Hydrogen-Bond-Promoted Palladium Catalysis: Allylic Alkylation of Indoles with Unsymmetrical 1,3-Disubstituted Allyl Acetates Using Chiral Bis(sulfoxide) Phosphine Ligands

Authors

  • Dr. Le Du,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
    3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (China)
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  • Prof. Dr. Peng Cao,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
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  • Dr. Junwei Xing,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
    3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (China)
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  • Yazhou Lou,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
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  • Liyin Jiang,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
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  • Dr. Liangchun Li,

    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
    3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (China)
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  • Prof. Dr. Jian Liao

    Corresponding author
    1. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
    3. College of Chemical Engineering, Sichuan University (China)
    • Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China)
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  • We thank the NSFC (No. 21272226, 21202160 and 21072186), West-Light Foundation of CAS, Chengdu Institute of Biology of CAS (Y0B1051100), the Major State Basic Research Development Program (973 program, 2010CB833300) for financial support and Prof. Zhanbin Wei (Xiamen University) for assistance with crystal structure analysis.

Abstract

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A DYKAT die hard: A new class of chiral BiSO-P ligands were effective for an unprecedented palladium-catalyzed asymmetric allylic alkylation of indoles with the racemic title acetates through a dynamic kinetic asymmetric transformation (DYKAT). The hydrogen bond formed between the sulfinyl group of the ligand and NH of indole plays an important role in the reaction.

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