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35348994434
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The NMR spectra of the dihydroxylated products 9a/9b were very difficult to characterize, due to the doubling of signals as a result of non-homogeneity in the N-CO bond of the urethane functionality.
-
The NMR spectra of the dihydroxylated products 9a/9b were very difficult to characterize, due to the doubling of signals as a result of non-homogeneity in the N-CO bond of the urethane functionality.
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52
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35349027866
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The mother liquor contained 9a and 9b in a 3:7 ratio.
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The mother liquor contained 9a and 9b in a 3:7 ratio.
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54
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a) J. K. Cha, W. J. Christ, Y Kishi, Tetrahedron 1984, 40, 2247-2255;
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35348939675
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As a result of delocalization of the lone pair of electrons on nitrogen bearing the carbonyl group (Cbz) the bulky substituents (CH2Ph and OCH2Ph) at the nitrogen and carbon orient syn to each other. The syn orientation of the substituents is possibly due to the stabilization arising from π-stacking of the phenyl groups. The presence of two distinct isomers of the conjugated ester as a result of delocalization is evident from the 1H NMR spectrum, which showed an isomeric ratio of 58:42
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1H NMR spectrum, which showed an isomeric ratio of 58:42.
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Y.-T. Li, S.-C. Li in Methods in Enzymology (Ed.: V. Ginsberg), Academic Press, 1972, 28, part B, p. 702;
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