ACS Publications. Most Trusted. Most Cited. Most Read
Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-Naphthols

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2024, 26, 30, 6390-6395
    Letter

    Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-Naphthols
    Click to copy article linkArticle link copied!

    • Chen-Ying Hou
      Chen-Ying Hou
      State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Chen-Ying Hou
    • Chun Yang
      Chun Yang
      State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Chun Yang
    • Yin Tian*
      Yin Tian
      State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
      *Email: [email protected]
      More by Yin Tian
      Orcidhttps://orcid.org/0000-0001-7039-0479
    • Ming-Sheng Xie*
      Ming-Sheng Xie
      State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      *Email: [email protected]
      More by Ming-Sheng Xie
      Orcidhttps://orcid.org/0000-0003-4113-2168
    • Hai-Ming Guo*
      Hai-Ming Guo
      State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      *Email: [email protected]
      More by Hai-Ming Guo
      Orcidhttps://orcid.org/0000-0003-0629-4524
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2024, 26, 30, 6390–6395
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c02156
    Published July 23, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    An achiral counteranion-induced reversal of enantioselectivity in Ni(II)-catalyzed Friedel–Crafts alkylation/annulation of 2-naphthols with β,γ-unsaturated α-keto esters was achieved. Using imidazolidine pyrroloimidazolone pyridine as the ligand and Ni(acac)2 as the Lewis acid, diverse naphthopyran derivatives were obtained in good yields (up to 94% yield) and high enantioselectivities (up to 99% ee). In the presence of Ni(OTf)2 as the Lewis acid, a series of chiral naphthopyran derivatives were obtained in good yields and with a controlled switch in stereoselectivity. DFT calculations reveal that the achiral counteranions regulate H-bonding interactions between counteranions with the N–H of the ligand and the O–H of 2-naphthol.

    Copyright © 2024 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c02156.

    • Experimental procedures, characterization data, X-ray crystallographic data, DFT calculation, and copy of NMR and HPLC spectra (PDF)

    Accession Codes

    CCDC 2311917, 2360442, and 2361236 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.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article has not yet been cited by other publications.

    Download PDF
    Go to Organic Letters
    Get e-Alerts
    Get e-Alerts

    Organic Letters

    Cite this: Org. Lett. 2024, 26, 30, 6390–6395
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c02156
    Published July 23, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

    Article Views

    770

    Altmetric

    -

    Citations

    -
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.