Enantioselective Intramolecular Nitrone Cycloaddition Route to 3-(Trifluoromethyl)-isoxazolidino[4,3-c]-chroman-4-ones and -quinolin-4-ones†

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Alberto Arnone, Gianluigi Broggini, Luca Bruche′, Giorgio Molteni and Gaetano Zecchi


Abstract

Optically active 3-(trifluoromethyl)isoxazolidino[4,3-c]-chroman-4-ones and -quinolin-4-ones are synthesised by the stereoselective intramolecular cycloaddition of homochiral nitrones.


References

  1. M. J. Silvester, Aldrichim. Acta, 1991, 24, 31 Search PubMed; Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Elsevier, New York, 1992 Search PubMed; M. J. Silvester, Adv. Heterocycl. Chem., 1994, 59, 1 Search PubMed; K. Burger, U. Wucherpfennig and E. Brunner, Adv. Heterocycl. Chem., 1994, 60, 1 CAS.
  2. P. Bravo, L. Bruché, G. Fronza and G. Zecchi, Tetrahedron, 1992, 48, 9775 CrossRef CAS; P. Bravo, L. Bruché, A. Farina, G. Fronza, S. V. Meille and A. Merli, Tetrahedron: Asymmetry, 1993, 4, 2131 CrossRef CAS; A. Arnone, P. Bandiera, P. Bravo, L. Bruché and M. Zanda, Gazz. Chim. Ital., 1996, 126, 773; A. Arnone, P. Bravo, L. Bruché, P. Seresini and M. Zanda, J. Heterocycl. Chem., 1997, 34, 489.
  3. A. Arnone, L. Bruché, L. Garanti and G. Zecchi, J. Chem. Res. (S), 1995, 282 Search PubMed.
  4. M. Cinquini and F. Cozzi, in Houben-Weyl, Methods of Organic Chemistry: Stereoselective Synthesis, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart, 1995, vol. E21c, ch. 1.6.1.2 Search PubMed.
  5. M. Frederickson, Tetrahedron, 1997, 53, 403 CrossRef CAS.
  6. K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH, New York, 1988, p. 85 Search PubMed; P. M. Wovkulich and M. R. Uskokovic, Tetrahedron, 1985, 41, 3455 Search PubMed.
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