Enantioselective organocatalytic route to trifluoromethyl-β-amino acids using chiral bases

Journal of Fluorine Chemistry

Volumn 128, Issue 5, 2007, Pages 500-506

  Michaut, Valérie ^a   Metz, François ^b   Paris, Jean Marc ^b   Plaquevent, Jean Christophe ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b Rhodia Recherches   (France)

Author keywords

Amino acids and derivatives; Asymmetric synthesis; Chiral bases; Proton shift transfer reaction; Trifluoromethyl compounds

Indexed keywords

EID: 34247112393     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.12.013     Document Type: Article

References (30)

1. J.P. Bégué, D. Bonnet-Delpon, Chimie bioorganique et médicinale du fluor EDP Sciences/CNRS Eds. (2005).
2. Smart B.E. J. Fluorine Chem. 109 (2001) 3-11
3. O'Hagan D., and Rzepa H.S. Chem. Commun. (1997) 645-652
4. Schlosser M. Angew. Chem. Int. Ed. 110 (1998) 1496-1513
5. Bégué J.P., and Bonnet-Delpon D. J. Fluorine Chem. 127 (2006) 992-1012
6. Isanbor C., and O'Hagan D. J. Fluorine Chem. 127 (2006) 303-319
7. Kirk K. J. Fluorine Chem. 127 (2006) 1013-1029
8. Liu M., and Sibi M.P. Tetrahedron 58 (2002) 7991-8035
9. Cheng R.P., Gellman S.H., and DeGrado W.F. Chem. Rev. 101 (2001) 3219-3232
10. Seebach D., Kimmerlin T., Sebesta R., Campo M.A., and Beck A.K. Tetrahedron 60 (2004) 7455-7506
11. Huguenot F., and Brigaud T. J. Org. Chem. 71 (2006) 2159-2162
12. Qiu X.L., Meng W.D., and Qing F.L. Tetrahedron 60 (2004) 6711-6745 and references cited therein
13. Lebouvier N., Laroche C., Huguenot F., and Brigaud T. Tetrahedron 43 (2002) 2827-2830
14. Ono T., Kukhar P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
15. Soloshonok V.A., Kirilenko A.G., and Kukhar V.P. Tetrahedron Lett. 34 (1993) 3621-3624
16. Soloshonok V.A., and Berbasov D.O. J. Fluorine Chem. 125 (2004) 1757-1763
17. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 889-893
18. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 924-929
19. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 930-935
20. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., and Svedas V.K. J. Org. Chem. 63 (1998) 1878-1884
21. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
22. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
23. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953-6964
24. Soloshonok V.A., Kirilenko A.G., Galushko S.V., and Kukhar V.P. Tetrahedron Lett. 35 (1994) 5063-5064
25. Mohar B., Baudoux J., Plaquevent J.C., and Cahard D. Angew. Chem. Int. Ed. 40 (2001) 4214-4216
26. Cahard D., Audouard C., Plaquevent J.C., and Roques N. Org. Lett. 2 (2000) 3699-3701
27. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
28. Soloshonok V.A., Kirilenko A.G., Fokina N.A., Shishkina I.P., Galushko S.V., Kukhar V.P., Svedas V.K., and Kozlova V. Tetrahedron Asymm. 5 (1994) 1119-1126
29. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
30. V. Michaut, Dissertation, Rouen University (France), 2006, and results to be published.