Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered ?-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters.

ABSTRACT: The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to ?-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared 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.

SUBMITTER: Kikushima K 

PROVIDER: S-EPMC3087848 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature