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Direct Asymmetric Hydrosilylation of Indoles: Combined Lewis Base and Brønsted Acid Activation

Authors

  • You-Cai Xiao,

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Dr. Chao Wang,

    1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China)
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  • Yuan Yao,

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Prof. Dr. Jian Sun,

    Corresponding author
    1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China)
    • Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China)
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  • Prof. Dr. Ying-Chun Chen

    Corresponding author
    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
    2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041(China)
    • Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • We are grateful for the financial support from the NSFC (20972101 and 21021001; for J.S.: 20972152 and 91013006), and the National Basic Research Program of China (973 Program, 2010CB833300). We also thank Prof. Xiao-Mei Zhang at the Chengdu Institute of Organic Chemistry for a gift of catalyst 1 c.

Abstract

original image

Quite a pair: The first organocatalytic direct asymmetric reduction of unprotected 1H-indoles to chiral indolines has been developed. The reaction proceeds through the generation of electrophilic indolenium ions by a Brønsted acid, and then chiral Lewis base (1) mediated enantioselective hydride transfer with HSiCl3. A variety of chiral indolines were obtained with moderate to excellent enantioselectivity. MOM=methoxymethyl.

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