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1 p.o. (p.o. = per os, oral administration).
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e) S. Marczak, K. Michalak, Z. Urbańczyk-Lipkowska, J. Wicha, J. Org. Chem. 1998, 63, 2218-2223; reviews:
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26
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0344801802
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note
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4 in a ratio of 3:1 or by parallel addition of both components. A modification of this reaction has meanwhile been carried out on a kilogram scale.
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27
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0344369938
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note
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1H NMR spectra suggest a hydrogen bond between the two groups (low-field shift and W-coupling of the OH hydrogen atom with an H atom of the neighboring AB system). By complexation with titanium this conformation should be maintained in the reaction mixture. Thus, the π orbitals of the carhonyl group and the σ C-H bond in the α position are almost orthogonal to each other. Therefore, acidification of the α H atom lacks conjugative stabilisation. In addition, elimination leads to greater steric hindrance of the neighboring substituents.
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28
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0344369939
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note
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1H NMR spectrum of this diastereomer indicates the absence of the intramolecular hydrogen bridge.
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29
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0028853158
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a) B. Di Simone, D. Savoia, E. Tagliavini, A. Umani-Ronchi, Tetrahedron: Asymmetry 1995, 6, 301-306;
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