View PDF Version
 
DOI: 10.1039/A706163C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 521-528

Enantioselective synthesis of 2-substituted 3-aminopropanoic acid (β-alanine) derivatives which are β-analogues of aromatic amino acids

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

Elena Arvanitis, Holger Ernst, Alice A. LudwigéD’Souza, Andrew J. Robinson and Peter B. Wyatt

Abstract

3-Aminopropanoic acid derivatives with a phenyl, 4-hydroxyphenyl, benzyl or indol-3-yl substituent at C-2 can be prepared enantioselectively by routes involving electrophilic attack of synthetic equivalents of [H2NCH2]+ upon enolates derived from chiral 3-acyl-1,3-oxazolidin-2-ones. tert-Butyl bromoacetate may be used as the electrophile, with subsequent introduction of nitrogen through the Curtius reaction, using the sequence of reagents (i) CF3CO2H; (ii) (PhO)2P(O)N3, Et3N, PhCH2OH; alternatively, direct electrophilic reaction with 1-[N-(benzyloxycarbonyl)aminomethyl]benzotriazole 4c or benzyl N-(acetoxymethyl)carbamate 2d introduces a protected aminomethyl group in a single step.

References

  1. D. C. Cole, Tetrahedron, 1994, 50, 9517 CrossRef CAS; Enantioselective Synthesis of β-Amino Acids, ed. E. Juaristi, Wiley-VCH, New York, 1997 Search PubMed.
  2. E. Juaristi, D. Quintana, M. Balderas and E. Garcia-Pérez, Tetrahedron: Asymmetry, 1996, 7, 2233 CrossRef CAS.
  3. E. Arvanitis, M. Motevalli and P. B. Wyatt, Tetrahedron Lett., 1996, 37, 4277 CrossRef CAS.
  4. A. Rottmann, M. Bartoczek and J. Liebsher, Synthesis, 1997, 313 CrossRef CAS.
  5. I. T. Barnish, M. Corless, P. J. Dunn, D. Ellis, P. W. Finn, J. D. Hardstone and K. James, Tetrahedron Lett., 1993, 34, 1323 CrossRef CAS.
  6. A. A. D'Souza, M. Motevalli, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1995, 1 RSC.
  7. J. F. Bower, R. Jumnah, A. C. Williams and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1997, 1411 RSC.
  8. D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark and M. T. Bilodeau, J. Am. Chem. Soc., 1990, 112, 8215 CrossRef CAS.
  9. J. J. Getz, R. J. Prankerd and K. B. Sloan, J. Org. Chem., 1992, 57, 1702 CrossRef CAS.
  10. A. R. Katritzky, X. Lan and W.-Q. Fan, Synthesis, 1994, 445 CrossRef CAS.
  11. P. C. B. Page, S. M. Allin, E. W. Collington and R. A. E. Carr, J. Org. Chem., 1993, 58, 6902 CrossRef CAS.
  12. R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661 CrossRef CAS.
  13. D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737 CrossRef CAS.
  14. J. W. Corse, R. G. Jones, Q. F. Soper, C. W. Whitehead and O. K. Behrens, J. Am. Chem. Soc., 1948, 70, 2837 CrossRef CAS.
  15. M. Chorev and Y. S. Klausner, J. Chem. Soc., Chem. Commun., 1976, 596 Search PubMed.
  16. A. Fadel and J. Salaün, Tetrahedron Lett., 1988, 29, 6257 CrossRef CAS.
  17. T. Shioiro, K. Ninomiya and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203 CrossRef CAS.
  18. J. E. Fagel and G. W. Ewing, J. Am. Chem. Soc., 1951, 73, 4360 CrossRef CAS.
  19. K. E. Harding, T. H. Marman and D. H. Nam, Tetrahedron, 1988, 44, 5605 CrossRef.
  20. J. A. Garbarino and O. Nuñez, J. Chem. Soc., Perkin Trans. 1, 1981, 906 RSC.
  21. E. Juaristi, J. Escalante, B. Lamatsch and D. Seebach, J. Org. Chem., 1992, 57, 2396 CrossRef CAS.
  22. S. Azam, A. A. D'Souza and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1996, 621 RSC.
  23. D. A. Evans, M. M. Morrisey and R. L. Dorow, J. Am. Chem. Soc., 1985, 107, 4346 CrossRef CAS.
  24. D. A. Evans, D. J. Mathre and W. L. Scott, J. Org. Chem., 1985, 50, 1830 CrossRef CAS.
  25. D. A. Evans, J. Bartroli and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127 CrossRef CAS.
  26. E. Testa, G. Cignarella, G. Pifferi, S. Füresz, M. T. Timbal, P. Schiatti and G. Maffii, Farmaco (Ed. Sci.), 1964, 19, 895 Search PubMed.