Evaluating continuous chirality measure as a 3D descriptor in chemoinformatics applied to asymmetric catalysis

Continuous Chirality Measure (CCM) is a computational metric by which to quantify the chirality of a compound. In enantioselective catalysis, prior work has postulated that CCM is correlated to selectivity and can be used to understand which structural features dictate catalyst efficacy. Herein, the...

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Bibliographic Details
Published in:Tetrahedron 2019-03, Vol.75 (13), p.1841-1851
Main Authors: Zahrt, Andrew F., Denmark, Scott E.
Format: Article
Language:English
Subjects:
Continuous chirality measure
Machine learning
Multivariate analysis
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Summary:Continuous Chirality Measure (CCM) is a computational metric by which to quantify the chirality of a compound. In enantioselective catalysis, prior work has postulated that CCM is correlated to selectivity and can be used to understand which structural features dictate catalyst efficacy. Herein, the investigation of CCM as a metric capable of guiding catalyst optimization is explored. Conformer-dependent CCM is also explored. Finally, CCM is used with Sterimol parameters to significantly improve the performance of Random Forest models. [Display omitted]
ISSN:0040-4020
0040-4039
1464-5416
DOI:10.1016/j.tet.2019.02.007