A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines
Yuka Takeuchi, Mutsumi Kobayashi, Yuuka Gotoh, Mari Ikeda, Yoichi Habata, Tomohiko Shirai, Shunsuke Kuwahara
TL;DR
This paper introduces a new method using a m-quaterphenyl probe and calculations to determine the 3D structure of chiral amines.
Contribution
A novel m-quaterphenyl probe combined with DFT calculations for assigning absolute configurations of amines.
Findings
The m-quaterphenyl probe forms conjugates with chiral amines that show ECCD.
DFT calculations correlate with the CD spectra's sign and intensity.
The method works for amino alcohols, amino acid esters, and secondary amines.
Abstract
We report a method for determining the absolute configurations of chiral amino alcohols, amino acid esters, and secondary amines through the combined use of a m-quaterphenyl probe 1 and theoretical calculations. The probe 1 is covalently attached to chiral amines to form conjugates that exhibit exciton-coupled circular dichroism (ECCD) in the m-quaterphenyl chromophores. The calculated ratios of the P and M conformers, obtained via DFT calculations, show a correlation with both the sign and intensity of the experimentally observed CD spectra.
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Taxonomy
TopicsMolecular spectroscopy and chirality · Analytical Chemistry and Chromatography · Axial and Atropisomeric Chirality Synthesis