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Organocatalytic Asymmetric Michael Addition of β-Ketoesters to Nitroalkenes

  • Published : 2009.07.20
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Abstract

Keywords

References

  1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
  2. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877 https://doi.org/10.1002/1099-0690(200206)2002:12<1877::AID-EJOC1877>3.0.CO;2-U
  3. Christoffers, J.; Baro, A. Angew. Chem. Int. Ed. 2003, 42, 1688 https://doi.org/10.1002/anie.200201614
  4. Connon, S. J. Synlett 2009, 354
  5. Yu, X.; Wang, W. Chem. Asian J. 2008, 3, 516 https://doi.org/10.1002/asia.200700415
  6. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713 https://doi.org/10.1021/cr068373r
  7. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701
  8. Almasi, D.; Alonso, D. A.; Najera, D. Tetrahedron: Asymmetry 2007, 18, 299 https://doi.org/10.1016/j.tetasy.2007.01.023
  9. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001
  10. Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017 https://doi.org/10.1016/j.tet.2003.11.016
  11. Czekelius, C.; Carreira, E. M. Angew. Chem. Int. Ed. 2005, 44, 612 https://doi.org/10.1002/anie.200461879
  12. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119 https://doi.org/10.1021/ja044370p
  13. Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem. Int. Ed. 2005, 44, 105 https://doi.org/10.1002/anie.200461923
  14. Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem. Int. Ed. 2006, 45, 947 https://doi.org/10.1002/anie.200502658
  15. 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
  16. 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
  17. 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
  18. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036 https://doi.org/10.5012/bkcs.2008.29.10.2036
  19. Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2093 https://doi.org/10.5012/bkcs.2008.29.11.2093
  20. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821
  21. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135
  22. Kim, S. M.; Kang, Y. K.; Cho, M. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2435 https://doi.org/10.5012/bkcs.2007.28.12.2435
  23. 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
  24. Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 27, 423 https://doi.org/10.5012/bkcs.2006.27.3.423
  25. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4265
  26. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115 https://doi.org/10.1016/j.tetlet.2005.02.164
  27. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309 https://doi.org/10.1021/ol050413a
  28. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897 https://doi.org/10.1021/jo0401772
  29. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545 https://doi.org/10.1021/ol010281v
  30. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299 https://doi.org/10.1016/S0040-4039(01)01237-0
  31. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933 https://doi.org/10.1016/S0040-4020(01)00891-2
  32. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659
  33. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527 https://doi.org/10.1016/j.tetlet.2008.07.041
  34. Mang, J. Y.; Kim. D. Y. Bull. Korean Chem. Soc. 2008, 29, 2091 https://doi.org/10.5012/bkcs.2008.29.11.2091

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