Synthesis of 5-fluoroalkyl isoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones

Chinese Journal of Chemistry

Volumn 22, Issue 9 SPEC.ISS., 2004, Pages 945-949

  Liu, Jin Tao ^a   Jin, Qi Hui ^a   Lü, He Jun ^a   Huang, Wei Yuan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

5 fluoroalkyl isoxazolidine; Cycloaddition; Ethyl 2 hydropolyfluoroalk 2 enoate; Nitrone; Synthesis

Indexed keywords

3,4 DIHYDROISOQUINOLINE N OXIDE; DICHLOROMETHANE; FLUORINE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; REACTION TIME; RING OPENING; ROOM TEMPERATURE; SYNTHESIS;

EID: 7044263063     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220914     Document Type: Article

References (19)

1. (a) Silvester, J. M. Aldrichimca Acta 1991, 24, 31.
2. (b) Filler, R.; Kobayashi, Y. Biomedical Aspects of Fluorine Chemistry, Elsevier, New York, 1992.
3. (c) Welch, J. T. Tetrahedron 1987, 43, 3123.
4. (a) Confalone, P. N.; Huie, E. M. Org. React. 1998, 36, 1.
5. (b) Tufariello, J. J. 1,3-Dipolar Cycloaddition Chemistry, Vol. 12, Ed.: Padwa, A., John Wiley and Sons, New York, 1984, p. 83.
6. (c) Torsell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Ed.: Feuer, H., VCH Publisher, New York, 1988.
7. (d) Padwa, A. Comprehensive Organic Synthesis, Vol. 4, Eds.: Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991, p. 1069.
8. (a) Zhang, X.-C.; Huang, W.-Y. J. Fluorine Chem. 1998, 92, 13.
9. (b) Zhang, X.-C.; Huang, W.-Y. J. Fluorine Chem. 1998, 87, 57.
10. (c) Zhang, X.-C.; Huang, W.-Y. Tetrahedron Lett. 1997, 27, 4827.
11. (d) Zhang, X.-C.; Huang, W.-Y. Tetrahedron 1998, 54, 12465.
12. Liu, J.-T.; Jin, Q.-H.; Lü, H.-J.; Huang, W.-Y. Tetrahedron Lett. 2001, 42, 5937.
13. Huang, W.-Y.; Lü, L.; Zhang, Y.-F. Chin. J. Chem. 1990, 281.
14. (a) Lunn, G.; Sansone, E. B. J. Org. Chem. 1986, 51, 513.
15. (b) Murahashi, S. I.; Shiota, T. Tetrahedron Lett. 1987, 28, 2383.
16. (c) Coperet, C.; Adolfsson, H.; Khuong, T. V.; Yudin, A. K.; Sharpless, K. B. J. Org. Chem. 1998, 63, 1740.
17. (d) Chan, K. S.; Yeung, M. L.; Chan, W.-K.; Wang, R.-J.; Mak, T. C. W. J. Org. Chem. 1995, 60, 1741.
18. -1. Data were measured at 293 K on a Bruker SMART CCD diffractometer with graphite monochromated Mo Kα radiation.
19. Iwao, M.; Kuraishi, T. J. Heterocycl. Chem. 1978, 15, 1425.