Intramolecular [4 + 2] cycloadditions involving transient phosphaalkene intermediates as dienophiles: a useful entry to phosphabicyclo[4.3.0]non-4-ene derivatives

(Note: The full text of this document is currently only available in the PDF Version )

Jean-François Pilard, Céline Friot and Jean-Marc Denis


Abstract

Three representative phosphabicyclo[4.3.0]non-4-ene derivatives are formed in high yields and various diastereomeric forms by [4 + 2] intramolecular cycloadditions involving transient phosphaalkenes as dienophiles; complete diastereoselectivity is observed with the P-substituted derivative.


References

  1. L. D. Quin and A. N. Hughes, The chemistry of organophosphorus compounds, ed. F. R. Hartley, Wiley, Chichester, 1990, vol. 1 Search PubMed.
  2. (a) F. Mathey, Acc. Chem. Res., 1992, 25, 90 CrossRef CAS; (b) M. Regitz and P. Binger, Angew. Chem., Int. Ed. Engl., 1988, 27, 1484 CrossRef; (c) R. Appel and F. Knoll, Adv. Org. Chem., 1989, 33, 258 Search PubMed; (d) A. C. Gaumont and J. M. Denis, Chem. Rev., 1994, 94, 1413 CrossRef CAS.
  3. L. D. Quin, A. N. Hughes and B. Pete, Tetrahedron Lett., 1987, 28, 5783 CrossRef CAS.
  4. P. Pellon, Y. Y. Yeung Lam Ko, P. Cosquer, J. Hamelin and R. Carrié, Tetrahedron Lett., 1986, 27, 5611 CrossRef CAS; P. Le Floch and F. Mathey, Tetrahedron Lett., 1989, 30, 817 CrossRef CAS.
  5. A. C. Gaumont, B. Pellerin, J. L. Cabioch, X. Morise, M. Lesvier, P. Savignac, P. Guenot and J. M. Denis, Inorg. Chem., 1996, 35, 6667 CrossRef CAS and references cited therein.
  6. P. Coutrot, C. Laurenco, J. F. Normant, P. Perriot, P. Savignac and J. Villieras, Synthesis, 1977, 615 CrossRef CAS.
  7. X. Morise, P. Savignac and J. M. Denis, J. Chem. Soc., Perkin Trans. 1, 1996, 2179 RSC.
  8. J. L. Cabioch and J. M. Denis, J. Organomet. Chem., 1989, 377, 227 CrossRef CAS.
  9. J. A. Marshall, J. Grote and J. E. Audia, J. Am. Chem. Soc., 1987, 108, 1186 CrossRef.
  10. For a general procedure see M. P. Teulade and P. Savignac, J. Organomet. Chem., 1988, 338, 295 Search PubMed.
  11. J. C. Guillemin, M. Le Guennec and J. M. Denis, J. Chem. Soc., Chem. Commun., 1989, 988 RSC.
  12. C. Grandin, E. Abbout-Joudet, N. Collignon, J. M. Denis and P. Savignac, Heteroatom Chem., 1992, 3, 337 CrossRef CAS.
  13. M. Abbadi, P. Cosquer, F. Tonnard, Y. Y. Yeung Lam Ko and R. Carrié, Tetrahedron, 1991, 47, 71 CrossRef.
  14. L. D. Quin and M. J. Gallagher, in Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, ed. J. G. Verkade and L. D. Quin, VCH, Weinheim, 1987 Search PubMed.
  15. R. Appel, J. Menzel and F. Knoch, Chem. Ber., 1985, 118, 4068 CAS.
  16. R. de Vaumas, A. Marinetti, L. Ricard and F. Mathey, J. Am. Chem. Soc., 1992, 114, 261 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.