Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Asymmetric Conjugate Addition of 1-Fluoro-1-nitro(phenylsulfonyl)methane to Chalcones Catalyzed by Binaphthyl-Derived Organocatalyst

  • Received : 2012.05.22
  • Accepted : 2012.05.29
  • Published : 2012.09.20
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Abstract

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References

  1. Isanobor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303. https://doi.org/10.1016/j.jfluchem.2006.01.011
  2. Kirk, K. L. J. J. Fluorine Chem. 2006, 127, 1013. https://doi.org/10.1016/j.jfluchem.2006.06.007
  3. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. https://doi.org/10.1021/op700134j
  4. Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359. https://doi.org/10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO;2-P
  5. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  6. Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. https://doi.org/10.1021/ja028464f
  7. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309. https://doi.org/10.1021/ol050413a
  8. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115. https://doi.org/10.1016/j.tetlet.2005.02.164
  9. 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
  10. Zhao, Y.; Pan, Y.; Sim, S.-B.; Tan, C.-H. Org. Biomol. Chem. 2012, 10, 479. https://doi.org/10.1039/c1ob05840a
  11. Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425. https://doi.org/10.5012/bkcs.2003.24.10.1425
  12. Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759. https://doi.org/10.1016/j.jfluchem.2009.06.002
  13. He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew. Chem. Int. Ed. 2008, 47, 9466. https://doi.org/10.1002/anie.200804140
  14. 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
  15. Mizuta, S.; Shibata, N.; Goto, Y.; Furukawa, T.; Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394. https://doi.org/10.1021/ja071509y
  16. Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896.
  17. Prakash, G. K. S.; Wang, F.; Stewart, T.; Mathew, T.; Olah, G. A. Proc. Natl. Acad. Sci. USA 2009, 106, 4090. https://doi.org/10.1073/pnas.0900179106
  18. Kamlar, M.; Bravo, N.; Alba, A.-N. R.; Hybelbauerova, S.; Cisarova, I.; Vesely, J.; Moyano, A.; Rios, R. Eur. J. Org. Chem. 2010, 5464.
  19. Pan, Y.; Zhao, Y.; Ma, T.; Yang, Y.; Liu, H.; Jiang, Z.; Tan, C.-H. Chem. Eur. J. 2010, 16, 779. https://doi.org/10.1002/chem.200902830
  20. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
  21. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.
  22. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  23. Lee, H. J.; Chae, Y. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 2875. https://doi.org/10.5012/bkcs.2011.32.8.2875
  24. Kang, Y. K.; Yoon, S. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 1195. https://doi.org/10.5012/bkcs.2011.32.4.1195
  25. Yoon, S. J.; Kang, Y. K.; Kim, D. Y. Synlett 2011, 420.
  26. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299. https://doi.org/10.1016/S0040-4039(01)01237-0
  27. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933. https://doi.org/10.1016/S0040-4020(01)00891-2
  28. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897. https://doi.org/10.1021/jo0401772
  29. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4265.
  30. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
  31. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
  32. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847. https://doi.org/10.1021/ja103786c
  33. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356. https://doi.org/10.1016/j.tetlet.2011.02.087

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