Metal-free reductive cleavage of N-O bonds in weinreb amides by an organic neutral super-electron donor

Synlett

Volumn , Issue 14, 2008, Pages 2132-2136

  Cutulic, Sylvain P Y ^a   Murphy, John A ^a   Farwaha, Hardeep ^a   Zhou, Sheng Ze ^a   Chrystal, Ewan ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

Electron transfer; Pyridinylidene; Reduction; Weinreb amide

Indexed keywords

AMIDE; UNCLASSIFIED DRUG; WEINREB AMIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT;

EID: 51149100131     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078240     Document Type: Article

References (20)

1. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
2. (b) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
3. (c) Aidhen, I. S.; Ahuja, J. Tetrahedron Lett. 1992, 33, 5431.
4. (d) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
5. (e) Selvamurugan, V.; Aidhen, I. S. Tetrahedron 2001, 57, 6065.
6. (f) Mislin, G. A.; Burger, A.; Abdallah, M. A. Tetrahedron 2004, 60, 12139.
7. (g) Murphy, J. A.; Commeureuc, A. G. J.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. Org. Lett. 2005, 7, 1427.
8. (h) Kangani, C. O.; Kelley, D. E.; Day, B. W. Tetrahedron Lett. 2006, 47, 6289.
9. (i) Hisler, K.; Tripoli, R.; Murphy, J. A. Tetrahedron Lett. 2006, 47, 6293.
10. Mattingly, P. G.; Miller, M. J. J. Org. Chem. 1980, 45, 410.
11. Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602.
12. Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755.
13. (a) Yus, M.; Radivoy, G.; Alonso, F. Synthesis 2001, 914.
14. (b) Taillier, C.; Bellosta, V.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2145.
15. Murphy, J. A.; Khan, T. A.; Zhou, S.; Thomson, D. W.; Mahesh, M. Angew. Chem. Int. Ed. 2005, 44, 1356.
16. Murphy, J. A.; Zhou, S.; Thomson, D. W.; Schoenebeck, F.; Mahesh, M.; Park, S. R.; Tuttle, T.; Berlouis, L. E. A. Angew. Chem. Int. Ed. 2007, 46, 5178.
17. Schoenebeck, F.; Murphy, J. A.; Zhou, S.; Uenoyama, Y.; Miclo, Y.; Tuttle, T. J. Am. Chem. Soc. 2007, 129, 13368.
18. Murphy, J. A.; Garnier, J.; Park, S. R.; Schoenebeck, F.; Zhou, S.-Z.; Turner, A. T. Org. Lett. 2008, 10, 1227.
19. Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, 103, 2167.
20. Giese, B. Bioorg. Med. Chem. 2006, 14, 6139.