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Synthesis
DOI: 10.1055/a-2806-4329
DOI: 10.1055/a-2806-4329
Short Review
Recent Progress in the Synthesis and Application of 2-Acylaziridines
Authors
This work was supported the Doctoral Research Foundation of Fuyang Normal University (No. 2025KYQD0075 to W. Xiong).
Abstract
2-Acylaziridines are versatile three-membered nitrogen heterocycles whose distinct reactivity stems from substantial ring strain and relatively weak C–N bonds. The appended acyl group exerts significant stereoelectronic influence and serves as a directing moiety, enabling stereoselective transformations that favor nucleophilic attack at the more substituted aziridine carbon and facilitate tandem cyclization processes. This review highlights recent advances over the past decade in the synthesis and applications of 2-acylaziridines, with an emphasis on innovative methodologies, detailed mechanistic studies, and practical implementations. It aims to inspire the development of advanced synthetic strategies and promote the broader use of these scaffolds in the construction of bioactive molecules and complex heterocyclic systems.
Publication History
Received: 15 January 2026
Accepted after revision: 05 February 2026
Accepted Manuscript online:
05 February 2026
Article published online:
17 February 2026
© 2026. Thieme. All rights reserved.
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References
- 1 De Proft F, Geerlings P. Top Heterocycl Chem. 2014 38
- 2a Wang Q, Chang H, Wei W. et al. Chin J Org Chem 2016; 36: 939
- 2b Sabir S, Kumar G, Verma VP, Jat JL. ChemistrySelect 2018; 3: 3702
- 2c Dank C, Ielo L. Org Biomol Chem 2023; 21: 4553
- 2d Dongbang S, Hwang J, Shin J, Baik E, Kim E. Synthesis 2025; 57: 1081
- 2e Crawley SL, Funk RL. Org Lett 2006; 8: 3995
- 3a Cardoso AL, Pinho e Melo TMVD. Eur J Org Chem 2012; 2012: 6479
- 3b Tang S, Zhang X, Sun J, Niu D, Chruma JJ. Chem Rev 2018; 118: 10393
- 3c Pohlhaus PD, Bowman RK, Johnson JS. J Am Chem Soc 2004; 126: 2294
- 4 Maurer SJ, Petrarca de Albuquerque JL, McCallum ME. Chembiochem 2024; 25: e202400295
- 5a Callebaut G, Meiresonne T, De Kimpe N, Mangelinckx S. Chem Rev 2014; 114: 7954
- 5b Ha HJ, Jung JH, Lee WK. Asian J Org Chem 2014; 3: 1020
- 5c Jarzyński S, Leśniak S. Chem Heterocycl Compd 2016; 52: 353
- 6 Jat JL, Paudyal MP, Gao HY. et al. Science 2014; 343: 61
- 7 Hashimoto T, Nakatsu H, Yamamoto K, Maruoka K. J Am Chem Soc 2011; 133: 9730
- 8 Xu J, Jiao P. J Chem Soc Perkin Trans 2002; 1: 1491
- 9 Patonay T, Hoffman RV. J Org Chem 2002; 60: 2368
- 10 Miyamoto Y, Wada N, Soeta T, Fujinami S, Inomata K, Ukaji Y. Chem Asian J 2013; 8: 824
- 11 Xing Q, Jiang D, Zhang J. et al. Commun Chem 2022; 5: 79
- 12 Farndon JJ, Young TA, Bower JF. J Am Chem Soc 2018; 140: 17846
- 13 Olaizola I, Ochoa de Retana AM, de los Santos JM.. Top Curr Chem 2025; 383: 40
- 14 Kwart H, Khan AA. J Am Chem Soc 1951; 1967: 89
- 15 Evans DA, Faul MM, Bilodeau MT. J Org Chem 1991; 56: 6744
- 16 Shikhar Srivastava O, Anand V, Rastogi N. Asian J Org Chem 2023; 12: e202300415
- 17 Dam D, Schoenmakers J, Bouwman E, Codée JDC. J Org Chem 2025; 90: 6577
- 18 Baris N, Dračínský M, Tarábek J. et al. Angew Chem Int Ed 2024; 63: e202315162
- 19 Wu C, Zhu Y. Chem Commun 2024; 60: 12449
- 20 Mitchell JK, Hussain WA, Bansode AH, O’Connor RM, Parasram M. J Am Chem Soc 2024; 146: 9499
- 21 Sabir S, Pandey CB, Yadav AK, Tiwari B, Jat JL. J Org Chem 2018; 83: 12255
- 22 Jat JL, Yadav AK, Pandey CB, Chandra D, Tiwari B. J Org Chem 2022; 87: 3751
- 23 Southwick PL, Christman DR. J Am Chem Soc 2002; 1886: 74
- 24 Ashitha KT, Vinaya PP, Krishna A. et al. Org Biomol Chem 2020; 18: 1588
- 25 Umeda T, Minakata S. RSC Adv 2021; 11: 22120
- 26 Wang S, Wang P, Li S-J, Chen Y-H, Sun Z-J, Lei A. Natl Sci Rev 2023; 10: nwad187
- 27 Gelato Y, Marraffa L, Pasca F. et al. J Am Chem Soc 2025; 147: 35567
- 28 Zhang X, Huang Q-F, Zou W-L. et al. Org Chem Front 2019; 6: 3321
- 29 Wang R, Jiang Q, Jiang L, Liu WH. J Am Chem Soc 2025; 147: 26298
- 30 Qu Y, Liu Z, Zhou Y, Feng X, Liu X. Chem Eur J 2025; 31: e202500302
- 31 Vásquez Tapia Vera C, Hughes WB, Klaus DR, Paton RS, Bandar JS. J Am Chem Soc 2025; 148: 494
- 32 de los Santos JM, Ochoa de Retana AM, Martínez de Marigorta E, Vicario J, Palacios F. ChemCatChem 2018; 10: 5092
- 33 Bew SP, Liddle J, Hughes DL, Pesce P, Thurston SM. Angew Chem Int Ed 2017; 56: 5322
- 34a Bierschenk SM, Pan JY, Settineri NS. et al. J Am Chem Soc 2022; 144: 11425
- 34b Zhou SB, Zhang ZC, Bai DJ. et al. Inorg Chem 2022; 61: 4009
- 34c Patamia V, Saccullo E, Zagni C. et al. Chem Eur J 2024; 30: e202303984
- 34d Li J, Kou M, Zhou S. et al. Nat Commun 2025; 16: 2169
- 35 Xie Z-Y, Xu C-L, Zhu Y. et al. Org Chem Front 2026; 13: 440
- 36 Lei X, Sun Y, Guo Q, Shi J. RSC Adv 2024; 14: 17178
- 37a Hu H, Liu Y, Lin L, Zhang Y, Liu X, Feng X. Angew Chem Int Ed 2016; 55: 10098
- 37b Nakamura S, Hayama D. Angew Chem Int Ed 2017; 129: 8911
- 38 An D, Guan X, Guan R, Jin L, Zhang G, Zhang S. Chem Commun 2016; 52: 11211
- 39 Peng Q, Guo D, Bie J, Wang J. Angew Chem Int Ed 2018; 57: 3767
- 40 Jiang J, Liu H, Lu C-D, Xu Y-J. Org Lett 2016; 18: 880
- 41 Trost BM, Saget T, Hung CI. Angew Chem Int Ed 2017; 56: 2440
- 42 Pan J, Wu JH, Zhang H. et al. Angew Chem Int Ed 2019; 58: 7425
- 43 Kodama Y, Imai S, Fujimoto J, Sato K, Mase N, Narumi T. Chem Commun 2021; 57: 6915
- 44 Kattamuri PV, Zhao JD, Das TK. et al. J Am Chem Soc 2022; 144: 10943
- 45 Baldwin JE, Pudussery RG, Qureshi AK, Sklarz B. J Am Chem Soc 1968; 90: 5325
- 46 Tangara S, Kanazawa A, Py S. Eur J Org Chem 2017; 6357
- 47 Tangara S, Aupic C, Kanazawa A, Poisson J-F, Py S. Org Lett 2017; 19: 4842
- 48 Lichtenstein YI, Golovanov IS, Ioffe SL, Tabolin AA. Tetrahedron 2022; 110: 132693
- 49 Bonner A, Baumann M. Org Process Res Dev 2023; 28: 1567
- 50 Smalley AP, Cuthbertson JD, Gaunt MJ. J Am Chem Soc 2017; 139: 1412
- 51 Ushimaru R. J Nat Med 2023; 78: 21
- 52 Tao H, Ushimaru R, Awakawa T, Mori T, Uchiyama M, Abe I. J Am Chem Soc 2022; 144: 21512
- 53 Zhou L, Awakawa T, Ushimaru R, Kanaida M, Abe I. Org Lett 2024; 26: 724
- 54 Cha L, Paris JC, Zanella B. et al. J Am Chem Soc 2023; 145: 6240
- 55 Hale EA, Zhu Q. Chem Sci 2025; 16: 15216
- 56a Sakla AP, Kansal P, Shankaraiah N. Org Biomol Chem 2020; 18: 8572
- 56b Pan B, Wang J, Yang Y, Huang G. Asian J Org Chem 2025; 15: e00617
- 57 Chung BKW, White CJ, Scully CCG, Yudin AK. Chem Sci 2016; 7: 6662
- 58 Scully CCG, White CJ, Yudin AK. Org Biomol Chem 2016; 14: 10230
- 59 Chung BKW, White CJ, Yudin AK. Nat Protoc 2017; 12: 1277
- 60 Jeong H, Yadav NN, Ha HJ. Synthesis 2017; 49: 1264
- 61 Srivastava N, Macha L, Ha HJ. Org Lett 2019; 21: 8992
- 62 Hajra S, Singha Roy S, Aziz SM, Das D. Org Lett 2017; 19: 4082
- 63 Hajra S, Abu Saleh SK, Hazra A, Singh MS. J Org Chem 2019; 84: 8194
- 64 Hajra S, Hazra A, Mandal P. Org Lett 2018; 20: 6471
- 65 Hajra S, Singha Roy S, Biswas A, Saleh SA. J Org Chem 2018; 83: 3633
- 66 Hajra S, Hazra A, Abu Saleh SK. J Org Chem 2019; 84: 10412
- 67 Bhandari S, Kulkarni N, Sakla AP, Shankaraiah N. Tetrahedron Lett 2020; 61: 152007
- 68 Bhandari S, Sakla AP, Shankaraiah N. ChemistrySelect 2020; 5: 2886
- 69 Hajra S, Biswas A. Org Lett 2020; 22: 4990
- 70 Mastandrea MM, Perulli S, Martini V. et al. Angew Chem Int Ed 2025; e16731
- 71a Wang B, Liang M, Tang J. et al. Org Lett 2016; 18: 4614
- 71b Zhan Y, Liu T, Ren J, Wang Z. Chemistry 2017; 23: 17862
- 71c Zou X, Liu Y, Shang S, Yang W, Deng W. Chin Chem Lett 2020; 31: 1293
- 71d Dong P, Chen L, Yang Z, Dong S, Feng X. Org Chem Front 2021; 8: 6874
- 71e Li H, Wu J, Zheng J, Li WZ. Chem Commun 2021; 57: 11092
- 72a Liao Y, Liu X, Zhang Y. et al. Chem Sci 2016; 7: 3775
- 72b Wu X, Zhou W, Wu HH, Zhang J. Chem Commun 2017; 53: 5661
- 72c Shi Z, Fan T, Lin J-S. et al. Org Chem Front 2025; 12: 5573
- 73 Liao Y, Zhou B, Xia Y, Liu X, Lin L, Feng X. ACS Catal 2017; 7: 3934
- 74 Li X, Zeng H, Lin L, Feng X. Org Lett 2021; 23: 2954