Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

Kazuya Saito; Shota Miwa; Asumi Iida; Yuuki Fujimoto; Elsa Caytan; Christian Roussel; Osamu Kitagawa

doi:10.1021/acs.orglett.1c02723

Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

Kazuya Saito, Shota Miwa, Asumi Iida, Yuuki Fujimoto, Elsa Caytan, Christian Roussel, Osamu Kitagawa

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.

Original language	English
Pages (from-to)	7492-7496
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.1c02723
Publication status	Published - 2021 Oct 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c02723

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title = "Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination",

abstract = "Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.",

author = "Kazuya Saito and Shota Miwa and Asumi Iida and Yuuki Fujimoto and Elsa Caytan and Christian Roussel and Osamu Kitagawa",

note = "Funding Information: We thank the Daicel Corporation for the support of the chiral HPLC separation attempts of rac- 4 . This work was partially supported by JSPS KAKENHI (C 20K06945). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c02723",

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T1 - Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

AU - Saito, Kazuya

AU - Miwa, Shota

AU - Iida, Asumi

AU - Fujimoto, Yuuki

AU - Caytan, Elsa

AU - Roussel, Christian

AU - Kitagawa, Osamu

N1 - Funding Information: We thank the Daicel Corporation for the support of the chiral HPLC separation attempts of rac- 4 . This work was partially supported by JSPS KAKENHI (C 20K06945). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.

AB - Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.

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EP - 7496

JO - Organic Letters

JF - Organic Letters

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ER -

Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

Abstract

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