Oxidative intramolecular bromo-amination of N-alkenyl sulfonamides via umpolung of alkali metal bromides

Journal of Organic Chemistry

Volumn 76, Issue 17, 2011, Pages 7249-7255

  Moriyama, Katsuhiko ^a   Izumisawa, Yuta ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMO-AMINATION; BROMOAMIDES; DIASTEREOSELECTIVITIES; HIGH YIELD; METAL BROMIDES; ORGANIC WASTES; UMPOLUNG;

ALKALI METALS; AMIDES; AMINES; BROMINE COMPOUNDS; SEWAGE;

SULFUR COMPOUNDS;

ALKALI METAL; BROMIDE; N ALKENOXYL SULFONAMIDE; N ALKENYL SULFONAMIDE; SODIUM PEROXIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL REACTION; ORGANIC WASTE; STEREOCHEMISTRY; STOICHIOMETRY;

ALKENES; AMINATION; BROMINE; CATALYSIS; CYCLIZATION; METALS, ALKALI; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; SULFONAMIDES;

EID: 80052183137     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201113r     Document Type: Article

References (47)

1. Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans. 1 2001, 1182-1203
2. Mccormick, J. L.; Osterman, R.; Chan, T.-M.; Das, P. R.; Pramanik, B. N.; Ganguly, A. K.; Girijavallabhan, V. M.; McPhail, A. T.; Saksena, A. K. Tetrahedron Lett. 2003, 44, 7997-8000
3. Minakata, S.; Morino, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335-3337
4. Marcotullio, M. C.; Campagna, V.; Sternativo, S.; Costantino, F.; Curini, M. Synthesis 2006, 2760-2766
5. Michael, F. E.; Sibbald, P. A.; Cochran, B. M. Org. Lett. 2008, 10, 793-796
6. Davies, S. G.; Nicholson, R.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Savory, E. D.; Smith, A. D.; Thomson, J. E. Tetrahedron: Asymmetry 2009, 20, 758-772
7. Majumdar, K. C.; Ray, K.; Ponra, S. Tetrahedron Lett. 2010, 51, 5437-5439
8. For a review, see: O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446
9. Gribble, G. W. Chemosphere 2003, 52, 289-297
10. Butler, A.; Carter-Franklin, J. N. Nat. Prod. Rep. 2004, 21, 180-188
11. Neumann, C. S.; Fujimori, D. G.; Walsh, C. T. Chem. Biol. 2008, 15, 99-109
12. Runguphan, W.; Qu, X.; O'Connor, S. E. Nature 2010, 468, 461-464
13. Qi, X.; Lee, S.-H.; Kwon, J. Y.; Kim, Y.; Kim, S.-H.; Lee, Y.-S.; Yoon, J. J. Org. Chem. 2003, 68, 9140-9143
14. Thakur, V. V.; Talluri, S. K.; Sudalai, A. Org. Lett. 2003, 5, 861-864
15. Manzoni, M. R.; Zabawa, T. P.; Kasi, D.; Chemler, S. R. Organometallics 2004, 23, 5618-5621
16. Jiang, F.; Wu, Z.; Zhang, W. Tetrahedron 2011, 67, 1501-1505
17. Jonasson, C.; Karstens, W. F. J.; Hiemstra, H.; Bäckvall, J.-E. Tetrahedron Lett. 2000, 41, 1619-1622
18. Jonasson, C.; Horváth, A.; Bäckvall, J.-E. J. Am. Chem. Soc. 2000, 122, 9600-9609
19. Sakakura, A.; Ukai, K.; Ishihara, K. Nature 2007, 445, 900-903
20. Tanuwidjaja, J.; Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2009, 131, 12084-12085
21. Zhou, L.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 10245-10247
22. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474-15476
23. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174-9177
24. Tanaka, A.; Oritani, T. Biosci. Biotech. Biochem. 1995, 59, 516-517
25. Snyder, S. A.; Treitler, D. S. Angew. Chem., Int. Ed. 2009, 48, 7899-7903
26. Eissen, M.; Lenoir, D. Chem.f - Eur. J. 2008, 14, 9830-9841
27. Podgorsek, A.; Zupan, M.; Iskra, J. Angew. Chem., Int. Ed. 2009, 48, 8424-8450
28. Tamaru, Y.; Kawamura, S.; Tanaka, K.; Yoshida, Z. Tetrahedron Lett. 1984, 25, 1063-1066
29. Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491-5501
30. Breternitz, H.-J.; Schaumann, E. J. Chem. Soc., Perkin Trans. 1 1999, 1927-1931
31. Fujioka, H.; Murai, K.; Ohba, Y.; Hirose, H.; Kita, Y. Chem. Commun. 2006, 832-834
32. Kumar, K. R. R.; Mallesha, H.; Basappa; Rangappa, K. S. Eur. J. Med. Chem. 2003, 38, 613-619
33. Minter, A. R.; Brennan, B. B.; Mapp, A. K. J. Am. Chem. Soc. 2004, 126, 10504-10505
34. Ishiyama, H.; Tsuda, M.; Endo, T.; Kobayashi, J. M lecules 2005, 10, 312-316
35. Pouilhès, A.; Amado, A. F.; Vidal, A.; Langlois, Y.; Kouklovsky, C. Org. Biomol. Chem. 2008, 6, 1502-1510
36. Frederickson, M. Tetrahedron 1997, 53, 403-425
37. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; Sarlo, F. D. Tetrahedron Lett. 1990, 31, 3351-3354
38. Murahashi, S.; Kodera, Y.; Hosomi, T. Tetrahedron Lett. 1988, 29, 5949-5952
39. Hanselmann, R.; Zhou, J.; Ma, P.; Confalone, P. N. J. Org. Chem. 2003, 68, 8739-8741
40. Piperno, A.; Chiacchio, U.; Iannazzo, D.; Giofrè, S. V.; Romeo, G.; Romeo, R. J. Org. Chem. 2007, 72, 3958-3960
41. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-910
42. Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449-1458
43. Peng, J.; Jiang, D.; Lin, W.; Chen, Y. Org. Biomol. Chem. 2007, 5, 1391-1396
44. Peng, J.; Lin, W.; Yuan, S.; Chen, Y. J. Org. Chem. 2007, 72, 3145-3148
45. Hay, M. B.; Wolfe, J. P. Angew. Chem., Int. Ed. 2007, 46, 6492-6494
46. Jiang, D.; Peng, J.; Chen, Y. Tetrahedron 2008, 64, 1641-1647
47. Lemen, G. S.; Giampietro, N. C.; Hay, M. B.; Wolfe, J. P. J. Org. Chem. 2009, 74, 2533-2540