Making Glycine Methyl Ester Chiral

Dennis Gerbig, Sarina Desch and Peter R. Schreiner
Chem. Eur. J. 2018, 24, 11904-11907. DOI: 10.1002/chem.201802119

We demonstrate that the simple achiral amino acid glycine as its methyl ester inherits the chiral imprint of methyl lactate upon complexation, resulting in induced vibrational optical activity of the methylene C−H bonds. To mimic conditions of ice on comets that are considered long‐term reaction as well as storage entities for (organic) molecules, we employ the matrix isolation technique in conjunction with vibrational circular dichroism spectroscopy and DFT computations. The observed chirality transfer is likely a key element for the realization of concepts rationalizing chirogenesis, that is, the generation of a chiral imbalance.