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Brønsted Acid Catalyzed Cycloisomerizations of 5,2-Enyne-1-ones: Highly Regioselective Synthesis of 2,3-Dihydro-4H-pyran-4-ones

Authors

  • Dr. Fang Yang,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Ke-Gong Ji,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Shu-Chun Zhao,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Shaukat Ali,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Yu-Ying Ye,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Xue-Yuan Liu,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Prof. Dr. Yong-Min Liang

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
    • State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 931-8912582
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Abstract

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Dual-action catalyst: A Brønsted acid catalyzed regioselective cycloisomerization was found to be highly effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones in a 6-exo-trig manner from the corresponding 5,2-enyne-1-ones. In this reaction, the Brønsted acid acts as a dual catalyst activating both the carbonyl and alkene moieties in a cascade manner (see scheme).

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