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 (KPO) does not cause the background racemic reaction and enhances the reactivity by serving as a co-catalyst.
A novel phosphine-catalyzed [3 + 2] cycloaddition of α-diazoacetates and β-trifluoromethyl enones has been developed that provides facile access to multisubstituted 4-(trifluoromethyl)pyrazolines in good to excellent yields at room temperature. In addition, a tandem [3 + 2] cycloaddition/Michael addition is also presented.
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