Synthesis of β-Trifluoromethylated Enones: An Unexpected Reactivity of Trifluoromethylated Weinreb Enamides towards Organolithium Species

Synlett

Volumn , Issue 8, 2009, Pages 1241-1244

  Marrec, Olivier ^a   Borrini, Julien ^a   Billard, Thierry ^a   Langlois, Bernard R ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Conjugate addition; Enones; Fluorine; Trifluoroacetoacetate; Weinreb enamide

Indexed keywords

BETA TRIFLUOROMETHYLATED ENONE; FLUORINE DERIVATIVE; ORGANOLITHIUM COMPOUND; TRIFLUOROACETAMIDE DERIVATIVE; TRIFLUOROMETHYLATED WEINREB ENAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; SYNTHESIS;

EID: 67649359770     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216748     Document Type: Article

References (43)

1. (a) Groß, U.; Rüdiger, S. Organo-Fluorine Compounds, In Methods of Organic Chemistry (Houben-Weyl), Vol.E10a; Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Thieme: Stuttgart, 1999, 18.
2. (b) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
3. (c) Hiyama, T. Organofluorine Compounds: Chemistry and Properties; Springer: Berlin, 2000.
4. (d) Dunitz, J. D. ChemBioChem 2004, 5, 614.
5. (e) Biffinger, J. C.; Kim, H. W.; DiMagno, S. G. ChemBioChem 2004, 5, 622.
6. (a) Dolbier, W. R. Jr. J. Fluorine Chem. 2005, 126, 157.
7. (b) Schofield, H. J. Fluorine Chem. 1999, 100, 7.
8. (c) Thayer, A. M. Chem. Eng. News 2006, 84, 15.
9. (d) Thayer, A. M. Chem. Eng. News 2006, 84, 27.
10. (a) Kirk, K. L. Curr. Top. Med. Chem. 2006, 6, 1447.
11. (b) Burger's Medicinal Chemistry and Drug Discovery, 6th ed., Vol.1 and 2; Abraham, D. J., Ed.; John Wiley and Sons: New York, 2003.
12. (c) Park, B. K.; Kitteringham, N. R.; O'Neill, P. M. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 443.
13. (d) Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303.
14. (e) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
15. (f) Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27.
16. (g) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645.
17. (a) Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
18. (b) Kirsch, P. Modern Fluoroorganic Chemisty; Wiley-VCH: Weinheim, 2004.
19. (c) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004.
20. (d) Fluorinated Synthons; Soloshonok, V. A., Ed.; ACS Symposium Series No. 911, American Chemical Society: Washington DC, 2005.
21. (e) Billard, T. Chem. Eur. J. 2006, 12, 974.
22. Leuger, J.; Blond, G.; Fröhlich, R.; Billard, T.; Haufe, G.; Langlois, B. R. J. Org. Chem. 2006, 71, 2735.
23. (a) Molines, H.; Wakselman, C. J. Fluorine Chem. 1980, 16, 97.
24. (b) Ogoshi, H.; Mizushima, H.; Toi, H.; Aoyama, Y. J. Org. Chem. 1986, 51, 2366.
25. (c) Jacobs, R. T.; Bernstein, P. R.; Cronk, L. A.; Vacek, E. P.; Newcomb, L. F.; Aharony, D.; Buckner, C. K.; Kusner, E. J. J. Med. Chem. 1994, 37, 1282.
26. (d) Ramachandran, P. V.; Teodorovic, A. V.; Gong, B.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1075.
27. (e) Ramachandran, P. V.; Gong, B.; Teodorovic, A. V.; Brown, H. C. Tetrahedron: Asymmetry 1994, 5, 1061.
28. (f) Prie, G.; Abarbri, M.; Thibonnet, J.; Parrain, J.-L.; Duchene, A. New J. Chem. 2003, 27, 432.
29. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729.
30. (h) Leroy, J.; Fisher, N.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1990, 1281.
31. (i) Jeong, I. H.; Jeon, S. L.; Kim, M. S.; Kim, B. T. J. Fluorine Chem. 2004, 125, 1629.
32. Blond, G.; Billard, T.; Langlois, B. R. J. Org. Chem. 2001, 66, 4826.
33. Jagodzinska, M.; Huguenot, F.; Zanda, M. Tetrahedron 2007, 63, 2042.
34. Tordeux, M.; Wakselman, C. J. Fluorine Chem. 1982, 20, 301.
35. (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
36. (b) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
37. Kessar, S. V.; Singh, P.; Singh, K. N.; Bharatam, P. V.; Sharma, A. K.; Lata, S.; Kaur, A. Angew. Chem. Int. Ed. 2008, 47, 4703.
38. (a) Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140.
39. (b) Yamazaki, T.; Kitazume, T. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; John Wiley and Sons: Chichester, 1999, Chap. 19, 575-600.
40. (c) Sini, G.; Tessier, A.; Pytkowicz, J.; Brigaud, T. Chem. Eur. J. 2008, 14, 3363.
41. Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527.
42. Lewandowska, E. Tetrahedron 2007, 63, 2107.
43. 4, filtered, and concentrated in vacuo to give 6.