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See the Supporting Information for full details.
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See the Supporting Information for full details.
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33748983040
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The diastereomeric influence of the substituted amine nucleophile had a significant effect on the nature of the product: 5 j was a colorless oil whereas 7 j was a white solid. For an example in which this nucleophile has been used in highly diastereoselective reactions, see.
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The diastereomeric influence of the substituted amine nucleophile had a significant effect on the nature of the product: 5 j was a colorless oil whereas 7 j was a white solid. For an example in which this nucleophile has been used in highly diastereoselective reactions, see:, S. G. Davies, G. D. Smyth, J. Chem. Soc. Perkin Trans. 1 1996, 2467-2477.
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79960899405
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CCDC 816868 (5 k) and 816869 (5 n) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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CCDC 816868 (5 k) and 816869 (5 n) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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22
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79960913492
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This process is remarkable owing to the high level of steric congestion at the alkene and the regioselective isomerization of the double bond away from the amine nitrogen atom. For recent reviews on rhodium-catalyzed isomerization of allylic alcohols, see
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This process is remarkable owing to the high level of steric congestion at the alkene and the regioselective isomerization of the double bond away from the amine nitrogen atom. For recent reviews on rhodium-catalyzed isomerization of allylic alcohols, see
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We suggest that the aldehyde α stereocentre rapidly epimerized under the reaction conditions. For a similar aldehyde, see.
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We suggest that the aldehyde α stereocentre rapidly epimerized under the reaction conditions. For a similar aldehyde, see:, M. C. Clasby, S. Chackalamannil, M. Czarniecki, D. Doller, K. Eagen, W. J. Greenlee, Y. Lin, J. R. Tagat, H. Tsai, Y. Xia, H.-S. Ahn, J. Agans-Fantuzzi, G. Boykow, M. Chintala, Y. Hsieh, A. T. McPhail, Bioorg. Med. Chem. Lett. 2007, 17, 3647-3651.
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79960914612
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1H NMR spectra of 11 a, indicating that the equilibrium lies towards the lactol form.
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1H NMR spectra of 11 a, indicating that the equilibrium lies towards the lactol form.
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There was no erosion of yield when oxygen was rigorously excluded from the reaction. See the Supporting Information for more details. For a similar example of oxidation within a rhodium-catalyzed domino sequence, see
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There was no erosion of yield when oxygen was rigorously excluded from the reaction. See the Supporting Information for more details. For a similar example of oxidation within a rhodium-catalyzed domino sequence, see
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