Citation: Zou Chuncheng, Han Yuanyuan, Zeng Chuikun, Zhang Tony Y., Ye Jinxing, Song Gonghua. Remote regioselective organocatalytic asymmetric [3+2] cycloaddition of N-2, 2, 2-trifluoroethyl isatin ketimines with cyclic 2, 4-dienones[J]. Chinese Chemical Letters, ;2020, 31(2): 377-380. doi: 10.1016/j.cclet.2019.07.052 shu

Remote regioselective organocatalytic asymmetric [3+2] cycloaddition of N-2, 2, 2-trifluoroethyl isatin ketimines with cyclic 2, 4-dienones

a.
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai Key Laboratory of Chemistry Biology, East China University of Science and Technology, Shanghai 200237, China

tyz@yahoo.com

yejx@ecust.edu.cn

Received Date: 26 May 2019
Revised Date: 16 July 2019
Accepted Date: 25 July 2019
Available Online: 27 July 2019

Figures(6)

An organocatalytic asymmetric [3+2] cycloaddition of trifluoromethyl-containing azomethine ylides with cyclic 2, 4-dienones was developed. The process enables efficient incorporation of CF₃ groups into functionalized spiro[pyrrolidin-3, 2'-oxindoles] in high yields with good to excellent enantio-and diastereoselectivities.
- Organocatalysis,
- Spiro oxindole skeleton,
- [3+2] cycloaddition,
- Cyclic 2, 4-dienones,
- CF₃ group
1. [1]
  (a) A. Gollner, D. Rudolph, H. Arnhof, et al., J. Med. Chem 59 (2016) 10147-10162;
  (b) M. Ito, M. Iwatani, T. Yamamoto, et al., Bioorg. Med. Chem 25 (2017) 4753-4767;
  (c) Y.A. Ivanenkov, S.V. Vasilevski, E.K. Beloglazkina, et al., Bioorg. Med. Chem. Lett. 25 (2015) 404-409;
  (d) A. Kumar, G. Gupta, A.K. Bishnoi, et al., Bioorg. Med. Chem. 23 (2015) 839-848.
2. [2]
  (a) B. Alcaide, P. Almendros, R. Rodriguez-Acebes, J. Org. Chem. 71 (2006) 2346-2351;
  (b) G. Lesma, N. Landoni, A. Sacchetti, A. Silvani, Tetrahedron 66 (2010) 4474-4478;
  (c) K. Jiang, Z.J. Jia, S. Chen, L. Wu, Y.C. Chen, Chem. -Eur. J. 16 (2010) 2852-2856;
  (d) M.P. Castaldi, D.M. Troast, J.A. Porco Jr, Org. Lett. 11 (2009) 3362-3365.
3. [3]
  (a) U.K.S. Kumar, H. Ila, H. Junjappa, Org. Lett. 3 (2001) 4193-4196;
  (b) Z. Szakonyi, F. Fülöp, D. Tourwé, N.D. Kimpe, J. Org. Chem. 67 (2002) 2192-2196;
  (c) E. Zhang, C.A. Fan, Y.Q. Tu, F.M. Zhang, Y.L. Song, J. Am. Chem. Soc.131 (2009) 14626-14627.
4. [4]
  (a) R. Rios, Chem. Soc. Rev. 41 (2012) 1060-1074;
  (b) G.S. Singh, Z.Y. Desta, Chem. Rev. 112 (2012) 6104-6155;
  (c) D. Cheng, Y. Ishihara, B. Tan, C.F. Barbas III, ACS Catal. 4 (2014) 743-762.
5. [5]
  (a) M. Bonin, A. Chauveau, L. Micouin, Synlett (2006) 2349-2363;
  (b) T.M.V.D. Pinho e Melo, Eur. J. Org. Chem (2006) (2006) 2873-2888;
  (c) G. Pandey, P. Banerjee, S.R. Gadre, Chem. Rev 106 (2006) 4484-4517;
  (d) H. Pellissier, Tetrahedron 63 (2007) 3235-3285;
  (e) L.M. Stanley, M.P. Sibi, Chem. Rev 108 (2008) 2887-2902;
  (f) C. Nájera, J.M. Sansano, Top. Heterocycl. Chem. 12 (2008) 117-145;
  (g) J. Adrio, J.C. Carretero, Chem. Commun 47 (2011) 6784-6794;
  (h) J. Adrio, J.C. Carretero, Chem. Commun 50 (2014) 12434-12446;
  (i) T. Hashimoto, K. Maruoka, Chem. Rev 115 (2015) 5366-5412.
6. [6]
  (a) I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, WileyBlackwell, Chichester, 2009;
  (b) V.A. Petrov, Fluorinated Heterocyclic Compounds: Synthesis Chemistry and Application, Wiley, Hoboken, 2009;
  (c) P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2nd, Wiley-VCH, Weinheim, 2013.
7. [7]
  (a) Q. Sun, X. Li, J. Su, et al., Adv. Synth. Catal. 357 (2015) 3187-3196;
  (b) M. Ma, Y. Zhu, Q. Sun, et al., Chem. Commn. 51 (2015) 8789-8792;
  (c) X. Li, J. Sun, Z. Liu, et al., Org. Lett. 18 (2016) 956-959;
  (d) Z.H. Wang, Z.J. Wu, D.F. Yue, et al., Chem. Commun. 52 (2016) 11708-11711;
  (e) M. Shi, Y.N. Gao, Eur. J. Org. Chem. (2017) (2017) 1552-1560;
  (f) Y. Zhi, K. Zhao, C. Essen, K. Rissanen, D. Enders, Synlett 28 (2017) 2876-2880;
  (g) W.J. Huang, Q. Chen, N. Lin, et al., Org. Chem. Front. 4 (2017) 472-482;
  (h) A. Ponce, I. Alonso, J. Adrio, J.C. Carretero, Chem. -Eur. J. 22 (2016) 4952-4959;
  (i) W.J. Huang, Q. Chen, W.R. Zhu, et al., Heterocycles 94 (2017) 879-893.
8. [8]
  (a) X. Tan, Y. Liu, P. Melchiorre, Angew. Chem. Int. Ed 51 (2012) 6439-6442;
  (b) T. Kitanosono, P. Xu, S. Kobayashi, Chem. Commun. 49 (2013) 8184-8186;
  (c) T. Kitanosono, P. Xu, S. Kobayashi, Chem. -Asian J. 9 (2014) 179-188;
  (d) X. Gu, T. Guo, Y. Dai, et al., Angew. Chem. Int. Ed 54 (2015) 10249-10253;
  (e) Y. Wei, Z. Liu, X. Wu, et al., Chem. -Eur. J. 21 (2015) 18921-18924;
  (f) C. Zou, C. Zeng, Z. Liu, et al., Angew. Chem. Int. Ed. 55 (2016) 14257-14261;
  (g) X. Sun, J. Fei, C. Zou, M. Lu, J. Ye, RSC Adv. 6 (2016) 106676-106679;
  (h) W. Xiao, Q.Q. Yang, Z. Chen, et al., Org. Lett. 20 (2018) 236-239.
9. [9]
  X. Tan, P. Melchiorre, Angew. Chem. Int. Ed. 52 (2013) 5360-5363. doi: 10.1002/anie.201301017
10. [10]
  X. Tan, N. Hofmann, P. Melchiorre, Angew. Chem. Int. Ed 53 (2014) 2997-3000. doi: 10.1002/anie.201310487
1. [1]
  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
2. [2]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
3. [3]
  Yong-Fang Shi , Sheng-Hua Zhou , Zuju Ma , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . From [Ba3S][GeS4] to [Ba3CO3][MS4] (M = Ge, Sn): Enhancing optical anisotropy in IR birefringent crystals via functional group implantation. Chinese Journal of Structural Chemistry, 2025, 44(1): 100455-100455. doi: 10.1016/j.cjsc.2024.100455
4. [4]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
5. [5]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
6. [6]
  Fei ZHOU , Xiaolin JIA . Co₃O₄/TiO₂ composite photocatalyst: Preparation and synergistic degradation performance of toluene. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2232-2240. doi: 10.11862/CJIC.20240236
7. [7]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
8. [8]
  Xiuzheng Deng , Changhai Liu , Xiaotong Yan , Jingshan Fan , Qian Liang , Zhongyu Li . Carbon dots anchored NiAl-LDH@In₂O₃ hierarchical nanotubes for promoting selective CO₂ photoreduction into CH₄. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942
9. [9]
  Yan Cheng , Hua-Peng Ruan , Yan Peng , Longhe Li , Zhenqiang Xie , Lang Liu , Shiyong Zhang , Hengyun Ye , Zhao-Bo Hu . Magnetic, dielectric and luminescence synergetic switchable effects in molecular material [Et₃NCH₂Cl]₂[MnBr₄]. Chinese Chemical Letters, 2024, 35(4): 108554-. doi: 10.1016/j.cclet.2023.108554
10. [10]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
11. [11]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
12. [12]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
13. [13]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
14. [14]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
15. [15]
  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
16. [16]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
17. [17]
  Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194
18. [18]
  Tong Su , Yue Wang , Qizhen Zhu , Mengyao Xu , Ning Qiao , Bin Xu . Multiple conductive network for KTi₂(PO₄)₃ anode based on MXene as a binder for high-performance potassium storage. Chinese Chemical Letters, 2024, 35(8): 109191-. doi: 10.1016/j.cclet.2023.109191
19. [19]
  Qingwang LIU . MoS₂/Ag/g-C₃N₄ Z-scheme heterojunction: Preparation and photocatalytic performance. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 821-832. doi: 10.11862/CJIC.20240148
20. [20]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(855)
HTML views(26)

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