Skip to main content
Log in

Synthesis of Novel Chiral C 2-symmetric Diaza-18-crown-6 Ether Derivatives and their Enantioselective Recognition of Amino Acid Derivatives

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

New chiral diaza-18-crown-6 ether derivatives, 5 and 6 were synthesized from (R)-(-)-2-amino-1-bütanol. These chiral artificial receptors exhibit pronounced chiral recognition toward the enantiomers of l- and d- amino acid derivatives. The highest enantioselectivity was observed in the case of Trp-OMe·HCl (K D /K L =12.5).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. E.B. Kyba K. Koga L.R. Sousa M.G. Siegel D.J. Cram (1973) J. Am. Chem. Soc. 95 2692 Occurrence Handle1:CAS:528:DyaE3sXhsVOqsb4%3D

    CAS  Google Scholar 

  2. For cyclophanes, see: (a) P.C. Kearney, L.S. Mizoue, R.A. Kumpf, J.E. Forman, A. McCurdy, and D.A. Dougherty: J. Am. Chem. Soc. 115, 9907 (1993); (b) R.J. Pieters, J. Cuntze, M. Bonnet, and F. Diedrich: J. Chem. Soc., Perkin Trans. 2, 1891 (1997); (c) S.M. Ngola, P.C. Kearney, S. Mecozzi, K. Russell, and D.A. Dougherty: J. Am. Chem. Soc. 121, 1192 (1999)

  3. For crown ethers, see: (a) J.S. Bradshaw, P. Huszthy, C.W. McDaniel, C.Y. Zhu, N.K. Dalley, R.M. Izatt, and S. Lifson: J. Org. Chem. 56, 4193 (1991); (b) X.X. Zhang, J.S. Bradshaw, and R.M. Izatt: Chem. Rew. 95, 3313 (1997); (c) E. Samu, P. Huszthy, L. Somogyi, and M. Hollosi: Tetrahed: Asymm. 10, 2775 (1999); (d) E. Samu, P. Huszthy, G. Horvath, A. Szöllosy, and A. Neszmelyi: Tetrahed: Asymm. 10, 3615 (1999); (e) H. Zhaou and W. Hua: J. Org. Chem. 65, 2933 (2000); (f) J.S. Bradshaw, K.E. Krakowiak, and R.M. Izatt: J. Heterocycl. Chem. 26, 565 (1989)

  4. For cyclodextrins, see: (a) M. Maletic, H. Wennemers, and D.Q. McDonald: Angew. Chem. Int. Ed. Engl. 35, 1490 (1996); (b) R. Breslow, Z. Yang, R. Ching, G. Trojiandt, and F. Odobel: J. Am. Chem. Soc. 120, 3536 (1998)

  5. J.F. Stoddart Chiral (1987) Top. Stereochem 17 207 Occurrence Handle1:CAS:528:DyaL1cXkvFWqtbk%3D

    CAS  Google Scholar 

  6. G.W. Gokel: In J.F. Stoddart (ed.), Crown Ethers and Cryptands, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, England (1991)

  7. J.-P. Joly G. Schröder (1997) Tetrahedron Lett 38 8197 Occurrence Handle10.1016/S0040-4039(97)10254-4 Occurrence Handle1:CAS:528:DyaK2sXns1alu7s%3D

    Article  CAS  Google Scholar 

  8. D.J. Chadwick, I.A. Cliffe, and I.O. Sutherland: J. Chem. Soc., Chem. Commun., 992 (1981).

  9. C.-P. Du J.-S. You X.-Q. Yu C.-L. Liu J.-B. Lan R.-G. Xie (2003) Tetrahed: Asymm 14 3651 Occurrence Handle1:CAS:528:DC%2BD3sXpt1yrs7s%3D Occurrence Handle10.1016/j.tetasy.2003.09.044

    Article  CAS  Google Scholar 

  10. X. Chen D.-M. Du W.-T. Hua (2003) Tetrahed: Asymm 14 999 Occurrence Handle1:CAS:528:DC%2BD3sXisleisLs%3D

    CAS  Google Scholar 

  11. N. Demirel Y. Bulut (2003) Tetrahed.: Asymm 14 2633 Occurrence Handle1:CAS:528:DC%2BD3sXmvV2ls7g%3D Occurrence Handle10.1016/S0957-4166(03)00594-9

    Article  CAS  Google Scholar 

  12. N. Demirel Y. Bulut H. Hoşgören (2004) Tetrahed: Asymm 15 2045 Occurrence Handle1:CAS:528:DC%2BD2cXls1Wltr4%3D

    CAS  Google Scholar 

  13. Y. Turgut H. Hoşgören (2003) Tetrahed.: Asymm 14 3815 Occurrence Handle1:CAS:528:DC%2BD3sXpt1yrsbs%3D Occurrence Handle10.1016/j.tetasy.2003.09.037

    Article  CAS  Google Scholar 

  14. Y. Turgut E. Şahin M. Toğrul H. Hoşgören (2004) Tetrahed: Asymm 15 1583 Occurrence Handle1:CAS:528:DC%2BD2cXktVeks70%3D Occurrence Handle10.1016/j.tetasy.2004.03.035

    Article  CAS  Google Scholar 

  15. M.Z. Köylü N. Demirel F. Doganal A. Yilmaz H. Hoşgören M. Balci (2005) J. Incl. Phenom. Macrocycl. Chem 52 51 Occurrence Handle10.1007/s10847-004-3842-x

    Article  Google Scholar 

  16. (a) J. Polster and H. Lachman, Spectrometric Titrations. VCH: Wienheim, 1989. (b) K.A. Connors, Binding Constans. The Measurement of Molecular Complex. Wiley: New York, 1987. (c) H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc. 71, 2703 (1949)

  17. K. Hirose (2001) J. Incl. Phenom. Macrocycl. Chem 39 193 Occurrence Handle10.1023/A:1011117412693 Occurrence Handle1:CAS:528:DC%2BD3MXktVWrtL4%3D

    Article  CAS  Google Scholar 

  18. G. Topal N. Demirel M. Toğrul Y. Turgut H. Hoşgören (2001) J. Heterocycl. Chem 38 281 Occurrence Handle1:CAS:528:DC%2BD3MXit1ehsbs%3D Occurrence Handle10.1002/jhet.5570380142

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yılmaz Turgut.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Turgut, Y., Demirel, N. & Hoşgören, H. Synthesis of Novel Chiral C 2-symmetric Diaza-18-crown-6 Ether Derivatives and their Enantioselective Recognition of Amino Acid Derivatives. J Incl Phenom Macrocycl Chem 54, 29–33 (2006). https://doi.org/10.1007/s10847-005-3125-1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-005-3125-1

Key words

Navigation