Assembly of 3-acyloxindoles via Cul/L-proline-catalyzed intramolecular arylation of β-keto amides

Organic Letters

Volumn 8, Issue 26, 2006, Pages 6115-6118

  Lu, Biao ^a   Ma, Dawei ^b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INDOLE DERIVATIVE; PROLINE;

ARTICLE; CATALYSIS; CHEMISTRY;

AMIDES; CATALYSIS; INDOLES; PROLINE;

EID: 33846123939     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0625886     Document Type: Article

References (42)

1. Heckel, A.; Roth, G. J.; Kley, J.; Hoerer, S.; Uphues, I. US 2005203104, 2005.
2. Parkes, K. E. B.; Ermert, P.; Fässler, J.; Ives, J.; Martin, J. A.; Merrett, J. H.; Obrecht, D.; Williams, G.; Klumpp, K. J. Med. Chem. 2003, 46, 1153.
3. (a) Robinson, R. P.; Reiter, L. A.; Barth, W. E.; Campeta, A. M.; Cooker, K.; Cronin, B. J.; Destito, R.; Donahue, K. M.; Falkner, F. C.; Fiese, E. F.; Johnson, D. L.; Kuperman, A. V; Liston, T. E.; Malloy, D.; Matin, J. J.; Mitchell, D. Y.; Rusek, F. W.; Shamblin, S. L.; Wright, C. F. J. Med. Chem. 1996, 39, 10.
4. (b) Golding, S.; Emery, P.; Young, S. P. J. Immunol. 1995, 154, 5384.
5. (c) LaLiberte, R.; Perregaux, D.; Svensson, L.; Pazoles, C. J.;Gabel, C. A. J. Immunol. 1994, 153, 2180.
6. (d) Sipe, J. D.; Bartle, L. M.; Loose, L. D. J. Immunol. 1992, 148, 480.
7. (a) Kosuge, T.; Ishida, H.; Inaba, A.; Nukaya, H. Chem. Pharm. Bull. 1985, 33, 1414.
8. (b) Beccalli, E. M.; Marchesini, A.; Pilati, T. Tetrahedron 1994, 50, 12697.
9. (c) Beccalli, E. M.; Clerici, F.; Marchesini, A. Tetrahedron 2001, 57, 4787.
10. (d) Smith, F. X.; Williams Gelsleichter, E.; Podcasy, J. A.; Sisko, J. T.; Hrubowchak, D. M. Synth. Commun. 2006, 36, 765.
11. (a) Porcs-Makkay, M.; Simig, G. Org. Proc. Res. Dev. 2000, 4, 10.
12. (b) Sechi, M.; Sannia, L.; Carta, F.; Palomba, M.; Dallocchio, R.; Dessi, A.; Derudas, M.; Zawahir, Z.; Neamati, N. Antiviral Chem. Chemother. 2005, 16, 41.
13. (c) Kumar, P. R.; Goud, P. S.; Raju, S.; Reddy, G. O. IN 182470, 1999.
14. (a) Lee, A.; Hartwig, J. J. Org. Chem. 2001, 66, 3402.
15. (b) Beckett, A. H.; Daisley, R. W.; Walker, J. Tetrahedron 1968, 24, 6093.
16. (c) Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835.
17. (d) Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. J. Med. Chem. 1998, 41, 2588.
18. Etkin, N.; Babu, S. D.; Fooks, C. J.; Durst, T. J. Org. Chem. 1990, 55, 1093.
19. (a) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693.
20. For related studies from this group, see: (b) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
21. (c) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
22. (d) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
23. (e) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
24. (f) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
25. (g) Ma, D.; Cai, Q. Synlett 2004, 1, 128.
26. (h) Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
27. (i) Ma, D.; Liu, F. Chem. Commun. 2004, 1934.
28. (j) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
29. (k) Zhu, W.; Ma, D. J. Org. Chem. 2005, 70, 2696.
30. (l) Ma, D.; Cai, Q.; Xie, X. Synlett 2005, 1767.
31. (m) Cai, Q.; Zou, B.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276.
32. (n) Cai, Q.; He, G.; Ma, D. J. Org. Chem. 2006, 71, 5268.
33. Jiang, Y.; Wu, N.; Wu, H.; He, M. Synlett 2005, 2703.
34. Hennessy, E. J.; Buchwald, S. L. Org. Lett. 2002, 4, 269.
35. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
36. Fang, Y.; Li, C. J. Org. Chem. 2006, 71, 6427.
37. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431.
38. (a) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
39. (b) Altenhoff, G.; Glorius, F. Adv. Synth. Catal. 2004, 346, 1661.
40. (c) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009.
41. (a) Gopalsamy, A.; Shi, M. Org. Lett. 2003, 5, 3907.
42. (b) Yamamoto, Y.; Watanabe, Y.; Ohnishi, S. Chem. Pharm. Bull. 1987, 35, 1860.