Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Pt(II)-Catalyzed Cyclization of Alkyne-aldehydes

  • Hong, Jong-Tai (Division of Energy Systems Research, Ajou University) ;
  • Kang, Min-Jung (Division of Energy Systems Research, Ajou University) ;
  • Jang, Hye-Young (Division of Energy Systems Research, Ajou University)
  • Received : 2010.05.10
  • Accepted : 2010.05.19
  • Published : 2010.07.20
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References

  1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. https://doi.org/10.1021/cr950065y
  2. Montgomery, J. Acc. Chem. Res. 2000, 33, 467. https://doi.org/10.1021/ar990095d
  3. Montgomery, J.; Amarashinghe, K. K. D.; Chowdhury, S. K.; Oblinger, E.; Seo, J.; Savchenko, A. V. Pure Appl. Chem. 2002, 74, 129. https://doi.org/10.1351/pac200274010129
  4. Ikeda, S.-I. Angew. Chem. Int. Ed. 2003, 42, 5120. https://doi.org/10.1002/anie.200301673
  5. Miller, K. M.; Molinaro, C.; Jamison, T. F. Tetrahedron Asymm. 2003, 3619.
  6. Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653. https://doi.org/10.1021/ar020108e
  7. Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063. https://doi.org/10.1021/jo061895m
  8. Rhee, J. U.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 10674. https://doi.org/10.1021/ja0637954
  9. Han, S. B.; Kong, J. R.; Krische, M. J. Org. Lett. 2008, 10, 4133. https://doi.org/10.1021/ol8018874
  10. Patman, R. L.; Chaulagain, M. R.; Villiams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066. https://doi.org/10.1021/ja809456u
  11. Lee, H.; Jang, M.-S.; Hong, J.-T.; Jang, H.-Y. Tetrahedron Lett. 2008, 49, 5785. https://doi.org/10.1016/j.tetlet.2008.07.117
  12. Shinde, M. P.; Wang, X.; Kang, E. J.; Jang, H.-Y. Eur. J. Org. Chem. 2009, 6091.
  13. Lee, H.; Jang, M.-S.; Song, Y.-J.; Jang, H.-Y. Bull. Korean Chem. Soc. 2009, 30, 327. https://doi.org/10.5012/bkcs.2009.30.2.327
  14. Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
  15. Trost, B. M.; Chen. D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. https://doi.org/10.1021/ja9624432
  16. Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116, 7915. https://doi.org/10.1021/ja00096a066
  17. Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. https://doi.org/10.1021/ja00021a040
  18. Li, H.; Loh, T.-P. J. Am. Chem. Soc. 2008, 130, 7194. https://doi.org/10.1021/ja801488z
  19. Johnson, T. O.; Overman, L. E. Tetrahedron Lett. 1991, 32, 7361. https://doi.org/10.1016/0040-4039(91)80107-H
  20. Takami, K.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Synlett 2001, 2, 293.
  21. Kang, S.-K.; Kim, Y.-M.; Ha, Y.-H.; Yu, C.-M.; Yang, H.; Lim, Y. Tetrahedron Lett. 2002, 43, 9105. https://doi.org/10.1016/S0040-4039(02)02241-4
  22. Zhao, Y.-J.; Loh, T.-P. J. Am. Chem. Soc. 2008, 130, 10024. https://doi.org/10.1021/ja802896n
  23. Harding, C. E.; Hanack, M. Tetrahedron Lett. 1971, 12, 1253. https://doi.org/10.1016/S0040-4039(01)96679-1
  24. Balf, R. J.; Rao, B.; Weiler, L. Can. J. Chem. 1971, 49, 3135. https://doi.org/10.1139/v71-523
  25. Hanack, M.; Harding, C. E.; Derocque, J. Chem. Ber. 1972, 105, 421. https://doi.org/10.1002/cber.19721050207
  26. Lange, G. L.; Hall, T.-W. J. Org. Chem. 1974, 39, 3819. https://doi.org/10.1021/jo00940a003
  27. Harding, C. E.; Stanford, G. R. J. Org. Chem. 1989, 54, 3054. https://doi.org/10.1021/jo00274a018
  28. Harding, C. E.; King, S. L. J. Org. Chem. 1992, 57, 883. https://doi.org/10.1021/jo00029a019
  29. Sisko, J.; Balog, A.; Curran, D. P. J. Org. Chem. 1992, 57, 4341. https://doi.org/10.1021/jo00042a007
  30. Balog, A.; Curran, D. P. J. Org. Chem. 1995, 60, 337. https://doi.org/10.1021/jo00107a011
  31. Wempe, M. F.; Grunwell, J. R. Tetrahedron Lett. 2000, 41, 6709. https://doi.org/10.1016/S0040-4039(00)01169-2
  32. Rhee, J. U.; Krische, M. J. Org. Lett. 2005, 7, 2493. https://doi.org/10.1021/ol050838x
  33. Saito, A.; Umakoshi, M.; Yagyu, N.; Hanzawa, Y. Org. Lett. 2008, 10, 1783. https://doi.org/10.1021/ol800539a
  34. Jin, T.; Yamamoto, Y. Org. Lett. 2008, 10, 3137. https://doi.org/10.1021/ol801265s

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