General direct transformation of secondary amides to ketones via amide activation

Acta Chimica Sinica

Volumn 70, Issue 18, 2012, Pages 1917-1922

  Xiao, Kaijiong ^a   Huang, Yinghong ^a   Huang, Peiqiang ^a  

^a Key Laboratory for Chemical Biology of Fujian Province   (China)

Author keywords

C C bond formation; Ketones; Molecular activation; Organocerium reagents; Reductive acylation; Secondary amides

Indexed keywords

EID: 84872581341     PISSN: 05677351     EISSN: None     Source Type: Journal    
DOI: 10.6023/A12080542     Document Type: Article

References (54)

1. Li, C.-J.; Trost, B. M. Proc. Natl. Acad. Sci. 2008, 105, 13197.
2. Albrecht, Ł.; Jiang, H.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2011, 50, 8492.
3. Pellissier, H. Tetrahedron 2006, 62, 1619 and 2143;
4. Guo, H.-C.; Ma, J.-A. Angew. Chem. Int. Ed. 2006, 45, 354.
5. Multicomponent Reactions, Eds.; Zhu, J.-P.; Bienaymé, H., Wiley-VCH, Weinheim, 2005.
6. Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505.
7. Xu, C.-P.; Xiao, Z.-H.; Zhuo, B.-Q.; Wang, Y.-H.; Huang, P.-Q. Chem. Commun. 2010, 46, 7834.
8. Liu, X.-K.; Zheng, X.; Ruan, Y.-P.; Ma, J.; Huang, P.-Q. Org. Biomol. Chem. 2012, 10, 1275.
9. Wang, Y.-H.; Ye, J.-L.; Wang, A.-E; Huang, P.-Q. Org. Biomol. Chem. 2012, 10, 6504.
10. Zheng. J.-L.; Liu, H.; Zhang, Y.-F.; Zhao, W.; Tong, J.-S.; Ruan, Y.-P.; Huang, P.-Q. Tetrahedron: Asymmetry 2011, 22, 257.
11. Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew. Chem. Int. Ed. 2010, 49, 3037.
12. Xiao, K.-J.; Wang, Y.; Ye, K.-Y.; Huang, P.-Q. Chem. Eur. J. 2010, 16, 12792;
13. Liao, J.-C.; Xiao, K.-J.; Zheng, X.; Huang, P.-Q. Tetrahedron 2012, 68, 5297.
14. Xiao, K.-J.; Wang, A.-E; Huang, P.-Q. Angew. Chem. Int. Ed. 2012, 51, 8314.
15. Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem. Int. Ed. 2007, 46, 5554;
16. Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 13864;
17. Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 15362;
18. Chen, Q.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 428.
19. Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600.
20. Abell, A. D.; Edmonds, M. K. In Organophosphorus Reagents; Ed.: Murphy, P. J., Oxford University Press, Oxford, 2004, p. 99;
21. Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Applications in Organic Chemistry, Wiley-VCH, New York, 1999;
22. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
23. Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 2, 171.
24. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
25. Balasubramaniam, S.; Aiden, I. S. Synthesis 2008, 3707.
26. Martín, R.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J. Synlett 1997, 1414.
27. Bechara, W. S.; Pelletier, G.; Charette, A. B. Nat. Chem. 2012, 4, 228. This work appeared while we were submitting our own manuscript. The two methods are complementary as a general methodology for the transformation of secondary amides to ketones in terms of the scope, reaction conditions and nucleophiles used.
28. Xiao, K.-J.; Wang, A.-E; Huang, Y.-H.; Huang, P.-Q. Asian J. Org. Chem. 2012, DOI:10.1002/ajoc.201200066.
29. Stang, P. J.; White, M. R. Aldrichimica Acta 1983, 16, 15.
30. Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
31. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829;
32. Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096;
33. Zhou, H.-B.; Liu, G.-S.; Yao, Z.-J. J. Org. Chem. 2007, 72, 6270;
34. Cui, S.-L.; Wang, J.; Wang, Y.-G. J. Am. Chem. Soc. 2008, 130, 13526;
35. Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 18;
36. Dong, Q.-L.; Liu, G.-S.; Zhou, H.-B.; Lin, C.; Yao, Z.-J. Tetrahedron Lett. 2008, 10, 1636.
37. Harder, I.; Hanack, M. Chem. Ber. 1984, 117, 3004.
38. Medley, J. W.; Movassaghi, M. J. Org. Chem. 2009, 74, 1341.
39. Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
40. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
41. Bartoli, G.; Marcantoni, E.; Marcolini, M.; Sambri, L. Chem. Rev. 2010, 110, 6104.
42. Enones, Eds.: Patai, S.; Rappoport, Z., Wiley, Chichester, 1989, Vol. 1.
43. Pohland, A. E.; Benson, W. R. Tetrahedron 1966, 66, 161;
44. Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 1268.
45. Yamaguchi, M.; Waseda, T.; Hirao, I. Chem. Lett. 1983, 12, 35.
46. Jeevanandam, A.; Narkunan, K.; Ling, Y.-C. J. Org. Chem. 2001, 66, 6014;
47. Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
48. Wang, X.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107;
49. Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67, 9200.
50. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120.
51. Fukuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2013.
52. Hosseini-Sarvari, M.; Mardaneh, Z. Bull. Chem. Soc. Jpn. 2011, 84, 778.
53. Liu, J.; Peng, X.; Sun, W.; Zhao, Y.; Xia, C. Org. Lett. 2008, 18, 3933.
54. Kawakami, T.; Miyatake, M.; Shibata, I.; Baba, A.; Matsuda, H. J. Org. Chem. 1996, 61, 376.