Effect of Multinuclear Copper/Aluminum Complexes in Highly Asymmetric Conjugate Addition of Trimethylaluminum to Acyclic Enones†
Corresponding Author
Prof. Dr. Kohei Endo
Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
Kohei Endo, Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
Takanori Shibata, Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorDaisuke Hamada
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorSayuri Yakeishi
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Takanori Shibata
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Kohei Endo, Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
Takanori Shibata, Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Kohei Endo
Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
PRESTO (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
Kohei Endo, Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
Takanori Shibata, Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorDaisuke Hamada
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorSayuri Yakeishi
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Takanori Shibata
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Kohei Endo, Department of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192 (Japan)
Takanori Shibata, Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Ohkubo, Shinjuku, Tokyo 169-8555 (Japan)
Search for more papers by this authorThis 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.
Graphical Abstract
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.
Supporting Information
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