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Synthesis of (−)‐Vulcanolide by Enantioselective Protonation
Author(s) -
Fehr Charles,
ChaptalGradoz Nathalie,
Galindo José
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020215)8:4<853::aid-chem853>3.0.co;2-5
Subject(s) - enantioselective synthesis , protonation , ketone , enantiomer , chemistry , stereochemistry , organic chemistry , catalysis , ion
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.