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Asymmetric Electrophilic Fluorination of β-Keto Phosphonates in Ionic Liquid Media Catalyzed by Chiral Palladium Complexes

  • Kim, Sung-Min (Department of Chemistry, Division of Applied Science, Soonchunhyang University) ;
  • Kang, Young-Ku (Department of Chemistry, Division of Applied Science, Soonchunhyang University) ;
  • Lee, Kil-Sung (Cheil Industries Inc.) ;
  • Mang, Joo-Yang (Department of Chemistry, Division of Applied Science, Soonchunhyang University) ;
  • Kim, Dae-Young (Department of Chemistry, Division of Applied Science, Soonchunhyang University)
  • Published : 2006.03.20
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References

  1. Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds: Chemistry and Applications; Springer-Verlag: Berlin, 2000
  2. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996
  3. Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions, ACS Symposium Series 746; Ramachandran, P. V., Ed.; American Chemical Society: Washington, DC, 2000
  4. Enantiocontrolled Synthesis of Fluoro-organic Compounds; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1999
  5. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661-692 https://doi.org/10.1016/S0957-4166(00)82374-5
  6. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755 https://doi.org/10.1021/cr941145p
  7. Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431-12477 https://doi.org/10.1016/S0040-4020(99)00748-6
  8. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1-16 https://doi.org/10.1021/cr030685w
  9. Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147-1155
  10. Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119-6149 https://doi.org/10.1021/cr030143e
  11. France, S.; Weatherwax, A.; Lectka, T. Eur. J. Org. Chem. 2005, 475-479
  12. Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 4359-4362 https://doi.org/10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO;2-P
  13. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547 https://doi.org/10.1021/ol010281v
  14. Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530-14531 https://doi.org/10.1021/ja028464f
  15. Baudequin, C.; Loubassou, J.-F.; Plaquevent, T.-C.; Cahard, D. J. Fluorine Chem. 2003, 122, 189-193 https://doi.org/10.1016/S0022-1139(03)00085-X
  16. Ma, J.-A.; Cahard, D. Tetrahedron: Asymmetry 2004, 15, 1007-1011 https://doi.org/10.1016/j.tetasy.2004.01.014
  17. Shibata, N.; Ishimaru, T.; Nagai, T.; Kohno, J.; Toru, T. Synlett 2004, 1703-1706
  18. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164-10165 https://doi.org/10.1021/ja0513077
  19. Blackburn, G. M. Chem. Ind. (London) 1981, 134-138
  20. McKenna, C. E.; Shen, P. J. Org. Chem. 1981, 46, 4573-4576 https://doi.org/10.1021/jo00335a053
  21. Nieschalk, J.; O'Hagan, D. Chem. Commun. 1995, 719-720
  22. Nieschalk, J.; O'Hagan, D. Chem. Commun. 1995, 719-720
  23. Jakeman, D. L.; Ivory, A. J.; Willamson, M. P.; Blackburn, G. M. J. Med. Chem. 1998, 41, 4493-4452
  24. Jakeman, D. L.; Ivory, A. J.; Willamson, M. P.; Blackburn, G. M. J. Med. Chem. 1998, 41, 4493-4452
  25. Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508 https://doi.org/10.1021/jo000220v
  26. Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001, 112, 13-33 https://doi.org/10.1016/S0022-1139(01)00478-X
  27. Yokomatsu, T.; Yamagishi, T.; Matsumoto, K.; Shibuya, S. Tetrahedron 1996, 52, 11725-11738 https://doi.org/10.1016/0040-4020(96)00671-0
  28. Glover, N. R.; Tracey, A. S. Biochemistry 1999, 38, 5256-5271 https://doi.org/10.1021/bi9825450
  29. Kotoris, C. C.; Wen, W.; Lough, A.; Taylor, S. D. J. Chem. Soc. Perkin Trans. 1 2000, 1271-1281
  30. Ruiz, M.; Ojea, V.; Quintela, J. M.; Guillin, J. J. Chem. Commun. 2002, 1600-1601
  31. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309-2311 https://doi.org/10.1021/ol050413a
  32. Bernardi, L.; Jorgensen, K. A. Chem. Commun. 2005, 1324-1326
  33. Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimizu, T.; Umebayashi, N.; Tamura, T.; Sasamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447-1450 https://doi.org/10.1016/j.tetlet.2005.01.018
  34. Dupont, J.; de Souza, R. F.; Saurez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692 https://doi.org/10.1021/cr010338r
  35. Seddon, R. Chem. Commum. 2001, 2399- 2407
  36. Wasserscheid, P.; Kein, W. Angew. Chem. Int. Ed. 2000, 39, 3772-3789 https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
  37. Welton, T. Chem. Rev. 1999, 99, 2071-2083 https://doi.org/10.1021/cr980032t
  38. Song, C. E.; Yoon, M. Y.; Choi, D. S. Bull. Korean Chem. Soc. 2005, 26, 1321-1330 https://doi.org/10.5012/bkcs.2005.26.9.1321
  39. Song, C. E. Chem. Commun. 2004, 1033-1043
  40. Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A.-C.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2003, 14, 3081-3093 https://doi.org/10.1016/S0957-4166(03)00596-2
  41. Davis Jr, J. H.; Fox, P. A. Chem. Commun. 2003, 1209-1212
  42. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115-3117 https://doi.org/10.1016/j.tetlet.2005.02.164
  43. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897-6899 https://doi.org/10.1021/jo0401772
  44. Park, E. J.; Kim, H. R.; Joung, C. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2004, 25, 1451-1452 https://doi.org/10.5012/bkcs.2004.25.10.1451
  45. Kim, D. Y.; Huh, S. C. Bull. Korean Chem. Soc. 2004, 25, 347-348 https://doi.org/10.5012/bkcs.2004.25.3.347
  46. Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425-1426 https://doi.org/10.5012/bkcs.2003.24.10.1425
  47. Kim, D. Y.; Choi, Y. J.; Park, H. Y.; Joung, C. U.; Koh, K. O.; Mang, J. Y.; Jung, K.-Y. Synth. Commun. 2003, 33, 435-443 https://doi.org/10.1081/SCC-120015774
  48. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299-6301 https://doi.org/10.1016/S0040-4039(01)01237-0
  49. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933-8938 https://doi.org/10.1016/S0040-4020(01)00891-2

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