Syntheses of α-fluoro-α,β-unsaturated thioamides and thiazolines from a fluorophosphonodithioacetate

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4670-4676

  Pfund, Emmanuel ^a   Masson, Serge ^a   Vazeux, Michel ^a   Lequeux, Thierry ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROCARBONS; ISOMERS; OLEFINS; SYNTHESIS (CHEMICAL);

DITHIOESTER; GLYCOSIDES; REAGENTS;

ESTERS;

CARBONYL DERIVATIVE; FLUORINE DERIVATIVE; FLUOROPHOSPHONOMETHYLTHIAZOLINE; FLUOROPHOSPHONOTHIOACETAMIDE; GLYCOSIDE; METHYL FLUORO(DIETHOXYPHOSPHONO)DITHIOACETATE; ORGANOMETALLIC COMPOUND; PEPTIDE; THIAZOLE DERIVATIVE; THIAZOLINE DERIVATIVE; THIOAMIDE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; FLUORINATION; MASS SPECTROMETRY; OLEFINATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; GLYCOSIDES; HYDROCARBONS, FLUORINATED; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM; THIAZOLES; THIOAMIDES;

EID: 3042699993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049560x     Document Type: Article

References (42)

1. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
2. Boeglin, D.; Heitz, A.; Martinez, J.; Fehrentz, J. A. Eur. J. Org. Chem. 2003, 3139-3146.
3. (a) Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 7297-7300.
4. (b) Otaka, A.; Wanatabe, H.; Mitsuyama, E.; Yukimasa, A.; Tamamura, M.; Fujii, N. Tetrahedron Lett. 2001, 42, 285-287.
5. (c) Okada, M.; Nakamura, Y.; Saito, A.; Sato, A.; Horikawa, H.; Taguchi, T. Tetrahedron Lett. 2002, 43, 5845-5847.
6. (a) Machleidt, H.; Wessendorf, R. Justus Liebigs Ann. Chem. 1964, 674, 1-10.
7. (b) Etemad-Moghadam, G.; Seyden-Penne, J. Bull. Soc. Chim. Fr. 1985, 448-454.
8. (a) Allmendinger, T. Tetrahedron 1991, 47, 4905-4914.
9. (b) Satoh, T.; Itoh, N.; Onda, K.; Kitoh, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn 1992, 65, 2800-2806.
10. (c) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107-3111.
11. (d) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291-304.
12. (e) Kawasaki, T.; Ichige, T.; Kitazume, T. J. Org. Chem. 1998, 63, 7525-7528.
13. (f) Xu, J.; Burton, D. J. Org. Lett. 2002, 4, 831-833.
14. (g) Chevrie, D.; Lequeux, T.; Pommelet, J. C. Tetrahedron 2002, 58, 4759-4767.
15. (a) Blackburn, G. M.; Rashid, A. J. Chem. Soc., Chem. Commun. 1989, 40-41.
16. (b) McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7740.
17. (c) Xu, Z.; DesMarteau, D. D. J. Chem. Soc., Perkin Trans 1 1992, 313-315.
18. (d) Burton, D. J.; Yang, Z.; Qui, W. Chem. Rev. 1996, 96, 1641-1715.
19. (e) Veenstra, S. J.; Hauser, K.; Felber, P. Bioorg. Med. Chem. Lett. 1997, 7, 351-354.
20. (f) Boumendjel, A., Nuzillard, J. M.; Massiot, G. Tetrahedron Lett. 1999, 40, 9033-9036.
21. (g) Van Steenis, J. H.; Boer, P. W. S.; Van der Hoeven, H. A.; Van der Gen, A. Eur. J. Org. Chem. 2001, 911-918.
22. Miwa, J. H.; Pallivathucal, L.; Gowda, S.; Lee, K. E. Org. Lett. 2002, 4, 4655-4657.
23. Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422.
24. Pfund, E.; Lequeux, T.; Masson, S.; Vazeux, M. Org. Lett. 2002, 4, 843-846.
25. Blackburn, G. M.; Brown, D.; Martin, S. F. J. Chem. Res., Synop. 1985, 92-93.
26. (a) Uneyama, K.; Mizutani, G. Chem. Commun. 1999, 613-614.
27. (b) Amii, H.; Kobayashi, T.; Matamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323-1324.
28. (c) Mae, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2000, 41, 7893-7896.
29. (d) Amii, H.; Koayashi, T.; Uneyama, K. Synthesis 2000, 2001-2003.
30. (e) Uneyama, K.; Amii, H. J. Fluorine Chem. 2002, 114, 127-131.
31. (f) Hata, H.; Kobayashi, T.; Amii, H.; Uneyama, K.; Welch, J. T. Tetrahedron Lett. 2002, 43, 6099-6102.
32. Léger, L.; Saquet, M. Bull. Soc. Chim. Fr. 1975, 657-666.
33. Meyers, A. I.; Tait, T. A.; Comins, D. L. Tetrahedron Lett. 1978, 4657-4660.
34. Portella, C.; Shermolovitch, Y. Tetrahedron Lett. 1997, 38, 4063-4064.
35. Hartke, K.; Hoederath, W. Sulfur Lett. 1983, 1, 191-198 (The NMR spectra of ketenedithioacetals agree with the characteristic patterns of the Z isomers, and for 4a, HOESY experiments showed a spatial proximity between the fluorine atom and the methylsulfanyl group).
36. Bulpin, A.; Masson, S. J. Org. Chem. 1992, 57, 4507-4512.
37. (a) Sundberg, R. J.; Biswas, S.; Murthi, K. K.; Rowe, D. J. Med. Chem. 1998, 41, 4317-4328.
38. (b) Leflemme, N.; Marchand, P. Gulea, M.; Masson, S. Synthesis 2000, 1143-1147.
39. (c) LeRoy-Gourvennec, S.; Masson, S. Synthesis 1995, 1393-1396.
40. (d) Shaumann, E.; Fittkau, S. Tetrahedron Lett. 1984, 25, 2325-2328.
41. Grison, C.; Genève, S.; Hablin, E.; Coutrot, P. Tetrahedron 2001, 57, 4903-4923.
42. Coutrot, P.; Grison, C.; Lecouvey, M. Bull. Soc. Chim. Fr. 1997, 134, 27-45.