ArticleJournal of the American Chemical Society2020
Connecting and Analyzing Enantioselective Bifunctional Hydrogen Bond Donor Catalysis Using Data Science Tools.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Accelerating Reaction Discovery through AI-HTE Integration: Nitrene-Mediated C-O Coupling as a Validated Case Study.JACS Au · 2026Article
- Best Practices and Considerations for Applying Multiple Linear Regression in Organic Chemistry Research.The Journal of organic chemistry · 2026Review
- Article
- Bifunctional Catalysis of Aldol Reactions by Foldamer Dihydrazides: Assessment of Conformational Preorganization.Journal of the American Chemical Society · 2025Article
- Studying Noncovalent Interactions in Molecular Systems with Machine Learning.Chemical reviews · 2025Review
- Applying statistical modeling strategies to sparse datasets in synthetic chemistry.Science advances · 2025Review
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- A substrate descriptor based approach for the prediction and understanding of the regioselectivity in caged catalyzed hydroformylation.Faraday discussions · 2023Article
- A deep learning framework for accurate reaction prediction and its application on high-throughput experimentation data.Journal of cheminformatics · 2023Article
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
- OSCAR: an extensive repository of chemically and functionally diverse organocatalysts.Chemical science · 2022Article
- Asymmetric Alkylation of Cyclic Ketones with Dehydroalanine via H-Bond-Directing Enamine Catalysis: Straightforward Access to Enantiopure Unnatural α-Amino Acids.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.Chemical science · 2022Article
- Identifying the true origins of selectivity in chiral phosphoric acid catalyzedChemical science · 2021Article
- Data Science Meets Physical Organic Chemistry.Accounts of chemical research · 2021Article
- Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts.Chemical science · 2021Article
- Linear Regression Model Development for Analysis of Asymmetric Copper-Bisoxazoline Catalysis.ACS catalysis · 2021Article
- Nucleophilicity PredictionThe Journal of organic chemistry · 2021Article
- Interrogation of 2,2'-Bipyrimidines as Low-Potential Two-Electron Electrolytes.Journal of the American Chemical Society · 2021Article
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2 authors.
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Abstract
The generalization of related asymmetric processes in organocatalyzed reactions is an ongoing challenge due to subtle, noncovalent interactions that drive selectivity. The lack of transferability is often met with a largely empirical approach to optimizing catalyst structure and reaction conditions. This has led to the development of diverse structural catalyst motifs and inspired unique design principles in this field. Bifunctional hydrogen bond donor (HBD) catalysis exemplifies this in which a broad collection of enantioselective transformations has been successfully developed. Herein, we describe the use of data science methods to connect catalyst and substrate structural features of an array of reported enantioselective bifunctional HBD catalysis through an iterative statistical modeling process. The computational parameters used to build the correlations are mechanism-specific based on the proposed transition states, which allows for analysis into the noncovalent interactions responsible for asymmetric induction. The resulting statistical models also allow for extrapolation to out-of-sample examples to provide a prediction platform that can be used for future applications of bifunctional hydrogen bond donor catalysis. Finally, this multireaction workflow presents an opportunity to build statistical models unifying various modes of activation relevant to asymmetric organocatalysis.
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