Reversal of diastereoselectivity of nitrile oxide 1,3-dipolar cycloadditions by Mg(II). Acceleration of cycloaddition by microwave irradiation

Tetrahedron

Volumn 56, Issue 30, 2000, Pages 5465-5472

  Mičúch, Peter ^a   Fišera, L'Ubor ^a   Cyrański, Michal K ^b   Krygowski, Tadeusz M ^b   Krajčík, Ján ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Cycloaddition; Diastereoselection; Isoxazolines; Microwave heating; Nitrile oxides

Indexed keywords

MAGNESIUM ION; MESITONITRILE OXIDE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; MICROWAVE IRRADIATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

EID: 0343953066     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00454-3     Document Type: Article

References (20)

1. Lang S.A. Jr, Lin Y.-I. Potts K.T. Comprehensive Heterocyclic Chemistry. 1984;Pergamon, Oxford.
2. Jäger V., Schohe R. Tetrahedron. 40:1984;2199.
3. Jäger V., Muller R., Leibold T., Hein M., Schwarz M., Fengler M., Jarošková L., Pätzel M., LeRoy P.-Y. Bull. Soc. Chim. Belg. 103:1994;491.
4. Curran D.P. J. Am. Chem. Soc. 105:1983;5826.
5. Fišera L., Goljer I., Jarošková L. Coll. Czech. Chem. Commun. 53:1988;1753.
6. Jäger V., Grund H., Bus V., Schwab W., Muller I., Schohe R., Franz R., Ehrler R. Bull. Soc. Chim. Belg. 92:1983;1039.
7. Raimondi L. Gazz. Chim. Ital. 127:1997;167.
8. Kanemasa S., Nishiuchi M., Kamimura A., Hori K. J. Am. Chem. Soc. 116:1994;2324.
9. Page P.C.B., Purdie M., Lathbury D. Tetrahedron. 53:1997;7365.
10. Mičúch P., Fišera L., Cyranski M.K., Krygowski T.M. Tetrahedron Lett. 40:1999;167.
11. Papageorgio C., Benezra C. J. Org. Chem. 50:1985;157.
12. Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001.
13. Foucaud A., Guemmout F.E. Bull. Soc. Chim. Fr. 1989;403.
14. Galema S.A. Chem. Soc. Rev. 26:1997;233.
15. Toma Š. Chemické Listy. 87:1993;627.
16. Longeon A., Guoyot M., Vacelet J. Experimentia. 46:1990;548.
17. Annunziata R., Benaglia M., Cinquini M., Cozi F., Raimondi L. J. Org. Chem. 60:1995;4697.
18. Sheldrick G.M. Acta Crystallogr. A46:1990;467.
19. Sheldrick, G. M. SHELXL 93, Program for Refinement of Crystal Structure; University of Göttingen, Germany 1993.
20. Further details of the crystal structure: list of structure factors, anisotropic displacement parameters, H-atom coordinates, complete geometry are deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 IEZ, UK (on quoting the depository no. CCCD 144970 and HOSSIR).