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  • Title: Chiral Bifunctional Phosphine Ligand-Enabled Cooperative Cu Catalysis: Formation of Chiral α,β-Butenolides via Highly Enantioselective γ-Protonation.
    Author: Cheng X, Li T, Gutman K, Zhang L.
    Journal: J Am Chem Soc; 2021 Jul 28; 143(29):10876-10881. PubMed ID: 34264076.
    Abstract:
    α,β-Butenolides with ≥96% enantiomeric excess are synthesized from β,γ-butenolides via a novel Cu(I)-ligand cooperative catalysis. The reaction is enabled by a chiral biphenyl-2-ylphosphine ligand featuring a remote tertiary amino group. Density functional theory studies support the cooperation between the metal center and the ligand basic amino group during the initial soft deprotonation and the key asymmetric γ-protonation. Remarkably, other coinage metals, that is, Ag and Au, can readily assume the same role as Cu in this asymmetric isomerization chemistry.
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