Efficient access to virtually enantiopure α-dialkyl-, α-acetoxy-, and α-acetamido esters

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8703-8706

  Cavé, Christian ^a   Porhiel Castellon, Yazmina Le ^a   Daley, Valérie ^a   Riche, Claude ^b   Chiaroni, Angèle ^b   D'Angelo, Jean ^a  

^a Centre Pharmaceutique   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ESTER;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0343580443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10339-2     Document Type: Article

References (14)

1. Tomioka, K;. Ando, K.; Yasuda, K.; Koga, K. Tetrahedron Lett. 1986, 27, 715-716.
2. Tomioka, K.; Seo, W.; Ando, K.; Koga, K. Tetrahedron Lett. 1987, 28, 6637-6640.
3. Brunner, H.; Kraus, J.; Lautenschlager, H.-J. Monatsh. Chem. 1988, 119, 1161-1167.
4. a) Guingant, A.; Hammami, H. Tetrahedron: Asymmetry 1991, 2, 411-414;
5. b) Guingant, A. ibid. 1991, 2, 415-418;
6. c) Guingant, A.; Hammami, H. ibid. 1993, 4, 25-26.
7. a) Cavé, C; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymmetry 1995, 6, 79-82;
8. b) Cavé, C.; Desmaële, D.; d'Angelo, J.; Riche, C; Chiaroni, A. J. Org. Chem. 1996, 61, 4361-4368;
9. c) Cavé, C.; Gassama, A.; Mahuteau, J.; d'Angelo, J.; Riche, C. Tetrahedron Lett. 1997, 38, 4773-4776;
10. d) d'Angelo, J.; Cavé, C.; Desmaële, D.; Gassama, A.; Thominiaux, C.; Riche, C. Heterocycles 1998, 47, in press.
11. Goering, H. L.; Chung Chyi Tseng J. Org. Chem. 1983, 48, 3986-3990.
12. Beausoleil, E.; L'Archevêque, B.; Bélec, L.; Aftani, M.; Lubell, W. D. J. Org. Chem. 1996, 61, 9447-9454.
13. Prepared through N-acetylation of commercially available (S)-glutamic acid 5-methyl ester (acetic anhydride, 12 h at 20 °C, 70 % yield).
14. Ambroise, L.; Desmaële, D.; Mahuteau, J.; d'Angelo, J. Tetrahedron Lett. 1994, 35, 9705-9708.