Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 20, Pages 7408-7412Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500050
Keywords
aldehyde; allylation; asymmetric synthesis; Bronsted acid; Lewis base
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Funding
- Ministry of Education, Youth, and Sports [MSM0021620857]
- Czech Science Foundation [P207/11/0587]
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Allylation, trans- and cis-crotylation of (2E,4E)-2,4-dimethylhexadienal, a representative alpha,beta,gamma,delta-unsaturated aldehyde, was carried out under different catalytic and stoichiometric conditions. The reactions catalyzed by organocatalysts TRIP-PA and N,N'-dioxides gave the best results with respect to yields, asymmetric induction, and catalyst load in comparison to other procedures. The developed methodology was applied in the enantioselective synthesis of (5R,6S)-(+)-pteroenone, a defensive metabolite (ichthyodeterrent) of the Antarctic pteropod Clione antarctica.
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