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  • Title: N-Heterocyclic Carbene-Catalyzed δ-Carbon LUMO Activation of Unsaturated Aldehydes.
    Author: Zhu T, Mou C, Li B, Smetankova M, Song BA, Chi YR.
    Journal: J Am Chem Soc; 2015 May 06; 137(17):5658-61. PubMed ID: 25910417.
    Abstract:
    An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.
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