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Effect of Multinuclear Copper/Aluminum Complexes in Highly Asymmetric Conjugate Addition of Trimethylaluminum to Acyclic Enones

Authors

  • Prof. Dr. Kohei Endo,

    Corresponding author
    1. Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
    2. PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
    • Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
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  • Daisuke Hamada,

    1. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
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  • Sayuri Yakeishi,

    1. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
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  • Prof. Dr. Takanori Shibata

    Corresponding author
    1. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
    • Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
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  • This work was supported by the JST PRESTO program, Grant-in-Aid for Young Scientists (B) from the Japan Society for the Promotion of Science, the Kurata Memorial Hitachi Science and Technology Foundation, and Hokuriku Bank. We thank Ryotaro Takayama (Waseda University) for his experimental assistance.

Abstract

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Al and friends: Asymmetric conjugate addition of Me3Al to β,β-disubstituted α,β-unsaturated ketones in the presence copper and L1 leads to a highly efficient construction of an all-carbon-substituted chiral quaternary center. This result is the first example of an asymmetric conjugate addition of Me3Al to acyclic enones to give a chiral quaternary carbon center with excellent yield and enantioselectivity under mild reaction conditions.

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