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Organocatalytic Asymmetric Michael Addition of 4-Hydroxycoumarin to β,γ-Unsaturated α-Keto Esters

  • Suh, Chang Won (Department of Chemistry, Soonchunhyang University) ;
  • Han, Tae Hyun (Department of Chemistry, Soonchunhyang University) ;
  • Kim, Dae Young (Department of Chemistry, Soonchunhyang University)
  • Received : 2013.03.08
  • Accepted : 2013.03.31
  • Published : 2013.06.20

Abstract

Keywords

References

  1. Manolov, I.; Danchev, N. D. Eur. J. Med. Chem. 1995, 30, 531. https://doi.org/10.1016/0223-5234(96)88266-3
  2. Shen, H. C. Tetrahedron 2009, 65, 3931. https://doi.org/10.1016/j.tet.2009.02.002
  3. Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Nicolaides, D. N. Curr. Pharm. Des. 2004, 10, 3813. https://doi.org/10.2174/1381612043382710
  4. O'Reilly, R. A. N. Engl. J. Med. 1976, 295, 354. https://doi.org/10.1056/NEJM197608122950702
  5. Thomassigny, C.; Prim, D.; Greck, C. Tetrahedron Lett. 2006, 47, 1117. https://doi.org/10.1016/j.tetlet.2005.12.028
  6. Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 947. https://doi.org/10.1002/anie.200502658
  7. Yang, J.; Li, W.; Jin, Z.; Liang, X.; Ye, J. Org. Lett. 2010, 12, 5218. https://doi.org/10.1021/ol102256v
  8. Dong, Z.-H.; Wang, L.-J.; Chen, X.-H.; Liu, X.-H.; Lin, L.-L.; Feng, X.-M. Eur. J. Org. Chem. 2009, 5192.
  9. Zhu, X.; Lin, A.; Shi, Y.; Guo, J.; Zhu, C.; Cheng, Y. Org. Lett. 2011, 13, 4382. https://doi.org/10.1021/ol201715h
  10. Lim, Y. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 1825. https://doi.org/10.5012/bkcs.2012.33.6.1825
  11. Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.-G.; Xia, A.-B.; Xu, Z.-Y. Chem. Eur. J. 2010, 16, 4177. https://doi.org/10.1002/chem.201000094
  12. Chen, X.- K.; Zheng, C.-W.; Zhao, S.-L.; Chai, Z.; Yang, Y. Q.; Zhao, G.; Cao, W.-G. Adv. Synth. Catal. 2010, 352, 1648. https://doi.org/10.1002/adsc.201000045
  13. Gao, Y.; Ren, Q.; Wang, L.; Wang, J. Chem. Eur. J. 2010, 16, 13068. https://doi.org/10.1002/chem.201002202
  14. Wang, J.-J.; Luo, J.-H.; Hu, Z.-P.; Lu, R.-J.; Nie, S.-Z.; Du, Q.-S.; Yan, M. ARKIVOC 2010, 229.
  15. Dong, Z.; Feng, J.; Cao, W.; Liu, X.; Lin, L.; Feng, X. Tetrahedron Lett. 2011, 52, 3433. https://doi.org/10.1016/j.tetlet.2011.04.089
  16. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  17. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897. https://doi.org/10.1021/jo0401772
  18. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309. https://doi.org/10.1021/ol050413a
  19. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115. https://doi.org/10.1016/j.tetlet.2005.02.164
  20. Kang, Y. K; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
  21. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  22. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734. https://doi.org/10.1021/jo900880t
  23. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847 https://doi.org/10.1021/ja103786c
  24. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783. https://doi.org/10.1002/adsc.201000515
  25. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917. https://doi.org/10.2174/138527210791111768
  26. Kang, Y. K. Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356. https://doi.org/10.1016/j.tetlet.2011.02.087
  27. Kang, Y. K.; Kim, H. H.; Koh, K. O.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3811. https://doi.org/10.1016/j.tetlet.2012.05.064
  28. Kwon, B. K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2481. https://doi.org/10.5012/bkcs.2012.33.8.2481
  29. Lee, H. J.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6984. https://doi.org/10.1016/j.tetlet.2012.10.051
  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. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565. https://doi.org/10.1016/j.tetlet.2006.05.003
  33. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
  34. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
  35. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527. https://doi.org/10.1016/j.tetlet.2008.07.041
  36. 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
  37. 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
  38. Oh, Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674. https://doi.org/10.1016/j.tetlet.2009.06.003
  39. Kang, S. H.; Kang, Y. K.; Kim, D. Y. Tetrahedron 2009, 65, 5676. https://doi.org/10.1016/j.tet.2009.05.037
  40. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906. https://doi.org/10.1016/j.tetlet.2010.03.105
  41. Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896. https://doi.org/10.1016/j.tetlet.2009.06.056
  42. Lee, H. J.; Kang, S. H.; Kim, D. Y. Synlett 2011, 1559.
  43. Kang, S. H.; Kwon, B. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 3247. https://doi.org/10.1016/j.tetlet.2011.04.084
  44. Kang, Y. K.; Suh, K. H.; Kim, D. Y. Synlett 2011, 1125.
  45. Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3537. https://doi.org/10.5012/bkcs.2012.33.11.3537
  46. Woo, S. B.; Kim, D. Y. Beilstein J. Org. Chem. 2012, 8, 699. https://doi.org/10.3762/bjoc.8.78
  47. Lee, H. J.; Woo, S. B.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3374. https://doi.org/10.1016/j.tetlet.2012.04.095
  48. Moon, H. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2845. https://doi.org/10.5012/bkcs.2012.33.9.2845
  49. Lee, H. J.; Woo, S. B.; Kim, D. Y. Molecules 2012, 17, 7523. https://doi.org/10.3390/molecules17067523
  50. Lee, H. J.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3437. https://doi.org/10.1016/j.tetlet.2012.04.072
  51. Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3171. https://doi.org/10.5012/bkcs.2012.33.10.3171
  52. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6569. https://doi.org/10.1016/j.tetlet.2012.09.100
  53. Kang, Y. K.; Lee, H. J.; Moon, H. W.; Kim, D. Y. RSC Adv. 2013, 3, 1332. https://doi.org/10.1039/c2ra21945j

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