Enantioselective Allylation of (2E,4E)‐2,4‐Dimethylhexadienal: Synthesis of (5R,6S)‐(+)‐Pteroenone |
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Authors: | Petr Koukal Prof?Dr Martin Kotora |
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Institution: | Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 123 43, Praha 2 (Czech Republic), Fax: (+420)?221‐951‐236 |
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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. |
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Keywords: | aldehyde allylation asymmetric synthesis Brø nsted acid Lewis base |
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