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Chiral Brønsted Acid-Promoted Enantioselective Desymmetrization in an Intramolecular Schmidt Reaction of Symmetric Azido 1,3-Hexanediones: Asymmetric Synthesis of Azaquaternary Pyrroloazepine Skeletons

Authors

  • Ming Yang,

    1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557
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  • Dr. Yu-Ming Zhao,

    1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557
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  • Dr. Shu-Yu Zhang,

    1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557
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  • Prof. Dr. Yong-Qiang Tu,

    Corresponding author
    1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557
    • Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557

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  • Prof. Dr. Fu-Min Zhang

    Corresponding author
    1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557
    • Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8915557

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Abstract

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The enantioselective desymmetrization of 2-substituted-2-azidopropyl 1,3-hexanediones through an asymmetric intramolecular Schmidt reaction using a chiral Brønsted acid has been developed for the first time. Synthetically interesting pyrroloazepine skeletons with an azaquaternary stereogenic center with up to 59 % ee are accessed effectively (see scheme; R=H, alkyl, or aryl).

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