Citation: Jun Liu, Zhaoyu Feng, Renming Pan, Xiaolong Yu, Meijuan Zhou, Gang Zhao, Hongyu Wang. Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides[J]. Chinese Chemical Letters, ;2025, 36(8): 110647. doi: 10.1016/j.cclet.2024.110647 shu

Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides

Jun Liu ^{a, c} ,
Zhaoyu Feng ^a ,
Renming Pan ^c ,
Xiaolong Yu ^d ,
Meijuan Zhou ^{d, *,} ,
Gang Zhao ^{c, *,} ,
Hongyu Wang ^{a, b, **,}

a.
Key Laboratory of Marine Drugs, Ministry of Education, Molecular Synthesis Center, and School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China
c.
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
SDU-ANU Joint Science College, Shandong University, Weihai 264209, China

^**

zhoumj@sdu.edu.cn

zhaog@sioc.ac.cn

why@ouc.edu.cn

Received Date: 5 August 2024
Revised Date: 10 November 2024
Accepted Date: 12 November 2024
Available Online: 15 November 2024

Figures(6)

Pyrazolidinones, as significant analogs of β-lactam antibiotics, have garnered substantial interest for their enantioselective synthesis. Azomethine imines, recognized as valuable building blocks for the construction of these nitrogen-containing compounds, underscore the continuous pursuit of novel building blocks and reaction methodologies within the chemical community. In this paper, we present a cascade cyclization between alkenyl azomethine imines and furan-2(5H)-one to generate chiral coronal polyheterocyclic compounds with high yields and enantioselectivities, catalyzed by dipeptide-derived phosphonium salts. In-vitro biological activity assays highlight the potential of these chiral compounds in drug discovery. Additionally, density functional theory (DFT) calculations elucidate the pivotal role of phosphonium salts, demonstrating their cooperative activations via hydrogen bonding and ion-pairing interactions.
- Asymmetric catalysis,
- Polyheterocycle,
- Peptide-phosphonium salt,
- Cycloaddition,
- Alkenyl azomethine imine
1. [1]
  L.M. Lima, B.N.M.d. Silva, G. Barbosa, E.J. Barreiro, Eur. J. Med. Chem. 208 (2020) 112829.
2. [2]
  M. Mora-Ochomogo, C.T. Lohans, RSC Med. Chem. 12 (2021) 1623–1639. doi: 10.1039/d1md00200g
3. [3]
  M. Typers, G.D. Wright, Nat. Rev. Microbiol. 17 (2019) 141–155.
4. [4]
  V.P. Sandanayaka, A.S. Prashad, Curr. Med. Chem. 9 (2002) 1145–1165. doi: 10.2174/0929867023370031
5. [5]
  R.J. Worthington, C. Melander, J. Org. Chem. 78 (2013) 4207–4213. doi: 10.1021/jo400236f
6. [6]
  N. Brown, E. Jacoby, Mini-Rev. Med. Chem. 6 (2006) 1217–1229. doi: 10.2174/138955706778742768
7. [7]
  S. Shaabani, C.G. Neochoritis, A. Twarda-Clapa, et al., Med. Chem. Commun. 8 (2017) 1046–1052.
8. [8]
  Y. Hu, D. Stumpfe, J. Bajorath, J. Med. Chem. 60 (2017) 1238–1246. doi: 10.1021/acs.jmedchem.6b01437
9. [9]
  L.O. Davis, Org. Prep. Proced. Int. 45 (2013) 437–464. doi: 10.1080/00304948.2013.834769
10. [10]
  M. Garg, M. Chauhan, P.K. Singh, J.M. Alex, R. Kumar, Eur. J. Med. Chem. 97 (2015) 444–461.
11. [11]
  U. Grošelj, J. Svete, ARKIVOC 6 (2015) 175–205. doi: 10.3998/ark.5550190.p009.129
12. [12]
  T. Hashimoto, K. Maruoka, Chem. Rev. 115 (2015) 5366–5412. doi: 10.1021/cr5007182
13. [13]
  C. Nájera, J. Sansano, M. Yus, Org. Biomol. Chem. 13 (2015) 8596–8636.
14. [14]
  L. Wei, X. Chang, C.J. Wang, Acc. Chem. Res. 53 (2020) 1084–1100. doi: 10.1021/acs.accounts.0c00113
15. [15]
  R. Shintani, Y.T. Soh, T. Hayashi, Org. Lett. 12 (2010) 4106–4109. doi: 10.1021/ol101700v
16. [16]
  R. Huber, R. Bigler, A. Mezzetti, Organometallics 34 (2015) 3374–3384. doi: 10.1021/acs.organomet.5b00357
17. [17]
  H.Y. Wang, C.W. Zheng, Z. Chai, J.X. Zhang, G. Zhao, Nat. Commun. 7 (2016) 12720.
18. [18]
  R. Shintani, G.C. Fu, J. Am. Chem. Soc. 125 (2003) 10778–10779.
19. [19]
  W. Chen, W. Du, Y.Z. Duan, et al., Angew. Chem. Int. Ed. 46 (2007) 7667–7670. doi: 10.1002/anie.200702618
20. [20]
  M. Hori, A. Sakakura, K. Ishihara, J. Am. Chem. Soc. 136 (2014) 13198–13201. doi: 10.1021/ja508441t
21. [21]
  Q. Du, J.M. Neudorfl, H.G. Schmalz, Chem. Eur. J. 24 (2018) 2379–2383. doi: 10.1002/chem.201800042
22. [22]
  G.L. Chai, E.Z. Yao, R.H. Liu, J. Chang, Org. Lett. 24 (2022) 6449–6454. doi: 10.1021/acs.orglett.2c02597
23. [23]
  B. Gu, S. Wu, H. Xu, et al., Chin. Chem. Lett. 32 (2021) 672–675.
24. [24]
  N. Luo, Z. Zheng, Z. Yu, Org. Lett. 13 (2011) 3384–3387. doi: 10.1021/ol201139w
25. [25]
  M. Zhang, F. Wu, H. Wang, J. Wu, W. Chen, Adv. Synth. Catal. 359 (2017) 2768–2772. doi: 10.1002/adsc.201700387
26. [26]
  T. Imaizumi, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 134 (2012) 20049–20052. doi: 10.1021/ja311150n
27. [27]
  L.P. Kong, N.K. Li, S.Y. Zhang, et al., Org. Biomol. Chem. 12 (2014) 8656–8670.
28. [28]
  R.H. Li, G.L. Chai, X. Wang, H.Y. Deng, J. Chang, J. Org. Chem. 88 (2023) 16566–16580. doi: 10.3390/ijms242316566
29. [29]
  X. Wu, Q. Liu, Y. Liu, et al., Adv. Synth. Catal. 355 (2013) 2701–2706. doi: 10.1002/adsc.201300383
30. [30]
  D. Cao, J. Zhang, H. Wang, G. Zhao, Chem. Eur. J. 21 (2015) 9998–10002. doi: 10.1002/chem.201501806
31. [31]
  H. Hong, H. Wang, C. Zheng, G. Zhao, Chin. Chem. Lett. 32 (2021) 708–712.
32. [32]
  F. Weinhold, J. Comb. Chem. 33 (2012) 2363–2379. doi: 10.1002/jcc.23060
33. [33]
  V. Rai, I.N.N. Namboothiri, Eur. J. Org. Chem. 2006 (2006) 4693–4703. doi: 10.1002/ejoc.200600505
34. [34]
  C. Nájera, J. Sansano, M. Yus, Org. Biomol. Chem. 13 (2015) 8596–8636.
35. [35]
  B.M. Trost, E. Gnanamani, J.S. Tracy, C.A. Kalnmals, J. Am. Chem. Soc. 139 (2017) 18198–18201. doi: 10.1021/jacs.7b11361
36. [36]
  T. Sakai, S. i. Hirashima, Y. Matsushima, et al., Org. Lett. 21 (2019) 2606–2609. doi: 10.1021/acs.orglett.9b00574
37. [37]
  B.M. Trost, E. Gnanamani, C.A. Kalnmals, C.I.J. Hung, J.S. Tracy, J. Am. Chem. Soc. 141 (2019) 1489–1493. doi: 10.1021/jacs.8b13367
38. [38]
  A.R. Choudhury, S. Mukherjee, Chem. Soc. Rev. 49 (2020) 6755–6788.
39. [39]
  H. Wang, C. Zheng, G. Zhao, Chin. J. Chem. 37 (2019) 1111–1119. doi: 10.1002/cjoc.201900276
40. [40]
  H. Li, H. Liu, H. Guo, Adv. Synth. Catal. 363 (2021) 2023–2036. doi: 10.1002/adsc.202001604
41. [41]
  S. Fang, Z. Liu, T. Wang, Angew. Chem. Int. Ed. 62 (2023) e202307258.
1. [1]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
2. [2]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
3. [3]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
4. [4]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
5. [5]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
6. [6]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
7. [7]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
8. [8]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
9. [9]
  Kai Zhu , Lei Yang , Yang Yang , Yanqi Wu , Fengzhi Zhang . Recent advances toward the catalytic enantioselective synthesis of planar chiral cyclophanes. Chinese Chemical Letters, 2025, 36(7): 110678-. doi: 10.1016/j.cclet.2024.110678
10. [10]
  Guodong Wang , Mengying Jia , Haitao Liu , Yong Liu , Zhiguo Zhang , Xianxiu Xu . Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives. Chinese Chemical Letters, 2025, 36(8): 110705-. doi: 10.1016/j.cclet.2024.110705
11. [11]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
12. [12]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
13. [13]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
14. [14]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
15. [15]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
16. [16]
  Min Yan , Zihao Ye , Ping Lu . Catalyst-free, visible-light-induced [2π + 2σ] cycloaddition towards azabicyclohexanes. Chinese Chemical Letters, 2025, 36(6): 110540-. doi: 10.1016/j.cclet.2024.110540
17. [17]
  Meixin Wang , Yizhi Zhang , Shanshan Liu , Xiao Shen . Synthesis of rigidified cyclohexanes enabled by visible-light-induced trifluoroacetylsilane-mediated [2 + 2] cycloaddition of cyclopropenes. Chinese Chemical Letters, 2025, 36(8): 110758-. doi: 10.1016/j.cclet.2024.110758
18. [18]
  Ruowen Liang , Chao Zhang , Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211
19. [19]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
20. [20]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(20)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142