title: Enantioselective Allylation of (2E,4E)-2,4-Dimethylhexadienal: Synthesis of (5R,6S)-(+)-Pteroenone.
abstract: Allylation, trans- and cis-crotylation of (2E,4E)-2,4-dimethylhexadienal, a representative α,β,γ,δ-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.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 123 43, Praha 2 (Czech Republic), Fax: (+420) 221-951-236.
authors.forename: Petr
authors.initials: P
authors.lastname: Koukal
authors.forename: Martin
authors.initials: M
authors.lastname: Kotora
keywords: Brønsted acid; Lewis base; aldehyde; allylation; asymmetric synthesis