Synthesis of N-alkoxycarbonyl ketimines derived from isatins and their application in enantioselective synthesis of 3-aminooxindoles

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2512-2515

  Yan, Wenjin ^a   Wang, Dong ^a   Feng, Jingchao ^a   Li, Peng ^a   Zhao, Depeng ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; INDOLE DERIVATIVE; ISATIN; KETIMINE; NITRILE; OXINDOLE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; IMINES; INDOLES; ISATIN; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 84862080990     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3007953     Document Type: Article

References (40)

1. For review, see: Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853
2. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
3. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
4. Zhou, F.; Liu, Y. L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
5. Shen, K.; Liu, X.; Lin, L.; Feng, X. Chem. Sci. 2012, 3, 327
6. Klein, J. E. M. N.; Taylor, R. J. K. Eur. J. Org. Chem. 2011, 6821
7. Cheng, L.; Liu, L.; Wang, D.; Chen, Y.-J. Org. Lett. 2009, 11, 3874
8. Bui, T.; Borregan, M.; Barbas, C. F., III. J. Org. Chem. 2009, 74, 4537
9. Qian, Z.-Q.; Zhou, F.; Du, T.-P.; Wang, B.-L.; Ding, M.; Zhao, X.-L.; Zhou, J. Chem. Commun. 2009, 6753
10. Bui, T.; Hernández-Torres, G.; Milite, C.; Barbas, C. F., III. Org. Lett. 2010, 12, 5696
11. Yang, Z.; Wang, Z.; Bai, S.; Shen, K.; Chen, D.; Liu, X.; Lin, L.; Feng, X. Chem.-Eur. J. 2010, 16, 6632
12. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255
13. Shen, K.; Liu, X.; Wang, G.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2011, 50, 4684
14. Lesma, G.; Landoni, N.; Pilati, T.; Sacchetti, A.; Silvani, A. J. Org. Chem. 2009, 74, 4537
15. Jung, H. H.; Buesking, A. W.; Ellman, J. A. Org. Lett. 2011, 13, 3912
16. Yan, W.; Wang, D.; Feng, J.; Li, P.; Wang, R. J. Org. Chem. 2012, 77, 3311
17. Liu, Y.-L.; Zhou, F.; Cao, J.-J.; Ji, C.-B.; Ding, M.; Zhou, J. Org. Biomol. Chem. 2010, 8, 3847
18. Guo, Q.-X.; Liu, Y.-W.; Li, X.-C.; Zhong, L.-Z.; Peng, Y.-G. J. Org. Chem. 2012, 77, 3589
19. Rajopadhye, M.; Popp, F. D. J. Heterocycl. Chem. 1987, 24, 1637
20. Konkel, M. J.; Lagu, B.; Boteju, L. M.; Jimenez, H.; Noble, S.; Walker, M. W.; Chandrasena, G.; Blackburn, T. P.; Nikam, S. S.; Wright, J. L.; Kornberg, B. E.; Gregory, T.; Pugsley, T. A.; Akunne, H.; Zoski, K.; Wise, L. D. J. Med. Chem. 2006, 49, 3757
21. Qian, Y.; Jing, C.; Zhai, C.; Hu, W. Adv. Synth. Catal. 2012, 354, 301
22. Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328
23. Sun, W.; Hong, L.; Liu, C.; Wang, R. Tetrahedron: Asymmetry 2010, 2493
24. Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124
25. Sun, W.; Zhu, G.; Wu, C.; Hong, L.; Wang, R. Chem.-Eur. J. 2012, 10.1002/chem.201200478
26. Jiang, X.; Sun, Y.; Yao, J.; Cao, Y.; Kai, M.; He, N.; Zhang, X.; Wang, Y.; Wang, R. Adv. Synth. Catal. 2012, 10.1002/adsc.201100796
27. Martell, A. E.; Herbst, R. M. J. Org. Chem. 1941, 6, 878
28. Sato, M. J. Org. Chem. 1961, 26, 770
29. Lwowski, W.; Mattingly, T. W. J. Am. Chem. Soc. 1965, 87, 1947
30. Reck, R.; Jochims, J. C. Chem. Ber. 1982, 115, 860
31. Kupfer, R.; Meier, S.; Wurthwein, E. U. Synthesis 1984, 688
32. Osipov, N. S.; Golubev, A. S.; Sewald, N.; Michel, T.; Kolomiets, A. F.; Fokin, A. V.; Burger, K. J. Org. Chem. 1996, 61, 752
33. Matsuo, J.; Tanaki, Y.; Kido, A.; Ishibashi, H. Chem.Commun. 2006, 2896
34. Hashimoto, T.; Yamamoto, K.; Maruoka, K. Chem. Lett. 2011, 40, 326
35. For selected examples in the synthesis of imines on aza-Wittig reactions, see: Saaby, S.; Fang, X.; Gathergood, N.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114
36. Kacprzak, K.; Gawronski, J. Synthesis 2001, 961
37. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621
38. Yeboah, E. M. O.; Yeboah, S. O.; Singh, G. S. Tetrahedron 2011, 67, 1725
39. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672
40. Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032