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
KAUST Grant NumberKUS-11-006-02
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AbstractThe 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.
CitationKikushima K, Holder JC, Gatti M, Stoltz BM (2011) 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. Journal of the American Chemical Society 133: 6902–6905. Available: http://dx.doi.org/10.1021/ja200664x.
SponsorsThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. K.K. acknowledges the Japan Society for the Promotion of Science for a postdoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship.
PublisherAmerican Chemical Society (ACS)
PubMed Central IDPMC3087848
CollectionsPublications Acknowledging KAUST Support
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