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Highly Efficient Catalytic Asymmetric Sulfa-Michael Addition of Thiols to trans-4,4,4-Trifluorocrotonoylpyrazole

Authors

  • Xiu-Qin Dong,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
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  • Xin Fang,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
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  • Hai-Yan Tao,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
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  • Xiang Zhou,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
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  • Chun-Jiang Wang

    Corresponding author
    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
    2. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
    • College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, Fax: (+86)-27-6875-4067
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Abstract

A new protocol for the efficient construction of chiral trifluoromethylated building blocks was developed via organocatalyzed sulfa-Michael addition of thiols to the cost-efficient trans-trifluorocrotonamide. Introducing the pyrazole moiety is crucial to providing H-bond acceptor sites for better activation and hence affording comparable asymmetric induction with that obtained when employing the expensive cis-4,4,4-trifluorocrotonate as the Michael acceptor.

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