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Enantioselective Iridium-Catalyzed Hydrogenation of 3,4-Disubstituted Isoquinolines

Authors

  • Dr. Lei Shi,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Zhi-Shi Ye,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Liang-Liang Cao,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Ran-Ning Guo,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Yue Hu,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Prof. Yong-Gui Zhou

    Corresponding author
    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
    • State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China)
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  • Financial support from the National Natural Science Foundation of China (21032003 and 21125208) and National Basic Research Program of China (2010CB833300).

Abstract

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Reining in the outliers: An efficient approach for enantioselective hydrogenation of 3,4-disubstituted isoquinolines was successfully developed. When isoquinolines are treated with [Ir(cod)Cl]2/(R)-synphos in the presence of 1-bromo-3-chloro-5,5-dimethyl-hydantoin (BCDMH), the chiral 3,4-disubstituted tetrahydroisoquinoline derivatives are obtained with ee values as high as 96 % (see scheme; cod=1,5-cyclooctadiene).

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