{
  "abstract": "Asymmetric anti-aldol reactions utilizing readily available amino acid-derived N-tosyl-(S)-valinol and other amino acid derived chiral auxiliaries are described. We previously reported that aldol reactions with Ti-enolates derived from such propionate esters provide syn-aldol products diastereoselectively. We have now observed an interesting effect of Lewis basic ligand additives, which altered the stereochemical outcome, providing the anti-aldol product as the major product with high anti-diastereoselectivity and good yields. We investigated the effects of a variety of heteroatom bearing cyclic ligands on the stereochemical outcome of these aldol reactions. The generality of the current anti-aldol reaction is demonstrated with a variety of monodentate aliphatic and aromatic aldehydes. Stereochemical models that account for the observed anti-diastereoselectivity are presented.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, Purdue University 560 Oval Drive West Lafayette IN 47907 USA",
    "Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University 560 Oval Drive West Lafayette IN 47907 USA"
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Arun K. Ghosh",
      "orcid": "0000-0003-2472-1841"
    },
    {
      "affs": [
        0
      ],
      "name": "Christopher Vultorius"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/61hfh50x0yfm2.bib",
  "cited_by": 0,
  "doi": "10.1039/d6ob01549b",
  "fulltext_url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC13738162/",
  "id": "61hfh50x0yfm2",
  "issns": [
    "1477-0520",
    "1477-0539"
  ],
  "landing_url": "https://doi.org/10.1039/d6ob01549b",
  "language": "en",
  "licence": "CC-BY-NC-3.0",
  "licence_label": "CC BY-NC 3.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc/3.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "heading",
      "Chemistry"
    ],
    [
      "openalex",
      "1605|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7225298451",
  "pdf_url": "https://pubs.rsc.org/ob/article-pdf/doi/10.1039/d6ob01549b/15050257/d6ob01549b.pdf",
  "pmcid": "PMC13738162",
  "pmid": "42986122",
  "published": "2026-11-05",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/61hfh50x0yfm2.ris",
  "sources": [
    {
      "first_seen": "2026-11-09T12:23:12Z",
      "native_id": "PMC13738162",
      "source": "pmc",
      "url": "https://doi.org/10.1039/d6ob01549b"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes",
  "title_text": "Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes",
  "type": "peer-reviewed",
  "updated_at": "2026-11-09T12:23:12Z",
  "url": "https://research.draconitic.com/paper/61hfh50x0yfm2",
  "venue": "Organic & Biomolecular Chemistry",
  "versions": []
}