Determination of enantiomeric excess in amine derivatives with molecular self-assemblies

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

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)
206 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)7130-7133
JournalAngewandte Chemie-International Edition
Volume54
Issue number24
Early online date21 May 2015
DOIs
Publication statusPublished - 8 Jun 2015

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