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Lewis Acid Catalyzed Protective Opening of Epoxides with Pivaloyl Halides
Corresponding Author(s) : Tulam Vijaya Kumar
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
An efficient protocol of shorter reaction times for protective opening of epoxides (POE) with pivaloyl halides under solvent-free conditions in presence of Lewis acid catalysts has been developed.
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- R.E. Parker and N.S. Isaacs, Chem. Rev., 59, 737 (1959); doi:10.1021/cr50028a006.
- B. Shivani, A. Pujala and K. Chakraborti, J. Org. Chem., 72, 3713 (2007); doi:10.1021/jo062674j.
- G. Sabitha, R.S. Babu, M. Rajkumar and J.S. Yadav, Org. Lett., 4, 343 (2002); doi:10.1021/ol016979q.
- A.S. Rao, S.K. Paknikar and J.G. Kirtane, Tetrahedron, 39, 2323 (1983); doi:10.1016/S0040-4020(01)91961-1.
- J. Gorzynski Smith, Synthesis, 629 (1984); doi:10.1055/s-1984-30921.
- J.L. Wee, K. Sundermann, P. Licari and J. Galazzo, J. Nat. Prod., 69, 1456 (2006); doi:10.1021/np060258o.
- A. Evidente, A. Cimmino, A. Berestetskiy, G. Mitina, A. Andolfi and A. Motta, J. Nat. Prod., 71, 31 (2008); doi:10.1021/np0703038.
- A. Bishara, A. Rudi, M. Aknin, D. Neumann, N. Ben-Califa and Y. Kashman, Org. Lett., 10, 153 (2008); doi:10.1021/ol702221v.
- K. Oguchi, M. Tsuda, R. Iwamoto, Y. Okamoto, J. Kobayashi, E. Fukushi, J. Kawabata, T. Ozawa, A. Masuda, Y. Kitaya and K. Omasa, J. Org. Chem., 73, 1567 (2008); doi:10.1021/jo702440s.
- S.E. Schaus and E.N. Jacobsen, Org. Lett., 2, 1001 (2000); doi:10.1021/ol005721h.
- D.M. Hodgson, M.J. Fleming and S.J. Stanway, J. Am. Chem. Soc., 126, 12250 (2004); doi:10.1021/ja045513a.
- E. Vedrenne, O.A. Wallner, M. Vitale, F. Schmidt and V.K. Aggarwal, Org. Lett., 11, 165 (2009); doi:10.1021/ol802651b.
- M. Escriba, V. Hessel, S. Rothstock, J. Eras, R. Canela and P. Lob, Green Chem., 13, 1799 (2011); doi:10.1039/c0gc00655f.
- R. Patil, W. Li, C.R. Ross II, E. Kraka, D. Cremer, M.L. Mohler, J.T. Dalton and D.D. Miller, Tetrahedron Lett., 47, 3941 (2006); doi:10.1016/j.tetlet.2006.03.154.
- O. Pamies and Jan-E. Backvall, J. Org. Chem., 67, 9006 (2002); doi:10.1021/jo026157m.
- C.B. Rao, D.C. Rao, M. Venkateswara and Y. Venkateswarlu, Green Chem., 13, 2704 (2011); doi:10.1039/c1gc15506g.
References
R.E. Parker and N.S. Isaacs, Chem. Rev., 59, 737 (1959); doi:10.1021/cr50028a006.
B. Shivani, A. Pujala and K. Chakraborti, J. Org. Chem., 72, 3713 (2007); doi:10.1021/jo062674j.
G. Sabitha, R.S. Babu, M. Rajkumar and J.S. Yadav, Org. Lett., 4, 343 (2002); doi:10.1021/ol016979q.
A.S. Rao, S.K. Paknikar and J.G. Kirtane, Tetrahedron, 39, 2323 (1983); doi:10.1016/S0040-4020(01)91961-1.
J. Gorzynski Smith, Synthesis, 629 (1984); doi:10.1055/s-1984-30921.
J.L. Wee, K. Sundermann, P. Licari and J. Galazzo, J. Nat. Prod., 69, 1456 (2006); doi:10.1021/np060258o.
A. Evidente, A. Cimmino, A. Berestetskiy, G. Mitina, A. Andolfi and A. Motta, J. Nat. Prod., 71, 31 (2008); doi:10.1021/np0703038.
A. Bishara, A. Rudi, M. Aknin, D. Neumann, N. Ben-Califa and Y. Kashman, Org. Lett., 10, 153 (2008); doi:10.1021/ol702221v.
K. Oguchi, M. Tsuda, R. Iwamoto, Y. Okamoto, J. Kobayashi, E. Fukushi, J. Kawabata, T. Ozawa, A. Masuda, Y. Kitaya and K. Omasa, J. Org. Chem., 73, 1567 (2008); doi:10.1021/jo702440s.
S.E. Schaus and E.N. Jacobsen, Org. Lett., 2, 1001 (2000); doi:10.1021/ol005721h.
D.M. Hodgson, M.J. Fleming and S.J. Stanway, J. Am. Chem. Soc., 126, 12250 (2004); doi:10.1021/ja045513a.
E. Vedrenne, O.A. Wallner, M. Vitale, F. Schmidt and V.K. Aggarwal, Org. Lett., 11, 165 (2009); doi:10.1021/ol802651b.
M. Escriba, V. Hessel, S. Rothstock, J. Eras, R. Canela and P. Lob, Green Chem., 13, 1799 (2011); doi:10.1039/c0gc00655f.
R. Patil, W. Li, C.R. Ross II, E. Kraka, D. Cremer, M.L. Mohler, J.T. Dalton and D.D. Miller, Tetrahedron Lett., 47, 3941 (2006); doi:10.1016/j.tetlet.2006.03.154.
O. Pamies and Jan-E. Backvall, J. Org. Chem., 67, 9006 (2002); doi:10.1021/jo026157m.
C.B. Rao, D.C. Rao, M. Venkateswara and Y. Venkateswarlu, Green Chem., 13, 2704 (2011); doi:10.1039/c1gc15506g.