{
  "abstract": "Enantioselective trapping of tertiary carbenium ions is often complicated by competing E1 elimination. Here, we show that a chiral oxazaborolidinium ion catalyst promotes ground-state intramolecular proton transfer from a phenolic OH group to an adjacent alkene, generating a catalyst-associated tertiary carbenium ion for enantioselective trapping. This activation mode allows alkenes formed by E1 elimination to regenerate reactive cations during the stereoconvergent conversion of racemic tertiary alcohols. Hydride and carbon trapping afford enantioenriched diarylalkanes and products bearing acyclic all-carbon quaternary stereocenters in up to 99% yield and 99% ee. Experimental and computational studies support competition between direct cation trapping and elimination followed by alkene protonation, with the balance depending on nucleophile reactivity. These findings establish intramolecular alkene protonation as a strategy for incorporating elimination into productive asymmetric catalysis.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "Sungkyunkwan University"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Jin Won Lee"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Hyojae Jung"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Hayoung Song"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Injoo Seo"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Do Hyun Ryu",
      "orcid": "0000-0001-7615-4661"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/08snq83phynak.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15008939/v1",
  "fulltext_url": null,
  "id": "08snq83phynak",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008939/v1",
  "language": null,
  "licence": "CC-BY-NC-ND",
  "licence_label": "CC BY-NC-ND",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7213452589",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15008939/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-16",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/08snq83phynak.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:19Z",
      "native_id": "10.26434/chemrxiv.15008939",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008939/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Intramolecular Alkene Protonation Enables Stereoconvergent Catalysis Through Tertiary Carbenium Ions",
  "title_text": "Intramolecular Alkene Protonation Enables Stereoconvergent Catalysis Through Tertiary Carbenium Ions",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:19Z",
  "url": "https://research.draconitic.com/paper/08snq83phynak",
  "venue": "ChemRxiv",
  "versions": []
}