A facile isomerization procedure for the access to thermodynamic silyl enol ethers

Synthetic Communications

Volumn 28, Issue 10, 1998, Pages 1817-1821

  Deyine, Abdallah ^a   Dujardin, Gilles ^a,b   Mammeri, Malika ^a   Poirier, Jean Marie ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; SILANE DERIVATIVE; SILYL ENOL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; EXTRACTION; ISOMERISM; SYNTHESIS; THERMODYNAMICS;

EID: 0031832945     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808007012     Document Type: Article

References (13)

1. Brownbridge, P. Synthesis 1983, 1 and 85.
2. Poirier, J-M. Org. Proc. Int., 1988, 20, 317.
3. For convenient methods in other cases (e.g. 2-alkylcyclohexanones), see : (a) Miller, R.D.; Mac Kean, D.R. Synthesis 1979, 730 (b) Krafft, M.E.; Holton, R.A. Tetrahedron Lett., 1983, 24, 1345.
4. For convenient methods in other cases (e.g. 2-alkylcyclohexanones), see : (a) Miller, R.D.; Mac Kean, D.R. Synthesis 1979, 730 (b) Krafft, M.E.; Holton, R.A. Tetrahedron Lett., 1983, 24, 1345.
5. (a) Duboudin, F.; Cazeau, P.; Moulines, F.; Laporte, O. J. Organomet. 1980, 201, C9.
6. (b) Cazeau, P.; Duboudin, F.; Moulines, F.; Barbot, O.; Dunoguès, J. Tetrahedron 1987, 43, 2075 and 2089.
7. Poirier, J-M.; Hennequin, L. Synth.Commun.. 1985, 15, 217.
8. Duhamel, P.; Dujardin, G.; Hennequin, L.; Poirier, J-M. J. Soc. Perkin Trans. 1 1992, 367.
9. House, H.O.; Czuba, L.J.; Gall, M.; Olmstead, H.D. J. Org. Chem., 1969, 34, 2324.
10. Poirier, J-M.; Hennequin, L.; Fomani, M. Bull. Soc. Chim. Fr. 1986, 436.
11. Emde, H.; Gôtz, A.; Hofmann, K.; Simchen, G. Ann. Chem, 1981, 1643.
12. Barzouin, A.; Dunoguès, J.; Lefort, M. Rhône Poulenc Industrie French Patent, 1436568, 1964 and extension 88358, 1965.
13. These procedures use the heating of trialkylsilyl enol ethers in a solvent, in the presence of an ammonium salt.