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Enantioselective Conjugate Addition of Fluoromalonate to Nitroalkenes Catalyzed by Chiral Nickel Complexes

  • Published : 2009.07.20
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Abstract

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References

  1. Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004
  2. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004
  3. Kirk, K. L. J. J. Fluorine Chem. 2006, 127, 1013 https://doi.org/10.1016/j.jfluchem.2006.06.007
  4. Isanobor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303 https://doi.org/10.1016/j.jfluchem.2006.01.011
  5. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881 https://doi.org/10.1126/science.1131943
  6. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305 https://doi.org/10.1021/op700134j
  7. Bohm, H.-J.; Banmer, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Muller, K.; Obstsander, U.; Stahl, M. ChemBioChem 2004, 5, 637 https://doi.org/10.1002/cbic.200301023
  8. Smart, B. R. J. J. Fluorine Chem. 2001, 109, 3 https://doi.org/10.1016/S0022-1139(01)00375-X
  9. Ismail, F. M. D. J. J. Fluorine Chem. 2002, 118, 27 https://doi.org/10.1016/S0022-1139(02)00201-4
  10. Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; Ramachandran, P. V., Ed.; ACS Symposium Series 746 American Chemical Society: Washington, DC, 2000
  11. Leonard, J. Contemp. Org. Synth. 1994, 1, 387 https://doi.org/10.1039/co9940100387
  12. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992
  13. Krause, N.; Hoffmann-Reder, A. Synthesis 2001, 171
  14. Berner, O. M.; Tedeschi, L.; Ender, D. Eur. J. Org. Chem. 2002, 1877
  15. Christoffers, J.; Baro, A. Angew. Chem. Int. Ed. 2003, 42, 1688 https://doi.org/10.1002/anie.200201614
  16. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701 https://doi.org/10.1002/ejoc.200600653
  17. Almasi, D.; Alonso, D. A.; Najera, D. Tetrahedron: Asymmetry 2007, 18, 299 https://doi.org/10.1016/j.tetasy.2007.01.023
  18. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001
  19. Calderari, G.; Seebach, D. Helv. Chim. Acta 1985, 68, 1592 https://doi.org/10.1002/hlca.19850680611
  20. Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017 https://doi.org/10.1016/j.tet.2003.11.016
  21. Czekelius, E.; Carreira, M. Angew. Chem. Int. Ed. 2005, 44, 612 https://doi.org/10.1002/anie.200461879
  22. Evans, D. A.; Seider, D. J. Am. Chem. Soc. 2005, 127, 9958 https://doi.org/10.1021/ja052935r
  23. Terada, M.; Ube, H.; Yaguchi, Y. J. Am. Chem. Soc. 2006, 128, 14545
  24. Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 947 https://doi.org/10.1002/anie.200502658
  25. Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Wu, X.-J. Chem. Commun. 2008, 1431 https://doi.org/10.1039/b718949d
  26. McGarraugh, P. G.; Brenner, S. E. Tetrahedron 2009, 65, 449 https://doi.org/10.1016/j.tet.2008.11.027
  27. Tan, B.; Zhang, X.; Chua, P. J.; Zhong, G. Chem. Commun. 2009, 779 https://doi.org/10.1039/b813915f
  28. Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y.; Lee, K. Bull. Korean Chem. Soc. 2003, 24, 1425 https://doi.org/10.5012/bkcs.2003.24.10.1425
  29. Nichols, P. J.; DeMattei, J. A.; Barnett, B. R.; LeFur, N. A.; Chuang, T.-H.; Piscopio, A. D.; Koch, K. Org. Lett. 2006, 8, 1495 https://doi.org/10.1021/ol060398p
  30. Kim, D. Y.; Park, E. J. Org Lett. 2002, 4, 545 https://doi.org/10.1021/ol010281v
  31. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897 https://doi.org/10.1021/jo0401772
  32. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309 https://doi.org/10.1021/ol050413a
  33. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115 https://doi.org/10.1016/j.tetlet.2005.02.164
  34. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4265 https://doi.org/10.1016/j.tetlet.2006.05.003
  35. Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 47, 423 https://doi.org/10.5012/bkcs.2006.27.3.423
  36. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135
  37. Cho, M. J.; Kang, Y. K.; Lee, N. R.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2191 https://doi.org/10.5012/bkcs.2007.28.12.2191
  38. Kim, S. M.; Kang, Y. K.; Cho, M. J.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2435 https://doi.org/10.5012/bkcs.2007.28.12.2435
  39. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821
  40. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659
  41. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527 https://doi.org/10.1016/j.tetlet.2008.07.041
  42. Mang, J. Y.; Kim. D. Y. Bull. Korean Chem. Soc. 2008, 29, 2091 https://doi.org/10.5012/bkcs.2008.29.11.2091
  43. Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2093 https://doi.org/10.5012/bkcs.2008.29.11.2093
  44. Lee, N. R.; Kim, S. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829 https://doi.org/10.5012/bkcs.2009.30.4.829
  45. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036 https://doi.org/10.5012/bkcs.2008.29.10.2036
  46. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259 https://doi.org/10.1016/j.jfluchem.2008.11.001
  47. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249 https://doi.org/10.5012/bkcs.2009.30.1.249
  48. Evans, D. A.; Mito, S.; Seidel, D. J. Am. Chem. Soc. 2007, 129, 11583 https://doi.org/10.1021/ja0735913
  49. Fossy, J. S.; Matsubara, R.; Kiyogara, H.; Kobayashi, S. Inorg. Chem. 2008, 47, 781 https://doi.org/10.1021/ic7017727
  50. Li, H.; Zu, L.; Xie, H.; Wang, W. Synthesis 2009, 1525
  51. Hashimoto, S.; Furukawa, I.; Kuroda, T. Tetrahedron Lett. 1980, 21, 2857 https://doi.org/10.1016/S0040-4039(00)78627-8

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