Detection of Isotopic Atropisomerism Based on <i>ortho</i>-H/D Discrimination

Abstract

Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N–C axial chirality) and a chiral carbon.