Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to 2-Nitrostyrenes by tert-Butanesulfinylphosphine Ligand

Authors

  • Feng Lang,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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    • These two authors contributed equally to this work.

  • Guihua Chen,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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    • These two authors contributed equally to this work.

  • Dr. Liangchun Li,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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  • Junwei Xing,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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  • Fuzhong Han,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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  • Linfeng Cun,

    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; Graduate School of Chinese Academy of Sciences, Beijing, 100049 (P.R. China)
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  • Prof. Dr. Jian Liao

    Corresponding author
    1. Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
    • Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (P.R. China), Fax: (+86) 28-8522-9250
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Abstract

original image

Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivities (up to 98 % ee) by using tert-butanesulfinylphosphine as a ligand (see scheme). Based on this method, (R)-cherylline was synthesized in 70 % overall yield.

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