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Highly Stereoselective Construction of β,β-Diaryl-α-Branched Ketones by the Chiral Primary Amine-Catalyzed Asymmetric Retro-Claisen Reaction

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2022, 24, 8, 1752-1756
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    Highly Stereoselective Construction of β,β-Diaryl-α-Branched Ketones by the Chiral Primary Amine-Catalyzed Asymmetric Retro-Claisen Reaction
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    • Yanfang Han
      Yanfang Han
      Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
      School of Chemical Science, University of Chinese Academy of Sciences, Beijing 100490, China
      More by Yanfang Han
    • Long Zhang
      Long Zhang
      Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China
      More by Long Zhang
    • Sanzhong Luo*
      Sanzhong Luo
      Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China
      *Email: [email protected]
      More by Sanzhong Luo
      Orcidhttps://orcid.org/0000-0001-8714-4047
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    Organic Letters

    Cite this: Org. Lett. 2022, 24, 8, 1752–1756
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    https://doi.org/10.1021/acs.orglett.2c00435
    Published February 21, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    Highly diastereo- and enantioselective retro-Claisen reaction of β-diketones with o-quinone methides has been developed by chiral primary amine catalysis. This reaction allows for efficient synthesis of chiral β,β-diaryl-α-branched ketones in moderate to good yields with excellent stereoselectivities. The reaction occurs via a tandem sequence of benzylic C–C bond formation, C–C bond cleavage, and stereospecific enamine protonation. This strategy uses o-quinone methides as diaryl precursors and features a broad substrate scope, mild conditions, and a high degree of stereocontrol.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.2c00435.

    • Experimental procedures, compound characterization data, NMR spectra, HPLC chart for products, and crystallographic data for 3bf (PDF)

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    CCDC 2046797 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 7 publications.

    1. Jia-Hui Liu, Xue-Jiao Lv, Yan-Kai Liu. Asymmetric Retro-Claisen Reaction Catalyzed by Chiral Aza-Bisoxazoline–Zn(II) Complex: Enantioselective Synthesis of α-Arylated Ketones. Organic Letters 2023, 25 (10) , 1706-1710. https://doi.org/10.1021/acs.orglett.3c00372
    2. Zhi-Yuan Yi, Lu Xiao, Xin Chang, Xiu-Qin Dong, Chun-Jiang Wang. Iridium-Catalyzed Asymmetric Cascade Allylation/Retro-Claisen Reaction. Journal of the American Chemical Society 2022, 144 (43) , 20025-20034. https://doi.org/10.1021/jacs.2c08811
    3. Durgaiah Chevella, Chiranjeevi Thota, Supriyo Majumder. Amberlyst-15 catalysed retro-Claisen condensation of β-diketones with alcohols: A practical approach to synthesize esters and ketoesters. Molecular Catalysis 2023, 548 , 113408. https://doi.org/10.1016/j.mcat.2023.113408
    4. Durgaiah Chevella, Chiranjeevi Thota, Supriyo Majumder. Zirconium oxychloride hydrate: an efficient and reusable catalyst for retro-Claisen condensation of alcohols with 1,3-diketones. Organic & Biomolecular Chemistry 2023, 21 (18) , 3837-3843. https://doi.org/10.1039/D3OB00116D
    5. Mao Cai, Runze Zhang, Chunming Yang, Sanzhong Luo. Bio‐inspired Small Molecular Catalysis. Chinese Journal of Chemistry 2023, 41 (5) , 548-559. https://doi.org/10.1002/cjoc.202200628
    6. Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α -Tertiary Carbonyl Compounds. Chinese Journal of Organic Chemistry 2023, 43 (3) , 961. https://doi.org/10.6023/cjoc202211045
    7. Yanfang Han, Mingying Shi, Xueling Mi, Sanzhong Luo. Chiral Primary Amine Catalyzed α ‐Arylation of Simple Ketones via Asymmetric Retro‐Claisen Cleavage. Chemistry – A European Journal 2022, 28 (71) https://doi.org/10.1002/chem.202202584
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    Organic Letters

    Cite this: Org. Lett. 2022, 24, 8, 1752–1756
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c00435
    Published February 21, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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