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Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)–H Functionalization

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    Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)–H Functionalization
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    • Jun Chen
      Jun Chen
      Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China
      More by Jun Chen
    • Zhan Shi
      Zhan Shi
      Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China
      More by Zhan Shi
    • Ping Lu*
      Ping Lu
      Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China
      *Email: [email protected]
      More by Ping Lu
      Orcidhttps://orcid.org/0000-0002-2259-2700
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    Organic Letters

    Cite this: Org. Lett. 2021, 23, 19, 7359–7363
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    https://doi.org/10.1021/acs.orglett.1c02513
    Published September 10, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C–H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey–Bakshi–Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C–H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.

    Copyright © 2021 American Chemical Society

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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.1c02513.

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    CCDC 2098966–2098967 contain 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. Isaac F. Yu, Jake W. Wilson, John F. Hartwig. Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules. Chemical Reviews 2023, 123 (19) , 11619-11663. https://doi.org/10.1021/acs.chemrev.3c00207
    2. Miho Oga, Yusei Takamatsu, Akihiro Ogura, Ken-ichi Takao. Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(−)-Puraquinonic Acid. The Journal of Organic Chemistry 2022, 87 (13) , 8788-8795. https://doi.org/10.1021/acs.joc.2c00753
    3. Anton Kudashev, Stefania Vergura, Marco Zuccarello, Thomas Bürgi, Olivier Baudoin. Methylene C(sp 3 )−H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products. Angewandte Chemie International Edition 2024, 63 (1) https://doi.org/10.1002/anie.202316103
    4. Anton Kudashev, Stefania Vergura, Marco Zuccarello, Thomas Bürgi, Olivier Baudoin. Methylene C(sp 3 )−H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products. Angewandte Chemie 2024, 136 (1) https://doi.org/10.1002/ange.202316103
    5. Martin Kamlar, Ivana Císařová, Jan Veselý. PCCP‐Catalyzed Synthesis of Tetrasubstituted Allenes Bearing Heteroaromatic Sulfenyl Group**. European Journal of Organic Chemistry 2023, 26 (32) https://doi.org/10.1002/ejoc.202300400
    6. Andrew Y. Hsieh, Ronald S. Haines, Jason B. Harper. The effects of ionic liquids on the ethanolysis of a chloroacenaphthene. Evaluation of the effectiveness of nucleofugality data to predict reaction outcome. RSC Advances 2023, 13 (30) , 21036-21043. https://doi.org/10.1039/D3RA04302A
    7. Li Li, Wei-Sheng Huang, Zheng Xu, Li-Wen Xu. Catalytic asymmetric silicon-carbon bond-forming transformations based on Si-H functionalization. Science China Chemistry 2023, 66 (6) , 1654-1687. https://doi.org/10.1007/s11426-022-1480-y
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    Organic Letters

    Cite this: Org. Lett. 2021, 23, 19, 7359–7363
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.1c02513
    Published September 10, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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