Lewis acid promoted aldol reaction of fluorinated silyl enol ethers from new fluoroacetylsilane derivatives

Tetrahedron Letters

Volumn 45, Issue 28, 2004, Pages 5403-5406

  Chung, Woo Jin ^a   Ngo, Silvana C ^a   Higashiya, Seiichiro ^a   Welch, John T ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

Aldol reaction; Fluorinated ketone; Fluorinated silyl enol ether; Lewis acid

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; ETHER DERIVATIVE; FLUORINE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; SILANE DERIVATIVE;

ALDOL REACTION; ARTICLE; FLUORINATION; SYNTHESIS;

EID: 2942693539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.055     Document Type: Article

References (21)

1. Ojima I., McCarthy J.R., Welch J.T. Biomedical Frontiers of Fluorine Chemistry. 1996;American Chemical Society, Washington, DC
2. Welch J.T., Eswarakrishnan S. Fluorine in Bioorganic Chemistry. 1991;John Wiley and Sons, New York
3. Tozer M.J., Herpin T.F. Tetrahedron. 52:1996;8619
4. Percy J.M. Top. Curr. Chem. 193:1997;131
5. Altenburger J.M., Schirlin D. Tetrahedron Lett. 32:1991;7255
6. Mukaiyama T., Kobayashi S. Org. React. 46:1994;1
7. Bednarski M.D., Lyssikatos J.P. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 2:1991;Pergamon, Oxford. Chapter 2.5
8. Kodama Y., Yamane H., Okumura M., Shiro M., Taguchi T. Tetrahedron. 51:1995;12217
9. Iseki K., Kuroki Y., Asada D., Takahashi M., Kishimoto S., Kobayashi Y. Tetrahedron. 53:1997;10271
10. Yamana M., Ishihara T., Ando T. Tetrahedron Lett. 24:1983;507
11. Amii H., Kobayashi T., Hatamoto T., Uneyama K. J. Chem. Soc., Chem. Commun. 1999;1323
12. Uneyama K., Amii H. J. Fluorine Chem. 114:2002;127
13. Brigaud T., Doussot P., Portella C. J. Chem. Soc., Chem. Commun. 1994;2117
14. Lefebvre O., Brigaud T., Portella C. J. Org. Chem. 66:2001;1941
15. Jin F., Jiang B., Hu Y. Tetrahedron Lett. 33:1992;1221
16. Jin F., Hu Y., Huang W. J. Chem. Soc., Chem. Commun. 1993;814
17. Jin F., Hu Y., Huang W. J. Chem. Soc., Perkin Trans. 1993;795
18. Higashiya, S.; Lim, D. S.; Ngo, S. C.; Toscano, P. J.; Welch, J. T. Abstract of Paper, 222nd National Meeting of the American Chemical Society, Chicago, IL, 2001; American Chemical Society: Washington, DC, ORGN 41
19. Ngo S.C., Chung W.C., Lim D.S., Higashiya S., Welch J.T. J. Fluorine Chem. 117:2002;207
20. 4, filtered, and concentrated. Product 5 was purified by recrystallization in hexane or silica gel column chromatography using a mixture of hexane and ethyl acetate (30:1 v/v)
21. 4, filtered, and concentrated. Purification via silica gel column chromatography afforded the spectroscopically pure products 8 and 9