{
  "abstract": "We report a straightforward one-step, highly diastereoselective [3 + 2] cycloaddition for the synthesis of cyclopentanones incorporating up to four stereogenic centres. Sulfoxonium ylides are readily available, safe-to-use reagents and were utilised as three-carbon synthons to introduce alkyl, aryl, and heteroatom substituents at the α-positions of the cyclopentanone. A variety of terminal and internal alkenes serve as two-carbon synthons for installation of alkyl, alkenyl, and (hetero)aryl substituents at the β-positions. Depending on the reactant combination, the cycloaddition is best performed either in hexafluoroisopropanol as the reaction solvent or with ZnCl2 as a Lewis acid in trifluoroethanol. Stereochemical analyses of the reaction products using trans- and cis-1,2-disubstituted alkenes support a stepwise cyclisation mechanism. The cyclopentanone products are versatile intermediates to other valuable compound classes such as diastereomerically pure δ-lactones and cyclopentanols.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, Yale University 226 Prospect St. New Haven CT 06520 USA"
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Jihyeon Yeo",
      "orcid": "0009-0005-1891-7858"
    },
    {
      "affs": [
        0
      ],
      "name": "Sebastian M. Krajewski",
      "orcid": "0000-0002-9755-2375"
    },
    {
      "affs": [
        0
      ],
      "name": "Jonathan A. Ellman",
      "orcid": "0000-0001-9320-5512"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/axsrp4rqq4ffh.bib",
  "cited_by": 0,
  "doi": "10.1039/d6sc05806j",
  "fulltext_url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC13591502/",
  "id": "axsrp4rqq4ffh",
  "issns": [
    "2041-6520",
    "2041-6539"
  ],
  "landing_url": "https://doi.org/10.1039/d6sc05806j",
  "language": "en",
  "licence": "CC-BY-3.0",
  "licence_label": "CC BY 3.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/3.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Chemistry"
    ],
    [
      "openalex",
      "1605|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7213878450",
  "pdf_url": "https://pubs.rsc.org/sc/article-pdf/doi/10.1039/d6sc05806j/14741516/d6sc05806j.pdf",
  "pmcid": "PMC13591502",
  "pmid": "42769507",
  "published": "2026-09-21",
  "publisher": "Royal Society of Chemistry",
  "ris": "https://research.draconitic.com/paper/axsrp4rqq4ffh.ris",
  "sources": [
    {
      "first_seen": "2026-11-07T12:23:30Z",
      "native_id": "PMC13591502",
      "source": "pmc",
      "url": "https://doi.org/10.1039/d6sc05806j"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Diastereoselective synthesis of substituted cyclopentanones via [3 + 2] cycloaddition of sulfoxonium ylides with alkenes",
  "title_text": "Diastereoselective synthesis of substituted cyclopentanones via [3 + 2] cycloaddition of sulfoxonium ylides with alkenes",
  "type": "peer-reviewed",
  "updated_at": "2026-11-08T12:20:59Z",
  "url": "https://research.draconitic.com/paper/axsrp4rqq4ffh",
  "venue": "Chemical Science",
  "versions": []
}