Bulletin of the Korean Chemical Society

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Deprotection of Tetrahydropyranyl Ethers Using a Catalytic Amount of Decaborane

  • Published : 2002.06.20
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Abstract

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References

  1. Kocienski, P. J. In Protecting Groups; Enders, D.; Noyori, R.; Trost, B. M, Eds.; Georg Thieme Verlag: New-York, 1994.
  2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons, Inc.: New York, 1991.
  3. Wagner, A.; Heitz, M. P.; Mioskowski, C. J. Chem. Soc, Chem. Commun. 1989, 1619.
  4. Zimmermann, K. Synth. Commun. 1995, 25, 2959. https://doi.org/10.1080/00397919508011426
  5. Nambiar, K. P.; Mitra, A. Tetrahedron Lett. 1994, 35, 3033. https://doi.org/10.1016/S0040-4039(00)76820-1
  6. Hon, Y.-S.; Lee, C.-F. Tetrahedron Lett. 1999, 40, 2389. https://doi.org/10.1016/S0040-4039(99)00274-9
  7. Marko, I. S.; Ates, A.; Augustyns, B.; Gautier, A.; Quesnel, Y; Turet, L.; Wiaux, M. Tetrahedron Lett. 1999, 40, 5613. https://doi.org/10.1016/S0040-4039(99)01043-6
  8. DattaGupta, A.; Singh, R.; Singh, V. K. Synlett 1996, 69.
  9. Raina, S.; Singh, V. K. Synth. Commun. 1995, 25, 2395 and references cited therein, https://doi.org/10.1080/00397919508015442
  10. Maiti, G.; Roy, S. C. J. Org. Chem. 1996, 61, 6038. https://doi.org/10.1021/jo9604898
  11. Caballero, G. M; Gros, E. G. Synthetic Commun. 1995, 25, 395.
  12. Srikrishna, A.; Sattigeri, J. A.; Viswajanani, R.; Yelamaggad, C. V. J. Org. Chem. 1995, 60, 2260. https://doi.org/10.1021/jo00112a056
  13. Campbell, Jr., In Press in Boron Chemistry; Steinberg, M, Ed.; Macmillan: New York, 1964; Vol. 1; pp 173-188.
  14. Lipscomb, W N. Science 1977, 196, 1047. https://doi.org/10.1126/science.196.4294.1047
  15. Muetterties, E. I. Boron Hydride Chemistry, Academic Press: New York, 1975.
  16. Tanaka, T.; Matsuda, T.; Kimijima, K.; Iwasaki, Y BuU. Chem. Soc. Jap. 1978, 51, 1259. https://doi.org/10.1246/bcsj.51.1259
  17. Reductive etherification: Lee, S. H.; Park, Y J.; Yoon, C. M. Tetrahedron Lett. 1999, 40, 6049. https://doi.org/10.1016/S0040-4039(99)01229-0
  18. Reductive animation: Bae, J. W; Cho, Y J.; Lee, S. H.; Maing Yoon, C. O.; Yoon, C. M. Chem. Commun. 2000, 1857.
  19. Lee, S. H.; Lee, J. H.; Yoon, C. M. Tetrahedron Lett, in press
  20. Olah, G. A.; Husain, A.; Singh, B. P. Synthesis 1983, 892.
  21. Miyashita, M; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772. https://doi.org/10.1021/jo00443a038
  22. Even if a drop of water added, the reaction was retarded clearly and the reaction was incomplete

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