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0343003061
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note
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(S)-(-)-2-Methyl-1-butanol, (1S,2S,3S,5R)-(+)-isopinocampheol and (1S,2R,5S)-(+)-menthol were purchased from Fluka Chemicals. (+)-8-Phenylmenthyl chloroacetate, which was hydrolysed (KOH, EtOH, reflux) to (-)-8-phenylmenthol, was purchased from the Aldrich Chemical Company.
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24
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0342568672
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All new compounds exhibited satisfactory spectral and analytical (high resolution mass) data
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All new compounds exhibited satisfactory spectral and analytical (high resolution mass) data.
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25
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0343874411
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note
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Preliminary studies using the enamine derived from ethyl pyruvate and benzylamine showed that N-acylation could be achieved in 46% yield using bromacetyl bromide. Attempted acylation using chloroacetyl chloride or chloroacetic anhydride was unsuccessful.
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26
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0343874409
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Lower yields were obtained using alternative bases including pyridine or triethylamine
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Lower yields were obtained using alternative bases including pyridine or triethylamine.
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28
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37049071529
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(b) Ozaki, S.; Matsushita, H.; Ohmori, H. J. Chem. Soc., Perkin Trans. 1, 1993, 2339.
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37049080023
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0001803004
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For related cyclisations using chiral N-protecting group auxiliaries see (a) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M. Synlett, 1995, 1159.
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