Synthesis of optically active 2,3-methanopipecolic acid

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4529-4532

  Hercouet, Alain ^a   Bessières, Bernard ^a   Le Corre, Maurice ^a   Toupet, Loïc ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 METHANOPIPECOLIC ACID; GLUTAMIC ACID; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; X RAY ANALYSIS;

EID: 0030600150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00875-1     Document Type: Article

References (20)

1. 1. For recent reviews see: (a), Stammer C. H., Tetrahedron, 1990, 46, 2231-2254.
2. (b) Alami A., Calmes M., Daunis J. and Jacquier R., Bull. Soc. Chim. Fr., 1993, 130, 5-24.
3. (c) Burgess K., Ho K. K. and Moye-Sherman D., Synlett, 1994, 575-583.
4. 2. Le Corre M., Hercouët A. and Bessières B., Tetrahedron: Asymmetry, 1995, 6, 683-684.
5. 3. Hercouët A., Bessières B. and Le Corre M., Tetrahedron: Asymmetry, 1996, 7, 283-284.
6. 4. a) Hockless D. C. R., Mayadunne R. C. and Wild S. B., Tetrahedron: Asymmetry, 1995, 6, 3031-3037.
7. b) Pauly, R., Sasaki, N.A. and Potier, P. Tetrahedron Lett., 1994, 35, 237-240.
8. c) Berrien, J. F., Royer, J. and Husson, H.-P.,J. Org. Chem. 1994, 59, 3769-3774.
9. d)Fernandez-Garcia, C. and McKervey, M.A., Tetrahedron: Asymmetry, 1995, 6, 2905-2906.
10. 5. Copeland T. D., Wondrack E. M., Tozser J., Roberts M. M. and Oroszlan S., Biochem. Biophys. Res. Commun., 1990, 769, 310-311.
11. 6. Flynn G. A., Giroux E. L. and Dage R.C., J. Am. Chem. Soc., 1987, 109, 7914-7915.
12. 7. Jones T. K., Mills S. G., Reamer R. A., Askin D., Desmond R., Volante R. P. and Shinkai I., J. Am. Chem. Soc., 1989, 111, 1157-1159.
13. 8. (a) Gringore O. H. and Rouessac F. P., Organic Syntheses, 1985, 63, 121.
14. (b) Larchevêque M. and Lalande J., Tetrahedron, 1984, 40, 1061-1065.
15. 3, 75.5 MHz) δ 27.70, 29.73, 43.85, 72.72 and 82.40.
16. 10. Gao Y. and Sharpless K. B., J. Am. Chem. Soc., 1988, 110, 7538-7539.
17. 3, 300 MHz) δ 1.13-1.18 (m, 1H), 1.50-1.58 (m, 2H), 1.68-1.92 (m, 3H); 3.48-3.54 (m, 3H), 3.69 (s, 3H); 7.38-7.42 (m, 3H), 7.75-7.79 (m, 2H) and 8.52 (s, 1H).
18. 3, 75.5 MHz) δ 19.75, 24.52, 25.81 ,32.00, 38.52, 44.19, 53.31 and 169.5.
19. + 141.0790; Found 141.0797.
20. 1, and Z = 2.