ArticleAngewandte Chemie (International ed. in English)2021
The Size-Accelerated Kinetic Resolution of Secondary Alcohols.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed.
- Size and Polarizability as Design Principles for Stereoselective Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
- Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Noncovalent CH-π and π-π Interactions in Phosphoramidite Palladium(II) Complexes with Strong Conformational Preference.Angewandte Chemie (International ed. in English) · 2021Article
- The Size-Accelerated Kinetic Resolution of Secondary Alcohols.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The factors responsible for the kinetic resolution of alcohols by chiral pyridine derivatives have been elucidated by measurements of relative rates for a set of substrates with systematically growing aromatic side chains using accurate competitive linear regression analysis. Increasing the side chain size from phenyl to pyrenyl results in a rate acceleration of more than 40 for the major enantiomer. Based on this observation a new catalyst with increased steric bulk has been designed that gives enantioselectivity values of up to s=250. Extensive conformational analysis of the relevant transition states indicates that alcohol attack to the more crowded side of the acyl-catalyst intermediate is favoured due to stabilizing CH-π-stacking interactions. Experimental and theoretical results imply that enantioselectivity enhancements result from accelerating the transformation of the major enantiomer through attractive non-covalent interactions (NCIs) rather than retarding the transformation of the minor isomer through repulsive steric forces.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.