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
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1.
沈阳化工大学材料科学与工程学院沈阳 110142