{
  "abstract": "Nitrones are reactive dipoles for cycloadditions that have been used for powerful alkene difunctionalization reactions, often stereocontrolled. Despite the wealth of knowledge generated over a half-century of study, reports of N-acyl nitrones are exceedingly rare, with limited options for their access. We report a new diverted Umpolung Amide Synthesis (UmAS) reaction that leads to N-acyl nitrones through an intermolecular carbon–nitrogen bond formation. These nitrones are rare examples of doubly acylated species (C- and N-acyl) that are expected to engage electron-rich alkenes in Type III dipolar cycloadditions. Our findings suggest, unexpectedly, that these species are more fleeting than previously reported, succumbing to a rapid N→O acyl transfer reaction that leads to stable O-acyl oximes.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States"
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Jeffrey S. Benner",
      "orcid": "0009-0008-1383-5302"
    },
    {
      "affs": [
        0
      ],
      "name": "Jeffrey N. Johnston",
      "orcid": "0000-0002-0885-636X"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/5ftven9kxyk16.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.joc.6c01600",
  "fulltext_url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC13711628/",
  "id": "5ftven9kxyk16",
  "issns": [
    "0022-3263",
    "1520-6904"
  ],
  "landing_url": "https://doi.org/10.1021/acs.joc.6c01600",
  "language": "en",
  "licence": "CC-BY-4.0",
  "licence_label": "CC BY 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Article"
    ],
    [
      "openalex",
      "1605|Organic Chemistry Cycloaddition Reactions"
    ]
  ],
  "openalex": "W7220915973",
  "pdf_url": "https://pubs.acs.org/joceah/article-pdf/doi/10.1021/acs.joc.6c01600/68792772/acs.joc.6c01600.pdf",
  "pmcid": "PMC13711628",
  "pmid": "42925078",
  "published": "2026-10-08",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/5ftven9kxyk16.ris",
  "sources": [
    {
      "first_seen": "2026-10-31T12:22:22Z",
      "native_id": "PMC13711628",
      "source": "pmc",
      "url": "https://doi.org/10.1021/acs.joc.6c01600"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organic Chemistry Cycloaddition Reactions",
      "subfield": "organic"
    }
  ],
  "title": "Umpolung Amide Synthesis with Nitrosoalkane Electrophiles: Pursuit of the Elusive N‑Acyl Nitrone for Dipolar Cycloadditions",
  "title_text": "Umpolung Amide Synthesis with Nitrosoalkane Electrophiles: Pursuit of the Elusive N‑Acyl Nitrone for Dipolar Cycloadditions",
  "type": "peer-reviewed",
  "updated_at": "2026-10-31T12:22:22Z",
  "url": "https://research.draconitic.com/paper/5ftven9kxyk16",
  "venue": "The Journal of Organic Chemistry",
  "versions": []
}