. N. Tetrahedron 2016, 72, 4273. |
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