Synthesis of new sulfonyloximes and their use in free-radical olefin carbo-oximation

Organic Letters

Volumn 17, Issue 8, 2015, Pages 1958-1961

  Ovadia, Benjamin ^a   Robert, Frédéric ^a   Landais, Yannick ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84928024773     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00672     Document Type: Article

References (27)

1. Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138
2. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982
3. Kim, S.; Lim, K.-C.; Kim, S. Chem. Commun. 2007, 4507
4. Schaffner, A.-P.; Darmency, V.; Renaud, P. Angew. Chem., Int. Ed. 2006, 45, 5847
5. Ryu, I. Multicomponent Radical Reactions. In Multicomponent Radical Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; p 169.
6. Liautard, V.; Landais, Y. Free-Radical Multicomponent Processes. In Multicomponent Reactions in Organic Synthesis, 2 nd ed.; Zhu, J.; Wang, Q.; Wang, M. X., Eds.; Wiley-VCH: Weinheim, Germany, 2014; p 401.
7. Godineau, E.; Landais, Y. J. Am. Chem. Soc. 2007, 129, 12662
8. Landais, Y.; Robert, F.; Godineau, E.; Huet, L.; Likhite, N. Tetrahedron 2013, 69, 10073
9. Chatgilialoglu, C. In The Chemistry of Sulfones and Sulfoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; p 1089.
10. Bertrand, M. P. Org. Prep. Proced. Int. 1994, 26, 257
11. Bertrand, F.; Le Guyader, F.; Liguori, L.; Ouvry, G.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. C. R. Acad. Sci. 2001, 4, 547
12. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
13. Le Guyader, F.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. J. Am. Chem. Soc. 1997, 119, 7410
14. Bertrand, F.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem., Int. Ed. 1999, 38, 1943
15. Kim, S.; Lim, C. J. Angew. Chem., Int. Ed. 2002, 41, 3265
16. Kim, S.; Kim, S. Bull. Chem. Soc. Jpn. 2007, 80, 809
17. Weidner, K.; Giroult, A.; Panchaud, P.; Renaud, P. J. Am. Chem. Soc. 2010, 132, 17511
18. A small amount of the oxime below is also formed from 3a, likely as a result of a Ramberg-Bäcklund rearrangement. Ramberg, L.; Bäcklund, B. Ark. Kemi, Mineral. Geol. 1940, 13A, 50
19. Darmency, V.; Renaud, P. Top. Curr. Chem. 2006, 263, 71
20. Quiclet-Sire, B.; Zard, S. Top. Curr. Chem. 2006, 264, 201
21. Curran, D. P.; Yoo, B. Tetrahedron Lett. 1992, 33, 6931
22. Denisov, E. T.; Denisova, T. G.; Pokidova, T. S. Handbook of Free Radical Initiators; Wiley & Sons: Hoboken, NJ, 2003.
23. Russell, G. A. J. Org. Chem. 1958, 23, 1407
24. Gilliom, R. D.; Ward, B. F. J. Am. Chem. Soc. 1965, 87, 3944
25. Gilliom, R. D. J. Org. Chem. 1985, 50, 4336
26. Bella, A. F.; Slawin, A. M. Z.; Walton, J. C. J. Org. Chem. 2004, 69, 5926
27. Godineau, E.; Schenk, K.; Landais, Y. J. Org. Chem. 2008, 73, 6983