Citation: Guo Shenquan, Zhang Niuniu, Tang Xiangzheng, Mao Zhifeng, Zhang Xuejing, Yan Ming, Xuan Yining. Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts[J]. Chinese Chemical Letters, ;2019, 30(2): 406-408. doi: 10.1016/j.cclet.2018.08.021 shu

Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts

a.
College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China
b.
Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

yanming@mail.sysu.edu.cn

xuanyn@mail3.sysu.edu.cn

Received Date: 26 June 2018
Revised Date: 17 July 2018
Accepted Date: 31 August 2018
Available Online: 5 February 2018

Figures(4)

An efficient synthesis of β-alkoxycarbonyl vinylsulfonium salts had been developed. Their reaction with indene-1, 3-diones and other active methylene compounds provided cyclopropane carboxylates in good yields. A tentative reaction mechanism was proposed.
- Vinylsulfonium salt,
- Active methylene compound,
- Cyclopropanation
1. [1]
  (a) Y. F. Wang,W. H. Zhang, V. J. Colandrea, L. S. Jimenez, Tetrahedron 55 (1999) 10659-10672;
  (b) Z. Wang, L. S. Jimenez, J. Am. Chem. Soc. 116 (1994) 4977-4978;
  (c) K. H. Kim, L. S. Jimenez, Tetrahedron Asymmetry 12 (2001) 999-1005;
  (d) M. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. Int. Ed. 45 (2006) 7066-7069;
  (e) M. G. Unthank, B. Tavassoli, V. K. Aggarwal, Org. Lett. 10 (2008) 1501-1504;
  (f) S. P. Fritz, T. H. West, E. M. McGarrigle, V. K. Aggarwal, Org. Lett. 14 (2012) 6370-6373.
2. [2]
  (a) M.Yar, E. M. McGarrigle, V. K. Aggarwal, Angew. Chem. Int. Ed. 47 (2008) 3784-3786;
  (b) M. Yar, E. M. McGarrigle, V. K. Aggarwal, Org. Lett. 11 (2009) 257-260;
  (c) E. M. McGarrigle, S. P. Fritz, L. Favereau, M. Yar, V. K. Aggarwal, Org. Lett. 13 (2011) 3060-3063;
  (d) J. An, N. J. Chang, L. D. Song, et al., Chem. Commun. 47 (2011) 1869-1871;
  (e) C. S. Xie, D. Y. Han, Y. Hu, J. H. Liu, T. Xie, Tetrahedron Lett. 51 (2010) 5238-5241.
3. [3]
  (a) H. Braun, G. Huber, Tetrahedron Lett. 17 (1976) 2121-2124;
  (b) K. Takaki, T. Agawa, J. Org. Chem. 42 (1977) 3303-3304;
  (c) R. Maeda, K. Oyama, R. Anno, et al., Org. Lett. 12 (2010) 2548-2550;
  (d) H. Lin, Q. L. Shen, L. Lu, J. Org. Chem. 76 (2011) 7359-7369.
4. [4]
  (a) M. E. Garst, J. Org. Chem. 44 (1979) 1578-1580;
  (b) M. E. Garst, P. Arrhenius, J. Org. Chem. 48 (1983) 16-24;
  (c) M. W. Rowbottom, N. Mathewsb, T. Gallagher, J. Chem. Soc. Perkin Trans. I 1 (1998) 3927-3930.
5. [5]
  (a) P. H. Jia, Q. L. Zhang, Q. M. Ou, Y. Huang, Org. Lett. 19 (2017) 4664-4667;
  (b) P. H. Jia, Q. L. Zhang, H. X. Jin, Y. Huang, Org. Lett. 19 (2017) 412-415.
6. [6]
  Z.C.Chen, L.Tong, Z.B.Du, et al., Org.Biomol.Chem.16(2018) 2634-2638. doi: 10.1039/C8OB00293B
7. [7]
  Y.M.Li, C.Mgck-Lichtenfeld, A.Studer, Angew.Chem.Int.Ed.55(2016) 14435-14438. doi: 10.1002/anie.v55.46
8. [8]
  T.Ishikawa, N.Kasai, Y.Yamada, T.Hanamoto, Tetrahedron Lett.17(2015) 1254-1260.
9. [9]
  Y.Y.Liu, X.Y.Yu, J.R.Chen, et al., Angew.Chem.Int.Ed.56(2017) 9527-9531. doi: 10.1002/anie.v56.32
1. [1]
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142