N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles

Authors

  • Bo Zhang,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (P.R. China), Fax: (+86) 10-82805297 http://sklnbd.bjmu.edu.cn/nj
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  • Peng Feng,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (P.R. China), Fax: (+86) 10-82805297 http://sklnbd.bjmu.edu.cn/nj
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  • Li-Hui Sun,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P.R. China), Fax: (+86) 10-62554449
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  • Dr. Yuxin Cui,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (P.R. China), Fax: (+86) 10-82805297 http://sklnbd.bjmu.edu.cn/nj
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  • Dr. Song Ye,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P.R. China), Fax: (+86) 10-62554449
    • Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P.R. China), Fax: (+86) 10-62554449
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  • Dr. Ning Jiao

    Corresponding author
    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (P.R. China), Fax: (+86) 10-82805297 http://sklnbd.bjmu.edu.cn/nj
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (P.R. China), Fax: (+86) 10-82805297 http://sklnbd.bjmu.edu.cn/nj
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Abstract

original image

In pole position: A simple and efficient approach to spirocyclic γ-lactam oxindoles by the N-heterocyclic carbene catalyzed addition of homoenloate equivalents to N-aryl isatinimines has been developed (see scheme). The use of N-aryl isatinimines as electrophiles in the NHC-catalyzed umpolung reaction of α,β-unsaturated aldehydes is demonstrated for the first time.

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