Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid. Part II. Enantioselective biomimetic transamination of 4,4,4-trifluoro-3-oxo-N-[(R)-1-phenylethyl]butanamide

Journal of Fluorine Chemistry

Volumn 127, Issue 7, 2006, Pages 930-935

  Soloshonok, Vadim A ^a   Ohkura, Hironari ^a   Yasumoto, Manabu ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Asymmetric synthesis; Biomimetic reductive methodology; Enamines; Fluorine and compounds; Imines; Operationally convenient conditions

Indexed keywords

EID: 33745197089     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.04.004     Document Type: Article

References (23)

1. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 924-929
2. For full papers on biomimetic transamination of fluorinated carbonyl compounds, see:
3. Ono T., Kukhar V.P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
4. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
5. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
6. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953-6964
7. Soloshonok V.A., and Kukhar V.P. Tetrahedron 53 (1997) 8307-8314
8. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., and Svedas V.K. J. Org. Chem. 63 (1998) 1878-1884
9. Jiang J., Shah H., and DeVita R.J. Org. Lett. 5 (2003) 4101-4103
10. Some details of this work were reported in the following short communication:
11. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
12. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
13. For our discussions on quite controversial issue of a stereochemical bulk of a trifluoromethyl group, see the following papers and references in them:
14. Soloshonok V.A., Kukhar V.P., Galushko S.V., Svistunova N.Y., Avilov D.V., Kuzmina N.A., Raevski N.I., Struchkov Y.T., Pisarevsky A.P., and Belokon Y.N. J. Chem. Soc. Perkin Trans. 1 (1993) 3143-3155
15. Soloshonok V.A., Hayashi T., Ishikawa K., and Nagashima N. Tetrahedron Lett. 35 (1994) 1055-1058
16. Soloshonok V.A., Avilov D.V., and Kukhar V.P. Tetrahedron 52 (1996) 12433-12442
17. Soloshonok V.A., Kacharov A.D., Avilov D.V., and Hayashi T. Tetrahedron Lett. 37 (1996) 7845-7848
18. Soloshonok V.A., Kacharov A.D., Avilov D.V., Ishikawa K., Nagashima N., and Hayashi T. J. Org. Chem. 62 (1997) 3470-3479
19. Kanai M., Yasumoto M., Kuriyama Y., Inomiya K., Katsuhara Y., Higashiyama K., and Ishii A. Org. Lett. 5 (2003) 1007-1010
20. Compounds 12 were found to undergo substantial enantiomer self-disproportionation on regular, achiral silica-gel columns:
21. Soloshonok V.A. Angew. Chem. In. Ed. Engl. 45 (2006) 766-769
22. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 127 (2006) 597-603
23. We found that this procedure is safe in regard of the enantiomer self-disproportionation effect.