Olefination of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate, a synthetic approach to new conformationally constrained prolines

Tetrahedron Asymmetry

Volumn 14, Issue 11, 2003, Pages 1479-1488

  Gil, Ana M ^a   Buñuel, Elena ^b   Díaz De Villegas, María D ^a   Cativiela, Carlos ^a  

^a CSIC   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

7 AZABICYCLO[2.2.1]HEPTANE; ALKENE DERIVATIVE; ALPHA (3 PHENYLPROPYL)GLYCINE; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID; GLYCINE DERIVATIVE; HEPTANE; HOMOGLUTAMIC ACID; METHYL N BENZOYL 2 FORMYL 7 AZABICYCLO[2.2.1]HEPTANE 1 CARBOXYLATE; NORLEUCINE; NORVALINE; PHOSPHORANE DERIVATIVE; PROLINE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIMERA; CONFORMATIONAL TRANSITION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED RADIATION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION; X RAY DIFFRACTION;

EID: 0037724159     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00200-3     Document Type: Article

References (30)

1. Giannis A., Kolter T. Angew. Chem., Int. Ed. Engl. 32:1993;1244-1267.
2. Liskamp R.M.J. Recl. Trav. Chim. Pays-Bas. 113:1994;1-19.
3. Gante J. Angew. Chem., Int. Ed. Engl. 33:1994;1699-1720.
4. Hruby V.J., Li G., Haskell-Luevano C., Shenderovich M. Biopolymers. 43:1997;219-266.
5. Cativiela C., Díaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645-732.
6. Some recent examples: Tetrahedron Symposium-in-Print Number 88. Asymmetric synthesis of novel sterically constrained amino acids, Hruby, V. J.; Soloshonok V. A., Eds. 2001; Vol. 57, pp. 6329-6650.
7. Thaisrivongs S., Pals D.T., Lawson J.A., Turner S.R., Harris D.W. J. Med. Chem. 30:1987;536-541.
8. Hinds M.G., Welsh J.H., Brennand D.M., Fisher J., Glennie M.J., Richards N.G.J., Turner D.L., Robinson J.A. J. Med. Chem. 34:1991;1777-1789.
9. Bisang C., Weber C., Inglis J., Schiffer C.A., van Gunsteren W.F., Jelesarov I., Bosshard H.R., Robinson J.A. J. Am. Chem. Soc. 117:1995;7904-7915.
10. Han W., Pelletier J.C., Mersinger L.J., Hodge C.N. Bioorg. Med. Chem. Lett. 8:1998;3615-3620.
11. Han W., Pelletier J.C., Mersinger L.J., Kettner C.A., Hodge C.N. Org. Lett. 1:1999;1875-1877.
12. Spand T.F., Garrafo H.M., Edwards M.W., Daly J.W. J. Am. Chem. Soc. 114:1992;3475-3478.
13. Chen Z., Trudell M.L. Chem. Rev. 96:1996;1179-1193.
14. Campbell J.A., Rapoport H. J. Org. Chem. 61:1996;6313-6325.
15. Hart B.P., Rapoport H. J. Org. Chem. 64:1999;2050-2056.
16. Avenoza A., Cativiela C., Fernández-Recio M.A., Peregrina J.M. Tetrahedron: Asymmetry. 10:1999;3999-4007.
17. Lennox J.R., Turner S.C., Rapoport H. J. Org. Chem. 66:2001;7078-7083.
18. Buñuel E., Gil A.M., Díaz-de-Villegas M.D., Cativiela C. Tetrahedron. 57:2001;6417-6427.
19. Sharma R., Lubell W.D. J. Org. Chem. 61:1996;202-209. and references 1-9 cited therein.
20. Evans M.C., Johnson R.L. Tetrahedron. 56:2000;9801-9808.
21. Khanapure S.P., Saha G., Powell W.S., Rokach J. Tetrahedron Lett. 41:2000;5807-5811.
22. Corey E.J., Winter R.A.E. J. Am. Chem. Soc. 85:1963;2677-2678.
23. Corey E.J., Carey F.A., Winter R.A.E. J. Am. Chem. Soc. 87:1965;934-935.
24. Corey E.J., Hopkins P.B. Tetrahedron Lett. 23:1982;1979-1982.
25. Carlsen H.J., Katsuki T., Martin V.S., Sharpless B. J. Org. Chem. 46:1981;3936-3938.
26. Abramovitch R.A., Cue B.W. Jr. J. Org. Chem. 45:1980;5316-5319.
27. Sheldrick, G. M. SHELXS-97. Program for the solution of crystal structures; University of Göttingen: Germany, 1997.
28. Sheldrick, G. M. SHELXL-97. Program for the refinement of crystal structures; University of Göttingen: Germany
29. Oliveros L., Lopez P., Minguillón C., Franco P. J. Liq. Chromatogr. 18:1995;1521-1532.
30. Oliveros L., Senso A., Minguillón C. Chirality. 9:1997;145-149.