Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 4, Pages 1257-1260Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.201002729
Keywords
allylic alcohols; fragrances hydrogenation; natural products; ruthenium
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(E)-Trisubstituted allylic alcohols are commonly prepared from the corresponding (E)-enals, themselves readily accessible by a simple aldol condensation reaction. We demonstrate that these very same (E)-enals can be converted into (Z)-trisubstituted allylic acetates (and thus alcohols) by a ruthenium-catalyzed 1,4-hydrogenation of the corresponding dienol acetates. This simple solution to a long-lasting problem was applied to an industrially feasible synthesis of (-)-beta-santalol.
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