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Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers

Authors

  • Wen-Dao Chu,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Le-Fen Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Xu Bao,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Xian-He Zhao,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Chao Zeng,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Ji-Yuan Du,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Guo-Biao Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Fang-Xin Wang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Xiao-Yan Ma,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
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  • Prof. Dr. Chun-An Fan

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)
    2. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Lu, Beijing 100191 (China)
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China)

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  • This research was supported by the 973 Program of MOST (2010CB833200), NSFC (21290180, 21072082), the Fok Ying Tung Education Foundation (121015), NCET (NCET-08-0254), PCSIRT (IRT1138), the Major New-Drug-Development Project of MOST (2012ZX09201101-003), FRFCU (lzujbky-2012-k39 and lzujbky-2013-ct02), and the 111 Project of MOE (111-2-17).

Abstract

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It′s just a phase: The title reaction sequence of para-quinone methides (p-QMs) has been developed with malonates under phase-transfer catalysis. The reaction also offers an alternative route to asymmetric construction of diarylmethine stereocenters in excellent enantioselectivities and high yields.

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