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

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

研究成果: Review article › 査読

3 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	13501-13507
ページ数	7
ジャーナル	Journal of Organic Chemistry
巻	87
号	21
DOI	https://doi.org/10.1021/acs.joc.2c02185
出版ステータス	Published - 2022 11月 4

ASJC Scopus subject areas

有機化学

文献へのアクセス

10.1021/acs.joc.2c02185

他のファイルとリンク

引用スタイル

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

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.",

author = "Shota Miwa and Ryunosuke Senda and Kazuya Saito and Azusa Sato and Yuko Nakamura and Osamu Kitagawa",

note = "Funding Information: This work was partly supported by JSPS KAKENHI Grant Number C 20K06945. Publisher Copyright: {\textcopyright} 2022 by the Author(s).",

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T1 - Asymmetric Synthesis of Isotopic Atropisomers based on ortho-CH3/CD3Discrimination and Their Structural Properties

AU - Miwa, Shota

AU - Senda, Ryunosuke

AU - Saito, Kazuya

AU - Sato, Azusa

AU - Nakamura, Yuko

AU - Kitagawa, Osamu

PY - 2022/11/4

Y1 - 2022/11/4

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AB - 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.

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