DOI QR코드

DOI QR Code

Electronic and Steric Effects in Diamine Recognition with a Highly Rigid Zn(II) Complex

  • Kim, Woo-Sung (Department of Chemistry, University of Toronto) ;
  • Chun, Cindy (Department of Chemistry, University of Toronto) ;
  • Kim, Hyun-Woo (Department of Chemistry, University of Toronto) ;
  • Lough, Alan J. (Department of Chemistry, University of Toronto) ;
  • Kim, B.-Moon (Department of Chemistry, Seoul National University) ;
  • Chin, Jik (Department of Chemistry, University of Toronto)
  • Published : 2007.01.20

Abstract

Keywords

References

  1. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley- VCH: New York, 2000
  2. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590 https://doi.org/10.1021/cr00097a012
  3. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3211 https://doi.org/10.1021/cr020025b
  4. Brunel, J. M. Chem. Rev. 2005, 105, 857-897 https://doi.org/10.1021/cr040079g
  5. Noyori, R. Acc. Chem. Res. 1990, 23, 345-350 https://doi.org/10.1021/ar00178a005
  6. Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801-1836 https://doi.org/10.1021/cr040652w
  7. Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627 https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L
  8. Le Gall, T.; Mioskowski, C., Angew. Chem. 1998, 110, 2724-2772 https://doi.org/10.1002/(SICI)1521-3757(19981002)110:19<2724::AID-ANGE2724>3.0.CO;2-4
  9. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195 https://doi.org/10.1021/cr9407577
  10. Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119-3154 https://doi.org/10.1021/cr020004h
  11. Larrow, J. F.; Jacobsen, E. N. Topics Organomet. Chem. 2004, 6, 123-152
  12. Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693 https://doi.org/10.1126/science.1083622
  13. Costas, M.; Que, L., Jr. Angew. Chem. Int. Ed. 2002, 41, 2179- 2181 https://doi.org/10.1002/1521-3773(20020617)41:12<2179::AID-ANIE2179>3.0.CO;2-F
  14. Costas, M.; Que, L., Jr., Angew. Chem. 2002, 114, 2283-2285 https://doi.org/10.1002/1521-3757(20020617)114:12<2283::AID-ANGE2283>3.0.CO;2-6
  15. Murphy, A.; Dubois, G.; Stack, T. D. P. J. Am. Chem. Soc. 2003, 125, 5250-5251 https://doi.org/10.1021/ja029962r
  16. Murphy, A.; Pace, A.; Stack, T. D. P. Org. Lett. 2004, 6, 3119-3122 https://doi.org/10.1021/ol048846l
  17. Schoumacker, S.; Hamelin, O.; Pécaut, J.; Fontecave, M. Inorg. Chem. 2003, 42, 8110-8116 https://doi.org/10.1021/ic0346533
  18. Segal, S.; Goldberg, I.; Kol, M. Organometallics 2005, 24, 200-202 https://doi.org/10.1021/om049556b
  19. Mason, A. F.; Coates, G. W. J. Am. Chem. Soc. 2004, 126, 16326-16327 https://doi.org/10.1021/ja044268s
  20. Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem. Int. Ed. 1999, 38, 2756-2759 https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18<2756::AID-ANIE2756>3.0.CO;2-6
  21. Chin, J.; Walsdorff, C.; Stranix, B.; Oh, J.; Chung, H. J.; Park, S.-M.; Kim, K. Angew. Chem. 1999, 111, 2923-2926 https://doi.org/10.1002/(SICI)1521-3757(19990917)111:18<2923::AID-ANGE2923>3.0.CO;2-P
  22. Chin, J.; Lee, S. S.; Lee, K. J.; Park, S.; Kim, D. H. Nature 1999, 401, 254-257 https://doi.org/10.1038/45751
  23. Bobb, R.; Alhakimi, B.; Studnicki, L.; Lough, A.; Chin, J. J. Am. Chem. Soc. 2002, 124, 4544-4545 https://doi.org/10.1021/ja017418x
  24. Mueller, R.; Gust, R.; Jennerwein, M.; Reile, H.; Laske, R.; Krischke, W.; Bernhardt, G.; Spruss, T.; Engel, J.; Schonenberger, H. Eur. J. Med. Chem. 1989, 24, 341-348 https://doi.org/10.1016/0223-5234(89)90076-7
  25. Crystallographic data for the structure reported here have been deposited with the Cambridge Crystallographic Data Centre (Deposition No. CCDC-627889).
  26. That data can be obtained free of charge via www.ccdc.cam.ac.uk (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk)
  27. Gust, R.; Schönenberger, H.; Kritzenberger, J.; Range, K. J.; Klement, U.; Burgemeister, T. Inorg. Chem. 1993, 32, 5939-5950 https://doi.org/10.1021/ic00078a009
  28. Hamada, T.; Manabe, K.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 7768-7769 https://doi.org/10.1021/ja048607t
  29. Essentially the same results were obtained when dach was used instead of dpen as the guest diamine https://doi.org/10.1016/j.pnmrs.2003.08.001
  30. Bain, A. D. Prog. Nucl. Magn. Reson. Spectrosc. 2003, 43, 63- 103 https://doi.org/10.1016/j.pnmrs.2003.08.001
  31. Jencks, W. P., Regenstein, J., Ionization Constants of Acids and Bases in Handbook of Biochemistry Selected Data for Molecular Biology; Sober, H. A., Ed.; The Chemical Rubber Co.: Ohio, USA, 1968; pp J-150 -J-189
  32. Equatorially positioned substituents are farther away from the metal than axially positioned substituents
  33. Molecular mechanics computation was performed using Spartan 04 Windows from Wavefunction, Inc
  34. Chun, C. P.; Kim, W.; Kim, H.; Chin, C.; Lough, A. J. Acta Cryst. 2005, E61, o4328-o4330

Cited by

  1. Controlling helical chirality of cobalt complexes by chirality transfer from vicinal diamines vol.49, pp.99, 2013, https://doi.org/10.1039/c3cc46887a