Synthesis and application in asymmetric synthesis of azacrown ethers derived from D-glucose

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

Péter Bakó, Kristóf Vizvárdi, Zoltán Bajor, Kristóf Vizvárdi and László Tõke


Abstract

New chiral monoaza-15-crown-5 derivatives and lariat ethers anellated to phenyl β-D-glucoside have been synthesized which show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (84% ee) and in the Darzens condensation of phenacyl chloride with benzaldehyde (74% ee).


References

  1. L. Tõke, P. Bakó, Gy. M. Keserû, M. Albert and L. Fenichel, Tetrahedron, 1998, 54, 213 CrossRef CAS and references cited therein.
  2. L. Tõke, L. Fenichel and M. Albert, Tetrahedron Lett., 1995, 36, 5951 CrossRef CAS.
  3. P. Bakó, Á. Szöllõsy, P. Bombicz and L. Tõke, Heteroatom Chem., 1997, 8, 333 CrossRef CAS.
  4. G. W. Gokel, Chem. Soc. Rev., 1992, 21, 39 RSC.
  5. P. Di Cesare and B. Gross, Synth. Commun., 1979, 4581.
  6. P. Bakó and L. Tõke, J. Inclusion Phenom., 1995, 23, 195 CrossRef CAS.
  7. B. Marsman and H. Wynberg, J. Org. Chem., 1979, 44, 2312 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.