{
  "abstract": "Stereogenic carbon loses its stereochemistry when it is converted into planar carbocation. Retention of the chirality is difficult unless static reference chirality is introduced within reactant to change the reactions diastereoselective. Herein we report a rare reaction in which a stereogenic alcohol gives a chiral twisted tricyclic skeleton by acid-mediated dehydrative cyclization. The intermediates are carbocations without any stereogenic centers, and their non-stereogenic conformational features relay the chiral information to the product. The chiral twist is computed to be flexible in the alcohol reactant and initial carbocation intermediate, but it is induced through the reaction steps to acquire thermal robustness. This chirality relay also provides an effective synthetic method for each enantiomer of the product, which is a valuable intrinsically chiral building block.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemical Science and Engineering, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, Japan, 615-8510",
    "Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, Japan, 615-8510",
    "Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Japan, 920-1192",
    "WPI Nano Life Science Institute, Kanazawa University, Kakuma-machi, Kanazawa, Japan, 920-1192"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 7,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Kenichi Kato",
      "orcid": "0000-0001-5348-5521"
    },
    {
      "affs": [
        0
      ],
      "name": "Nagisa Kawabata"
    },
    {
      "affs": [
        1
      ],
      "name": "Yori Kajiwara"
    },
    {
      "affs": [
        2
      ],
      "name": "Tatsuya Nishimura",
      "orcid": "0000-0002-8416-4007"
    },
    {
      "affs": [
        2,
        3
      ],
      "name": "Katsuhiro Maeda",
      "orcid": "0000-0002-5341-8799"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Shunsuke Ohtani",
      "orcid": "0000-0002-8669-1089"
    },
    {
      "affs": [
        0,
        1,
        3
      ],
      "name": "Tomoki Ogoshi",
      "orcid": "0000-0002-4464-0347"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/cbt98q6hm34p5.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010075/v1",
  "fulltext_url": null,
  "id": "cbt98q6hm34p5",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010075/v1",
  "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|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7221000728",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010075/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-08",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/cbt98q6hm34p5.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:22Z",
      "native_id": "10.26434/chemrxiv.15010075",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010075/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Chirality Relay via Non-stereogenic Carbocations: from Stereogenic Alcohol to Twisted Tricyclic Skeleton",
  "title_text": "Chirality Relay via Non-stereogenic Carbocations: from Stereogenic Alcohol to Twisted Tricyclic Skeleton",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:22Z",
  "url": "https://research.draconitic.com/paper/cbt98q6hm34p5",
  "venue": "ChemRxiv",
  "versions": []
}