Sodium hydroxide-promoted reaction of 1-substituted 2,3,3-trifluoroprop-1-enyl toluene-p-sulfonates with alcohols. First efficient and convenient access to α-fluoro-β,β-dialkoxy ketones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 18, 1997, Pages 2679-2680

  Funabiki, Kazumasa ^a   Suzuki, Chisato ^a   Takamoto, Seizi ^a   Matsui, Masaki ^a   Shibata, Katsuyoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748619261     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705495e     Document Type: Article

References (34)

1. For recent examples, see: K. Iseki, S. Oishi, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1996, 37, 9081;
2. K. Mikami, T. Yazima, T. Takasaki, S. Matsukawa, M. Terada, T. Uchimura and M. Murata, Tetrahedron, 1996, 52, 85;
3. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199;
4. V. A. Soloshonok, A. D. Kacharov and T. Hayashi, Tetrahedron, 1996, 52, 245.
5. V. Kameswaran and B. Jiang, Synthesis, 1997, 530;
6. I. K. Khanna, R. M. Weier, Y. Yu, X. D. Xu, F. J. Koszyk, P. W. Collins, C. M. Koboldt, A. W. Veenhuizen, W. E. Perkins, J. J. Casler, J. L. Masferrer, Y. Y. Zhang, S. A. Gregory, K. Seibert and P. C. Isakson, J. Med. Chem., 1997, 40, 1634.
7. For our contribution to fluorine-containing heterocyclic compounds, see: I. Katsuyama, S. Ogawa, Y. Yamaguchi, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Synthesis, in the press;
8. I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Synlett, 1997, 591;
9. I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Tetrahedron Lett., 1996, 37, 4177.
10. For synthetic applications of fluorinated acetals, see: T.-P. Loh and X.-R. Li, Chem. Commun., 1996, 1929;
11. S. Kaneko, T. Yamazaki and T. Kitazume, J. Org. Chem., 1993, 58, 2302;
12. T. Ishihara, H. Hayashi and H. Yamanaka, Tetrahedron Lett., 1993, 34, 5777;
13. T. Tsukamoto and T. Kitazume, J. Chem. Soc., Perkin Trans. 1, 1993, 1177;
14. T. Kubota, M. Iijima and T. Tanaka, Tetrahedron Lett., 1992, 33, 1351;
15. T. Tsukamoto and T. Kitazume, Chem. Lett., 1992, 1377;
16. T. Fuchigami, K. Yamamoto and Y. Nakagawa, J. Org. Chem., 1991, 56, 137;
17. T. Fuchigami, Y. Nakagawa and T. Nonaka, J. Org. Chem., 1987, 87, 5489;
18. A. Guy, A. Lobgeois and M. Lemaire, J. Fluorine Chem., 1986, 32, 361.
19. R. J. Linderman, Rev. Pestic. Toxicol., 1993, 2, 231;
20. R. H. Abeles, Drug Dev. Res., 1987, 10, 221.
21. H. Kamaya, M. Sato and C. Kaneko, Tetrahedron Lett., 1997, 38, 587;
22. D. F. Andrés, E. G. Laurent and B. S. Marquet, Tetrahedron Lett., 1997, 38, 1049.
23. For the preparation of α-fluorinated β-diketones, see: R. E. Banks, N. J. Lawrence and A. L. Popplewell, J. Chem. Soc., Chem. Commun., 1994, 343;
24. G. Resnati and D. D. DesMarteau, J. Org. Chem., 1992, 57, 4281;
25. G. Resnati and D. D. DesMarteau, J. Org. Chem., 1991, 56, 4925.
26. K. Funabiki, T. Kurita, M. Matsui and K. Shibata, Chem. Lett., 1997, 739;
27. K. Funabiki, C. Ohtake, H. Muramatsu, M. Matsui and K. Shibata, Synlett, 1996, 444;
28. K. Funabiki, T. Ohtsuki, T. Ishihara and H. Yamanaka, Chem. Lett., 1996, 5;
29. K. Funabiki, T. Ohtsuki, T. Ishihara and H. Yamanaka, Chem. Lett., 1995, 239;
30. K. Funabiki, T. Ohtsuki, T. Ishihara and H. Yamanaka, Chem. Lett., 1994, 1075.
31. For the effective synthesis of polyfluoroalkylated compounds by the use of fluorinated enol derivatives, see: B. Dondy, P. Doussot, M. Iznaden, M. Muzard and C. Portella, Tetrahedron Lett., 1994, 35, 4357;
32. T. Ishihara, M. Kuroboshi, K. Yamaguchi and Y. Okada, J. Org. Chem., 1990, 55, 3107.
33. J. Ichikawa, M. Kobayashi, N. Yokota, Y. Noda and T. Minami, Tetrahedron, 1994, 50, 11 637;
34. N. Ishikawa, A. Takaoka, H. Iwakiri, S. Kubota and S. R. F. Kagaruki, Chem. Lett., 1980, 1107.