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Doubly Stereocontrolled Asymmetric Aza-Henry Reaction with in situ Generation of N-Boc-Imines Catalyzed by Novel Rosin-Derived Amine Thiourea Catalysts

Authors

  • Xianxing Jiang,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong
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    • These authors contributed equally to this work.

  • Yifu Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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    • These authors contributed equally to this work.

  • Lipeng Wu,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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  • Gen Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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  • Xing Liu,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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  • Hailong Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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  • Dan Fu,

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
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  • Rui Wang

    1. State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-8911255
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong
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Abstract

The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Boc-imines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee), and satisfactory diastereoselectivies (anti/syn up to 98:2). Furthermore, these organocatalysts based on rosin have been proved to be the very effective promoters for this catalytic asymmetric process along side the Cinchona alkaloid-derived catalysts.

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