Bulletin of the Korean Chemical Society

  • 제34권3호
  • /
  • Pages.993-996
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  • 2013
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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An Expedient Synthesis of Cinnamyl Fluorides from Morita-Baylis-Hillman Adducts

  • Lim, Cheol Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Se Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyun Ju (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Hyung Jin (School of Applied Chemical Engineering, Chonnam National University) ;
  • Kim, Jae Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • 투고 : 2012.12.13
  • 심사 : 2012.12.30
  • 발행 : 2013.03.20
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참고문헌

  1. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811. https://doi.org/10.1021/cr010043d
  2. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447. https://doi.org/10.1021/cr900291g
  3. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511. https://doi.org/10.1016/j.tet.2008.02.087
  4. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1. https://doi.org/10.1021/cr068057c
  5. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, p 201.
  6. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627. https://doi.org/10.2174/1385272023374094
  7. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481. https://doi.org/10.5012/bkcs.2005.26.10.1481
  8. Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769. https://doi.org/10.1016/j.tet.2009.07.034
  9. Shi, M.; Wang, F.-J.; Zhao, M.-X.; Wei, Y. The Chemistry of the Morita-Baylis-Hillman Reaction; RSC Publishing: Cambridge, UK, 2011.
  10. Gowrisankar, S.; Kim, S. H.; Kim, J. N. Bull. Korean Chem. Soc. 2009, 30, 726 https://doi.org/10.5012/bkcs.2009.30.3.726
  11. Basavaiah, D.; Reddy, K. R.; Kumaragurubaran, N. Nature Protocols 2007, 2, 2665. https://doi.org/10.1038/nprot.2007.369
  12. Das, B.; Banerjee, J.; Ravindranath, N. Tetrahedron 2004, 60, 8357. https://doi.org/10.1016/j.tet.2004.07.022
  13. Fernandes, L.; Bortoluzzi, A. J.; Sa, M. M. Tetrahedron 2004, 60, 9983. https://doi.org/10.1016/j.tet.2004.08.018
  14. Sa, M. M.; Ramos, M. D.; Fernandes, L. Tetrahedron 2006, 62, 11652. https://doi.org/10.1016/j.tet.2006.09.059
  15. Deng, J.; Hu, X.-P.; Huang, J.-D.; Yu, S.-B.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 2015. https://doi.org/10.1021/jo702510m
  16. Lee, K. Y.; Lee, Y. J.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 143. https://doi.org/10.5012/bkcs.2007.28.1.143
  17. Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1489. https://doi.org/10.5012/bkcs.2006.27.9.1489
  18. Das, B.; Damodar, K.; Bhunia, N.; Shashikanth, B. Tetrahedron Lett. 2009, 50, 2072. https://doi.org/10.1016/j.tetlet.2009.02.132
  19. Baumann, M.; Baxendale, I. R.; Ley, S. V. Synlett 2008, 2111.
  20. Farrington, E.; Franchini, M. C.; Brown, J. M. Chem. Commun. 1998, 277.
  21. Bernardi, L.; Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Folegatti, M.; Grilli, S.; Mazzanti, A.; Ricci, A. Tetrahedron: Asymmetry 2004, 15, 245. https://doi.org/10.1016/j.tetasy.2003.11.008
  22. Baumann, M.; Baxendale, I. R.; Martin, L. J.; Ley, S. V. Tetrahedron 2009, 65, 6611. https://doi.org/10.1016/j.tet.2009.05.083
  23. Zemtsov, A. A.; Levin, V. V.; Dilman, A. D.; Struchkova, M. I.; Belyakov, P. A.; Tartakovsky, V. A.; Hu, J. Eur. J. Org. Chem. 2010, 6779.
  24. Boukerb, A.; Gree, D.; Laabassi, M.; Gree, R. J. Fluorine Chem. 1998, 88, 23. https://doi.org/10.1016/S0022-1139(98)00115-8
  25. Bresciani, S.; Slawin, A. M. Z.; O'Hagan, D. J. Fluorine Chem. 2009, 130, 537. https://doi.org/10.1016/j.jfluchem.2009.03.003
  26. Yoneda, N.; Fukuhara, T. Chem. Lett. 2001, 222.
  27. Liu, Y.; Lai, H.; Rong, B.; Zhou, T.; Hong, J.; Yuan, C.; Zhao, S.; Zhao, X.; Jiang, B.; Fang, Q. Adv. Synth. Catal. 2011, 353, 3161. https://doi.org/10.1002/adsc.201100339
  28. Hafner, A.; Brase, S. Adv. Synth. Catal. 2011, 353, 3044. https://doi.org/10.1002/adsc.201100528
  29. Nowak, I.; Robins, M. J. J. Org. Chem. 2007, 72, 2678. https://doi.org/10.1021/jo062544a
  30. Pang, W.; Zhu, S.; Jiang, H.; Zhu, S. Tetrahedron 2006, 62, 11760. https://doi.org/10.1016/j.tet.2006.09.041
  31. Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4873. https://doi.org/10.1021/ol048069p
  32. Zhang, X.; Qing, F.-L.; Peng, Y. J. Fluorine Chem. 2001, 108, 79. https://doi.org/10.1016/S0022-1139(00)00400-0
  33. Zhang, X.; Qing, F.-L.; Yu, Y. J. Org. Chem. 2000, 65, 7075. https://doi.org/10.1021/jo005520r
  34. Allmendinger, T.; Lang, R. W. Tetrahedron Lett. 1991, 32, 339. https://doi.org/10.1016/S0040-4039(00)92622-4
  35. Jadhav, V. H.; Jang, S. H.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Kim, J.-Y.; Lee, S.; Lee, J. W.; Song, C. E.; Kim, D. W. Chem. Eur. J. 2012, 18, 3918. https://doi.org/10.1002/chem.201102455
  36. Jadhav, V. H.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Kim, D. W. Org. Lett. 2011, 13, 2502. https://doi.org/10.1021/ol200751e
  37. Jadhav, V. H.; Jang, S. H.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Chi, D. Y.; Kim, D. W. Org. Lett. 2010, 12, 3740. https://doi.org/10.1021/ol101485n
  38. Kim, D. W.; Jeong, H.- J.; Lim, S. T.; Sohn, M.-H.; Chi, D. Y. Tetrahedron 2008, 64, 4209. https://doi.org/10.1016/j.tet.2008.02.094
  39. Kim, D. W.; Hong, D. J.; Jang, K. S.; Chi, D. Y. Adv. Synth. Catal. 2006, 348, 1719. https://doi.org/10.1002/adsc.200606119
  40. Kim, D. W.; Ahn, D.-S.; Oh, Y.- H.; Lee, S.; Kil, H. S.; Oh, S. J.; Lee, S. J.; Kim, J. S.; Ryu, J. S.; Moon, D. H.; Chi, D. Y. J. Am. Chem. Soc. 2006, 128, 16394. https://doi.org/10.1021/ja0646895
  41. Kim, D. W.; Chi, D. Y. Angew. Chem. Int. Ed. 2004, 43, 483. https://doi.org/10.1002/anie.200352760
  42. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281. https://doi.org/10.1021/jo034109b
  43. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278. https://doi.org/10.1021/ja026242b
  44. Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 15902. https://doi.org/10.1021/ja206960k
  45. Hollingworth, C.; Hazari, A.; Hopkinson, M. N.; Tredwell, M.; Benedetto, E.; Huiban, M.; Gee, A. D.; Brown, J. M.; Gouverneur, V. Angew. Chem. Int. Ed. 2011, 50, 2613. https://doi.org/10.1002/anie.201007307
  46. Gustafsson, T.; Gilmour, R.; Seeberger, P. H. Chem. Commun. 2008, 3022.
  47. Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050. https://doi.org/10.1021/ja0440497
  48. Makosza, M.; Bujok, R. J. Fluorine Chem. 2005, 126, 209. https://doi.org/10.1016/j.jfluchem.2004.12.003
  49. Kim, D. W.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H. Tetrahedron Lett. 2010, 51, 432. https://doi.org/10.1016/j.tetlet.2009.11.058
  50. Kim, D. W.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H. Angew. Chem. Int. Ed. 2008, 47, 8404. https://doi.org/10.1002/anie.200803150
  51. Kim, D. W.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Katzenellenbogen, J. A.; Chi, D. Y. J. Org. Chem. 2008, 73, 957. https://doi.org/10.1021/jo7021229
  52. Shinde, S. S.; Lee, B. S.; Chi, D. Y. Org. Lett. 2008, 10, 733. https://doi.org/10.1021/ol702679d

피인용 문헌

  1. ChemInform Abstract: An Expedient Synthesis of Cinnamyl Fluorides from Morita-Baylis-Hillman Adducts. vol.44, pp.40, 2013, https://doi.org/10.1002/chin.201340057
  2. Synthesis of Tetrahydropyridines from Morita-Baylis-Hillman Acetates of α,β-Unsaturated Aldehydes Via an Intramolecular 1,6-Conjugate Addition vol.37, pp.1, 2015, https://doi.org/10.1002/bkcs.10610
  3. Synthesis of Morita–Baylis–Hillman-fluorides using 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine vol.97, pp.None, 2013, https://doi.org/10.1016/j.tet.2021.132387