Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Design and Synthesis of Binaphthol-Derived Chiral Ketone Catalysts for Dioxirane-Mediated Asymmetric Epoxidation of Olefins

  • Published : 1999.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Binaphthol-derived chiral ketones 1a-c were synthesized and were shown to serve as active catalysts for asymmetric epoxidation of olefins using Oxone, although their enantioselectivities were not high. However, very interestingly, the stereochemical outcome of the resulting epoxides implicates that in the epoxidation using 1a-c, the planar transition state may be more favorable than the spiro transition state.

Keywords

References

  1. Catalytic Asymmetric synthesis Jacobsen, E. N.;Ojima, I.(ed.)
  2. J. Am. Chem. Soc. v.118 Yang, D.;Yip, Y.-C.;Tang, M.-W.;Wong, M.-K.;Zheng, J.-H.;Cheung, K.-K.
  3. J. Am. Chem. Soc. v.118 Yang, D.;Wang, X.-C.;Wong, M.-K,;Yip, Y.-C.;Tang. M.-W.
  4. J. Am. Chem. Soc. v.120 Yang, D.;Wong, M.-K.;Yip, Y.-C.;Wang, S.-C.;Tang, M.-W.;Zheng, J.-H.;Cheung, K.-K.
  5. J. Am. Chem. Soc. v.118 Tu, Y.;Wang, Z.-X.;Shi, Y.
  6. J. Org. Chem. v.62 Wang, Z.-X.;Tu, Y.;Frohn, M.;Shi, Y.
  7. J. Am .Chem. Soc. v.119 Wang, Z.-X.;Tu, Y.;Frohn, M.;Zhang, J.-R.;Shi, Y.
  8. J. Org. Chem. v.63 Frohn, M.;Dalkiewicz, M.;Tu, Y.;Wang, Z.-X.;Shi Y.
  9. J. Org. Chem. v.63 Wang, Z.-X.;Shi, Y.
  10. Tetrahedron Lett. v.39 Gao, G.-A.;Wang, Z.-X.;Tu, Y.;Shi, Y.
  11. J. Org. Chem. v.63 Tu, Y.;Wang, Z.-X.;Frohn, M.;He, M.;Yu, H.;Tang, Y.;Shi, Y.
  12. Tetrahedron: Asymmetry v.8 Song, C. E.;Kim, Y. H.;Lee, K. S.;Lee, S.-g.;Jin, B. W.
  13. Tetrahedron: Asymmetry v.8 Adam, W.;Zhao, C.-G.
  14. J. Org. Chem. v.62 Denmark, S. E.;Wu, Z.;Crudden, C. M.;Matsuhashi, H.
  15. Chemtracts: Org. Chem. v.10 Bergbreiter, D. E.
  16. Chem. Commun. Amstrong, A.;Hayter, B. R.
  17. Chemtracts: Org. Chem. v.11 Dakin, L. A.;Panek, J. S.
  18. J. Org. Chem. v.46 Cram, D. J.;Lingenfelter, D. S.;Helgeson, R. C.
  19. J. Org. Chem. v.30 Berti, C.;Gottari, F.;Ferrani, P. L.;Machia, B.
  20. Bull. Soc. Chim. Fr. Audier, H. E.;Dupin, J. F.;Tullien, J.
  21. Aldrich catalog
  22. Tetrahedron: Asymmetry v.8 Brandes, B. D.;Jacobsen, E. N.
  23. Tetrahedron: Asymmetry v.4 Hudlicky, T.;Boros, E. E.;Boros, C. H.
  24. Tetrahedron Lett. v.28 Baumstark, A. L.;McCloskey, C. J.
  25. J. Am. Chem. Soc. v.114 Bach, R. D.;Andres, J. L.;Owensby, A. L.;Schlegl, H. B.;MaDouall, J. W.
  26. Tetrahedron: Asymmetry v.9 Adam, W.;Fell, R. T.;Saha-Moller, C. R.;Zhao, C.-G.