{
  "abstract": "Catalytic stereoselective hydrogenation of unfunctionalized polyenes remains a major challenge because multiple stereogenic centers must be generated in the absence of directing groups. Here we investigate squalene, a flexible hydrocarbon containing six isolated trisubstituted double bonds, as a demanding substrate for assessing stereochemical bias in the complete hydrogenation of an unfunctionalized polyene. Evaluation of Rh- and Ir-based homogeneous catalysts identified one Ir–P,N complex that promotes complete conversion to squalane while inducing a highly non-statistical diastereomeric distribution, reaching up to 90% d.e. The stereochemical outcome was quantified directly by 13C NMR spectroscopy of crude reaction mixtures, without derivatization or chromatographic separation. Buried-volume analysis was used to compare the steric environment of the selective Ir catalyst with representative non-selective systems, providing a qualitative interpretation of the observed behaviour. To our knowledge, this work provides the first catalytic access to stereoregular squalane and establishes a practical NMR-based approach to evaluate stereochemical bias in hydrogenated isoprenoid hydrocarbons.",
  "abstract_shown": true,
  "affiliations": [
    "Dipartimento di Scienze Chimiche, Università di Napoli Federico II 80126 Napoli Italy",
    "DPI P.O. Box 902 5600 AX Eindhoven the Netherlands",
    "Department of Chemistry, University of Florida, Center for Catalysis P.O. Box 117200 Gainesville Florida 32611 USA"
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 6,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Teresa Iovine"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Christian Ehm",
      "orcid": "0000-0002-2538-5141"
    },
    {
      "affs": [
        2,
        1
      ],
      "name": "Umesh I. Kaluarachchige Don"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Vincenzo Busico",
      "orcid": "0000-0001-7079-1651"
    },
    {
      "affs": [
        2,
        1
      ],
      "name": "Adam S. Veige",
      "orcid": "0000-0002-7020-9251"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Roberta Cipullo",
      "orcid": "0000-0003-3846-1999"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/5w772k1264dxc.bib",
  "cited_by": 0,
  "doi": "10.1039/d6ra05192h",
  "fulltext_url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC13548352/",
  "id": "5w772k1264dxc",
  "issns": [
    "2046-2069"
  ],
  "landing_url": "https://doi.org/10.1039/d6ra05192h",
  "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",
      "1604|Asymmetric Hydrogenation and Catalysis"
    ]
  ],
  "openalex": "W7211869420",
  "pdf_url": null,
  "pmcid": "PMC13548352",
  "pmid": "42707489",
  "published": "2026-09-07",
  "publisher": "Royal Society of Chemistry",
  "ris": "https://research.draconitic.com/paper/5w772k1264dxc.ris",
  "sources": [
    {
      "first_seen": "2026-11-01T12:23:32Z",
      "native_id": "PMC13548352",
      "source": "pmc",
      "url": "https://doi.org/10.1039/d6ra05192h"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1604|Asymmetric Hydrogenation and Catalysis",
      "subfield": "inorganic"
    }
  ],
  "title": "Ir/Rh-catalyzed hydrogenation of squalene: access to stereoregular squalane",
  "title_text": "Ir/Rh-catalyzed hydrogenation of squalene: access to stereoregular squalane",
  "type": "peer-reviewed",
  "updated_at": "2026-11-02T12:20:46Z",
  "url": "https://research.draconitic.com/paper/5w772k1264dxc",
  "venue": "RSC Advances",
  "versions": []
}