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DOI: 10.1039/A604899D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 487-492

Reaction of 4-ethoxycarbonyl-2-phenyl-4,5-dihydrooxazol-5-one with organolead(IV) triacetates. A route to some α-arylglycine and α-vinylglycine derivatives

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Mark J. Koen, Jacqueline Morgan, John T. Pinhey and Christopher J. Sherry

Abstract

4-Ethoxycarbonyl-2-phenyl-4,5-dihydrooxazol-5-one undergoes rapid arylation and vinylation with arylead triacetates and (E)-styryllead triacetates, respectively. The resulting moisture-sensitive 4-aryl- and 4-styryl-oxazolones undergo hydrolysis and decarboxylation under mild conditions to provide a short efficient route to derivatives of α-arylglycines and α-vinylglycines.

References

  1. M. J. Koen, J. Morgan and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1993, 2383 RSC.
  2. J. T. Pinhey, Aust. J. Chem., 1991, 44, 1353 CAS.
  3. J. T. Pinhey, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. II, p. 461 Search PubMed.
  4. M. G. Moloney and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1988, 2847 RSC.
  5. M. G. Moloney, J. T. Pinhey and M. J. Stoermer, J. Chem. Soc., Perkin Trans. 1, 1990, 2645 RSC.
  6. C. J. Parkinson, J. T. Pinhey and M. J. Stoermer, J. Chem. Soc., Perkin Trans. 1, 1992, 1911 RSC.
  7. M. G. Moloney, J. T. Pinhey and E. G. Roche, J. Chem. Soc., Perkin Trans. 1, 1989, 333 RSC.
  8. R. P. Kopinski, J. T. Pinhey and B. A. Rowe, Aust. J. Chem., 1984, 37, 1245 CAS.
  9. J. W. Cornforth, in The Chemistry of Penicillin, ed. H. T. Clarke, J. R. Johnson and R. Robinson, Princeton University Press, Princeton, 1949, p. 775 Search PubMed.
  10. R. P. Kozyrod and J. T. Pinhey, Tetrahedron Lett., 1983, 24, 1031; R. P. Kozyrod, J. Morgan and J. T. Pinhey, Aust. J. Chem., 1985, 38, 1147 CAS.
  11. D. H. R. Barton, D. M. X. Donelly, J.-P. Finet and P. J. Guiry, J. Chem. Soc., Perkin Trans. 1, 1992, 1365 RSC.
  12. J. Morgan and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1990, 715 RSC.
  13. P. Rocca, F. Morais, A. Godard and G. Queguiner, Tetrahedron, 1993, 49, 49 CrossRef CAS.
  14. R. P. Kozyrod and J. T. Pinhey, Org. Synth., 1984, 64, 24.
  15. L. C. Williamsens, D. De Vos, J. Spierenberg and J. Wolters, J. Organomet. Chem., 1972, 39, C61 CrossRef.
  16. M.-L. Huber and J. T. Pinhey, J. Chem. Soc., Perkin Trans. 1, 1990, 721 RSC.
  17. D. Ben-Ishai, I. Sataty and Z. Bernstein, Tetrahedron, 1976, 32, 1571 CrossRef CAS.
  18. W.-D. Sprung, M. Kobow and E. Schulz, Pharmazie, 1989, 44, 540 Search PubMed.
  19. A. Alavanipour, C. Eaborn and D. R. M. Walton, J. Organomet. Chem., 1980, 201, 233 CrossRef.
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