Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Diastereoselectivity in the Reaction of 2-Piperidineacetates

  • Published : 1999.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

In the reactions of the enolates of various 2-piperidineacetates with iodomethane or trisyl azide, the anti isomer was always predominant over the syn one, independent of the stereochemistry of the piperidineacetates. The piperidineacetates having OTBDMS moiety at C5 proceeded more diastereoselectively than the compounds without the substituent. The diastereoselectivity could be explained by perpendicular model for the electrophilic substitution reaction.

Keywords

References

  1. J. Org. Chem. v.38 Boeckman, R. K. Jr.
  2. J. Am. Chem. Soc. v.97 Posner, G. H.;Sterling, J. J.;Whitten, C. E.;Lenz, C. M.;Brunelle, D. J.
  3. J. Chem. Soc., Chem. Commun. Takano, S.;Tamura, N.;Ogasawara, K.
  4. J. Am. Chem. Soc v.110 Tomioka, K.;Kawasaki, K.;Yasuda, K.;Koga, K.
  5. Tetrahedron v.37 Kogen, H.;Hashimoto, S.;Tomioka, K.;Koga, K.
  6. Helv. Chim. Acta v.62 Frater, G.
  7. Helv. Chim. Acta v.63 Seebach, D.;Wasmuth, D.
  8. Angew Chem., Int. Ed. Engl. v.20 Seebach, D.;Wasmuth, D.
  9. Tetrahedron v.40 Frater, G.
  10. J. Chem. Soc., Chem. Commun. v.28 Bernhard, W.;Fleming, I.;Waterson, D.
  11. J. Org. Chem. v.56 Panek, J. S.;Beresis, R.;Xu, F.;Yang, M.
  12. J. Am. Chem. Soc. v.104 Evans, D. A.;ennis, m. D.;Mathre, D. J.
  13. J. Am. Chem. Soc. v.112 Evans, D. A.;Britton, T. C.;Ellman, J. A.;Dorrow, R. L.
  14. J. Am. Chem. Soc. v.107 Evans, D. A.;Morrissey, M. M.;Dorrow, R. L.
  15. Tetrahedron Lett v.26 Kawasaki, H.;Tomioka, K.;Koga, K.
  16. J. Am. Chem. Soc. v.107 Mcgarvey, G. J.;Williams, J. M.
  17. Tetrahedron Lett v.27 Morizawa, Y.;Yasuda, A.;Uchida, K.
  18. J. Am. Chem. Soc. v.1104 Paddon-Row, M. N.;Rondan, N. G.;Houk, K. N.
  19. J. Org. Chem. v.60 Fleischer, J. M.;Gushurst, A. J.;Jorgensen, W. L.
  20. J. Antibiot. v.23 Gitterman, C. O.;Rickes, E. L.;Wolf, D. E.;Mada, J.;Zimmerman, S. B.;Stoudt, T. H.;Demny, T. C.
  21. J. Am. Chem. Soc. v.102 Fukuyama, T.;Frank, R. K.;Jewell, C. F.
  22. J. chem. Soc., Chem. Commun. Golding, B. T.;Smith, A. J.
  23. Ann. Chem. Herdeis, C.;Held, W. A.;Kirfel, A.
  24. Heterocycles Herdeis, C.;Nagel, U.
  25. Tetrahedron:Asymmetry v.1 Morley, C.;Knight, D. W.;Share, A. C.
  26. J. Korean Chem. Soc. v.39 Chung, K.-H.;An, S.-O.
  27. Tetrahedron v.52 Herdeis, C.;Held, W. A.;Kirfel, A.;Schwabenlander, F.
  28. Bull. Korean Chem. Soc. v.19 Reddy, P. N.;Han, S. S.;Chung, K.-H.
  29. Can. J. Chem. v.46 Chow, Y. L.;Colon, C. J.;Tam, J. N. S.
  30. Chem. Rev. v.89 Hoffman, R. W.