Efficient copper-mediated reactions of nitrenes derived from sulfonimidamides

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3573-3575

  Leca, Dominique ^a   Toussaint, Aurélie ^a   Mareau, Camille ^a   Fensterbank, Louis ^a   Lacôte, Emmanuel ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COPPER; NITROGEN DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; ATOM; CHEMICAL REACTION KINETICS; MOLECULE; PRODUCTIVITY; QUANTUM YIELD;

EID: 6444230448     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0485520     Document Type: Article

References (35)

1. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
2. (a) Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S.; Baird, C. P.; Sparey, T. J.; Taylor, P. C. J. Org. Chem. 1997, 62, 6512-6518.
3. (b) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805-4806.
4. Bolm, C.; Muniz, K.; Aguilar, N.; Kesselgruber, M.; Raabe, G. Synthesis 1999, 1251-1260.
5. Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073-2074.
6. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915-916.
7. (a) Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309-312.
8. (b) Albone, D. P.; Aujla, P. S.; Taylor, P. C.; Challenger, S.; Derrick, A. M. J. Org. Chem. 1998, 63, 9569-9571.
9. (a) Abramovitch, R. A.; Bailey, T. D.; Takaya, T.; Uma, V. J. Org. Chem. 1974, 39, 340-345.
10. (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
11. Mansuy, D.; Mahy, J. P.; Duréault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., Chem. Commun. 1984, 1161-1163.
12. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5, 5326-5327.
13. Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202-16203.
14. Jensen, M. P.; Mehn, M. P.; Que, L., Jr. Angew. Chem. Int. Ed. 2003, 42, 4357-4360.
15. Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087-1105.
16. Evans, D. A.; Bilodeau, M. T.; Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742-2753. For a mechanistic study of this reaction, see: Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013-8020.
17. Evans, D. A.; Bilodeau, M. T.; Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742-2753. For a mechanistic study of this reaction, see: Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013-8020.
18. (a) Espino, C. G.; Du Bois, J. Angew. Chem. Int. Ed. 2001, 40, 598-600.
19. (b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
20. Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.
21. (a) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
22. (b) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
23. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Angew. Chem. Int. Ed. 2002, 41, 3465-3468.
24. Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305-1307.
25. Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
26. (a) Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 127, 11395-11401.
27. (b) Brebion, F.; Delouvrié, B.; Nàjera, F.; Fensterbank, L.; Malacria, M.; Vaissermann, J. Angew. Chem. Int. Ed. 2003, 42, 5342-5345.
28. (a) Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Org. Lett. 2002, 4, 4093-4095.
29. (b) Leca, D.; Song, K.; Amatore, M.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906-916.
30. Johnson, C. R.; Jonsson, E. U.; Bacon, C. C. J. Org. Chem. 1979, 44, 2055-2061.
31. (a) Jones, M. R.; Cram, D. J. J. Am. Chem. Soc. 1974, 96, 2183-2190.
32. (b) Toth, J. E.; Ray, J.; Deeter, J. J. Org. Chem. 1993, 58, 3469-3472.
33. See Supporting Information for the HPLC spectra.
34. Roh, K. R.; Kim, K. S.; Kim, Y. H. Tetrahedron Lett. 1991, 32, 793-796.
35. Toth, J. E.; Grindey, G. B.; Ehlhardt, W. J.; Ray, J. E.; Boder, G. B.; Bewley, J. R.; Klingerman, K. K.; Gates, S. B.; Rinzel, S. M.; Schultz, R. M.; Weir, L. C.; Worzalla, J. F. J. Med. Chem. 1997, 40, 1018-1025.