A Highly Efficient Synthesis of Optically Active Ferrocenylethylamines via Hydride Reduction of Chiral Ferrocenylketimines

Authors

  • Hengyu Qian,

    1. Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China
    2. Henan Key Laboratory of Surface & Interface Science, School of Material & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou, Henan 450002, China
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  • Shihai Yan,

    1. Lab of Biofuel, Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, Shandong 266101, China
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  • Xiuling Cui,

    Corresponding author
    1. Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China
    • Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: 0086-0371-67767753; Fax: 0086-0371-67767753
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  • Chao Pi,

    1. Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China
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  • Cheng Liu,

    1. Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China
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  • Yangjie Wu

    Corresponding author
    1. Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China
    • Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: 0086-0371-67767753; Fax: 0086-0371-67767753
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Abstract

Due to using (R)- or (S)-α-methylbenzylamine as a chiral auxiliary, and low-temperature regime for reduction of the intermediate ferrocenyl-mono- or 1,1′-bis-ketimines, the corresponding secondary mono- or 1,1′-bis-amines were prepared with high diastereoselectivity. Removal of the α-methylbenzyl group afforded the optically active primary mono- and bis-ferrocenylethylamines in high yields. The absolute configuration of (R,R)-3a and (S,S)-3b was determined by X-ray single crystal diffraction.

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