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Synthesis of (-)-Vulcanolide by enantioselective protonation
Charles Fehr1, Nathalie Chaptal-Gradoz, José Galindo
1Firmenich SA, Corporate R&D Division P.O. Box 239, 1211 Geneva 8, Switzerland. charles.fehr@firmenich.com
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 22, 2002
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.