Development of a palladium-catalyzed enantioselective conjugate addition of arylboronic acids to cyclic conjugate acceptors

Abstract

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addn. of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepd. from Pd(OCOCF_3)_2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.

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