Cobalt-catalyzed regioselective synthesis of pyrrolidinone derivatives by reductive coupling of nitriles and acrylamides

Journal of the American Chemical Society

Volumn 131, Issue 51, 2009, Pages 18252-18253

  Wong, Ying Chieh ^a   Parthasarathy, Kanniyappan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDES; CHEMICAL EQUATIONS; PYRROLIDINONE; REDUCTIVE COUPLING REACTION; REDUCTIVE COUPLINGS; REGIOSELECTIVE METHOD; REGIOSELECTIVE SYNTHESIS;

AMIDES; CHEMICAL BONDS; COBALT; CYANIDES; HYDROGELS;

SYNTHESIS (CHEMICAL);

2 PYRROLIDONE DERIVATIVE; ACRYLAMIDE; COBALT; NITRILE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; DEHYDRATION; ELECTRON; HYDROLYSIS; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 73249142066     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9088296     Document Type: Article

References (50)

1. (a) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
2. (b) Ikeda, S. Acc. Chem. Res. 2000, 33, 511.
3. (c) Song, M.; Montgomery, J. Tetrahedron 2005, 61, 11440.
4. (d) Ng, S.-S.; Jamison, T. F. Tetrahedron 2005, 61, 11405.
5. (e) Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653.
6. (f) Moslin, R. M.; Moslin, K. M.; Jamison, T. F. Chem. Commun. 2007, 4441.
7. (g) Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2007, 40, 971.
8. (h) Jeganmohan, M.; Cheng, C.-H. Chem.sEur. J. 2008, 14, 10876.
9. (a) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
10. (b) Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782.
11. (c) Ng, S.-S.; Ho, C.-Y.; Jamison, T. F. J. Am. Chem. Soc. 2006, 128, 11513.
12. (d) Takimoto, M.; Kajima, Y.; Sato, Y.; Mori, M. J. Org. Chem. 2005, 70, 8605.
13. (e) Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320.
14. (f) Hratchian, H. P.; Chowdhury, S. K.; Gutierrez-Garcia, V. M.; Amarasinghe, K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636.
15. (g) Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 201.
16. (h) Shirakawa, E.; Yamamoto, Y.; Nakao, S.; Oda, T.; Tsuchimoto, T.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 3448.
17. (i) Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043.
18. (j) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
19. (k) Ikeda, S.; Cui, D. M.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 4712.
20. (l) Zhao, L.; Lu, X. Org. Lett. 2002, 4, 3903.
21. (m) Zhao, L.; Lu, X.; Xu, W. J. Org. Chem. 2005, 70, 4059.
22. (n) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
23. (o) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
24. (p) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
25. (q) Ikeda, S. Angew. Chem., Int. Ed. 2003, 42, 5120.
26. (r) Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743.
27. (s) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
28. (t) Yeh, C.-H.; Korivi, R. P.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 4892.
29. (a) Trost, B. M. Science 1991, 254, 1471.
30. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
31. (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
32. (d) Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R.; Williams, T. J.; Zhang, L. Pure Appl. Chem. 2002, 74, 25.
33. Druliner, J. D.; Blackstone, R. C. J. Organomet. Chem. 1982, 240, 277.
34. (a) Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. J. Am. Chem. Soc. 2002, 124, 9696.
35. (b) Chang, H.-T.; Jayanth, T. T.; Cheng, C.-H. J. Am. Chem. Soc. 2007, 129, 4166.
36. (c) Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. Tetrahedron Lett. 2004, 45, 6203.
37. (d) Chang, H.-T.; Jayanth, T. T.; Cheng, C.-H. J. Am. Chem. Soc. 2007, 129, 12032.
38. Hilt, G.; Treutwein, J. Angew. Chem., Int. Ed. 2007, 46, 8653.
39. (a) Rayabarapu, D. K.; Sambaiah, T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2001, 40, 1286.
40. (b) Jayanth, T. T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2007, 46, 5921.
41. (c) Mannathan, S.; Jeganmohan, M.; Cheng, C.-H. Angew. Chem., Int. Ed. 2009, 48, 2192.
42. (d) Garcia, P.; Moulin, S.; Miclo, Y.; Leboeuf, D.; Aubert, C.; Malacria, M. Chem.-Eur. J. 2009, 15, 2129.
43. (a) Murray, W. V.; Lalan, P.; Gill, A.; Addo, M. F.; Lewis, J. M.; Lee, D. K. H.; Wachter, M. P.; Rampulla, R.; Underwood, D. C. Bioorg. Med. Chem. Lett. 1993, 369, 785.
44. (b) James, G. D.; Pattendon, G.; Mills, S. D. Tetrahedron Lett. 1985, 26, 3617.
45. (c) Wu, B.; Kuhen, K.; Nguyen, T. N.; Ellis, D.; Anaclerio, B.; He, X.; Yang, K.; Karanewsky, D.; Yin, H.; Wolf, K.; Bieza, K.; Caldwell, J.; He, Y. Bioorg. Med. Chem. Lett. 2006, 16, 3430.
46. (d) Piracetam, Doxapram, and Cotine are widely used pyrrolidinone drugs.
47. Mori, M.; Uesaka, N.; Shibasaki, M. Chem. Commun. 1990, 1222.
48. (a) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193.
49. Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. J. Org. Chem. 1996, 61, 5013.
50. Fillon, H.; Gosmini, C.; Perichon, J. J. Am. Chem. Soc. 2003, 125, 3867.