Electrochemical cleavage of sulfonamides: An efficient and tunable strategy to prevent β-fragmentation and epimerization

Organic Letters

Volumn 14, Issue 3, 2012, Pages 942-945

  Viaud, Pierre ^a   Coeffard, Vincent ^a   Thobie Gautier, Christine ^a   Beaudet, Isabelle ^a   Galland, Nicolas ^a   Quintard, Jean Paul ^a   Le Grognec, Erwan ^a  

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856710173     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300003f     Document Type: Article

References (38)

1. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4 th ed.; Wiley-Interscience: New York, 2006.
2. Kocienski, P. J. Protecting Groups, 3 rd ed.; Georg Thieme Verlag: New York, 2005.
3. Vedejs, E.; Lin, S. J. Org. Chem. 1994, 59, 1602-1603
4. Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128-8129
5. Blay, G.; Cardona, L.; Climent, E.; Pedro, J. R. Angew. Chem., Int. Ed. 2008, 47, 5593-5596
6. Ankner, T.; Hilmersson, G. Org. Lett. 2009, 11, 503-506
7. Jensen, K. L.; Franke, P. T.; Nielsen, L. T.; Daasbjerg, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 129-133
8. Moussa, Z.; Romo, D. Synlett 2006, 3294-3298
9. Kong, K.; Romo, D.; Lee, C. Angew. Chem., Int. Ed. 2009, 48, 7402-7405
10. Parsons, A. F.; Pettifer, R. M. Tetrahedron Lett. 1996, 37, 1667-1670
11. Knowles, H. S.; Parsons, A. F.; Pettifer, R. M.; Rickling, S. Tetrahedron 2000, 56, 979-988
12. Nyasse, B.; Grehn, L.; Ragnarsson, U. Chem. Commun. 1997, 1017-1018
13. Das, I.; Pathak, T. Org. Lett. 2006, 8, 1303-1306
14. Deck, J. A.; Martin, S. F. Org. Lett. 2010, 12, 2610-2613
15. Yasuhara, A.; Sakamoto, T. Tetrahedron Lett. 1998, 39, 595-596
16. Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284
17. Shohji, N.; Kawaji, T.; Okamoto, S. Org. Lett. 2011, 13, 2626-2629
18. Dunach, E.; Medeiros, M. J.; Olivero, S. New. J. Chem. 2006, 30, 1534-1548
19. Yoshida, J.-i.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265-2299
20. Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 2099-2119
21. Horner, L.; Neumann, H. Chem. Ber. 1965, 98, 3462-3469
22. Mairanovsky, V. G. Angew. Chem., Int. Ed. Engl. 1976, 15, 281-291
23. Lebouc, A.; Martigny, P.; Carlier, R.; Simonet, J. Tetrahedron 1985, 41, 1251-1258
24. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1992, 57, 834-840
25. Lund, H.; Hammerich, O. Organic Electrochemistry, 4 th ed.; Marcel Dekker: New York, 2001.
26. Coeffard, V.; Thobie-Gautier, C.; Beaudet, I.; Le Grognec, E.; Quintard, J.-P. Eur. J. Org. Chem. 2008, 383-391
27. Senboku, H.; Nakahara, K.; Fukuhara, T.; Hara, S. Tetrahedron Lett. 2010, 51, 435-438
28. Knowles, H. S.; Parsons, A. F.; Pettifer, R. M. Synlett 1997, 271-272
29. Kozuka, S.; Takahashi, H.; Oae, S. Bull. Chem. Soc. Jpn. 1970, 43, 129-134
30. Liu, Y.; Zhang, Y. Tetrahedron Lett. 2003, 44, 4221-4291
31. Coeffard, V.; Beaudet, I.; Evain, M.; Le Grognec, E.; Quintard, J.-P. Eur. J. Org. Chem. 2008, 3344-3351
32. Coeffard, V.; Beaudet, I.; Quintard, J.-P.; Le Grognec, E. Chirality 2010, 22, 864-869
33. Kells, K. W.; Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666-15667
34. Cintrat, J.-C.; Léat, V.; Parrain, J.-L.; Le Grognec, E.; Beaudet, I.; Toupet, L.; Quintard, J.-P. Organometallics 2004, 23, 943-945
35. Cintrat, J.-C.; Leat-Crest, V.; Parrain, J.-L.; Le Grognec, E.; Beaudet, I.; Quintard, J.-P. Eur. J. Org. Chem. 2004, 4251-4267
36. Cintrat, J.-C.; Léat-Crest, V.; Parrain, J.-L.; Le Grognec, E.; Beaudet, I.; Toupet, L.; Quintard, J.-P. Eur. J. Org. Chem. 2004, 4268-4279
37. Coeffard, V.; Le Grognec, E.; Beaudet, I.; Evain, M.; Quintard, J.-P. J. Org. Chem. 2009, 74, 5822-5838
38. Fains, O.; Vernon, J. M. Tetrahedron Lett. 1997, 38, 8265-8266