Construction of Enantiomerically Enriched Diazo Compounds Using Diazo Esters as Nucleophiles: Chiral Lewis Base Catalysis

Authors

  • Haibin Mao,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Aijun Lin,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Yan Shi,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Zhijie Mao,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Xuebin Zhu,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Weipeng Li,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Prof. Dr. Hongwen Hu,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Prof. Dr. Yixiang Cheng,

    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
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  • Prof. Dr. Chengjian Zhu

    Corresponding author
    1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai, 200032 (P. R. China)
    • State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China)

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  • We gratefully acknowledge the National Natural Science Foundation of China (21172106, 21074054), the National Science Fund for Talent Training in Basic Science (No. J1103310), the National Basic Research Program of China (2010CB923303), and the Research Fund for the Doctoral Program of Higher Education of China (20120091110010) for their financial support.

Abstract

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Amazing diazo: The title reaction leads to highly functionalized diazo compounds in good yields with excellent enantioselectivities (see scheme; Boc=tert-butoxycarbonyl). The utility of the products was demonstrated by the rapid synthesis of a number of optically pure nitrogen heterocycles. The key to this process was the use of 2,2,2-trifluoroethyl diazoacetate as a superior nucleophilic reagent.

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