Regioselective 1,4-trifluoromethylation of α,β-enones using 'protect-in-situ' methodology

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7623-7627

  Sevenard, Dmitri V ^a   Sosnovskikh, Vyacheslav Ya ^b   Kolomeitsev, Alexander A ^c   Königsmann, Martin H ^a   Röschenthaler, Gerd Volker ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b URAL FEDERAL UNIVERSITY   (Russian Federation)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

(trifluoromethyl)trimethylsilane; Nucleophilic addition; Regioselectivity; Trifluoromethylation

Indexed keywords

(TRIFLUOROMETHYL)TRIMETHYLSILANE; ALUMINUM; CARBONYL DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL NUCLEUS; CHEMICAL PROCEDURES; METHODOLOGY; METHYLATION; STEREOCHEMISTRY;

EID: 0141741270     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.050     Document Type: Article

References (42)

1. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993 Organofluorine Chemistry-Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994.
2. Burton D.J., Yang Z.-Y. Tetrahedron. 48:1992;189.
3. McClinton M.A., McClinton D.A. Tetrahedron. 48:1992;6555.
4. Ruppert I., Schlich K., Volbach W. Tetrahedron Lett. 25:1984;2195.
5. Prakash G.K.S., Yudin A.K. Chem. Rev. 97:1997;757.
6. Singh R.P., Shreeve J.M. Tetrahedron. 56:2000;7613.
7. Prakash G.K.S., Mandal M. J. Fluorine Chem. 112:2001;123.
8. Prakash G.K.S., Krishnamurti R., Olah G.A. J. Am. Chem. Soc. 111:1989;393.
9. Krishnamurti R., Bellew D.R., Prakash G.K.S. J. Org. Chem. 56:1991;984.
10. Singh R.P., Cao G., Kirchmeier R.L., Shreeve J.M. J. Org. Chem. 64:1999;2873.
11. Petrov V.A. Tetrahedron Lett. 41:2000;6959.
12. Sevenard D.V., Kirsch P., Röschenthaler G.-V., Movchun V.N., Kolomeitsev A.A. Synlett. 2001;379.
13. Bardin V.V., Kolomeitsev A.A., Furin G.G., Yagupolskii Yu.L. Izv. Akad. Nauk SSSR, Ser. Khim. 1990;1693.
14. Kolomeitsev A.A., Movchun V.N., Yagupolskii Yu.L., Porwisiak J., Dmowski W. Tetrahedron Lett. 33:1992;6191.
15. Movchun V.N., Kolomeitsev A.A., Yagupolskii Yu.L. J. Fluorine Chem. 70:1995;255.
16. Wiedemann J., Heiner T., Mloston G., Prakash G.K.S., Olah G.A. Angew. Chem. 110:1998;880.
17. Watanabe S., Fujita T., Sakamoto M., Mino Y., Kitazume T. J. Fluorine Chem. 73:1995;21.
18. Allen A.D., Fujio M., Mohammed N., Tidwell T.T., Tsuji Y. J. Org. Chem. 62:1997;246.
19. Singh R.P., Kirchmeier R.L., Shreeve J.M. Org. Lett. 1:1999;1047.
20. Prakash G.K.S., Tongco E.C., Mathew T., Vankar Y.D., Olah G.A. J. Fluorine Chem. 101:2000;199.
21. Large S., Roques N., Langlois B.R. J. Org. Chem. 65:2000;8848.
22. Billard T., Bruns S., Langlois B.R. Org. Lett. 2:2000;2101.
23. (a) Sosnovskikh, V. Ya.; Sevenard, D. V.; Usachev, B. I.; Röschenthaler, G.-V. Tetrahedron Lett. 2003, 44, 2097;
24. Sosnovskikh, V. Ya.; Usachev, B. I.; Sevenard, D. V.; Röschenthaler, G.-V. J. Org. Chem., in press.
25. Larock R.C. Comprehensive Organic Transformations. 2nd ed. 1999;1599-1609 Wiley-VCH, New York.
26. Sato K., Tamura M., Tamoto K., Omote M., Ando A., Kumadaki I. Chem. Pharm. Bull. 48:2000;1023.
27. Sato K., Nakazato S., Enko H., Tsujita H., Fujita K., Yamamoto T., Omote M., Ando A., Kumadaki I. J. Fluorine Chem. 121:2003;105.
28. Saito S., Yamamoto H. Chem. Commun. 1997;1585.
29. Yamamoto H., Saito S. Pure Appl. Chem. 71:1999;239.
30. Saito S., Yamamoto H. Chem. Eur. J. 5:1999;1959.
31. Gassman P.G., O'Reilly N.J. J. Org. Chem. 52:1987;2481.
32. Maruoka K., Shimada I., Akakura M., Yamamoto H. Synlett. 1994;847.
33. Kolomeitsev A.A., Seifert F.U., Röschenthaler G.-V. J. Fluorine Chem. 71:1995;47.
34. Movchun, V. N.; Kirij, N. V.; Rusanov, E. B.; Kolomeitsev, A. A.; Yagupolskii, Yu. L. 15th International Symposium on Fluorine Chemistry, Vancouver, Canada, August 2-7, 1997, In (2) C-8.
35. Nonoshita K., Banno H., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 112:1990;316.
36. Usachev, B. I., private communication.
37. Sevenard, D. V., unpublished data.
38. 2,6-Diphenylphenol used for ATPH synthesis was recovered after hydrolysis of the complex and work up of the reaction mixture in all cases.
39. F-H=5.8 Hz).
40. Sosnovskikh, V. Ya.; Ovsyannikov, I. S. Zh. Org. Khim. 1993, 29, 89 (Russ. J. Org. Chem. 1993, 29, 74).
41. Schoo N., Schäfer H.-J. Liebigs Ann. Chem. 1993;601.
42. 19F NMR and MS data of all synthesized compounds are in accordance with proposed structures.