Publication date: Jul 07, 2023
Chiral ligands are important components in asymmetric homogeneous catalysis, but their synthesis and screening can be both time-consuming and resource-intensive. Data-driven approaches, in contrast to screening procedures based on intuition, have the potential to reduce the time and resources needed for reaction optimization by more rapidly identifying an ideal catalyst. These approaches, however, are often non-transferable and cannot be applied across different reactions. To overcome this drawback, we introduce a general featurization strategy for bidentate ligands that is coupled with an automated feature selection pipeline and Bayesian ridge regression to perform multivariate linear regression modeling. This approach, which is applicable to any reaction, incorporates electronic, steric, and topological features (rigidity/flexibility, branching, geometry, constitution) and is well-suited for early-stage ligand optimization. Using only a limited number of points per dataset, our workflow capably predicts the enantioselectivity of four metal-catalyzed asymmetric reactions. Uncertainty estimates provided by Bayesian ridge regression permit the use of Bayesian optimization to efficiently explore pools of prospective new ligands. Using this procedure, a new library of 312 chiral bidentate ligands was screened to identify promising ligand candidates for a challenging asymmetric oxy-alkynylation reaction.
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chemiscopify.ipynb
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19.5 KiB | Notebook to generate Chemiscope files |
lit_xyz.tar.gz
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93.3 KiB | xyz literature ligand structures |
csd_xyz.tar.gz
MD5md5:6256d527c7b0a5d379cc93b27e51c07e
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217.3 KiB | xyz CSD ligand structures |
mc_lit.csv
MD5md5:61a8c13d3b8b713ab2ffd39d26ac7285
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402.0 KiB | literature ligand features |
mc_csd.csv
MD5md5:60e4a156d4248d2cd446ac72ee483324
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1.2 MiB | CSD ligand features |
lit_ligs-chemiscope.json.gz
MD5md5:60b33dab6d34ab68a6ca8cb54d6c6dce
Visualize on Chemiscope
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262.0 KiB | literature ligand chemiscope JSON |
csd_ligs-chemiscope.json.gz
MD5md5:303a4c57f0ff537bc1088866733c72a7
Visualize on Chemiscope
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731.7 KiB | CSD ligand chemiscope JSON |
README.md
MD5md5:86b1ace8149bb6a6b0ded8a7d936223c
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594 Bytes | Read me |
2023.107 (version v1) [This version] | Jul 07, 2023 | DOI10.24435/materialscloud:1m-gv |