DOI QR코드

DOI QR Code

One-Pot Synthesis of 5-Arylpent-4-enoate Derivatives from Baylis-Hillman Acetates: Use of Phosphorous Ylide

  • Im, Yang-Jin (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Na, Jeong-Eun (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 : 2003.04.20

Abstract

Keywords

References

  1. Basavaiah, D.; Pandiaraju, S. Tetrahedron Lett. 1995, 36, 757. https://doi.org/10.1016/0040-4039(94)02360-N
  2. Basavaiah, D.; Pandiaraju, S.; Krishnamacharyulu, M. Synlett 1996, 747.
  3. Shen, Y.; Zhang, Z. Synth. Commun. 2000, 30, 445. https://doi.org/10.1080/00397910008087341
  4. Shen, Y.; Zhang, Z. J. Chem. Res. (S) 1999, 556.
  5. Im, Y. J.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1361. https://doi.org/10.5012/bkcs.2002.23.10.1361
  6. Taber, D. F.; Amedio, J. C. Jr.; Gulino, F. J. Org. Chem. 1989, 54, 3474. https://doi.org/10.1021/jo00275a038
  7. Taber, D. F.; Amedio, J. C. Jr.; Patel, Y. K. J. Org. Chem. 1985, 50, 3618. https://doi.org/10.1021/jo00219a035
  8. Miles, D. H.; Huang, B.-S. J. Org. Chem. 1976, 41, 208. https://doi.org/10.1021/jo00864a006
  9. Huang, B.-S.; Parish, E. J.; Miles, D. H. J. Org. Chem. 1974, 39, 2647. https://doi.org/10.1021/jo00931a051
  10. Zaragoza, F. J. Org. Chem. 2002, 67, 4963. https://doi.org/10.1021/jo025731r
  11. Johnson, A. W.; Kaska, W. C.; Strazewski, K. A. O.; Dixon, D. A. Ylides and Imines of Phosphorus; John Wiley & Sons, Inc.: 1993; pp 166-178.
  12. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627. https://doi.org/10.2174/1385272023374094
  13. Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675. https://doi.org/10.1016/S0040-4039(02)00884-5
  14. Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209. https://doi.org/10.1016/S0040-4039(02)01314-X
  15. Kim, J. N.; Im, Y. J.; Kim, J. M. Tetrahedron Lett. 2002, 43, 6597. https://doi.org/10.1016/S0040-4039(02)01441-7
  16. Kim, J. N.; Lee, H. J.; Gong, J. H. Tetrahedron Lett. 2002, 43, 9141. https://doi.org/10.1016/S0040-4039(02)02274-8
  17. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Gong, J. H. Synlett 2002, 173.
  18. Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247. https://doi.org/10.1016/S0040-4039(01)02344-9
  19. Chung, Y. M.; Gong, J. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2001, 42, 9023. https://doi.org/10.1016/S0040-4039(01)01971-2
  20. Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341. https://doi.org/10.1016/S0040-4039(01)01791-9
  21. Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195. https://doi.org/10.1016/S0040-4039(01)00687-6
  22. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737. https://doi.org/10.1016/S0040-4039(01)00552-4
  23. Kim, H. S.; Kim, T. Y.; Lee, K. Y.; Chung, Y. M.; Lee, H. J.; Kim, J. N. Tetrahedron Lett. 2000, 41, 2613. https://doi.org/10.1016/S0040-4039(00)00229-X
  24. Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343. https://doi.org/10.1021/ol9903741
  25. Lee, H. J.; Seong, M. R.; Kim, J. N. Tetrahedron Lett. 1998, 39, 6223. https://doi.org/10.1016/S0040-4039(98)01280-5
  26. Lee, H. J.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 1999, 40, 4363. https://doi.org/10.1016/S0040-4039(99)00749-2
  27. Chung, Y. M.; Lee, H. J.; Hwang, S. S.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 799.
  28. Im, Y. J.; Kim, J. M.; Mun, J. H.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 349.

Cited by

  1. Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isatylidene Malononitriles vol.13, pp.13, 2011, https://doi.org/10.1021/ol201094f
  2. Diels–Alder dimerization of Morita–Baylis–Hillman acetates catalyzed by organocatalysts vol.39, pp.1, 2013, https://doi.org/10.1007/s11164-012-0626-6
  3. PPh3-mediated intramolecular conjugation of alkyl halides with electron-deficient olefins: facile synthesis of chromans and relevant analogues vol.49, pp.40, 2013, https://doi.org/10.1039/c3cc41435c
  4. 2′ Allylation–Wittig Strategy vol.79, pp.8, 2014, https://doi.org/10.1021/jo500375q
  5. Synthesis of 1,3,4-Trisubstituted Benzenes from Morita-Baylis-Hillman Adducts of α-Bromocinnamaldehyde via [5+1] Annulation Strategy vol.36, pp.12, 2015, https://doi.org/10.1002/bkcs.10577
  6. 2′ Reaction of Phosphorous Ylides with Carbonates of Isatin-derived Moritas-Baylis-Hillman Adducts vol.38, pp.9, 2017, https://doi.org/10.1002/bkcs.11193
  7. One-Pot Synthesis of 5-Arylpent-4-enoate Derivatives from Baylis—Hillman Acetates: Use of Phosphorous Ylide. vol.34, pp.35, 2003, https://doi.org/10.1002/chin.200335081
  8. A Facile Synthesis of 4-Arylidene-2-substituted Isoxazolidin-5-ones from Baylis-Hillman Acetates vol.25, pp.1, 2003, https://doi.org/10.5012/bkcs.2004.25.1.033
  9. Synthesis of deuterium labeled compounds by KCN-assisted hydrolysis of phosphonium salts vol.45, pp.31, 2004, https://doi.org/10.1016/j.tetlet.2004.06.058
  10. Microwave accelerated SN2' substitution of Baylis-Hillman acetates: A comparative study of conventional heating versus microwave irradiation vol.274, pp.1, 2003, https://doi.org/10.1016/j.molcata.2007.03.073
  11. Asymmetric synthesis of chiral glutaric acid derivatives via Rh-catalyzed enantioselective hydrogenation vol.20, pp.5, 2003, https://doi.org/10.1016/j.tetasy.2009.02.046
  12. Recent advances in the Pd-catalyzed chemical transformations of Baylis-Hillman adducts vol.65, pp.43, 2009, https://doi.org/10.1016/j.tet.2009.07.034