Premium
Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self‐Assemblies
Author(s) -
Shcherbakova Elena G.,
Minami Tsuyoshi,
Brega Valentina,
James Tony D.,
Anzenbacher Pavel
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501736
Subject(s) - chirality (physics) , diastereomer , chemistry , enantiomer , amine gas treating , enantiomeric excess , covalent bond , diol , fluorescence , self assembly , organic chemistry , amino acid , combinatorial chemistry , dynamic covalent chemistry , enantioselective synthesis , supramolecular chemistry , catalysis , molecule , biochemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
We 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.