The first enantioselective palladium-catalyzed, asymmetric construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to cyclic, �-substituted enones is reported. A wide range of arylboronic acids and cyclic enones are reacted utilizing a catalyst prepared from palladium(II) trifluoroacetate and a chiral pyridinooxazoline ligand to yield enantioenriched products bearing benzylic stereocenters. Recently, this methodology has been expanded to support the reaction of heterocyclic chromone and 4-quinolone conjugate acceptors. Notably, this transformation is insensitive to air or moisture, providing a practical and operationally simple method of synthesizing enantioenriched  stereocenters. The application of this reaction toward the total syntheses of members of the taiwaniaquinone sesquiterpenoid family of natural products is discussed.

Development and application of a palladium-catalyzed enantioselective conjugate addition

248th National Meeting (2014)

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