View PDF Version
 
DOI: 10.1039/A801450G (Paper) Reference Section for: Chem. Commun., 1998, 1159-1160

New procedures for the Juliá–Colonna asymmetric epoxidation: synthesis of (+)-clausenamide

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

Michael W. Cappi, Robert W. Flood, Stanley M. Roberts, John Skidmore, Natalie M. Williamson, Wei-Ping Chen, Yong-Wei Liao and John A. Smith

Abstract

The oxidation of chalcone 1 to optically active epoxide 2 [a precursor of (+)-clausenamide (+)-3] may be effected using a 15-mer or 20-mer of L-leucine bound to a PEG based support; poly-L-leucines of this type may be used as immobilised catalysts in a fixed-bed reactor.

References

  1. S. Banfi, S. Colonna, H. Molinari, S. Juliá and J. Guixer, Tetrahedron, 1984, 40, 5207 CrossRef CAS and references cited thereinFor recent reviews, see M. E. Lasterra-Sánchez and S. M. Roberts, Curr. Org. Chem., 1997, 187 Search PubMed; S. Ebrahim and M. Wills, Tetrahedron: Asymmetry, 1997, 8, 3163 Search PubMed.
  2. J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich and L. Snyder, J. Org. Chem., 1993, 58, 6247 CrossRef CAS.
  3. J. A. N. Augustyn, B. C. B. Bezuidenhoudt, A. Swanepoel and D. Ferreira, Tetrahedron, 1990, 46, 4429 CrossRef CAS; H. van Rensburg, P. S. van Heerden, B. C. B. Bezuidenhoudt and D. Ferreira, Chem. Commun., 1996, 2747 RSC.
  4. P. A. Bentley, S. Bergeron, M. W. Cappi, D. E. Hibbs, M. B. Hursthouse, T. C. Nugent, R. Pulido, S. M. Roberts and L. E. Wu, Chem. Commun., 1997, 739 RSC.
  5. B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. McCague, T. C. Nugent and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1997, 3501 RSC.
  6. J. V. Allen, M. W. Cappi, P. D. Kary, S. M. Roberts, N. M. Williamson and L. E. Wu, J. Chem. Soc., Perkin Trans. 1, 1997, 3297 RSC.
  7. P. A. Bentley, W. Kroutil, J. A. Littlechild and S. M. Roberts, Chirality, 1997, 9, 198 CrossRef CAS.
  8. H. R. Kricheldorf, Comp. Polym. Sci., 1989, 3, 531 Search PubMed.
  9. The peptide chain is linked via a hydroxymethylphenoxyacetic acid linker and via a polyethylene glycol graft to polystyrene particles of 75–150 µm in diameter. The density of attachment was 0.17 mmol peptide per gram of starting resin.
  10. S. Juliá, J. Masana and J. C. Vega, Angew. Chem., Int. Ed. Engl., 1980, 19, 929 CrossRef.
  11. S. Itsuno, M. Sakakura and K. Ito, J. Org. Chem., 1990, 55, 6047 CrossRef CAS.
  12. A. A. Oswald and D. L. Guertin, J. Org. Chem., 1963, 28, 651 CAS.
  13. Y. Liu, C. Z. Shi and J. T. Zhang, Yaoxue Xuebao, 1991, 26, 166 Search PubMed; T. G. Lin, G. T. Liu, K. J. Li, B. L. Zhao and W. J. Xin, Zhongguo Yaolixue Yu Dulixue Zhazhi, 1992, 16, 97 Search PubMed.
  14. P. W. Baures, D. S. Eggleston, J. R. Flisak, K. Gombatz, I. Lantos, W. Mendelson and J. J. Remich, Tetrahedron Lett., 1990, 31, 6501 CrossRef CAS.
  15. D. F. Huang and L. Huang, Tetrahedron, 1990, 46, 3135 CrossRef CAS; J. Q. Wang and W. S. Tian, J. Chem. Soc., Perkin Trans. 1, 1996, 209 RSC.
  16. M. H. Yang, Y. Y. Chen and H. Liang, Huaxue Xuebao, 1987, 45, 1170 CAS.
  17. W. Hartwig and L. Born, J. Org. Chem., 1987, 52, 4352 CrossRef CAS; M. H. Yang, Y. Y. Chen and L. Huang, Phytochemistry, 1988, 27, 445 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.