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β-Keto esters are known to cyclise through oxygen rather than carbon, see: T. R. Hoye, A. J. Caruso and M. J. Kurth, J. Org. Chem., 1981, 46, 3550; J. D. White, R. W. Skeean and G. L. Trammell, J. Org. Chem., 1985, 50, 1939.
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0344263074
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note
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Tanis showed that the benzyl ether of the epoxy alcohol was superior to silyl protected analogues: See ref. 7.
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26
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0001277528
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For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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Frejd, T.1
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0030025329
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For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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Jung, M.E.1
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0030749246
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For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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Stork, G.1
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37049106917
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J. Andrieux, D. H. R. Barton and H. Patin, J. Chem. Soc., Perkin Trans. 1, 1977, 359.
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30
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0344694786
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note
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From molecular modelling it was found that 22 was lower in energy than the conjugated tetrasubstituted double bond isomer.
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31
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0345557022
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note
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The optimised procedure required refluxing 11 with NaH (5 equiv.) in THF for 4 h followed by addition of BnBr and refluxing for a further 2 h. Less isomerisation was observed if 11 was refluxed with NaH for a shorter time.
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32
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0345557021
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note
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13C NMR, mass and IR analyses.
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