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N-Heterocyclic Carbene Catalysis: Enantioselective Formal [2+2] Cycloaddition of Ketenes and N-Sulfinylanilines

Authors

  • Teng-Yue Jian,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Dr. Lin He,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Cen Tang,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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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 (China)
    • Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Financial support from the National Natural Science Foundation of China (No. 20872143, 20932008), the Ministry of Science and Technology of China (2011CB808600), and the Chinese Academy of Sciences is gratefully acknowledged.

Abstract

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Sultam of swing: Both enantiomers of 1,2-thiazetidin-3-one oxides were obtained in very good yields with excellent enantioselectivities when using N-heterocyclic carbene catalysts (see scheme; M.S.=molecular sieves, TBS=tert-butyldimethylsilyl). The products were easily converted into 3-oxo-β-sultams, α-mercapto amides, and β-mercapto amines through oxidation or reduction.

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