TY - JOUR
T1 - Determining the Absolute Configuration of Small Molecules by Diffusion NMR Experiments
AU - Cabral, Tadeu Luiz Gomes
AU - Dal Poggetto, Guilherme
AU - Brussolo da Silva, João Pedro
AU - Nilsson, Mathias
AU - Tormena, Claudio F.
PY - 2024/10/8
Y1 - 2024/10/8
N2 - Enantiomers are ubiquitous in many areas of science, such as pharmaceuticals, agriculture, and food. Nuclear magnetic resonance (NMR) alone is not able to differentiate enantiomers as their spectra are identical. However, these can be distinguished using chiral auxiliaries (such as chiral complexing agents) that form diastereomeric complexes, but absolute identification is still troublesome, usually requiring a chemical reaction with a chiral derivatizing agent. Here, we propose a new method that uses a hybrid mixture of solvating agents in a simple comparison of diffusion NMR experiments, which can discriminate enantiomers in both frequency and diffusion domains, dubbed CHIMERA (CHIral Micelle Enantiomer Resolving Agent). The new method was assessed for twenty-three small chiral molecules using a combination of BINOL and (-)-DMEB, a chiral surfactant, and initial results indicate that absolute configuration can be obtained from a simple experiment.
AB - Enantiomers are ubiquitous in many areas of science, such as pharmaceuticals, agriculture, and food. Nuclear magnetic resonance (NMR) alone is not able to differentiate enantiomers as their spectra are identical. However, these can be distinguished using chiral auxiliaries (such as chiral complexing agents) that form diastereomeric complexes, but absolute identification is still troublesome, usually requiring a chemical reaction with a chiral derivatizing agent. Here, we propose a new method that uses a hybrid mixture of solvating agents in a simple comparison of diffusion NMR experiments, which can discriminate enantiomers in both frequency and diffusion domains, dubbed CHIMERA (CHIral Micelle Enantiomer Resolving Agent). The new method was assessed for twenty-three small chiral molecules using a combination of BINOL and (-)-DMEB, a chiral surfactant, and initial results indicate that absolute configuration can be obtained from a simple experiment.
U2 - 10.1002/anie.202418508
DO - 10.1002/anie.202418508
M3 - Article
SN - 0044-8249
JO - Angewandte Chemie
JF - Angewandte Chemie
M1 - e202418508
ER -