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Gallium(III) Iodide Mediated Mild and Efficient Method for Synthesis of 4-Iodotetrahydropyrans by Cross-Cyclization of Epoxides and Homoallylic Alcohols
Corresponding Author(s) : K. Rajasekhar
Asian Journal of Chemistry,
Vol. 29 No. 12 (2017): Vol 29 Issue 12
Abstract
The synthesis of 4-iodotetrahydropyran derivatives has been achieved via gallium(III) iodide mediated cyclization of epoxides and homo-allylic alcohols. This is a single step diastereoselective method for the preparation of 4-iodotetrahydropyrans.
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- Same as ref 30).
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References
T. Voigt, C. Gerding-Reimers, T.T. Ngoc Tran, S. Bergmann, H. Lachance, B. Schölermann,A. Brockmeyer, P. Janning, S. Ziegler and H. Waldmann, Angew. Chem. Int. Ed., 52, 410 (2013); https://doi.org/10.1002/anie.201205728.
F. Colobert, R.D. Mazery, G. Solladié and M.C. Carreño, Org. Lett., 4, 1723 (2002); https://doi.org/10.1021/ol025778z.
I. Louis, N.L. Hungerford, E.J. Humphries and M.D. McLeod, Org. Lett., 8, 1117 (2006); https://doi.org/10.1021/ol053092b.
C.W. Cheung, P. Ren and X. Hu, Org. Lett., 16, 2566 (2014); https://doi.org/10.1021/ol501087m.
D. Zurwerra, J. Gertsch and K.-H. Altmann, Org. Lett., 12, 2302 (2010); https://doi.org/10.1021/ol100665m.
J.S. Yadav, B.V. Subba Reddy, G.G.K.S. Narayana Kumar and T. Swamy, Tetrahedron Lett., 48, 2205 (2007); https://doi.org/10.1016/j.tetlet.2007.01.076.
A.K. Saikia, S. Bondalapati, K. Indukuri and P. Gogoi, Chem. Lett., 40, 1176 (2011); https://doi.org/10.1246/cl.2011.1176.
D. Clarisse, B. Pelotier, O. Piva and F. Fache, Chem. Commun., 48, 157 (2012); https://doi.org/10.1039/C1CC16501A.
J.S. Yadav, B.V.S. Reddy, M.K. Gupta and S.K. Biswas, Synthesis, 2711 (2004); https://doi.org/10.1055/s-2004-831220.
J.S. Yadav, B.V.S. Reddy, N. Kumar and M. Reddy, Chem. Lett., 36, 426 (2007); https://doi.org/10.1246/cl.2007.426.
G. Sabitha, K.B. Reddy, M. Bhikshapathi and J.S. Yadav, Tetrahedron Lett., 47, 2807 (2006); https://doi.org/10.1016/j.tetlet.2006.02.094.
M.G. Safarov, N.G. Nigmatullin, U.G. Ibatullin and S.R. Rafikov, Russ. Chem. Bull., 31, 792 (1982); https://doi.org/10.1007/BF00950021.
R.F. Talipov, R.F. Talipov, G.R. Talipova and M.G. Safarov, Russ. J. Gen. Chem., 66, 1344 (1996).
J. Madhukar and S. Nagavani, Orient. J. Chem., 26, 1151 (2010).
N.M. Raju, K. Rajasekhar, J.M. Babu and B.V. Rao, Res. J. Chem. Sci., 6, 48 (2016).
T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 45, 49 (2004); https://doi.org/10.1016/j.tetlet.2003.10.129.
I.M. Baltork and H. Aliyan, Synth. Commun., 28, 3943 (1998); https://doi.org/10.1080/00397919808004952.
I. Mohammadpoor-Baltork, S. Tangestaninejad, H. Aliyan and V. Mirkhani, Synth. Commun., 30, 2365 (2000); https://doi.org/10.1080/00397910008086878.
I. Mohammadpoor-Baltork, A.R. Khosropour and H. Aliyan, Synth. Commun., 31, 3411 (2001); https://doi.org/10.1081/SCC-100106198.
N.R. Swamy, G. Kondaji and K. Nagaiah, Synth. Commun., 32, 2307 (2002); https://doi.org/10.1081/SCC-120006000.
T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 43, 7891 (2002); https://doi.org/10.1016/S0040-4039(02)01896-8.
N. Chatani, H. Inoue, T. Kotsuma and S. Murai, J. Am. Chem. Soc., 124, 10294 (2002); https://doi.org/10.1021/ja0274554.
H. Inoue, N. Chatani and S. Murai, J. Org. Chem., 67, 1414 (2002); https://doi.org/10.1021/jo016232d.
M. Yamaguchi, T. Tsukagoshi and M. Arisawa, J. Am. Chem. Soc., 121, 4074 (1999); https://doi.org/10.1021/ja984022l.
N. Asao, T. Asano, T. Ohishi and Y. Yamamoto, J. Am. Chem. Soc., 122, 4817 (2000); https://doi.org/10.1021/ja994000e.
K. Kobayashi, M. Arisawa and M. Yamaguchi, J. Am. Chem. Soc., 124, 8528 (2002); https://doi.org/10.1021/ja026108r.
G.S. Viswanathan, M. Wang and C.J. Li, Angew. Chem. Int. Ed., 41, 2138 (2002); https://doi.org/10.1002/1521-3773(20020617)41:12<2138::AIDANIE2138>3.0.CO;2-T.
G.S. Viswanathan and C.J. Li, Synlett, 1553 (2002); https://doi.org/10.1055/s-2002-33530.
G.S. Viswanathan and C.J. Li, Tetrahedron Lett., 43, 1613 (2002); https://doi.org/10.1016/S0040-4039(02)00082-5.
C.K.Z. Andrade and N.R. Azevedo, Tetrahedron Lett., 42, 6473 (2001); https://doi.org/10.1016/S0040-4039(01)01306-5.
Same as ref 30).
C. Kleber, Z. Andrade and R.A. Matos, Synlett, 1189 (2003); https://doi.org/10.1055/s-2003-39902.
P.C. Andrews, A.C. Peatt and C.L. Raston, Tetrahedron Lett., 45, 243 (2004); https://doi.org/10.1016/j.tetlet.2003.10.188.
R. Amemiya, A. Fujii and M. Yamaguchi, Tetrahedron Lett., 45, 4333 (2004); https://doi.org/10.1016/j.tetlet.2004.03.187.