Detection of Isotopic Atropisomerism Based on ortho -H/D Discrimination.

Authors :: Saito K
Miwa S
Iida A
Fujimoto Y
Caytan E
Roussel C
Kitagawa O
Source :: Organic letters [Org Lett] 2021 Oct 01; Vol. 23 (19), pp. 7492-7496. Date of Electronic Publication: 2021 Sep 13.
Publication Year :: 2021
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.