Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage

  • Zuliang Chen ,
  • Yingjing Wei ,
  • Junliang Zhang
Expand
  • a College of Chemistry and Bio-engineering, Yichun University, Yichun, Jiangxi 333600
    b Department of Chemistry, Fudan University, Shanghai 200438

Received date: 2023-03-17

  Revised date: 2023-04-27

  Online published: 2023-05-15

Supported by

National Natural Science Foundation of China(21861041)

Abstract

There are two different ring-opening modes of aziridines: ring-opening of aziridines via carbon-nitrogen bond cleavage, and ring-opening of aziridines via carbon-carbon bond cleavage. Among them, the reaction of aziridines via carbon-nitrogen bond cleavage has been reported in many reviews. The cycloaddition reactions of donor-acceptor (D-A) aziridines via carbon-carbon bond cleavage in recent 20 years are mainly summarized. Under some proper catalysts, the ring-opening of D-A aziridines via carbon-carbon bond cleavage yield azomethine ylides, which can undergo [3+n] cycloaddition reaction with aldehydes, imines, alkenes, alkynes, indoles etc.

Cite this article

Zuliang Chen , Yingjing Wei , Junliang Zhang . Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3078 -3088 . DOI: 10.6023/cjoc202303026

References

[1]
(a) Wakaki S.; Marumo H.; Tomoika K.; Shimizu E.; Kato G.; Kamada H.; Kudo S.; Fujimoto Y. Antibiot. Chemother. 1958, 8, 228.
[1]
(b) Hata T.; Sano Y.; Sugawara R.; Matsumae A.; Kanamori K.; Shima T.; Hoshi T. J. Antibiot. 1956, 9, 141.
[2]
(a) Ohno H. Chem. Rev. 2014, 114, 7784.
[2]
(b) Wang Q.; Chang H.; Wei W.; Liu Q.; Gao W.; Li Y.; Li X. Chin. J. Org. Chem. 2016, 36, 939. (in Chinese)
[2]
(王清宇, 常宏宏, 魏文珑, 刘强, 高文超, 李彦威, 李兴, 有机化学, 2016, 36, 939.)
[2]
(c) Ilardi E. A.; Njardarson J. T. J. Org. Chem. 2013, 78, 9533.
[2]
(d) Mack D. J.; Njardarson J. T. ACS Catal. 2013, 3, 272.
[2]
(e) Kuznetsov M. A.; Kuznetsova L. M.; Pankova A. S. Tetrahedron Lett. 2016, 57, 3575.
[3]
Vaultier M.; Carrie R. Tetrahedron Lett. 1978, 19, 1195.
[4]
Pohlhaus P. D.; Bowman R. K.; Johnson J. S. J. Am. Chem. Soc. 2004, 126, 2294.
[5]
Li L.; Wu X.; Zhang J. Chem. Commun. 2011, 47, 5049.
[6]
Zhan Y.; Liu T.; Ren J.; Wang Z. Chem. Eur. J. 2017, 23, 17862.
[7]
Zhang J.-H.; Pan C.-L.; Zhang H.-H.; Xu P.-F.; Luo Y.-C. Org. Chem. Front. 2021, 8, 2203.
[8]
Li L.; Zhang J. Org. Lett. 2011, 13, 5940.
[9]
Wang B.; Liang M.; Tang J.; Deng Y.; Zhao J.; Sun H.; Tung C.-H.; Jia J.; Xu Z. Org. Lett. 2016, 18, 4614.
[10]
Wu X.; Li L.; Zhang J. Chem. Commun. 2011, 47, 7824.
[11]
Jiang Z.; Wang J.; Lu P.; Wang Y. Tetrahedron 2011, 67, 9609.
[12]
Wu X.; Zhang J. Synthesis 2012, 44, 2147.
[13]
(a) Feng L.-W.; Ren H.; Xiong H.; Wang P.; Wang L.; Tang Y. Angew. Chem. Int. Ed. 2017, 56, 3055.
[13]
(b) Shenje R.; Martin M. C.; France S. Angew. Chem. Int. Ed. 2014, 53, 13907.
[13]
(c) Zhang J.; Chen Z.; Wu H.-H.; Zhang J. Chem. Commun. 2012, 48, 1817.
[14]
Liu H.; Zheng C.; You S.-L. Chin. J. Chem. 2014, 32, 709.
[15]
Cui B.; Ren J.; Wang Z. J. Org. Chem. 2014, 79, 790.
[16]
Tong D.; Wu J.; Bazinski N.; Koo D.; Vemula N.; Pagenkopf B. L. Chem. Eur. J. 2019, 25, 15244.
[17]
Zhou H.; Zeng X.; Ding L.; Xie Y.; Zhong G. Org. Lett. 2015, 17, 2385.
[18]
Zuo Q.; Shi Z.; Zhan F.; Wang Z.; Lin J.-S.; Jiang Y. Tetrahedron Lett. 2020, 61, 151576.
[19]
Garve L. K. B.; Kreft A.; Jones P. G.; Werz D. B. J. Org. Chem. 2017, 82, 9235.
[20]
Shi Z.; Fan T.; Zhang X.; Zhan F.; Wang Z.; Zhao L.; Lin J.-S.; Jiang Y. Adv. Synth. Catal. 2021, 363, 2619.
[21]
Alajarin M.; Ba?on D.; Egea A.; Marín-Luna M.; Orenes R.-A.; Vidal A. Org. Chem. Front. 2018, 5, 2020.
[22]
Varshnaya R. K.; Banerjee P. Org. Biomol. Chem. 2017, 15, 5182.
[23]
(a) Lee S. G.; Sin S.; Kim S.; Kim S.-G. Tetrahedron Lett. 2018, 59, 1480.
[23]
(b) Lee S. G.; Kim S.-G. Tetrahedron 2018, 74, 3671.
[24]
Zou X.; Liu Y.; Shang S.; Yang W.; Deng W. Chin. Chem. Lett. 2020, 31, 1293.
[25]
(a) Gulevich A. V.; Zhdanko A. G.; Orru R. V. A.; Nenajdenko V. G. Chem. Rev. 2010, 110, 5235.
[25]
(b) Qiu G.; Ding Q.; Wu J. Chem. Soc. Rev. 2013, 42, 5257.
[26]
Soeta T.; Miyamoto Y.; Fujinami S.; Ukaji Y. Tetrahedron 2014, 70, 6623.
[27]
Ghosh A.; Pandey A. K.; Banerjee P. J. Org. Chem. 2015, 80, 7235.
[28]
Liao Y.; Liu X.; Zhang Y.; Xu Y.; Xia Y.; Lin L.; Feng X. Chem. Sci. 2016, 7, 3775.
[29]
Wu X.; Zhou W.; Wu H.-H.; Zhang J. Chem. Commun. 2017, 53, 5661.
[30]
Liao Y.; Zhou B.; Xia Y.; Liu X.; Lin L.; Feng X. ACS Catal. 2017, 7, 3934.
[31]
Dong P.; Chen L.; Yang Z.; Dong S.; Feng X. Org. Chem. Front. 2021, 8, 6874.
[32]
Xu Y.; Chang F.; Cao W.; Liu X.; Feng X. ACS Catal. 2018, 8, 10261.
[33]
(a) Kim S.; Kim S.-G. Asian J. Org. Chem. 2019, 8, 1621.
[33]
(b) Kim S.-G. B. Korean Chem. Soc. 2019, 40, 747.
[34]
Zhang F.; Sang X.; Zhou Y.; Cao W.; Feng X. Org. Lett. 2022, 24, 1513.
Outlines

/