Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Indium-Mediated Allylation of Hydroxyphthalides with Acetic Acid as an Additive

  • Lee, Ji-Hee (Graduate School of Biotechnology, Korea University) ;
  • Park, Young-Sang (Graduate School of Biotechnology, Korea University) ;
  • Nam, Mi-Hye (Department of New Material Chemistry, Korea University) ;
  • Lee, Seung-Hwan (Graduate School of Biotechnology, Korea University) ;
  • Cho, Min-Young (Department of New Material Chemistry, Korea University) ;
  • Yoon, Cheol-Min (Department of New Material Chemistry, Korea University)
  • Published : 2005.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Shan, R.; Stadler, M.; Anke, H.; Sterner, O. J. Nat. Prod. 1997, 60, 804 https://doi.org/10.1021/np970145s
  2. Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorganic & Medicinal Chem. 1999, 7, 1445 https://doi.org/10.1016/S0968-0896(99)00058-9
  3. Ogawa, Y.; Wakamatsu, T.; Maruno, M.; Isono, M. Jpn. Kokai Tokkyo Koho JP 07206,844, 1995
  4. Ogawa, Y.; Wakamatsu, T.; Maruno, M.; Isono, M. Chem. Abstr. 1995, 123, 256503d
  5. Garibay, P.; Vedso, P.; Begtrup, M.; Hoeg-Jensen, T. J. Comb. Chem. 2001, 3, 332
  6. Mukhopadhyay, R.; Kundu, N. G. Tetrahedron 2001, 57, 9475 https://doi.org/10.1016/S0040-4020(01)00943-7
  7. Hayat, S.; Rahman, A.-U.; Choudhary, M. I.; Khan, K. M.; Bayer, E. Tetrahedron Lett. 2001, 42, 1647
  8. Sakamoto, M.; Sekine, N.; Miyoshi, H.; Mino, T.; Fujita, T. J. Am. Chem. Soc. 2000, 122, 10210
  9. Jayaraman, M.; Fanwick, P. E.; Cushman, M. J. Org. Chem. 1998, 63, 5736 https://doi.org/10.1021/jo980928y
  10. Ciattini, P. G.; Mastropietro, G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1993, 34, 3763 https://doi.org/10.1016/S0040-4039(00)79222-7
  11. Mori, S.; Takechi, S.; Shimizu, S.; Kida, S.; Iwakura, H.; Hajima, M. Tetrahedron Lett. 1999, 40, 1165 https://doi.org/10.1016/S0040-4039(98)02554-4
  12. Mali, R. S.; Babu, K. N. J. Org. Chem. 1998, 63, 2488 https://doi.org/10.1021/jo971622e
  13. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 https://doi.org/10.1021/cr00022a010
  14. Hosomi, A. Acc. Chem. Res. 1988, 21, 200 https://doi.org/10.1021/ar00149a004
  15. Nair, V.; Jayan, C. N. Tetrahedron Lett. 2000, 1091
  16. Paquette, L. A.; Rothhaar, R. R.; Isaac, M.; Rogers, L. M.; Roger, R. D. J. Org. Chem. 1998, 63, 5463 https://doi.org/10.1021/jo980372e
  17. Li, C. J. Tetrahedron 1996, 52, 5643 https://doi.org/10.1016/0040-4020(95)01056-4
  18. Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228 https://doi.org/10.1021/ja984359n
  19. Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581 https://doi.org/10.1016/S0040-4039(00)99525-X
  20. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920 https://doi.org/10.1021/jo00112a005
  21. Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453 https://doi.org/10.1080/00397918808064009
  22. Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931 https://doi.org/10.1021/ja953682c
  23. Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500 https://doi.org/10.1021/jo00072a038
  24. Canonne, P.; Plamondon, J.; Akssira, M. Tetrahedron 1988, 44, 2903
  25. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130 https://doi.org/10.1021/ja00172a040
  26. Frye, S. V.; Eliel, E. L.; Cloux, R. J. Am. Chem. Soc. 1987, 109, 1862 https://doi.org/10.1021/ja00240a047

Cited by

  1. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2013, https://doi.org/10.1021/cr300051y
  2. Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis vol.114, pp.12, 2014, https://doi.org/10.1021/cr400524q
  3. A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D vol.13, pp.22, 2015, https://doi.org/10.1039/C5OB00575B
  4. Three-Component Indium-Mediated Domino Allylation of 1H-Indole-3-carbaldehyde with Electron-Rich (Hetero)arenes: Highly Efficient Access to Variously Functionalized Indolylbutenes vol.2008, pp.16, 2008, https://doi.org/10.1002/ejoc.200701160
  5. Indium-Mediated Allylation of Hydroxyphthalides with Acetic Acid as an Additive. vol.36, pp.30, 2005, https://doi.org/10.1002/chin.200530092
  6. Indium-mediated Allylation of α-Imino Esters in Aqueous Media vol.28, pp.1, 2007, https://doi.org/10.5012/bkcs.2007.28.1.139