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

Shota Miwa; Ryunosuke Senda; Kazuya Saito; Azusa Sato; Yuko Nakamura; Osamu Kitagawa

doi:10.1021/acs.joc.2c02185

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

J Org Chem. 2022 Nov 4;87(21):13501-13507. doi: 10.1021/acs.joc.2c02185. Epub 2022 Oct 10.

Authors

Shota Miwa¹, Ryunosuke Senda¹, Kazuya Saito¹, Azusa Sato², Yuko Nakamura², Osamu Kitagawa¹

Affiliations

¹ 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.
² Division of Basic Sciences, Center for Medical and Nursing Education, Tokyo Women's Medical University, 8-1 Kawada-cho, Shinjuku-ku, Tokyo 162-8666, Japan.

PMID: 36214390
DOI: 10.1021/acs.joc.2c02185

Abstract

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 ortho-CH₃/CD₃ discrimination and were revealed to possess a slight optical rotation and high rotational stability.

Publication types

Review
Research Support, Non-U.S. Gov't

MeSH terms

Stereoisomerism*