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33747029733
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note
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It was important to reduce the amount of allylic chloride present in the reaction mixture as it was found to be inefficient in the subsequent alkylation reaction.
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28
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0001428613
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5) resulted in lower yields of the allylic bromide 21 and led to bromohydrin formation. 20 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;
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33747016195
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note
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From molecular modelling (SPARTAN) it was found that 27 was lower in energy than the conjugated tetrasubstituted double bond isomer 2.
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31
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33747022246
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13C NMR, mass and IR analyses
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13C NMR, mass and IR analyses.
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32
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33746982868
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note
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The recovered isomer 28 was enriched in one diastereomer after 2 h reflux with NaH. After 4 h reflux, the recovered isomer 28 appeared to be one diastereomer only, suggesting a difference in deprotonation rates for the two diastereomeric esters.
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33
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37049106917
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