title: Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-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 β-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.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Kotaro
authors.initials: K
authors.lastname: Kikushima
authors.forename: Jeffrey C
authors.initials: JC
authors.lastname: Holder
authors.forename: Michele
authors.initials: M
authors.lastname: Gatti
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D003512:Cyclohexanones; D009942:Organometallic Compounds; D010165:Palladium