Citation: Rui-Hua Liu, Qi-Chao Shan, Ya Gao, Teck-Peng Loh, Xu-Hong Hu. Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides[J]. Chinese Chemical Letters, ;2021, 32(4): 1411-1414. doi: 10.1016/j.cclet.2020.10.007 shu

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Rui-Hua Liu ^{a, 1} ,
Qi-Chao Shan ^{a, 1} ,
Ya Gao ^a ,
Teck-Peng Loh ^{a, b, *,} ,
Xu-Hong Hu ^{a, *,}

a.
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
b.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

teckpeng@ntu.edu.sg

ias_xhhu@njtech.edu.cn

Received Date: 2 August 2020
Revised Date: 8 October 2020
Accepted Date: 10 October 2020
Available Online: 12 October 2020

Figures(7)

Disclosed herein is an efficient Ag-catalyzed [4+1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.
- Enamides,
- Sulfoxonium ylides,
- Oxazolines,
- Silver catalysis,
- Heteroannulation
1. [1]
  (a) X.L. Sun, Y. Tang, Acc. Chem. Res. 41 (2008) 937-948;
  (b) L.Q. Lu, J.R. Chen, W.J. Xiao, Acc. Chem. Res. 45 (2012) 1278-1293;
  (c) G. Li, L. Wang, Y. Huang, Chin. J. Org. Chem. 33 (2013) 1900-1918;
  (d) L.Q. Lu, T.R. Li, Q. Wang, W.J. Xiao, Chem. Soc. Rev. 46 (2017) 4135-4149;
  (e) D. Kaiser, I. Klose, R. Oost, J. Neuhaus, N. Maulide, Chem. Rev. 119 (2019) 8701-8780.
2. [2]
  (a) Q. Wang, T.R. Li, L.Q. Lu, et al., J. Am. Chem. Soc. 138 (2016) 8360-8363;
  (b) Y. Xu, G. Zheng, X. Yang, X. Li, Chem. Commun. 54 (2018) 670-673;
  (c) X. Wu, H. Xiong, S. Sun, J. Cheng, Org. Lett. 20 (2018) 1396-1399;
  (d) D. Clare, B.C. Dobson, P.A. Inglesby, C. Aïssa, Angew. Chem. Int. Ed. 58 (2019) 16198-16202;
  (e) Z. Tang, Y. Zhou, Q. Song, Org. Lett. 21 (2019) 5273-5276;
  (f) X. Chen, M. Wang, X. Zhang, X. Fan, Org. Lett. 21 (2019) 2541-2545;
  (g) S. Hu, S. Du, Z. Yang, L. Ni, Z. Chen, Adv. Synth. Catal. 361 (2019) 3124-3136;
  (h) Z. Shen, C. Pi, X. Cui, Y. Wu, Chin. Chem. Lett. 30 (2019) 1374-1378;
  (i) T.B. Hua, C. Xiao, Q.Q. Yang, J.R. Chen, Chin. Chem. Lett. 31 (2020) 311-323;
  (j) Y. Kommagalla, S. Ando, N. Chatani, Org. Lett. 22 (2020) 1375-1379;
  (k) S. Zhu, K. Shi, H. Zhu, et al., Org. Lett. 22 (2020) 1504-1509.
3. [3]
  (a) R. Matsubara, S. Kobayashi, Acc. Chem. Res. 41 (2008) 292-301;
  (b) D.R. Carbery, Org. Biomol. Chem. 6 (2008) 3455-3460;
  (c) K. Gopalaiah, H.B. Kagan, Chem. Rev. 111 (2011) 4599-4657.
4. [4]
  (a) M.X. Wang, Chem. Commun. 51 (2015) 6039-6049;
  (b) X.M. Xu, L. Zhao, J. Zhu, M.X. Wang, Angew. Chem. Int. Ed. 55 (2016) 3799-3803;
  (c) J. Wu, C. Zhao, J. Wang, J. Am. Chem. Soc. 138 (2016) 4706-4709;
  (d) M.N. Zhao, L. Yu, R.R. Hui, et al., ACS Catal. 6 (2016) 3473-3477.
5. [5]
  (a) J.R. Chen, X.Q. Hu, L.Q. Lu, W.J. Xiao, Chem. Rev. 115 (2015) 5301-5365;
  (b) C. Zhu, Y. Ding, L.W. Ye, Org. Biomol. Chem. 13 (2015) 2530-2536;
  (c) P. Sivaguru, S. Cao, K.R. Babu, X. Bi, Acc. Chem. Res. 53 (2020) 662-675.
6. [6]
  (a) A.W. Goering, R.A. McClure, J.R. Doroghazi, et al., ACS Cent. Sci. 2 (2016) 99-108;
  (b) J.B. Neupana, R.P. Neupane, Y. Luo, et al., Org. Lett. 21 (2019) 8449-8453;
  (c) J. Maier, F.P. Mayer, S.D. Brandt, H.H. Sitte, ACS Chem. Neurosci. 9 (2018) 2484-2502;
  (d) L. Liu, L. Yin, H. Bian, N. Zhang, Chin. Chem. Lett. 31 (2020) 501-504.
7. [7]
  (a) G. Helmchen, A. Pfaltz, Acc. Chem. Res. 33 (2000) 336-345;
  (b) G.C. Hargaden, P.J. Guiry, Chem. Rev. 109 (2009) 2505-2550.
8. [8]
  (a) P. Wipf, C.P. Miller, Tetrahedron Lett. 33 (1992) 907-910;
  (b) A.J. Phillips, Y. Uto, P. Wipf, M.J. Reno, D.R. Williams, Org. Lett. 2 (2000) 1165-1168.
9. [9]
  (a) S. Rajaram, M.S. Sigman, Org. Lett. 4(2002) 3399-3401;
  (b) T. Ohshima, T. Iwasaki, K. Mashima, Chem. Commun. (2006) 2711-2713;
  (c) M. Trose, F. Lazreg, M. Lesieur, C.S.J. Cazin, J. Org. Chem. 80 (2015) 9910-9914.
10. [10]
  (a) T. Saegusa, Y. Ito, H. Kinoshita, S. Tomita, J. Org. Chem. 36 (1971) 3316-3323;
  (b) F. Sladojevich, A. Trabocchi, A. Guarna, D.J. Dixon, J. Am. Chem. Soc. 133 (2011) 1710-1713.
11. [11]
  M.S.A. Mehedi, J.J. Tepe, J. Org. Chem. 84(2019) 7219-7226. doi: 10.1021/acs.joc.9b00883
12. [12]
  P. Bellotti, J. Brocus, F.E. Orf, et al., J. Org. Chem. 84(2019) 6278-6285.
13. [13]
  (a) P.D. Morse, D.A. Nicewicz, Chem. Sci. 6 (2015) 270-274;
  (b) W.C. Gao, F. Hu, Y.M. Huo, et al., Org. Lett. 17 (2015) 3914-3917;
  (c) H. Wang, J. Zhang, J. Tan, et al., Org. Lett. 20 (2018) 2505-2508;
  (d) S.S. Chavan, B.D. Rupanawar, R.B. Kamble, A.M. Shelke, G. Suryavanshi, Org. Chem. Front. 5 (2018) 544-548;
  (e) H. Luo, Z. Yang, W. Lin, Y. Zheng, S. Ma, Chem. Sci. 9 (2018) 1964-1969.
14. [14]
  Y. He, C. Pi, Y. Wu, X. Cui, Chin. Chem. Lett. 31(2020) 396-400.
15. [15]
  (a) S. Pankajakshan, Y.H. Xu, J.K. Cheng, M.T. Low, T.P. Loh, Angew. Chem. Int. Ed. 51 (2012) 5701-5705;
  (b) Z.Y. Shen, J.K. Cheng, C. Wang, et al., ACS Catal. 9 (2019) 8128-8135;
  (c) P. Shi, S. Li, L.M. Hu, et al., Chem. Commun. 55 (2019) 11115-11118;
  (d) R.H. Liu, Z.Y. Shen, C. Wang, T.P. Loh, X.H. Hu, Org. Lett. 22 (2020) 944-948;
  (e) S. Li, Q.C. Shan, L.M. Hu, X.Q. Ma, X.H. Hu, Chem. Commun. 56 (2020) 7969-7972.
16. [16]
  (a) B. Maji, S. Lakhdar, H. Mayr, Chem. Eur. J. 18 (2012) 5732-5740;
  (b) L. Yang, Q. Wen, F. Xiao, G.J. Deng, Org. Biomol. Chem. 12 (2014) 9519-9523;
  (c) X.M. Xu, C.H. Lei, S. Tong, J. Zhu, M.X. Wang, Org. Chem. Front. 5 (2018) 3138-3142;
  (d) Y. He, J. Lou, Z. Yu, Y.G. Zhou, Chem. Eur. J. 26 (2020) 4941-4946.
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