Asymmetric Synthesis of Isotopic Atropisomers based on ortho-CH3/ CD3 Discrimination and Their Structural Properties

N-C axially chiral 3-(2-trideuteriomethyl-4,6-dimethylphenyl)-2-ethyl-quinazolin-4-ones and 3-(2-trideuteriomethyl-4,6-dimethylphenyl)-2-(1-phenylpropan-2-yl)quinazolin-4-ones were prepared in high enantio-and diastereomeric purities (98% ee). These quinazolinone derivatives are isotopic atropisomers based on ortho- CH3/CD3 discrimination and were revealed to possess a slight optical rotation and high rotational stability.

Automated summary

High enantiomeric and diastereomeric purities (98% ee) were achieved in the preparation of N-C axially chiral quinazolinone derivatives. These derivatives, characterized by ortho- CH3/CD3 discrimination, display slight optical rotation and high rotational stability.