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Zinc triflate: A mild and efficient catalyst for deprotection of tetrahydropyranyl ethers

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Abstract

Treatment of tetrahydropyranyl (THP) ethers with zinc triflate in methanol provides a simple and efficient process for deprotection of these ethers and the parent alcohols are obtained in excellent yields.

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References

  1. Greene, T.W. and Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd ed., John Wiley and Sons, New York, 1999, p. 102.

    Book  Google Scholar 

  2. Bongini, A., Cardillo, G., Orena, M., and Sandri, S., Synthesis., 1979, vol. 8, pp. 618–620.

    Article  Google Scholar 

  3. Miyashita, M., Yoshikoshi, A., and Grieco, P.A., J. Org. Chem., 1977, vol. 42, pp. 3772–3774.

    Article  CAS  Google Scholar 

  4. Hajipour, A.R., Zarei, A., Khazdooz, L., Pourmousavi, S.A., Zahmatkesh, S., and Ruoho, A.E. Indian. J. Chem. B, 2006, no. 45, pp. 305–308.

    Google Scholar 

  5. Wang, J., Zhang, C., Qu, Z., Hou, Y., Chan, B., and Wu, P., J. Chem. Research (S), 1999, pp. 294–295.

    Google Scholar 

  6. Gupta, A.D., Singh, R.S., and Singh, V.K., Synlett., 1996, no. 1, pp. 69–71.

    Google Scholar 

  7. Baltork, I.M. and Pouranshirvani, S., Synthesis., 1997, no. 7, pp. 756–758.

    Google Scholar 

  8. Jung, Y.J., Park, E.S., Lee, J.H., and Yoom, C.M., Bull. Korean Chem. Soc., 2002, vol. 23, pp. 791–792.

    Article  CAS  Google Scholar 

  9. Li, Z. and Ganesan, A., Synth. Commun., 1998, vol. 28, pp. 3209–3212.

    Article  CAS  Google Scholar 

  10. Reddy, G.S., Neelakantan, P., and Iyengar, D.S. Synth. Commun., 2000, vol. 30, pp. 4107–4111.

    Article  CAS  Google Scholar 

  11. Narendar, M., Reddy, M.S., and Rao, K.R., Synthesis. 2004, vol. 11, pp. 1741–1743.

    Google Scholar 

  12. Raina, S., and Singh, V.K., Synth. Commun., 1995, vol. 25, pp. 2395–2400.

    Article  CAS  Google Scholar 

  13. Wang, Y.G., Wu, X.X., and Jiang, Z.Y., Tetrahedron Lett., 2004, vol. 45, pp. 2973–2976.

    Article  CAS  Google Scholar 

  14. Habibi, M.H., Tangestaninejad, S., Baltork, I.M., Mirkhani, V., and Yadollahi, B., Tetrahedron Lett., 2001, vol. 42, pp. 2851–2853.

    Article  CAS  Google Scholar 

  15. Naik, S., Gopinath, R., and Patel, B.K., Tetrahedron Lett. 2001, vol. 42, pp. 7679–7681.

    Article  CAS  Google Scholar 

  16. Yeom, C.E., Shin, Y.J., and Kim, B.M., Bull. Korean. Chem. Soc., 2007, vol. 28, pp. 103–107.

    Article  CAS  Google Scholar 

  17. Namboodiri, V.V. and Varma, R.S., Tetrahedron Lett., 2002, vol. 43, pp. 1143–1146.

    Article  CAS  Google Scholar 

  18. Mineno, T., Tetrahedron Lett., 2002, vol. 43, pp. 7975–7978.

    Article  CAS  Google Scholar 

  19. Stephens, J.R., Butler, P.R., Clow, C.H., Oswald, M.C., Smith, R.C., and Mohan, R S., Eur. J. Org. Chem., 2003, vol. 19, pp. 3827–3831.

    Article  Google Scholar 

  20. Hon, Y.S., Lee, C.F., Chen, R.J., and Szu, P.H., Tetrahedron. 2001, vol. 57, pp. 5991–6001.

    Article  CAS  Google Scholar 

  21. Reddy, M.A., Reddy, L.R., Bhanumathi, N., and Rao, K.R., Synth. Commun., 2000, vol. 30, pp. 4323–4328.

    Article  CAS  Google Scholar 

  22. Rezai, N., Meybodi, F.A., and Salahi, P., Synth. Commun., 2000, vol. 30, pp. 1799–1805.

    Article  CAS  Google Scholar 

  23. Kim, S. and Park, J.H., Tetrahedron Lett., 1987, vol. 28, pp. 439–440.

    Article  CAS  Google Scholar 

  24. Ogawa, Y. and Shibasaki, M., Tetrahedron Lett., 1984, vol. 25, pp. 663–664.

    Article  CAS  Google Scholar 

  25. Ravi Kumar, K., Satyanarayana, P.V.V., and Reddy, B.S., Chin. J. Chem., 2012, vol. 30, pp. 1189–1191.

    Article  Google Scholar 

  26. Lekhok, K.C., Bhuyan, D., Prajapati, D., and Boruah, R.C., Mol. Divers., 2010, vol. 14, pp. 841–846.

    Article  CAS  Google Scholar 

  27. Kumar, V.N., Sridhar, G., Laxminarayana, E., Mallaiah, B., and Giri, T., J. Drug. Chem. (IJPI), 2012, no. 2, p. 10.

    Google Scholar 

  28. Atukuri, D., Ravindra, R.K., and Pramod, P.K., Lett. Org. Chem., 2013, no. 10, pp. 510–517.

    Google Scholar 

  29. Corey, E. J., and Shimoji, K. Tetrahedron Lett., 1983, vol. 24, 169–172.

    Article  CAS  Google Scholar 

  30. Miyashita, M., Yoshikoshi, A., and Grieco, P.A., J. Org. Chem., 1977, vol. 42, p. 3772.

    Article  CAS  Google Scholar 

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Correspondence to R. Srinivasulu.

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Srinivasulu, R., Satyanarayana, P.V.V. & Ravi Kumar, K. Zinc triflate: A mild and efficient catalyst for deprotection of tetrahydropyranyl ethers. Russ J Gen Chem 83, 2419–2422 (2013). https://doi.org/10.1134/S1070363213120384

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  • DOI: https://doi.org/10.1134/S1070363213120384

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