Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones

Chemistry Letters

Volumn 44, Issue 10, 2015, Pages 1407-1409

  Sekine, Kohei ^a   Kobayashi, Ryo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84946901952     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.150584     Document Type: Article

References (33)

1. a) Y. Tsuji, T. Fujihara, Chem. Commun. 2012, 48, 9956.
2. b) M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem., Int. Ed. 2011, 50, 8510.
3. c) A. Correa, R. Martín, Angew. Chem., Int. Ed. 2009, 48, 6201.
4. d) T. Sakakura, K. Kohno, Chem. Commun., 2009, 1312.
5. e) T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365.
6. a) H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc. 2006, 128, 11040.
7. b) H. Yoshida, T. Morishita, J. Ohshita, Org. Lett. 2008, 10, 3845.
8. c) T. Kaicharla, M. Thangaraj, A. T. Biju, Org. Lett. 2014, 16, 1728.
9. d) W.-J. Yoo, T. V. Q. Nguyen, S. Kobayashi, Angew. Chem., Int. Ed. 2014, 53, 10213.
10. a) M. Yoshida, T. Murao, K. Sugimoto, M. Ihara, Synlett 2007, 575.
11. b) C.-R. Qi, H.-F. Jiang, Green Chem. 2007, 9, 1284.
12. c) N. Eghbali, J. Eddy, P. T. Anastas, J. Org. Chem. 2008, 73, 6932.
13. d) W.-J. Yoo, C.-J. Li, Adv. Synth. Catal. 2008, 350, 1503.
14. e) P. Foley, N. Eghbali, P. T. Anastas, Green Chem. 2010, 12, 888.
15. J. Zhao, H. Huang, C. Qi, H. Jiang, Eur. J. Org. Chem. 2012, 5665.
16. S. Li, J. Ye, W. Yuan, S. Ma, Tetrahedron 2013, 69, 10450.
17. T. Stalling, J. Pauly, M. Schmidtmann, J. Martens, Eur. J. Org. Chem. 2014, 833.
18. b) S. Sharma, A. K. Singh, D. Singh, D.-P. Kim, Green Chem. 2015, 17, 1404.
19. c) W. Xiong, C. Qi, H. He, L. Ouyang, M. Zhang, H. Jiang, Angew. Chem., Int. Ed. 2015, 1, 3084.
20. a) S. Yoshida, K. Fukui, S. Kikuchi, T. Yamada, Chem. Lett. 2009, 38, 786.
21. b) S. Kikuchi, S. Yoshida, Y. Sugawara, W. Yamada, H.-M. Cheng, K. Fukui, K. Sekine, I. Iwakura, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2011, 84, 698.
22. a) M. Sai, S. Matsubara, Org. Lett. 2011, 13, 4676.
23. b) T. Xu, X. Mu, H. Peng, G. Liu, Angew. Chem., Int. Ed. 2011, 50, 8176.
24. c) T. Xu, G. Liu, Synlett 2012, 23, 955.
25. d) C. Schäfer, M. Miesch, L. Miesch, Chem.-Eur. J. 2012, 18, 8028.
26. e) J. Liu, X. Xie, Y. Liu, Chem. Commun. 2013, 49, 11794.
27. Y. Takeda, S. Okumura, S. Tone, I. Sasaki, S. Minakata, Org. Lett. 2012, 14, 4874.
28. a) M. J. Bougault, C. R. Hebd. Seances Acad. Sci. 1904, 139, 864.
29. b) M. D. Dowle, D. I. Davies, Chem. Soc. Rev. 1979, 8, 171.
30. a) B. G. Davis, M. A. T. Maughan, T. M. Chapman, R. Villard, S. Courtney, Org. Lett. 2002, 4, 103.
31. b) E. J. Grayson, B. G. Davis, Org. Lett. 2005, 7, 2361.
32. c) G. Wang, Z. Li, C. Ha, K. Ding, Synth. Commun. 2008, 38, 1629.
33. J. Huang, H. Wang, A.-Y. Peng, Eur. J. Org. Chem. 2014, 8126.