{
  "abstract": "A formal ring-expansion reaction of azetidine nitrones has been developed for the synthesis of 5-aminoisoxazolidines. Nucleophilic addition of an amine, alcohol or water to an azetidine nitrone is proposed to initiate azetidine nitrone ring-opening followed by cyclization to the corresponding 5-membered ring. A variety of examples are presented highlighting the scope of the method as well as the differences in stereochemical preference between primary aniline and secondary amine nucleophiles. A two-step, one-pot process is also described for the direct conversion of N-alkenylnitrones to 5-aminoisoxazolidines.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, University of Illinois Chicago, 845 W. Taylor St., MC 111, Chicago, IL, USA, 60607"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 8,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Dylan C. Keane"
    },
    {
      "affs": [
        0
      ],
      "name": "Abdullah S. Alshreimi"
    },
    {
      "affs": [
        0
      ],
      "name": "Laura Alonso"
    },
    {
      "affs": [
        0
      ],
      "name": "Oishik Sarkar"
    },
    {
      "affs": [
        0
      ],
      "name": "Lam Minh Uyen Phan"
    },
    {
      "affs": [
        0
      ],
      "name": "Benjamin Stageberg"
    },
    {
      "affs": [
        0
      ],
      "name": "Donald J. Wink"
    },
    {
      "affs": [
        0
      ],
      "name": "Laura L. Anderson",
      "orcid": "0000-0002-8764-7522"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/cb0etb0djqjq7.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15007888/v2",
  "fulltext_url": null,
  "id": "cb0etb0djqjq7",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007888/v2",
  "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|Synthesis and Reactions of Organic Compounds"
    ]
  ],
  "openalex": "W7213448910",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15007888/v2",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-17",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/cb0etb0djqjq7.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:19Z",
      "native_id": "10.26434/chemrxiv.15007888",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007888/v2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Synthesis and Reactions of Organic Compounds",
      "subfield": "organic"
    }
  ],
  "title": "Synthesis of 5-Aminoisoxazolidines from Azetidine Nitrones via Formal Ring Expansion",
  "title_text": "Synthesis of 5-Aminoisoxazolidines from Azetidine Nitrones via Formal Ring Expansion",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:19Z",
  "url": "https://research.draconitic.com/paper/cb0etb0djqjq7",
  "venue": "ChemRxiv",
  "versions": []
}