{
  "abstract": "Chiral 3-amino-4-methylpiperidines are valuable structural motifs in biologically active molecules, yet their efficient asymmetric synthesis remains challenging. We developed a Rh/JosiPhos-catalyzed asymmetric hydrogenation of tetrasubstituted cyclic enamides that provides direct access to enantioenriched 3-amino-4-methylpiperidines under exceptionally mild conditions with an H₂ balloon at room temperature. A broad range of substrates was well tolerated, affording the corresponding products in up to 96% yield and 99% ee. The catalytic system showed high efficiency, achieving a turnover number of 10 000 on gram scale. The utility of the method was further demonstrated by the preparation of a key intermediate for the formal synthesis of tofacitinib. This practical and scalable protocol provides efficient access to chiral 3-amino-4-methylpiperidines and expands the scope of asymmetric hydrogenation of highly substituted enamides.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology Shenzhen 518055 China lixx7@sustech.edu.cn yincc@sustech.edu.cn zhangxm@sustech.edu.cn."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Qishu Chen"
    },
    {
      "affs": [
        0
      ],
      "name": "Qin Feng"
    },
    {
      "affs": [
        0
      ],
      "name": "Xiuxiu Li"
    },
    {
      "affs": [
        0
      ],
      "name": "Congcong Yin"
    },
    {
      "affs": [
        0
      ],
      "name": "Xumu Zhang",
      "orcid": "0000-0001-5700-0608"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/ehtjdzr6ce23p.bib",
  "cited_by": 0,
  "doi": "10.1039/d6sc05491a",
  "fulltext_url": "https://europepmc.org/articles/PMC13681836",
  "id": "ehtjdzr6ce23p",
  "issns": [
    "2041-6520",
    "2041-6539"
  ],
  "landing_url": "https://europepmc.org/article/MED/42904087",
  "language": "eng",
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1604|Asymmetric Hydrogenation and Catalysis"
    ]
  ],
  "openalex": "W7221813404",
  "pdf_url": "https://europepmc.org/articles/PMC13681836?pdf=render",
  "pmcid": "PMC13681836",
  "pmid": "42904087",
  "published": "2026-10-15",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/ehtjdzr6ce23p.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:19:53Z",
      "native_id": "MED:42904087",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42904087"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1604|Asymmetric Hydrogenation and Catalysis",
      "subfield": "inorganic"
    }
  ],
  "title": "Practical asymmetric hydrogenation of tetrasubstituted cyclic enamides for enantioenriched 3-amino-4-methylpiperidines.",
  "title_text": "Practical asymmetric hydrogenation of tetrasubstituted cyclic enamides for enantioenriched 3-amino-4-methylpiperidines.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:19:53Z",
  "url": "https://research.draconitic.com/paper/ehtjdzr6ce23p",
  "venue": "Chemical science",
  "versions": []
}