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An Unprecedented Ruthenium-Catalyzed Reductive Amination of Aldehydes with Tertiary Amines

  • Cho, Chan-Sik (Research Institute of Industrial Technology, Kyungpook National University) ;
  • Park, Ji-Hyuk (Department of Industrial Chemistry, College of Engineering, Kyungpook National University) ;
  • Kim, Tae-Jeong (Department of Industrial Chemistry, College of Engineering, Kyungpook National University) ;
  • Shim, Sang-Chul (Department of Industrial Chemistry, College of Engineering, Kyungpook National University)
  • Published : 2002.01.20

Abstract

Keywords

References

  1. Dayagi, S. In The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: London, 1970; Chapter 2, pp 61-147
  2. Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 8.
  3. Hudlicky, M. Reactions in Organic Chemistry; American Chemical Society: Washington, D. C., 1996.
  4. Cho, C. S.; Lim, H. K.; Shim, S. C.; Kim, T. J.; Choi, H.-J. Chem. Commun. 1998, 995
  5. Cho, C. S.; Kim, J. H.; Shim, S. C. Tetrahedron Lett. 2000, 41, 1811 https://doi.org/10.1016/S0040-4039(00)00035-6
  6. Cho, C. S.; Kim, J. H.; Kim, T.-J.; Shim, S. C. Tetrahedron 2001, 57, 3321 https://doi.org/10.1016/S0040-4020(01)00202-2
  7. Cho, C. S.; Kim, T. K.; Yoon, S. W.; Kim, T.-J.; Shim, S. C. Bull. Korean Chem. Soc. 2001, 22, 545.
  8. Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499 https://doi.org/10.1016/S0040-4039(98)02661-6
  9. Cho, C. S.; Oh, B. H.; Shim, S. C. J. Heterocyclic Chem. 1999, 36, 1175 https://doi.org/10.1002/jhet.5570360510
  10. Cho, C. S.; Oh, B. H.; Shim, S. C.; Oh, D. H. J. Heterocyclic Chem. 2000, 37, 1315 https://doi.org/10.1002/jhet.5570370549
  11. Cho, C. S.; Kim, J. S.; Oh, B. H.; Kim, T.-J.; Shim, S. C.; Yoon, N. S. Tetrahedron 2000, 56, 7747 https://doi.org/10.1016/S0040-4020(00)00694-3
  12. Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885
  13. Cho, C. S.; Kim, T. K.; Kim, T.-J.; Shim, S. C.; Yoon, N. S. J. Heterocyclic Chem. in press.
  14. Cho, C. S.; Kim, B. T.; Lee, M. J.; Kim, T.-J.; Shim, S. C. Angew. Chem. Int. Ed. Engl. 2001, 40, 958 https://doi.org/10.1002/1521-3773(20010302)40:5<958::AID-ANIE958>3.0.CO;2-4
  15. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020 https://doi.org/10.1021/jo0108459
  16. Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998
  17. Yoshimura, N.; Moritani, I.; Shimamura, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1973, 95, 3038. https://doi.org/10.1021/ja00790a064
  18. Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. https://doi.org/10.1021/ja00469a093
  19. Shvo, Y.; Laine, R. M. J. Chem. Soc., Chem. Commun. 1980, 753.
  20. Khai, B.-T.; Concilio, C.; Porzi, G. J. Organomet. Chem. 1981, 208, 249. https://doi.org/10.1016/S0022-328X(00)82680-7
  21. Khai, B.-T.; Concilio, C.; Porzi, G. J. Org. Chem. 1981, 46, 1759. https://doi.org/10.1021/jo00321a056
  22. Arcelli, A.; Khai, B.-T.; Porzi, G. J. Organomet. Chem. 1982, 231, C31. https://doi.org/10.1016/S0022-328X(00)81961-0
  23. Murahashi, S.-I.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229. https://doi.org/10.1016/S0040-4039(00)86792-1
  24. Laine, R. M.; Thomas, D. W.; Cary, L. W. J. Am. Chem. Soc. 1982, 104, 1763. https://doi.org/10.1021/ja00370a064
  25. Jung, C. W.; Fellmann, J. D.; Garrou, P. E. Organometallics 1983, 2, 1042. https://doi.org/10.1021/om50002a018
  26. Murahashi, S.-I. Angew. Chem. Int. Ed. Engl. 1995, 34, 2443. https://doi.org/10.1002/anie.199524431
  27. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. https://doi.org/10.1021/jo00291a035
  28. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum: New York, 1991; pp 205-255.

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