Direct coupling procedure for the synthesis of N-acyl-2-oxazolidinones derived from α,β-unsaturated carboxylic acids

Synthetic Communications

Volumn 26, Issue 2, 1996, Pages 261-268

  Knol, Joop ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030050998     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003613     Document Type: Article

References (14)

1. For a recent review see: Kagan, H.B.; Riant, O. Chem. Rev. 1992, 92, 1007.
2. (a) Castellino, S.; Dwight, J. J. Am. Chem. Soc. 1993, 115, 2986.
3. (b) Gothelf, K.V.; Hazell, R.G.; Jørgensen, K.A. J. Am, Chem. Soc. 1995, 117, 4435.
4. Selected examples: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Narashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
5. (b) Evans, D.A.; Miller, S.J.; Leckta, T. J. Am. Chem Soc. 1993, 115, 6460.
6. (c) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535.
7. (d) Evans, D.A.; Leckta, T.; Miller, S.J. Tetrahedron Lett. 1993, 34, 7027.
8. (e) Seebach, D.; Dahinden, R.; Marti, R.E.; Beck, A.K.; Plattner, D.A.; Kühnle, F.N.M. J. Org. Chem. 1995, 60, 1788.
9. Evans, D.A.; Chapman, K.T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
10. For recent modified procedures, see: (a) Thom, C.; Kocieński, P. Synthesis, 1992, 582.
11. (b) Ho, G.-J.; Mathre, D.J. J. Org. Chem. 1995, 60, 2271.
12. This reagent is commercially available; for a review see: Mukaiyama, T. Angew. Chem. Int. Ed. Engl. 1979, 18, 707.
13. Spatz, S.M.; Stone, H. J. Org. Chem. 1958, 23, 1559.
14. See supplementary material of ref. 3b.