A new approach to the synthesis of N-alkylated 2-substituted azetidin-3-ones

European Journal of Organic Chemistry

Volumn , Issue 10, 2006, Pages 2440-2445

  Gérard, Stéphane ^a   Raoul, Marion ^a   Sapi, Janos ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Azetidin 3 ones; Domino nucleophilic substitution addition; Levulinic acid; Small ring systems

Indexed keywords

EID: 33646751954     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500987     Document Type: Article

References (27)

1. J. Kobayashi, J. Cheng, M. Ishibashi, M. R. Wälchli, S. Yamamura, Y. Ohizumi, J. Chem. Soc., Perkin Trans. 1 1991, 1135-1137.
2. S. Hanessian, J.-M. Fu, J.-L. Chiara, R. Di Fabio, Tetrahedron Lett. 1993, 34, 4157-4160.
3. G. Emmer, Tetrahedron 1992, 48, 7165-7172.
4. For examples on the chemistry of azetidin-3-ones, see: Y. Dejaegher, N. M. Kuz'menok, A. M. Zvonok, N. De Kimpe, Chem. Rev. 2002, 102, 29-60.
5. J. Podlech, D. Seebach, Helv. Chim. Acta 1995, 78, 1238-1246.
6. Y. K. Ramtohul, M. N. G. James, J. C. Vederas, J. Org. Chem. 2002, 67, 3169-3178.
7. A. Salgado, M. Boeykens, C. Gauthier, J.-P. Declercq, N. De Kimpe, Tetrahedron 2002, 58, 2763-2775.
8. G. S. Singh, Tetrahedron 2003, 59, 7631-7649 and references cited therein.
9. J. Y. Cha, M. A. Hanna, Industrial Crops Products 2002, 16, 109-118.
10. a) S.W. Fitzpatrick, Production of levulinic acid from carbohydrate-containing materials. 1995, US Patent 5,608,105;
11. b) V. Ghorpade, M. A. Hanna, Method and apparatus for production of levulinic acid via reactive extrusion. 1999, US Patent 5,859,263;
12. c) W. A. Farone, J. Cuzens, Method for production of levulinic acid and its derivatives. 2000, US Patent 6,054,611.
13. J. J. Bozell, L. Moens, D. C. Elliott, Y Wang, G. G. Neuenschwander, S. W. Fitzpatrick, R. J. Bilski, J. L. Jarnefeld, Resources Conservation Recycling 2000, 28, 227-239.
14. For a review on the chemistry of levulinic acid, see: B. V. Timokhin, V. A. Baransky, G. D. Eliseeva, Russ. Chem. Rev. 1999, 68, 73-84 and references cited therein.
15. G. Stajer, A. E. Szabo, A. Csampai, P. Sohar, Eur. J. Org. Chem. 2004, 1318-1322.
16. A. Sorg, F. Blank, R. Brückner, Synlett 2005, 8, 1286-1290.
17. J. E. Mc Murry, L. C. Blaszczak, J. Org. Chem. 1974, 39, 2217-2222.
18. H.-J. Cristau, E. Torreilles, P. Morand, H. Christol, Phosphorus Sulfur 1985, 25, 357-367.
19. a) R. Zimmer, M. Colas, M. Roth, H.-U. Reissig, Liebigs Ann. Chem. 1992, 709-714;
20. b) Y. Jahng, J. Kim, Arch. Pharm. Research (Korea) 1994, 17, 104-108.
21. N. Gouault, J.-F. Cupif, M. Amoros, M. David, J. Chem. Soc., Perkin Trans. 1 2002, 2234-2236.
22. D. Berkes, A. Kolarovic, R. Manduch, P. Baran, F. Povazanec, Tetrahedron: Asymmetry 2005, 16, 1927-1934.
23. A. Westerlund, J.-L. Gras, R. Carlson, Tetrahedron 2001, 57, 5879-5883.
24. For a review on reactivity of conjugated haloenoates, see: D. Caine, Tetrahedron 2001, 57, 2643-2684.
25. R. A. Bunce, C. J. Peeples, P. B. Jones, J. Org. Chem. 1992, 57, 1727-1733.
26. H. Urbach, R. Henning, Tetrahedron Lett. 1984, 25, 1143-1146.
27. M. Knollmüller, M. Ferencic, P. Gärtner, U. Girreser, M. Klinge, L. Gaischin, K. Mereiter, C. R. Noe, Monatsh. Chem. 1999, 130, 769-782.