Enantioselective Intramolecular Crossed Rauhut–Currier Reactions through Cooperative Nucleophilic Activation and Hydrogen-Bonding Catalysis: Scope and Mechanistic Insight

Authors

  • Xu-Fan Wang,

    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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  • Liang Peng,

    1. Center for Computational Quantum Chemistry, South China Normal University, West 55 Zhongshan Road, Guangzhou, Guangdong 510009 (P.R. China), Fax: (+86) 20-3931-0544
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  • Jing An,

    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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  • Chao Li,

    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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  • Qing-Qing Yang,

    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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  • Liang-Qiu Lu,

    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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  • Prof. Dr. Feng-Long Gu,

    Corresponding author
    1. Center for Computational Quantum Chemistry, South China Normal University, West 55 Zhongshan Road, Guangzhou, Guangdong 510009 (P.R. China), Fax: (+86) 20-3931-0544
    • Center for Computational Quantum Chemistry, South China Normal University, West 55 Zhongshan Road, Guangzhou, Guangdong 510009 (P.R. China), Fax: (+86) 20-3931-0544
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  • Prof. Dr. Wen-Jing Xiao

    Corresponding author
    1. Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
    • Key laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China), Fax: (+86) 27-6786-2041
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Abstract

A highly efficient and enantioselective intramolecular crossed Rauhut–Currier (RC) reaction of nitroolefins with tethered enonates has been developed through cooperative nucleophilic activation and a hydrogen-bonding catalytic strategy (≤98 % ee and 98 % yield). The reaction features simple experimental procedures and is completely chemoselective and atom-economic in character. The potential synthetic applications have been demonstrated by the conversion of the RC reaction products into biologically and pharmaceutically valuable compounds with highly diastereoselectivity. In addition, computational investigations were employed to support the proposed mechanism and to obtain a good understanding of the origin of the stereoselectivity in RC reactions.

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