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Synthesis of 4-Benzylidene-2,5-dimethyl-3,4-dihydro-2H-pyrrole Derivatives from Baylis-Hillman Adducts and Their Chemical Transformations

  • Lee, Mi-Jung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Park, Da-Yeon (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2005.08.20

Abstract

Keywords

References

  1. Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621 https://doi.org/10.1016/j.tetlet.2003.12.133
  2. Black, D. St. C.; Edwards, G. L.; Evans, R. H.; Keller, P. A.; Laaman, S. M. Tetrahedron 2000, 56, 1889 https://doi.org/10.1016/S0040-4020(00)00094-6
  3. Taniguchi, M.; Ra, D.; Mo, G.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2001, 66, 7342 https://doi.org/10.1021/jo0104835
  4. Nsanzumuhire, C.; Clement, J.-L.; Ouari, O.; Karoui, H.; Finet, J.-P.; Tordo, P. Tetrahedron Lett. 2004, 45, 6385 https://doi.org/10.1016/j.tetlet.2004.07.016
  5. Ningsanont, N.; Black, D. St. C.; Chanphen, R.; Thebtaranonth, Y. J. Med. Chem. 2003, 46, 2397 https://doi.org/10.1021/jm020452h
  6. Turner, M. J.; Luckenbach, L. A.; Turner, E. L. Synth. Commun. 1986, 16, 1377 https://doi.org/10.1080/00397918608056386
  7. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331 https://doi.org/10.1021/jo0261449
  8. Cariou, M.; Jubault, H. M.; Tallec, et A. Tetrahedron Lett. 1982, 22, 3961 https://doi.org/10.1016/S0040-4039(01)82038-4
  9. Cheruku, S. R.; Padmanilayam, M. P.; Vennerstrom, J. L. Tetrahedron Lett. 2003, 44, 3701 https://doi.org/10.1016/S0040-4039(03)00740-8
  10. van Esseveldt, B. C. J.; Vervoort, P. W. H.; van Delft, F. L.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 1791 https://doi.org/10.1021/jo0484023
  11. Kitamura, M.; Mori, Y.; Narasaka, K. Tetrahedron Lett. 2005, 46, 2373 https://doi.org/10.1016/j.tetlet.2005.02.062
  12. Gawley, R. E.; Termine, E. J. J. Org. Chem. 1984, 49, 1946 https://doi.org/10.1021/jo00185a022
  13. Black, D. St. C.; Craig, D. C.; Edwards, G. L.; Laaman, S. M. Tetrahedron Lett. 1998, 39, 5849 https://doi.org/10.1016/S0040-4039(98)01159-9
  14. Desvergnes, S.; Py, S.; Vallee, Y. J. Org. Chem. 2005, 70, 1459 https://doi.org/10.1021/jo048237r
  15. Lee, C. G.; Lee, K. Y.; Kim, S. C.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 485 https://doi.org/10.1007/s11814-009-0082-1
  16. Lee, C. G.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 481 https://doi.org/10.5012/bkcs.2005.26.3.481
  17. Lee, M. J.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 477 https://doi.org/10.5012/bkcs.2005.26.3.477
  18. Gowrisankar, S.; Na, J. E.; Lee, M. J.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 319 https://doi.org/10.5012/bkcs.2005.26.2.319
  19. Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493 https://doi.org/10.1016/j.tet.2004.11.082
  20. Lee, K. Y.; Kim, T. H.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 1966 https://doi.org/10.5012/bkcs.2004.25.12.1966
  21. Gowrisankar, S.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6949 https://doi.org/10.1016/j.tetlet.2004.07.070
  22. Gowrisankar, S.; Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6141 https://doi.org/10.1016/j.tetlet.2004.06.057
  23. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 5485 https://doi.org/10.1016/j.tetlet.2004.05.064
  24. Kim, J. M.; Lee, K. Y.; Lee, S.-k.; Kim, J. N. Tetrahedron Lett. 2004, 45, 2805 https://doi.org/10.1016/j.tetlet.2004.02.047
  25. Monnier-Benoit, N.; Jabin, I.; Selkti, M.; Tomas, A.; Revial, G. Tetrahedron: Asymmetry 2003, 14, 2747 https://doi.org/10.1016/S0957-4166(03)00527-5
  26. Camara, C.; Keller, L.; Dumas, F. Tetrahedron: Asymmetry 2003, 14, 3263 https://doi.org/10.1016/S0957-4166(03)00573-1
  27. d'Angelo, J.; Guingant, A. Tetrahedron Lett. 1988, 29, 2667 https://doi.org/10.1016/0040-4039(88)85255-9
  28. Desmaele, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345 https://doi.org/10.1016/S0040-4039(00)95197-9
  29. Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273 https://doi.org/10.1021/ja00287a061
  30. Aube, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965 https://doi.org/10.1021/ja00023a065
  31. Milligan, G. L.; Mossman, C. J.; Aube, J. J. Am. Chem. Soc. 1995, 117, 10449 https://doi.org/10.1021/ja00147a006
  32. Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371 https://doi.org/10.1016/S0040-4020(01)80761-4
  33. Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4965 https://doi.org/10.1016/S0040-4039(00)74058-5
  34. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398 https://doi.org/10.1021/jo00107a019
  35. Mori, M.; Hashimoto, A.; Shibasaki, M. J. Org. Chem. 1993, 58, 6503 https://doi.org/10.1021/jo00075a062
  36. Schumann, D.; Naumann, A.; Wirtz, K.-P. Chem. Ber. 1979, 112, 734 https://doi.org/10.1002/cber.19791120235
  37. Padwa, A.; Sheehan, S. M.; Straub, C. S. J. Org. Chem. 1999, 64, 8648 https://doi.org/10.1021/jo9911600
  38. Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812 https://doi.org/10.1021/jo00281a022
  39. Maison, W.; Prenzel, A. H. G. P. Synthesis 2005, 1031

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