An efficient and general entry to (Z)-α-fluoro-β-substituted acrylaldehydes based on the coupling reaction of α-fluoro-β-amino acrylaldehydes with organolithium reagents

Chemistry Letters

Volumn , Issue 8, 1997, Pages 739-740

  Funabiki, Kazumasa ^a   Kurita, Takao ^a   Matsui, Masaki ^a   Shibata, Katsuyoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002662870     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.739     Document Type: Article

References (22)

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12. Our contribution for the synthesis of α-fluoro-β-substituted acrylaldehyde, for β-amino-substituted, see: a) K. Funabiki, T. Ohtsuki, T. Ishihara, and H. Yamanaka, Chem. Lett., 1994, 1075. For β-thio-substituted, see:
13. b) K. Funabiki, C. Ohtake, H. Muramatsu, M. Matsui, and K. Shibata, Synlett, 1996, 444. For other reports on α-fluoroacrylaldehyde, see. For β-amino-substituted, see:
14. C. Reichart and K. Halbritter, Liebigs Ann. Chem., 737, 99 (1970);
15. H. Yamanaka, S. Yamashita, and T. Ishihara, Synlett, 1993, 353. For β-thio-substituted, see: Ref. 4.
16. Addition of some organomethallic reagents to α-fluoro-β-substituted α,β-unsaturated aldehydes and/or ketones were reported. For Grignard reagents, see: Ref. 4 and a) P. E. Elkik and M. I. Imbeaux-Oudotte, Bull. Soc. Chim. Fr., 1976, 439. For dimethylcuprate, see:
17. b) C. Chuit, R. Sâuvetre, D. Masure, J. F. Normant, Tetrahedron, 35, 2645 (1979). For the regioselective addition of some hetero nucleophiles to α-fluoro-β-polyfluoroalkyl-β-substituted α,β-unsaturated carbonyl compounds, see: B. Dondy, P. Doussot, M. Iznaden, M. Muzard, and C. Portella, Tetrahedron Lett., 35, 4357 (1994).
18. b) C. Chuit, R. Sâuvetre, D. Masure, J. F. Normant, Tetrahedron, 35, 2645 (1979). For the regioselective addition of some hetero nucleophiles to α-fluoro-β-polyfluoroalkyl-β-substituted α,β-unsaturated carbonyl compounds, see: B. Dondy, P. Doussot, M. Iznaden, M. Muzard, and C. Portella, Tetrahedron Lett., 35, 4357 (1994).
19. 4FO: M, 150.0481.
20. 2Zn at 0 °C did not cause the reaction at all to furnish the trace amount of 3a.
21. For a recent review, see: T. Yamazaki and T. Kitazume, J. Syn. Org. Chem. Jpn., 54, 665 (1996).
22. K. Funabiki, T. Ohtsuki, T. Ishihara, and H. Yamanaka, Chem. Lett., 1996, 5.