Easy synthesis of (E)- or (Z)-perfluorinated β-enaminaoesters

Journal of Fluorine Chemistry

Volumn 117, Issue 1, 2002, Pages 35-41

  Prié, Gildas ^a   Richard, Sébastien ^a   Parrain, Jean Luc ^b   Duchêne, Alain ^a   Abarbri, Mohamed ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Ethylperfluoroalkynoate; Perfluorinated enaminoesters; Stereoselectivity

Indexed keywords

AMINE; ESTER DERIVATIVE; PERFLUORO COMPOUND;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; FLUORINATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

EID: 0037190254     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(02)00162-8     Document Type: Article

References (35)

1. P.W. Hickmott, Tetrahedron 38 (1982) 1975;
2. P.W. Hickmott, Tetrahedron 40 (1984) 2989;
3. M.A. Whitesell, Synthesis (1983) 517.
4. J.T. Welch, Tetrahedron 4 (1987) 3123 and references cited therein;
5. R. Filler, Y. Kobayashi, L. Yagupolskii (Eds.), Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993;
6. J.T. Welch, S. Eswara-Krishnan (Eds.), Fluorine in Bioorganic Chemistry, Wiley, New York, 1991;
7. A. Francesch, R. Alvarez, S. Lopez, A.R. de Lera, J. Org. Chem. 62 (1997) 310;
8. M. Groesbeck, S.O. Smith, J. Org. Chem. 62 (1997) 3638.
9. V.P. Kukhar, V.A. Soloshonok (Eds.), Fluorine-Containing Aminoacids, Synthesis and Properties, Wiley, New York, 1995.
10. D.C. Poulter, P.L. Wiggins, T.L. Plummer, J. Org. Chem. 46 (1981) 1532;
11. J. Froissard, J. Greiner, R. Pastor, J. Fluorine Chem. 17 (1981) 249;
12. A. Chauvin, J. Greiner, R. Pastor, A. Cambon, Tetrahedron 42 (1986) 663;
13. C. Portella, M. Iznaden, J. Fluorine Chem. 51 (1991) 1;
14. J.P. Bégué, D. Bonnet-Delpon, D. Bouvet, M.H. Rock, J. Chem. Soc. Perkin Trans. 1 (1998) 1797;
15. M.A. Decock-Plancquaert, F. Evariste, N. Guillot, Z. Janousek, C. Maliverney, R. Merényi, H.G. Viehe, Bull. Soc. Chim. Belg. 101 (1992) 313;
16. J.P. Bouillon, C. Maliverney, Z. Janousek, H.G. Viehe, Bull. Soc. Chim. Fr. 134 (1997) 47;
17. H.M. Park, T. Uegaki, T. Konno, T. Ishihara, H. Yamanaka, Tetrahedron Lett. 40 (1999) 2985 and references cited therein.
18. J.P. Bégué, D. Mesureur, Synthesis (1989) 309;
19. J.P. Bégué, D. Bonnet-Delpon, D. Mesureur, G. Née, S.W. Wu, J. Org. Chem. 57 (1992) 3807.
20. H. Yamanaka, K. Shiomi, T. Ishihara, Tetrahedron Lett. 40 (1995) 7267.
21. B.C. Hamper, M.L. Kurtzweil, J.B. Beck, J. Org. Chem. 57 (1992) 5680;
22. W. Cen, Y. Ni, Y. Shen, J. Fluorine Chem. 73 (1995) 161;
23. Y. Shen, S. Gao, J. Fluorine Chem. 76 (1996) 37.
24. G. Prié, J. Thibonnet, M. Abarbri, A. Duchêne, J.-L. Parrain, Synlett (1998) 839;
25. J. Thibonnet, G. Prié, M. Abarbri, A. Duchêne, J.-L. Parrain, Tetrahedron Lett. 40 (1999) 3151.
26. M. Abarbri, J. Thibonnet, J.-L. Parrain, A. Duchêne, Synthesis (2002) 543.
27. B.C. Hamper, Org. Synth. 70 (1991) 246.
28. F. Camps, R. Canela, J. Coll, A. Messeguer, A. Roca, Tetrahedron 34 (1978) 2179;
29. J.-P. Bégué, D. Bonnet-Delpon, D. Mesureur, M. Ourevitch, Magn. Resonance Chem. 29 (1991) 675;
30. K. Tamura, T. Ishihara, H. Yamanaka, J. Fluorine Chem. 68 (1994) 25;
31. P. Palmas, J. Thibonnet, J.-L. Parrain, M. Abarbri, F. David-Quillot, A. Duchêne, Magn. Resonance Chem. 40 (2002) 537.
32. S. Fustero, B. Pina, A. Simon-Fuentes, Tetrahedron Lett. 38 (1997) 6771;
33. S. Fustero, M. Garcia de la Torre, B. Pina, A Simon-Fuentes, J. Org. Chem. 64 (1999) 5551.
34. K. Funabiki, K. Tamura, T. Ishihara, H. Yamanaka, Bull. Chem. Soc. Jpn. 67 (1994) 3021.
35. J. Birch, D.H. Williamson, Org. React. 24 (1976) 1.