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Asymmetric Synthesis of Isotopic Atropisomers based on ortho-CH3/CD3Discrimination and Their Structural Properties

Authors :
Miwa, Shota
Senda, Ryunosuke
Saito, Kazuya
Sato, Azusa
Nakamura, Yuko
Kitagawa, Osamu
Source :
The Journal of Organic Chemistry; November 2022, Vol. 87 Issue: 21 p13501-13507, 7p
Publication Year :
2022

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/CD3discrimination and were revealed to possess a slight optical rotation and high rotational stability.

Details

Language :
English
ISSN :
00223263
Volume :
87
Issue :
21
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs60977144
Full Text :
https://doi.org/10.1021/acs.joc.2c02185