Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Approch for Catalyst Optimization: Host/Guest Complexes of Chiral Bisphosphine Bearing Imidazolidinone and Their Application in Rh-Catalyzed Asymmetric Hydrogenation

  • Park, Jung-Hwan (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Shin, Hyun-Ik (Chemical Development Division, LG Life Sciences, Ltd./R&D) ;
  • Park, Doo-Han (Department of Chemistry, Sahmyook University) ;
  • Lee, Sang-Gi (Department of Chemistry and Nano Science (BK21), Ewha Womans University)
  • Published : 2010.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

As a new strategy for the optimization of a chiral catalyst, the catalytic activity of the host-guest complexes of chiral bisphosphine bearing imidazolidinone was investigated in Rh-catalyzed asymmetric hydrogenation of enamide. Marginal enhancement in enantioselectivity was observed and the nature of interaction between host-guest was experimentally elucidated.

Keywords

References

  1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley:New York, 1994
  2. Comprehensive Asymmetric Catalysis; Jacobson, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1-3
  3. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.:Wiley-VCH: New York, 2000.
  4. Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297. https://doi.org/10.1021/cr0000630
  5. Roelfes, G.; Feringa, B. L. Angew. Chem. Int. Ed. 2005, 44, 3230. https://doi.org/10.1002/anie.200500298
  6. Lee, S.-g.; Zhang, Y. J.; Song, C. E.; Lee, J. K.; Choi, C. H.Angew. Chem. Int. Ed. 2002, 41, 847. https://doi.org/10.1002/1521-3773(20020301)41:5<847::AID-ANIE847>3.0.CO;2-F
  7. Bell, D. A.; Anslyn, E. V. Hydrogen-bonding Receptors: OpenchainCatalytic System in Comprehensive Supramolecular Chemistry;Lehn, J.-M., ed.: Pergamon Elsevier Science: 1996; Vol. 2,Chapter 14, pp. 439-475.
  8. Mazik, M.; Radunz, W.; Boese, R. J. Org. Chem. 2004, 69, 7448. https://doi.org/10.1021/jo048979k
  9. Hedge, V.; Hung, C.-Y.; Madhukar, P.; Cunningham, R.;Höphner, T.; Thummel, R. P. J. Am. Chem. Soc. 1993, 115, 872. https://doi.org/10.1021/ja00056a008
  10. Fielding, L. Tetrahedron 2000, 56, 6151. https://doi.org/10.1016/S0040-4020(00)00492-0
  11. Cowart, M. D.; Sucholeiki, I.; Bukownik, R. R.; Wilcox, C. S. J.Am. Chem. Soc. 1988, 110, 6204. https://doi.org/10.1021/ja00226a040
  12. Mohamedi, F.; Richards, N. G. T.; Liskamp, W. C. H.; Lipton,M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comp.Chem. 1990, 11, 440. https://doi.org/10.1002/jcc.540110405
  13. Allinger, N. L.; Yuh, Y. QCPE 1980, 12,395.
  14. Burker, U.; Allinger, N. L. Molecular Mechanics; AmericanChemical Society: Washington, DC, 1982.
  15. Saunders, M.; Houk,K. N.; Wu, Y. D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W.C. J. Am. Chem. Soc. 1990, 112, 1419. https://doi.org/10.1021/ja00160a020