VCD study of alpha-methylbenzyl amine derivatives: detection of the unchanged chiral motif
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Updated: Jun 15, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Christian Merten1, Marc Amkreutz, Andreas Hartwig
1Fraunhofer Institute of Manufacturing Technology and Applied Materials Science (IFAM), Department of Adhesive Bonding Technology and Surfaces, 28359 Bremen, Germany. christian.merten@ifam.fraunhofer.de
Abstract:
Chiral alpha-methylbenzyl amine is a well known and often used chiral auxiliary, e.g., in the resolution of racemates or asymmetric catalysis. In this work, alpha-methylbenzyl amine and its derivatives N,alpha-dimethylbenzyl amine, N,N,alpha-trimethylbenzyl amine, and bis[alpha-methylbenzyl] amine were investigated by vibrational circular dichroism (VCD) spectroscopy and density functional theory (DFT). For all compounds, stable low energy conformers were obtained by the DFT calculations and based on those, the theoretical vibrational absorption (VA) and VCD spectra were calculated and compared with experimental spectra. Hence, the absolute configurations and conformational preferences were determined. A qualitative comparison of all the experimental VCD spectra of the investigated chiral molecules supported by the calculated ones is given which clearly shows similarities between the spectra of the different chiral amines. These can be assigned to vibrations of the unchanged chiral center.
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