Spontaneous aldol and Michael additions of simple enoxytrimethylsilanes in DMSO

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4881-4884

  Génisson, Yves ^a   Gorrichon, Liliane ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

Aldol addition; Enoxysilanes; Michael additions; Mukaiyama reaction; Solvent effect

Indexed keywords

DIMETHYL SULFOXIDE; SOLVENT; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; REACTION ANALYSIS;

EID: 0037777381     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00725-5     Document Type: Article

References (25)

1. Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389 and references cited therein.
2. Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389 and references cited therein.
3. Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889-892 and references cited therein.
4. Carreira, E. M.; Singer R. A. Tetrahedron Lett. 1994, 35, 4323-4326. Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581. Ellis, W. W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1998, 193-194.
5. Carreira, E. M.; Singer R. A. Tetrahedron Lett. 1994, 35, 4323-4326. Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581. Ellis, W. W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1998, 193-194.
6. Carreira, E. M.; Singer R. A. Tetrahedron Lett. 1994, 35, 4323-4326. Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581. Ellis, W. W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1998, 193-194.
7. Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181-187 and references cited therein.
8. Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103-107.
9. Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991 and references cited therein.
10. Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7704-7405.
11. Activation of trimethylsilyl enol ethers under high pressure: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Am. Chem. Soc. 1983, 105, 6963-6965. Or by water: Lubineau, A. J. Org. Chem. 1986, 51, 2142-2144.
12. Activation of trimethylsilyl enol ethers under high pressure: Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Am. Chem. Soc. 1983, 105, 6963-6965. Or by water: Lubineau, A. J. Org. Chem. 1986, 51, 2142-2144.
13. Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922-7923.
14. Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026-7043.
15. Kobayashi, S.; Nishio, K. J. Org. Chem. 1993, 58, 2647-2649.
16. Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585-2588.
17. Early unexplained solvent assisted additions of trimethylsilyl ketene acetals have been reported. Michael additions in hot acetonitrile: Kita, Y.; Segawa, J.; Haruta, J.-I.; Yasuda, H.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1982, 1099-1104. Michael additions in nitromethane: RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083-2089. Aldol additions in hot acetonitrile: Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Kishino, H.; Ke, Y. Y.; Tamura, Y. J. Org. Chem. 1988, 53, 554-561.
18. Early unexplained solvent assisted additions of trimethylsilyl ketene acetals have been reported. Michael additions in hot acetonitrile: Kita, Y.; Segawa, J.; Haruta, J.-I.; Yasuda, H.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1982, 1099-1104. Michael additions in nitromethane: RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083-2089. Aldol additions in hot acetonitrile: Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Kishino, H.; Ke, Y. Y.; Tamura, Y. J. Org. Chem. 1988, 53, 554-561.
19. Early unexplained solvent assisted additions of trimethylsilyl ketene acetals have been reported. Michael additions in hot acetonitrile: Kita, Y.; Segawa, J.; Haruta, J.-I.; Yasuda, H.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1982, 1099-1104. Michael additions in nitromethane: RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083-2089. Aldol additions in hot acetonitrile: Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Kishino, H.; Ke, Y. Y.; Tamura, Y. J. Org. Chem. 1988, 53, 554-561.
20. Acetonitrile and nitromethane gave the poorest results (ca. 20% yield along with ca. 10% yield of nitroaldol product in the latter case) while NMP, propylene carbonate and sulfolane revealed moderately efficient (ca. 50% yield).
21. Creger, P. L. Tetrahedron Lett. 1972, 1, 79-80.
22. Reaction of the representative trimethylsilyl enol ether derived from cyclohexanone with benzaldehyde in anhydrous DMF proceeded extremely slowly (ca. 10% yield after four days at room temperature).
23. The strongest propensity of 1 to give 1,4-addition could be rationalised by the intervention of a radical reaction pathway, treatment of cyclopentenone with enoxysilane 1 in dry DMSO and in the presence of a free-radical scavenger (Galvinoxyl) giving the aldol product in only 60% yield (instead of 95%).
24. Chan, T. H.; Aida, T.; Lau, P. W. K.; Gorys, V.; Harpp, D. N. Tetrahedron Lett. 1979, 42, 4029-4032.
25. Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707-709 and references cited therein.