ArticleAngewandte Chemie (International ed. in English)2017
Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- 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
- Feed-Forward Neural Network for Predicting Enantioselectivity of the Asymmetric Negishi Reaction.ACS central science · 2023Article
- Noncovalent Stabilization of Radical Intermediates in the Enantioselective Hydroamination of Alkenes with Sulfonamides.Journal of the American Chemical Society · 2022Article
- Data Science Meets Physical Organic Chemistry.Accounts of chemical research · 2021Article
- Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System.Journal of the American Chemical Society · 2021Article
- Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.Journal of the American Chemical Society · 2020Article
- Strategies for remote enantiocontrol in chiral gold(iii) complexes applied to catalytic enantioselective γ,δ-Diels-Alder reactions.Chemical science · 2020Article
- Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.Chemical science · 2019Article
- Disulfonimides versus Phosphoric Acids in Brønsted Acid Catalysis: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Reactivity.The Journal of organic chemistry · 2019Article
- Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.Chemical science · 2018Article
- Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.Angewandte Chemie (International ed. in English) · 2018Article
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Abstract
The study of the oxidative amination of tetrahydroisoquinolines under chiral-anion phase-transfer (CAPT) catalysis by multidimensional correlation analysis (MCA) is revisited. The parameterization of the transition states (TSs) for the uncatalyzed reaction, the introduction of conformational descriptors, and the use of computed interaction energies and distances as parameters allowed access to a considerably simplified mathematical correlation of substrate and catalyst structure to enantioselectivity. The equation obtained is suggestive of key interactions occurring at the TS. Specifically, the CAPT catalyst is proposed to coordinate the intermediate iminium cation by P=O⋅⋅⋅H-O hydrogen-bonding and N⋅⋅⋅H-C electrostatic interactions. The conformational freedom of the benzyl substituent of the substrate was also found to be important in providing an efficient mode of molecular recognition.
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