Enantioselective synthesis of β-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: Application to the synthesis of (R)-(-)-baclofen

Tetrahedron Asymmetry

Volumn 8, Issue 22, 1997, Pages 3801-3805

  Brenna, Elisabetta ^a   Caraccia, Nicola ^a   Fuganti, Claudio ^a   Fuganti, Daniela ^a   Grasselli, Piero ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BACLOFEN; BUTYRIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030844225     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00538-7     Document Type: Article

References (13)

1. Fronza, G.; Fuganti, C.; Grasselli, P.; Malpezzi, L.; Mele, A. J. Org. Chem., 1994, 59, 3487; Fogliato, G.; Fronza, G.; Fuganti, C.; Grasselli, P.; Servi, S. J. Org. Chem., 1995, 60, 5693; Fuganti, C.; Grasselli, P.; Mendozza, M.; Servi, S.; Zucchi, G. Tetrahedron, 1997, 53, 2617.
2. Fronza, G.; Fuganti, C.; Grasselli, P.; Malpezzi, L.; Mele, A. J. Org. Chem., 1994, 59, 3487; Fogliato, G.; Fronza, G.; Fuganti, C.; Grasselli, P.; Servi, S. J. Org. Chem., 1995, 60, 5693; Fuganti, C.; Grasselli, P.; Mendozza, M.; Servi, S.; Zucchi, G. Tetrahedron, 1997, 53, 2617.
3. Fronza, G.; Fuganti, C.; Grasselli, P.; Malpezzi, L.; Mele, A. J. Org. Chem., 1994, 59, 3487; Fogliato, G.; Fronza, G.; Fuganti, C.; Grasselli, P.; Servi, S. J. Org. Chem., 1995, 60, 5693; Fuganti, C.; Grasselli, P.; Mendozza, M.; Servi, S.; Zucchi, G. Tetrahedron, 1997, 53, 2617.
4. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc., 1970, 92, 741.
5. Ziegler, F. E. Chem. Rev., 1988, 88, 1423.
6. Poppe, L.; Novak, L. In Selective Biocatalysis, VCH-Weinheim, 1992, pp. 67-155.
7. (a) Caira, M. R.; Clauss, R.; Nassimbeni, L. R.; Scott, J. L.; Wildervanck, A. F. J. Chem. Soc., Perkin Trans. 2, 1997, 763;
8. (b) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett., 1997, 38, 1195, and references therein for previous syntheses.
9. Hudgson, P.; Weightman, D. Brit. Med. J., 1971, 4, 15.
10. Olpe, H. R.; Demiéville, H.; Baltzer, V.; Benzce, W. L.; Koella, W. P.; Wolf, P.; Haas, H. L. Eur. J. Pharmacol., 1978, 52, 133.
11. The extent of conversion (c) and the enantiomeric ratio (E) of the enzymatic kinetic resolution were calculated according to Chen, C-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc., 1982, 104, 7294.
12. Fuganti, C.; Grasselli, P.; Servi, S.; Spreafico, F.; Zirotti, C.; Casati, P. J. Chem. Res. (M), 1984, 976.
13. Koch, S. S. C.; Chamberlin, A. R. J. Org. Chem., 1993, 58, 2725.