Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1960-1964Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409591
Keywords
Bronsted acid catalysis; enol catalysis; fragrances; Michael addition; structure-activity relationships
Categories
Funding
- Max Planck Society
- Fonds der Chemischen Industrie
- X-ray department of the MPI fur Kohlenforschung
- GC department of the MPI fur Kohlenforschung
- HPLC department of the MPI fur Kohlenforschung
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Novel Cashmeran odorants were designed by molecular modeling. Their short syntheses involve a novel asymmetric BrOnsted acid catalyzed Michael addition of unactivated -substituted ketones. This key transformation was realized by utilizing a new type of enol activation catalysis and affords different cyclic ketones bearing -quaternary stereocenters in good to excellent yields and with high enantioselectivity. Subsequent McMurry coupling and Saegusa-Ito oxidation furnished the enantiopure target odorants, one enantiomer of which indeed possesses the typical olfactory aspects of Cashmeran.
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