Synthesis of nonracemic 3-fluoro-aspartic acids

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5103-5106

  Charvillon, F Burgat ^a   Amouroux, R ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID BETA HYDROXAMIC ACID; ASPARTIC ACID DERIVATIVE; ESTER; FLUORINE DERIVATIVE; TARTARIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; DEAMINATION; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; HYDROXYLATION; ION EXCHANGE CHROMATOGRAPHY; ISOMER; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030586219     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01044-1     Document Type: Article

References (26)

1. 1. a) Thomasset, N. ; Hamedi-Sangsari, F. ; Toumaire, R. ; Navarro, C. ; Malley, S. ; Goetsch, L. ; Grange, J. ; Vila., J. Int. J. Cancer 1991, 49, 421-424.
2. b) Tournaire, R. ; Malley, S. ; Hamedi-Sangsari, F. ; Thomasset, N. ; Grange, J. ; Doré, J. F. ; Vila, J. Int. J. Cancer 1994, 58, 420-425.
3. c) Malley, S. ; Grange, J. ; Hamedi-Sangsari, F. ; Vila, J. Proc. Natl. Acad. Sci. USA 1994, 91, 11017-11021.
4. 2. Matsumoto, K. ; Ozaki, Y. ; Iwasaki, T. ; Horikawa, H. ; Miyoshi, M. Experientia 1979, 35, 850-851.
5. 3. Wanner, M. J. ; Hageman, J. J. M. ; Koomen, G. J. ; Pandit, U. K. J. Med. Chem. 1980, 23, 85-87.
6. 4. a) Kollonitsch, J. ; Marburg, S. ; Perkins, L. M. J. Org. Chem. 1979, 44, 771-777.
7. b) Stern, A. M. ; Foxman, B. M. ; Tashjian, Jr, A. H. ; Abeles, R. H. J. Med. Chem. 1982, 25, 544-550.
8. 5. Hudlicky, M. J. Fluorine Chem. 1988, 40, 99-108.
9. 6. a) Burgat Charvillon, F. ; Amouroux, R. Biomed. Chem. Lett., submitted,
10. b) Saito, S. ; Bunya, N. ; Inaba, M. ; Moriwake, T. ; Torii, S. Tetrahedron Lett. 1985, 26, 5309-5312.
11. 7. a) Tewson, T. J. ; Welch, M. J. J. Org. Chem. 1978, 43, 1090-1092.
12. b) Pansare, S. V. ; Vederas, J. C. J. Org. Chem. 1987, 52, 4804-4810.
13. c) Hayakawa, H. ; Takai, F. ; Tanaka, H. ; Miyasaka, T. ; Yamaguchi, K. Chem. Pharm. Bull. 1990, 38, 1136-1139.
14. d) Focella, A. ; Bizzarre, F. ; Exon, C. Synth. Com. 1991, 21, 2165-2170.
15. e) Pankiewicz, K. W. ; Krzeminski, J. ; Ciszewski, L. A. ; Ren, W-Y. ; Watanabe, K. A. J. Org. Chem. 1992, 57, 553-559.
16. 8. Somekh, L. ; Shanzer, A. J. Am. Chem. Soc. 1982, 104, 5836-5837.
17. 9. Chini, M. ; Crotti, P. ; Favero, L. ; Macchia, F. Tetrahedron Lett. 1994, 55, 761-764.
18. 2).
19. 11. Atmospheric pressure and a short reaction time (4h) are crucial since a higher pressure and a longer time gave rise to an enamine by loss of HF. In addition, because of its relative instability, the fluoroamine 9 must be stored in the hydrochloride form.
20. D = - 23 (c 0.85, MeOH).
21. D = -18 (c 0.53, HCl 1N).
22. 14. Gao, Y. ; Sharpless, B. J. Am. Chem. Soc. 1988, 110, 7538-7539.
23. 15. The elimination of HF was observed in the final product with temperature reaction above 0°C.
24. 2O).
25. 2O).
26. D = + 5 (c 0.19, HCl 1N).