Phosphine-Catalyzed Diastereo- and Enantioselective Michael Addition of β-Carbonyl Esters to β-Trifluoromethyl and β-Ester Enones: Enhanced Reactivity by Inorganic Base

Abstract

A novel chiral biamide-phosphine multifunctional catalyst has been developed that mediates the asymmetric intermolecular Michael addition of β-carbonyl esters to β-trifluoromethyl enones and 3-aroyl acrylates in the presence of competing methyl acrylate and the inorganic base. This method provides a facile access to structurally diverse trifluoromethyl and quaternary stereogenic centers with excellent enantioselectivity (up to 99% ee) and good diastereoselectivity (up to 13:1 dr). The addition of the inorganic base (K₃PO₄) does not cause the background racemic reaction and enhances the reactivity by serving as a co-catalyst.