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  • Title: Favoring trienamine activation through unconjugated dienals: organocatalytic enantioselective remote functionalization of alkenes.
    Author: Prieto L, Talavera G, Uria U, Reyes E, Vicario JL, Carrillo L.
    Journal: Chemistry; 2014 Feb 17; 20(8):2145-8. PubMed ID: 24478203.
    Abstract:
    Unconjugated 2,5-dienals are more reactive substrates than the corresponding fully conjugated α,β,γ,δ-unsaturated aldehydes towards organocatalytic activation through trienamine intermediates. This difference in reactivity has been demonstrated in the Diels-Alder reaction with nitroalkenes, a reaction that proceeds with clean β,ε-selectivity to afford the final products in high yields and stereoselectivities, the related polyconjugated 2,4-dienals being completely unreactive.
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