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Updated: Aug 24, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ruthenium-Catalyzed Nitrile-Acrylate Reductive Coupling by 2-Propanol: Synthesis of Enantioenriched β-Amino Esters
Sebastian Höthker1, Colin E Hayter1, Weijia Shen1
1Department of Chemistry, University of Texas at Austin, Austin, Texas, USA.
Abstract:
Using a ruthenium catalyst derived from RuHCl(CO)(PPh3)3 and Cy-BIPHEP, 2-propanol-mediated reductive coupling of phenyl acrylate with aromatic or aliphatic nitriles occurs to form α,β-unsaturated β-amino esters. Although the reaction products, which incorporate acyclic tetrasubstituted alkenes, are challenging substrates for asymmetric hydrogenation, trifluoroethanol (TFE) enabled rhodium-Walphos-catalyzed hydrogenation occurs with high levels of enantioselectivity. Thus, through successive transfer hydrogenative coupling-asymmetric hydrogenation events, abundant nitrile and acrylate feedstocks are converted to enantioenriched β-amino esters. This method represents a new catalytic transformation of nitriles and the first reductive C─C coupling of nitriles beyond the use of stoichiometric metals or metalloids.
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