Asymmetric functionalization of a chiral non-racemic oxazolidine ester enolate. A new route towards the preparation of quaternary serine esters

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1737-1740

  Alezra, Valérie ^a   Bonin, Martine ^a   Chiaroni, Angèle ^b   Micouin, Laurent ^a   Riche, Claude ^b   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE; SERINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034635889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00026-5     Document Type: Article

References (14)

1. Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599.
2. (a) Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sazaki, S.; Toyama, R.; Chiba, K.; Hoshino, Y.; Okumoto, T. J. Antibiotics 1994, 47, 208-215.
3. (b) Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sazaki, S.; Toyama, R.; Chiba, K.; Hoshino, Y.; Okumoto, T. J. Antibiotics 1994, 47, 216-224.
4. (c) Kawatsu, M.; Yamashita, T.; Ishizuka, M.; Takeuchi, T. J. Antibiotics 1995, 48, 222-225.
5. (d) Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiotics 1992, 45, 1692-1696.
6. Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429.
7. (a) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
8. (b) Seebach, D.; Aebi, J. D.; Tetrahedron Lett. 1984, 25, 2545-2548.
9. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194-1216.
10. For a recent review, see: Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
11. Bureau, R.; Mortier, J.; Joucla, M. Bull. Soc. Chim. Fr. 1993, 130, 584-596. Toluene has to be degassed prior to reflux to avoid formation of ca. 10% N-methylation.
12. For a general discussion on β-elimination with oxazolidine esters, see Ref. 4a.
13. 4, filtered and concentrated. The crude mixture was purified by flash chromatography on silica gel (cyclohexane:AcOEt, 80:20) to give the pure compound 8a (126 mg, 0.41 mmol, 63% overall yield).
14. -3. Lists of the fractional atomic coordinates, thermal parameters, distances, bond and torsion angles have been deposited at the Cambridge Crystallographic Data Centre, UK, as Supplementary Material (CIF file).