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Angewandte Chemie
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Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self‐Assemblies

Authors: Shcherbakova, Elena G.; Minami, Tsuyoshi; Brega, Valentina; James, Tony D.; Anzenbacher, Pavel;

Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self‐Assemblies

Abstract

AbstractWe report the first fluorescence‐based assay for the rapid determination of the ee value of amines, amino alcohols, and amino acid esters. The method uses the self‐assembly of 2‐formylphenylboronic acid with a chiral diol and a chiral amine or derivatives (of unknown chirality) to produce two diastereomeric iminoboronates that differ in their fluorescence intensity and polarization. The approach allows for the accurate determination of the ee value of chiral amines with errors of just 1–2 %. We believe that this application of orthogonal dynamic covalent self‐assembly in the determination of the enantioselectivity will lead to the development of high‐throughput procedures for the determination of chirality.

Country
United Kingdom
Related Organizations
Keywords

Kinetics, Support Vector Machine, Benzaldehydes, Molecular Conformation, Stereoisomerism, Amines, Amino Acids, Amino Alcohols, Boronic Acids, Fluorescent Dyes

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
100
Top 10%
Top 10%
Top 1%
Green
bronze
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