{
  "source": "ORD Dataset Wishlist",
  "snapshot_date": "2026-09-25",
  "ord_wishlist_status_at_snapshot": "Available",
  "ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570083",
  "ord_data_issue": null,
  "title": "Automated, Accelerated Nanoscale Synthesis of Iminopyrrolidines",
  "doi": "10.1002/anie.202000887",
  "journal": "Angewandte Chemie International Edition",
  "publication_date": "2020-02-12",
  "authors": [
    "Angelina Osipyan",
    "Shabnam Shaabani",
    "Robert Warmerdam",
    "Svitlana Valentinovna Shishkina",
    "Harry Böltz",
    "Alexander S. S. Dömling"
  ],
  "article_open_access": {
    "status": "hybrid",
    "license": "cc-by-nc-nd"
  },
  "dataset_size_estimate": null,
  "experiment_type": null,
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "plate_images_or_heatmaps",
  "smiles_in_source": "no",
  "needs_author_contact": true,
  "data_locations": [
    {
      "url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC7383484/",
      "what": "Full text and SI PDF (ANIE-59-12423-s001.pdf): randomized plate design (p. S5), MS classification (p. S43, Fig. S3), plate results (pp. S91-S92), mmol resynthesis",
      "license": "CC BY-NC-ND 4.0 (article, per PMC/Crossref); SI licence not separately stated"
    },
    {
      "url": "https://doi.org/10.1002/anie.202000887",
      "what": "Angewandte Chemie version of record and SI",
      "license": "CC BY-NC-ND 4.0 (article)"
    }
  ],
  "notes": "Source: Osipyan et al., Angew. Chem. Int. Ed. 2020, doi:10.1002/anie.202000887 (open access, CC BY-NC-ND 4.0; PMC7383484). Chemistry: an Ugi-type multicomponent reaction of L-glutamine with oxo components and isocyanides that gives iminopyrrolidine-2-carboxylic acid derivatives. 1152 reactions were run at nanoscale (660 nL per well, 0.125 M) in three 384-well plates, using I-DOT dispensing with building blocks combined at random. Outcomes were classified by direct-injection MS into three classes: major product peak, product peak present but not major, or no product. They are shown as colour-coded plate maps. Twelve compounds were resynthesized at mmol scale with isolated yields. Curation needs a per-well mapping of building blocks to outcomes. If the SI does not tabulate it, the raw plate data must be obtained from the authors. The mmol-scale resynthesis (12 reactions, isolated yields) can be curated from the SI alone as a small separate dataset.",
  "verification_caveats": "Outcomes are qualitative (3-class MS detection), not yields; the ORD encoding needs a product-detection or qualitative outcome. Randomized well layout makes image-based transcription error-prone. Two wells were flagged for reagent-transfer failure. Stereochemistry (Gln stereocentre retention, diastereomers from prochiral ketones) must be encoded carefully. Likely two datasets (nanoscale plates, mmol resynthesis)."
}