N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Nitroalkenes with Oxodienes

Authors

  • Xiang-Yu Chen,

    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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  • 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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  • Prof. 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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Abstract

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NHC catalysis: N-heterocyclic carbenes were found to be efficient catalysts for the unprecedented [4+2] cycloaddition of nitroalkenes and oxodienes, giving the corresponding dihydropyrans in good yield with good diastereoselectivity (see scheme). Deuteration experiment reveals that the reaction is possibly initiated by the addition of N-heterocylic carbene to nitroalkenes.

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