Highly stereoselective ring expansion of enantiopure α-hydroxyalkyl azetidines

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5209-5212

  Couty, François ^a   Durrat, François ^a   Prim, Damien ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZETIDINE DERIVATIVE; CHLOROFORM; METHYL GROUP; N,N DIMETHYLFORMAMIDE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHLORINATION; CHROMATOGRAPHY; ENANTIOMER; HEATING; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0038684522     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01227-9     Document Type: Article

References (23)

1. Hesse M. Ring Enlargements in Organic Chemistry. 1991;VCH, Weinheim; New York; Basel; Cambridge.
2. For some recent examples see: (a) Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569-1576; (b) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890; (c) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron 2001, 57, 1801-1812; (d) Friedolin, W.; Eberbach, W. Tetrahedron 2001, 57, 4349-4358; (e) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4688-4691.
3. For some recent examples see: (a) Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569-1576; (b) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890; (c) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron 2001, 57, 1801-1812; (d) Friedolin, W.; Eberbach, W. Tetrahedron 2001, 57, 4349-4358; (e) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4688-4691.
4. For some recent examples see: (a) Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569-1576; (b) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890; (c) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron 2001, 57, 1801-1812; (d) Friedolin, W.; Eberbach, W. Tetrahedron 2001, 57, 4349-4358; (e) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4688-4691.
5. For some recent examples see: (a) Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569-1576; (b) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890; (c) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron 2001, 57, 1801-1812; (d) Friedolin, W.; Eberbach, W. Tetrahedron 2001, 57, 4349-4358; (e) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4688-4691.
6. For some recent examples see: (a) Papa, C.; Tomasini, C. Eur. J. Org. Chem. 2000, 1569-1576; (b) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890; (c) Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron 2001, 57, 1801-1812; (d) Friedolin, W.; Eberbach, W. Tetrahedron 2001, 57, 4349-4358; (e) Ducray, R.; Ciufolini, M. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4688-4691.
7. Cossy J., Dumas C., Gomez Pardo D. Eur. J. Org. Chem. 1999;1693-1699.
8. Calvez O., Chiaroni A., Langlois N. Tetrahedron Lett. 39:1998;9447-9450.
9. Cossy J., Mirguet O., Gomez Pardo D., Desmurs J.-R. Tetrahedron Lett. 42:2001;5705-5707.
10. Cossy J., Dumas C., Gomez Pardo D. Bioorg. Med. Chem. Lett. 7:1997;1343-1344.
11. Wasserman H.H., Robinson R.P., Matsuyama H. Tetrahedron Lett. 21:1980;3493-3497.
12. Lednicer D., Hauser C.R. J. Am. Chem. Soc. 79:1957;4449-4451.
13. Manhas M.S., Amin S.G., Bose A.K. Heterocycles. 5:1976;669-673.
14. Fugami K., Miura K., Morizawa Y., Oshima K., Utimoto K., Nozaki H. Tetrahedron. 45:1989;3089-3098.
15. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596-9604. See also references cited therein for other 4 to 5 ring enlargements.
16. Ungureanu I., Klotz P., Schoenfelder A., Mann A. J. Chem. Commun. 2001;958-959.
17. Agami C., Couty F., Rabasso N. Tetrahedron Lett. 43:2002;4633-4636.
18. Carlin-Sinclair A., Couty F., Rabasso N. Synlett. 2003;726-729.
19. Outurquin F., Pannecoucke X., Berthe B., Paulmier C. Eur. J. Org. Chem. 2002;1007-1014.
20. Agami C., Couty F., Evano G. Tetrahedron: Asymmetry. 2002;297-302.
21. Couty F., Prim D. Tetrahedron: Asymmetry. 13:2002;2619-2624.
22. Joucla M., Fouchet B., Hamelin J. Tetrahedron. 41:1985;2707-2715.
23. 3), 7.21-7.60 (m, 15H, Ar).