First catalytic C-acylation of enoxysilanes: An efficient route to β-diketones

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3885-3887

  Le Roux, Christophe ^a   Mandrou, Stéphanie ^a   Dubac, Jacques ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000935716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960090j     Document Type: Article

References (25)

1. For our previous work on bismuth catalysts, see: Labrouillère, M.; Le Roux, C.; Oussaid, A.; Gaspard-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1995, 132, 522.
2. (a) House, H.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514.
3. (b) Beck, A. K.; Hoekstra, M. S.; Seebach, D. Tetrahedron Lett. 1977, 13, 1187.
4. Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron Lett. 1979, 15, 1339.
5. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
6. (a) Mao, C. L.; Frostick, F. C.; Man, E. H.; Manyik, R. M.; Wells, R. L.; Hauser, C. R. J. Org. Chem. 1969, 34, 1425.
7. (b) Manyik, R. M.; Frostick, F. C.; Sanderson, J. J.; Hauser, C. R. J. Am. Chem. Soc. 1953, 75, 5030.
8. Murai, S.; Kuroki, Y.; Hasegawa, K.; Tsutsumi, S. J. Chem. Soc., Chem. Commun. 1972, 946.
9. (a) Murai, S.; Hasegawa, K.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1975, 14, 636.
10. (b) Effenberger, F.; Ziegler, T.; Schönwälder, K. H.; Kesmarszky, T.; Bauer, B. Chem. Ber. 1986, 119, 3394.
11. Hopka, I.; Rathke, M. W. J. Org. Chem. 1981, 46, 3771.
12. Tirpak, R. E.; Rathke, M. W. J. Org. Chem. 1982, 47, 5099.
13. Kramarova, E. N.; Baukov, Y. I.; Lutsenko, I. F. Zh. Obshch. Khim. 1973, 43, 1857.
14. Limat, D.; Schlosser, M. Tetrahedron 1995, 51, 5799.
15. Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J.; Jaud, J.; Vignaux, P. J. Org. Chem. 1993, 58, 1835.
16. Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1993, 130, 832.
17. As suggested by a referee the assistance of the silicon to stabilize the cationic intermediate would be also described in K, although silicon is known to stabilize positive charges at the beta position through hyperconjugation. However, the intermediate K would explain the selective desilylation in our mechanism. (Formula Presented)
18. Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J. Org. Chem. 1994, 59, 2238.
19. Hoffmann, H. M. R.; Haase, K. Synthesis 1981, 715.
20. (a) Dill, K.; Mc Gown, E. L. In The Chemistry of Organic Compounds of Arsenic, Antimony and Bismuth; Patai, S., Ed.; J. Wiley: New York, 1994; pp 695-713.
21. (b) Irwing Sax, N.; Bewis, R. J. Dangerous Properties of Industrial Materials; Van Nostrand Reinhold: New York, 1989; pp 283-284 and 522-523.
22. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: New York, 1992.
23. Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunoguès, J. Tetrahedron 1987, 43, 2075.
24. (a) Jacquier, R.; Petrus, C.; Petrus, F. Bull. Soc. Chim. Fr. 1986, 2845.
25. (b) Nakano, T.; Umano, S.; Kino, Y.; Ishii, Y.; Ogawa, M. J. Org. Chem. 1988, 53, 3752.