Enantioselective Allylation of (2 E,4 E)‐2,4‐Dimethylhexadienal: Synthesis of (5 R,6 S)‐(+)‐Pteroenone

Abstract Allylation, trans‐ and cis‐ crotylation of (2 E ,4 E )‐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 result...

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Bibliographic Details
Published in:Chemistry – A European Journal
Main Authors: Koukal, Petr, Kotora, Martin
Other Authors: Ministry of Education, Youth, and Sports, Czech Science Foundation
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2015
Subjects:
Antarctic
The Antarctic
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/chem.201500050
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201500050
https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201500050
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Summary:Abstract Allylation, trans‐ and cis‐ crotylation of (2 E ,4 E )‐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 (5 R ,6 S )‐(+)‐pteroenone, a defensive metabolite (ichthyodeterrent) of the Antarctic pteropod Clione antarctica .

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