Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts

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{
  "metadata": {
    "is_last": true, 
    "version": 1, 
    "title": "Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts", 
    "keywords": [
      "catalysis", 
      "machine learning", 
      "enantioselectivity", 
      "organocatalyst", 
      "MARVEL"
    ], 
    "description": "Hundreds of catalytic methods are developed each year to meet the demand for high-purity chiral compounds. The computational design of enantioselective organocatalysts remains a significant challenge, as catalysts are typically discovered through experimental screening. Recent advances in combining quantum chemical computations and machine learning (ML) hold great potential to propel the next leap forward in asymmetric catalysis. Within the context of quantum chemical machine learning (QML, or atomistic ML), the ML representations used to encode the structure of molecules and evaluate their similarity cannot easily capture the subtle energy differences that govern enantioselectivity. Here, we present a general strategy for improving molecular representations within an atomistic machine learning model to predict the enantiomeric excess of asymmetric propargylation organocatalysts solely from the structure of catalytic cycle intermediates. Mean absolute errors as low as 0.25 kcal mol-1 were achieved in predictions of the activation energy. This strategy opens the door for quickly and accurately predicting higher-selectivity catalysts for any reaction from available structural information.", 
    "license": "Creative Commons Attribution 4.0 International", 
    "references": [
      {
        "comment": "Manuscript under consideration for publication.", 
        "citation": "S. Gallarati, R. Fabregat, R. Laplaza, S. Bhattacharjee, M. D. Wodrich, C. Corminboeuf, Chem. Sci., under consideration.", 
        "type": "Journal reference"
      }
    ], 
    "doi": "10.24435/materialscloud:vp-h5", 
    "conceptrecid": "765", 
    "publication_date": "Mar 05, 2021, 18:06:22", 
    "edited_by": 100, 
    "_oai": {
      "id": "oai:materialscloud.org:766"
    }, 
    "contributors": [
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Gallarati", 
        "givennames": "Simone"
      }, 
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Fabregat", 
        "givennames": "Raimon"
      }, 
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland", 
          "National Center for Competence in Research - Catalysis  (NCCR-Catalysis), Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Laplaza", 
        "givennames": "Rub\u00e9n"
      }, 
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland", 
          "Indian Institute of Science Education and Research, Dr. Homi Bhabha Rd, Ward No. 8, NCL Colony, Pashan, Pune, Maharashtra 4110008, India"
        ], 
        "familyname": "Bhattacharjee", 
        "givennames": "Sinjini"
      }, 
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Wodrich", 
        "givennames": "Matthew"
      }, 
      {
        "affiliations": [
          "Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland", 
          "National Center for Competence in Research - Catalysis  (NCCR-Catalysis), Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland", 
          "National Center for Computational Design and Discovery of Novel Materials (MARVEL), Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL), 1015 Lausanne, Switzerland"
        ], 
        "email": "clemence.corminboeuf@epfl.ch", 
        "familyname": "Corminboeuf", 
        "givennames": "Clemence"
      }
    ], 
    "owner": 341, 
    "license_addendum": null, 
    "mcid": "2021.40", 
    "_files": [
      {
        "size": 2315445, 
        "checksum": "md5:e9de7acb257e7b092ac8e4ab9dc5ca00", 
        "description": "See README.txt", 
        "key": "Propargylation_ML_data.zip"
      }
    ], 
    "id": "766", 
    "status": "published"
  }, 
  "revision": 7, 
  "updated": "2021-12-06T13:34:19.050121+00:00", 
  "created": "2021-03-05T07:47:41.386129+00:00", 
  "id": "766"
}