Lewis Acid Catalyzed SN2-Type Domino Ring-Opening Cyclization (DROC) of Aziridines with Alkynes: A Synthetic Route to 2,3-Dihydropyrroles

Dipti Shukla; Suraj Kashyap; Bharat Singh; Amit Kumar Sharma; Aditya Bhattacharyya; Noimur Rahman; Manas K. Ghorai

doi:10.1055/a-2415-1629

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(02): 447-456
DOI: 10.1055/a-2415-1629

paper

Special Topic Dedicated to Prof. H. Ila

Lewis Acid Catalyzed S_N2-Type Domino Ring-Opening Cyclization (DROC) of Aziridines with Alkynes: A Synthetic Route to 2,3-Dihydropyrroles

Dipti Shukla

,

Suraj Kashyap

,

Bharat Singh

,

Amit Kumar Sharma

,

Aditya Bhattacharyya

,

Noimur Rahman

,

Manas K. Ghorai ∗

Abstract

Alle Artikel dieser Rubrik

Dedicated to Prof. H. Ila on the occasion of her 80^th birthday.

Abstract

A simple strategy for the synthesis of a variety of dihydropyrroles in good to excellent yields via a Lewis acid catalyzed, quaternary ammonium salt mediated S_N2-type ring opening followed by cyclization of activated aziridines with alkynes in a domino fashion is described. The formation and the observed stereoselectivities of the products via an S_N2-/double S_N2-type ring-opening pathway are rationalized by mechanistic studies.

Key words

aziridines - alkynes - dihydropyrroles - S_N2-type ring opening - DROC

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References

1a Green MP, Prodger JC, Hayes CJ. Tetrahedron Lett. 2002; 43: 6609
1b Castellano S, Fiji HD. G, Kinderman SS, Watanabe M, de Leon P, Tamanoi F, Kwon O. J. Am. Chem. Soc. 2007; 129: 5843
1c O’Hagan D. Nat. Prod. Rep. 2000; 17: 435 ; and references cited therein
1d Dewick PM. Medicinal Natural Products, Chap. 6. J. Wiley & Sons; Chichester: 1997
1e Shen H.-F, Chen X, Liao P, Shao X.-S, Li Z, Xu X.-Y. Chin. Chem. Lett. 2015; 26: 509

2a Misra N, Luthra R, Singh KL, Kumar S. In Comprehensive Natural Products Chemistry, , Chap. 4.03. Barton D, Nakanishi K, Methcohn O, Kelly IW. Elsevier; Amsterdam: 1999
2b Terssell KB. G. Natural Product Chemistry, 2nd ed., Chap. 8. Apotekarsocieteten; Stockholm: 1977
2c Ye Z, Shi L, Shao X, Xu X, Xu Z, Li Z. J. Agric. Food Chem. 2013; 61: 312

3a Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
3b Hou G.-H, Hie J.-H, Yan P.-C, Zhou Q.-L. J. Am. Chem. Soc. 2009; 131: 1366
3c Qin H, Guo T, Lin K, Li G, Lu H. Nat. Commun. 2023; 14: 7307 ; and references cited therein

4a Li X.-Z, He Y.-P, Wu H. Angew. Chem. Int. Ed. 2024; 63: e202317182
4b Wang P, Leng Y, Wu Y. Eur. J. Org. Chem. 2022; e202201091
4c Hegedus LS, McKearin JM. J. Am. Chem. Soc. 1982; 104: 2444
4d Ichikawa J, Fujiwara M, Wada Y, Okauchi T, Minami T. Chem. Commun. 2000; 1887
4e Ma S, Yu F, Li J, Gao W. Chem. Eur. J. 2007; 13: 247
4f Brichacek M, Njardarson JT. Org. Biomol. Chem. 2009; 7: 1761 ; and references cited therein
4g Knight DW, Redfern AL, Gilmore J. J. Chem. Soc., Perkin Trans. 1 2002; 622
4h Wu Q, Hu J, Ren X, Zhou J. Chem. Eur. J. 2011; 17: 11553

For some reviews and examples of the synthesis of pyrrolidine derivatives, see:

5a Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
5b Coldham I, Hufton R. Chem. Rev. 2005; 105: 2765
5c Mitchinson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 2000; 2862
5d Sardina FJ, Rapoport H. Chem. Rev. 1996; 96: 1825
5e Pichon M, Figadère B. Tetrahedron: Asymmetry 1996; 7: 927
5f Sundberg RJ. In Comprehensive Heterocyclic Chemistry II, Vol. 2. Bird CW. Pergamon; Oxford: 1996: 119
5g Davis FA, Zhang J, Qiu H, Wu Y. Org. Lett. 2008; 10: 1433
5h Jiang C, Frontier AJ. Org. Lett. 2007; 9: 4939
5i Trost BM, Silverman SM, Stambuli JP. J. Am. Chem. Soc. 2007; 129: 12398
5j Murruzzu C, Riera A. Tetrahedron: Asymmetry 2007; 18: 149
5k Rios R, Ibrahem I, Vesely J, Sundén H, Córdova A. Tetrahedron Lett. 2007; 48: 8695
5l Jiang W, Tran JA, Tucci FC, Fleck BA, Hoare SR, Markison S, Wen J, Chen CW, Marinkovic D, Arellano M, Foster AC, Chen C. Bioorg. Med. Chem. Lett. 2007; 17: 6546
5m Anxionnat B, Robert B, George P, Ricci G, Perrin M.-A, Pardo DG, Cossy J. J. Org. Chem. 2012; 77: 6087
5n Lim HJ, RajanBabu TV. Org. Lett. 2011; 13: 6596
5o Wang D, Fan Y, Yu P, Désaubry L. Chem. Commun. 2020; 56: 5584

For some examples of the synthesis of 2,3-dihydropyrrole derivatives, see:

6a Yaragorla S, Tangellapally R, Arun D. Eur. J. Org. Chem. 2024; 27: e202400238
6b Gong K, Ma Y, Yu P, Gao S, Li Y, Liang D, Sun S, Wang B. Adv. Synth. Catal. 2024; 366: 2352
6c Ji X, He R, Shi L, Sun S, Liang D. Eur. J. Org. Chem. 2024; 27: e202301246
6d Saini RK, Borpatra PJ, Pandey SK. Eur. J. Org. Chem. 2023; 26: e202300693
6e Hu X, Tao M, Gong K, Feng Q, Hu X, Li Y, Sun S, Liang D. J. Org. Chem. 2023; 88: 12935
6f Permingeat CP, Bianchini MA, Delpiccolo CM. L. J. Org. Chem. 2023; 88: 16091
6g Lei T, Cheng Y.-Y, Han X, Zhou C, Yang B, Fan X.-W, Chen B, Tung C.-H, Wu L.-Z. J. Am. Chem. Soc. 2022; 144: 16667
6h Guo C, Xue M.-X, Zhu M.-K, Gong L.-Z. Angew. Chem. Int. Ed. 2008; 47: 3414 ; Angew. Chem. 2008, 120, 3462
6i Zhou X, Zhang H, Yuan J, Mai L, Li Y. Tetrahedron Lett. 2007; 48: 7236
6j Wurz RP, Charette AB. Org. Lett. 2005; 7: 2313
6k Doyle MP, Yan M, Hu W, Gronenberg LS. J. Am. Chem. Soc. 2003; 125: 4692

7a Chiang H.-L, Zhao W.-T, Chen Y.-A, Lin Y.-C, Chen P.-L, Wu Y.-K. Synlett 2024; 35: 1145
7b Mohamadpour F. Sci. Rep. 2022; 12: 16911
7c Shi D, Zeng T, Lei X, Wu X, Li M, Zhang Y. Synthesis 2022; 54: 5434
7d Liu S, Zhuang Z, Qiao JX, Yeung K.-S, Su S, Cherney EC, Ruan Z, Ewing WR, Poss MA, Yu J.-Q. J. Am. Chem. Soc. 2021; 143: 21657
7e Surmont R, Verniest G, De Kimpe N. Org. Lett. 2009; 11: 2920
7f D’hooghe M, Buyck C, Contreras J, De Kimpe N. Org. Biomol. Chem. 2008; 6: 3667
7g Surmont R, Verniest G, Colpaert F, Macdonald G, Thuring JW, Deroose F, De Kimpe N. J. Org. Chem. 2009; 74: 1377
7h Brabandt WV, Landeghem RV, De Kimpe N. Org. Lett. 2006; 8: 1105

8a Hiyama T, Koide H, Fujita S, Nozaki H. Tetrahedron 1973; 29: 3137
8b DeShong P, Kell DA, Sidler DR. J. Org. Chem. 1985; 50: 2309
8c Bergmeier SC, Fundy SL, Seth PP. Tetrahedron 1999; 55: 8025
8d Bucciarelli M, Forni A, Moretti I, Prati F, Torre G. Tetrahedron: Asymmetry 1995; 6: 2073
8e Papa C, Tomasini C. Eur. J. Org. Chem. 2000; 1569
8f Concellόn JM, Riego E, Suárez JR, García-Granda S, Díaz MR. Org. Lett. 2004; 6: 4499
8g Wu J, Sun X, Xia H.-G. Tetrahedron Lett. 2006; 47: 1509
8h Ney JE, Wolfe JP. J. Am. Chem. Soc. 2006; 128: 15415
8i Ishii K, Sone T, Shigeyama T, Noji M, Sugiyama S. Tetrahedron 2006; 62: 10865
8j Vetica F, Bailey SJ, Kumar M, Mahajan S, von Essen C, Rissanen K, Enders D. Synthesis 2020; 52: 2038
8k Xing S, Xia H, Wang C, Wang Y, Hao L, Wang K, Zhu B. Adv. Synth. Catal. 2021; 363: 1044
8l Xing S, Wang Y, Jin C, Shi S, Zhang Y, Liao Z, Wang K, Zhu B. J. Org. Chem. 2022; 87: 6426
8m Wang Q, Fan T, Song J. Org. Lett. 2023; 25: 1246
8n Xing S, Jin C, Zhang P, Yang J, Liang Y, Ao X, Pi W, Wang K, Zhu B. J. Org. Chem. 2024; 89: 5153
8o Wu H, Li Y, Sun M, Zhang J, Li J, Yang J. Org. Lett. 2024; 26: 751

9a Yadav VK, Sriramurthy V. J. Am. Chem. Soc. 2005; 127: 16366
9b Gandhi S, Bisai A, Bhanu Prasad BA, Singh VK. J. Org. Chem. 2007; 72: 2133
9c Shi Z, Fan T, Zhang X, Zhan F, Wang Z, Zhao L, Lin J.-S, Jiang Y. Adv. Synth. Catal. 2021; 363: 2619
9d Wang C.-C, Wang X.-L, Zhang Q.-L, Liu J, Ma Z.-W, Liu Z.-J, Chen Y.-J. Org. Chem. Front. 2022; 9: 1574
9e Hashimoto K, Higuchi D, Matsubara S, Murakami K. Front. Chem. 2023; 11: 1272034
9f Qiao J, Wang S, Liu X, Feng X. Chem. Eur. J. 2023; 29: e202203757
9g Mazzarella D, Bortolato T, Pelosi G, Dell’Amico L. Chem. Sci. 2024; 15: 271

10a Ungureanu I, Bologa C, Chayer S, Mann A. Tetrahedron Lett. 1999; 40: 5315
10b Ungureanu I, Klotz P, Mann A. Angew. Chem. Int. Ed. 2000; 39: 4615
10c Ungureanu I, Klotz P, Schoenfelder P, Mann A. Tetrahedron Lett. 2001; 42: 6087
10d Drew MA, Tague AJ, Richardson C, Pyne SG, Hyland CJ. T. Org. Lett. 2021; 23: 4635
10e Zhu G.-S, Yang P.-J, Ma C.-X, Yang G, Chai Z. Org. Lett. 2021; 23: 7933
10f Wani IA, Sk S, Mal A, Sengupta A, Ghorai MK. Org. Lett. 2022; 24: 7867
10g Wu KJ. Y, Benedetto AE, Myers AG. J. Org. Chem. 2023; 88: 1907
10h Wang F, Xu X, Yan Y, Zhang J, Bai W.-J, Chen J, Yang Y. Org. Lett. 2023; 25: 6853
10i Wang F, Xu X, Yan Y, Zhang J, Yang Y. Org. Chem. Front. 2024; 11: 668

11a Ghorai MK, Ghosh K, Das K. Tetrahedron Lett. 2006; 47: 5399
11b Ghorai MK, Ghosh K. Tetrahedron Lett. 2007; 48: 3191
11c Westermeyer A, Guillamot G, Phansavath P, Ratovelomanana-Vidal V. Tetrahedron 2020; 76: 131221
11d Dong P, Chen L, Yang Z, Dong S, Feng X. Org. Chem. Front. 2021; 8: 6874
11e Xiao S, Chen B, Jiang Q, He L, Chu W.-D, He C.-Y, Liu Q.-Z. Org. Chem. Front. 2021; 8: 3729
11f Li Y, Chen F, Zhu S, Chu L. Org. Chem. Front. 2021; 8: 2196

12a Gaebert C, Mattay J. Tetrahedron 1997; 53: 14297
12b Madhushaw RJ, Hu C.-C, Liu R.-S. Org. Lett. 2002; 4: 4151
12c Zhu W, Cai G, Ma D. Org. Lett. 2005; 7: 5545
12d Ding C.-H, Dai L.-X, Hou X.-L. Tetrahedron 2005; 61: 9586
12e Gomes PJ. S, Nunes CM, Pais AA. C. C, Pinho e Melo TM. V. D, Arnaut LG. Tetrahedron Lett. 2006; 47: 5475
12f Wender PA, Strand D. J. Am. Chem. Soc. 2009; 131: 7528
12g Fan J, Gao L, Wang Z. Chem. Commun. 2009; 5021
12h Feng J.-J, Lin T.-Y, Zhu C.-Z, Wang H, Wu H.-H, Zhang J. J. Am. Chem. Soc. 2016; 138: 2178
12i Nguyen TN, May JA. Org. Lett. 2018; 20: 3618
12j Rong J, Jiang H, Wang S, Su Z, Wang H, Tao C. Org. Biomol. Chem. 2020; 18: 3149
12k Kapoor R, Chawla R, Verma A, Keshari T, Siddiqui IR. Synlett 2023; 34: 1621

13a Kashyap S, Singh B, Ghorai MK. J. Org. Chem. 2024; 89: 11429
13b Singh B, Kashyap S, Singh S, Gupta S, Ghorai MK. J. Org. Chem. 2024; 89: 2247
13c Goswami G, Singh B, Wani IA, Mal A, Ghorai MK. J. Org. Chem. 2024; 89: 11576
13d Singh B, Kumar M, Goswami G, Verma I, Ghorai MK. J. Org. Chem. 2023; 88: 4504
13e Pradhan S, Chauhan N, Shahi CK, Bhattacharyya A, Ghorai MK. Org. Lett. 2020; 22: 7903
13f Bhattacharyya A, Das S, Chauhan N, Biswas PK, Ghorai MK. Synlett 2020; 31: 708
13g Wani IA, Goswami G, Sk S, Mal A, Sayyad M, Ghorai MK. Org. Biomol. Chem. 2020; 18: 272
13h Tarannum S, Sk S, Das S, Wani IA, Ghorai MK. J. Org. Chem. 2020; 85: 367
13i Goswami G, Chauhan N, Mal A, Das S, Das M, Ghorai MK. ACS Omega 2018; 3: 17562
13j Ghorai MK, Shukla D, Das K. J. Org. Chem. 2009; 74: 7013
13k Ghorai MK, Das K, Shukla D. J. Org. Chem. 2007; 72: 5859
13l Ghorai MK, Kumar A, Das K. Org. Lett. 2007; 9: 5441

14a Ghorai MK, Kumar A, Tiwari DP. J. Org. Chem. 2010; 75: 137
14b Ghorai MK, Shukla D, Bhattacharyya A. J. Org. Chem. 2012; 77: 3740
14c Bhattacharyya A. Synlett 2012; 23: 2142

15 See the Supporting Information for details.
16 The dihydropyrroles are sensitive to acidic impurities and were partially hydrolyzed during column chromatographic purification of the crude reaction mixture and during the preparation of analytical samples.
17 Perrin DD, Armarego WL. F. Purification of Laboratory Chemicals, 3rd ed. Pergamon Press; Oxford: 1988
18 Jenkins CL, Kochi JK. J. Am. Chem. Soc. 1972; 94: 843

Zusatzmaterial

Supporting Information