Synthesis of (-)-Vulcanolide by enantioselective protonation |
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Authors: | Fehr Charles Chaptal-Gradoz Nathalie Galindo José |
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Institution: | Firmenich SA, Corporate R&D Division P.O. Box 239, 1211 Geneva 8, Switzerland. charles.fehr@firmenich.com |
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Abstract: | Two efficient enantioselective syntheses of the more active (S,S)-enantiomer of the powerful musk odorant Vulcanolide are described. In both syntheses, the key step is an enantioselective protonation of a ketone enolate. A third enantioselective protonation, of a thiol ester enolate, was applied for the determination of the absolute configuration of Vulcanolide by comparison with a known compound. |
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