Asymmetric Synthesis of Isotopic Atropisomers based on -CH/CD Discrimination and Their Structural Properties.

J Org Chem

Department of Applied Chemistry (Japanese Association of Bio-intelligence for Well-being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.

Published: November 2022

N-C axially chiral 3-(2-trideuteriomethyl-4,6-dimethylphenyl)-2-ethylquinazolin-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 -CH/CD discrimination and were revealed to possess a slight optical rotation and high rotational stability.

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http://dx.doi.org/10.1021/acs.joc.2c02185DOI Listing

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