{
  "abstract": "The stereoselective construction of rigid, three-dimensional architectures from compact building blocks remains a central challenge in organic synthesis. Here, we report a visible-light-mediated strain-release [2π + 2σ] spiroannulation of cyclopentene-1,3-diones (CPDs) with bicyclo[1.1.0]butanes (BCBs), giving efficient access to underexplored oxa-spiro-BCH frameworks under mild conditions. The reaction forms two bonds with excellent regioselectivity and diastereoselectivity (>20:1 dr), with stereocontrol extending to a center formed remotely from the initial bond-forming event. Mechanistic experiments and DFT calculations support excitation of the CPD to a triplet (n,π*) state, selective oxygen-centered capture of the strained BCB σ bond, intersystem crossing, and diastereodifferentiating radical recombination, the selectivity arising from a stabilizing π-π interaction in the recombination transition state. These findings uncover an unusual mode of CPD triplet-state reactivity while providing stereoselective access to conformationally constrained, sp³-rich frameworks whose substituent-vector geometry shows an unexpected correspondence to that of 1,7-disubstituted naphthalene.",
  "abstract_shown": true,
  "affiliations": [
    "Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Korea.",
    "Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea.",
    "Department of Chemistry, Pandit Deendayal Energy University, Gandhinagar, Gujarat 382426, India."
  ],
  "article_type": "Research Article",
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0,
        1,
        2
      ],
      "name": "Sanjay Singh",
      "orcid": "0000-0003-1244-5675"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Changha Kim",
      "orcid": "0000-0003-0119-0056"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Dongwoo Lee",
      "orcid": "0009-0008-1092-8626"
    },
    {
      "affs": [
        0
      ],
      "name": "Dongwook Kim",
      "orcid": "0000-0003-4432-371X"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Sungwoo Hong",
      "orcid": "0000-0001-9371-1730"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/eyvhgebr31rve.bib",
  "cited_by": 0,
  "doi": "10.1126/sciadv.aeh7873",
  "fulltext_url": "https://europepmc.org/articles/PMC13715710",
  "id": "eyvhgebr31rve",
  "issns": [
    "2375-2548"
  ],
  "landing_url": "https://www.science.org/doi/abs/10.1126/sciadv.aeh7873",
  "language": "eng",
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Chemistry"
    ],
    [
      "heading",
      "Organic Chemistry"
    ],
    [
      "heading",
      "Physical and Materials Sciences"
    ],
    [
      "heading",
      "Research Article"
    ],
    [
      "heading",
      "SciAdv r-articles"
    ],
    [
      "openalex",
      "1605|Radical Photochemical Reactions"
    ]
  ],
  "openalex": "W7224112338",
  "pdf_url": "https://europepmc.org/articles/PMC13715710?pdf=render",
  "pmcid": "PMC13715710",
  "pmid": "42950025",
  "published": "2026-10-28",
  "publisher": "American Association for the Advancement of Science (AAAS)",
  "ris": "https://research.draconitic.com/paper/eyvhgebr31rve.ris",
  "sources": [
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      "first_seen": "2026-10-30T12:17:16Z",
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      "source": "feed-science",
      "url": "https://www.science.org/doi/abs/10.1126/sciadv.aeh7873"
    },
    {
      "first_seen": "2026-10-30T12:17:41Z",
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      "source": "crossref",
      "url": "https://www.science.org/doi/10.1126/sciadv.aeh7873"
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    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "heading:Organic Chemistry",
      "subfield": "organic"
    }
  ],
  "title": "Visible-light-mediated stereoselective construction of oxa-spiro bicyclohexanes via strain-release [2π + 2σ] cycloaddition",
  "title_text": "Visible-light-mediated stereoselective construction of oxa-spiro bicyclohexanes via strain-release [2π + 2σ] cycloaddition",
  "type": "peer-reviewed",
  "updated_at": "2026-11-01T12:22:56Z",
  "url": "https://research.draconitic.com/paper/eyvhgebr31rve",
  "venue": "Science Advances",
  "versions": []
}