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N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents

Authors

  • Prof. Dr. Changsheng Yao,

    Corresponding author
    1. School of Chemistry and Engineering, Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou, Jiangsu 221116 (P.R. China), Fax: (+86) 516-83500365
    • School of Chemistry and Engineering, Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou, Jiangsu 221116 (P.R. China), Fax: (+86) 516-83500365
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  • Donglin Wang,

    1. School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)
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  • Jun Lu,

    1. School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)
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  • Prof. Dr. Tuanjie Li,

    1. School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)
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  • Weihui Jiao,

    1. School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)
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  • Prof. Chenxia Yu

    1. School of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou Jiangsu 221116 (P.R. China)
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Abstract

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Carbenes ring true: N-Heterocyclic carbene (NHC) catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents, such as 1,3-dicarbonyl compounds, β-enamino ketones, and β-enamino esters through umpolung processes gave functionalized 3,4-dihydropyranones and 3,4-dihydropyridinones (see scheme). The availability of the starting materials, lack of external oxidant, and usefulness of the products make this strategy attractive.

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