Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1349-1352

  Ishino, Yoshio ^a   Kita, Yoshio ^a,b   Maekawa, Hirofumi ^a,c   Ohno, Toshinobu ^a   Yamasaki, Yasuhiro ^a,b   Miyata, Toshiyuki ^a   Nishiguchi, Ikuzo ^a,c  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b ORIENT CHEMICAL INDUSTRIES CO LTD   (Japan)

^c NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Carbonyl compounds; Enol ethers; Magnesium and compounds; Silicon halides

Indexed keywords

CARBONYL DERIVATIVE; ETHER DERIVATIVE; MAGNESIUM; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033547954     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02659-8     Document Type: Article

References (15)

1. Brownbridge P., Synthesis, 1983, 1 and 85.
2. Reets von M.T., Angew. Chem., 94, 97 (1982).
3. Colvin E.W., Silicon in Organic Synthesis, Butterworths, London, 1981.
4. Pawkinko S., Organo Silicon Chemistry, Walter de Gruyter, Berlin, 1986.
5. Weber W.P., Silicon Reagents for Organic Synthesis, Spring-Verlag, Berlin, 1983.
6. Negishi E, Organometallics in Organic Synthesis, John Wiley & Sons, New York, Vol.1, Chap. 6, 1980.
7. Bonafoux D., Bordeau M., Biran C., Cazeau P., and Dunogues J., J. Org. Chem., 61, 5532 (1996).
8. Bonafoux D., Bordeau M., Biran C., and Dunogues J., J. Organomet. Chem., 493, 27 (1995).
9. Davis F.A., Sheppard A.C. Chen B.C., and Haque M., J. Am. Chem. Soc., 112, 6679 (1990).
10. Takai K., Kataoka Y., Okazoe T., and Utimoto K., Tetrahedron Lett., 29, 1065 (1988).
11. Davis F.A., Lal G.S., and Wei J., Tertahedron Lett., 29, 4269 (1988).
12. Dedier J., Gerval P., and Frainnet E., J. Organomet. Chem., 185, 183 (1980).
13. House H.O., Czuba L.J., Gall M.,and Olmstead H.D., J. Org. Chem., 34, 2324 (1969).
14. Cazeau P., Duboudin F., Moulines F., Babot O., Dunogues J., Tetrahedron., 43, 2075 (1987).
15. Ishino Y., Maekawa H., Takeuchi H., Sukata K., and Nishiguchi I., Chem. Lett., 1995, 829.