{
  "abstract": "We report two Sm-catalyzed reductive transformations of enones. Using catalytic Sm(OTf)3 and Zn0 as the terminal reductant, Wieland–Miescher-type ketones underwent ring contraction to trans-hydrindanes bearing vicinal quaternary stereogenic centers. Under similar conditions but with 2-naphthalenethiol as a hydrogen atom donor, diastereoselective enone reduction outcompeted the ring contraction pathway, furnishing decalin products. The diastereoselectivity of the enone reduction was shown to be controlled primarily by the substrate structure; however, for certain substrates, the thiol structure could be used to improve the diastereoselectivity. Mechanistic investigation by cyclic voltammetry is also reported.",
  "abstract_shown": true,
  "affiliations": [
    "Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering",
    "California Institute of Technology",
    "Department of Chemistry",
    "University of Minnesota"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Nathan C. Friede"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Kristen E. Gardner"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Nhu H. Quach"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Matthew Neurock"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Sarah E. Reisman"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/68myma28xjyea.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010939/v1",
  "fulltext_url": null,
  "id": "68myma28xjyea",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010939/v1",
  "language": null,
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7223291918",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010939/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-23",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/68myma28xjyea.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:26Z",
      "native_id": "10.26434/chemrxiv.15010939",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010939/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Sm-Catalyzed Reductive Transformations of Enones",
  "title_text": "Sm-Catalyzed Reductive Transformations of Enones",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:26Z",
  "url": "https://research.draconitic.com/paper/68myma28xjyea",
  "venue": "ChemRxiv",
  "versions": []
}