Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation

Abstract The chirality of winding vine-shaped heterobiaryls with molecular asymmetry is recognized by a sugar-based chiral oxidant. Kinetic resolution of (±)-bisbenzoimidazole bearing an olefin moiety takes place with Shi’s asymmetric epoxidation to observe krel value up to ca. 35 affording the corr...

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Autores principales:	Kazuki Maruhashi, Yoichi Okayama, Ryo Inoue, Shiomi Ashida, Yuka Toyomori, Kentaro Okano, Atsunori Mori
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2018
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/c04e0dd87eb9419b8009fd40035080e4
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spelling	oai:doaj.org-article:c04e0dd87eb9419b8009fd40035080e42021-12-02T15:09:06ZChirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation10.1038/s41598-018-19878-x2045-2322https://doaj.org/article/c04e0dd87eb9419b8009fd40035080e42018-01-01T00:00:00Zhttps://doi.org/10.1038/s41598-018-19878-xhttps://doaj.org/toc/2045-2322Abstract The chirality of winding vine-shaped heterobiaryls with molecular asymmetry is recognized by a sugar-based chiral oxidant. Kinetic resolution of (±)-bisbenzoimidazole bearing an olefin moiety takes place with Shi’s asymmetric epoxidation to observe krel value up to ca. 35 affording the corresponding epoxide. The reaction of a (±)-bithiophene derivative also recognized the chirality to give the corresponding epoxide with er of 96:4 at 39% conversion. Dynamic kinetic resolution is found to take place when unsymmetrical biaryl composed of benzoimidazole/thiophene is subjected to Shi’s epoxidation, whose conversion of the racemic substrate exceeds to 50%.Kazuki MaruhashiYoichi OkayamaRyo InoueShiomi AshidaYuka ToyomoriKentaro OkanoAtsunori MoriNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 8, Iss 1, Pp 1-8 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Kazuki Maruhashi Yoichi Okayama Ryo Inoue Shiomi Ashida Yuka Toyomori Kentaro Okano Atsunori Mori Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
description	Abstract The chirality of winding vine-shaped heterobiaryls with molecular asymmetry is recognized by a sugar-based chiral oxidant. Kinetic resolution of (±)-bisbenzoimidazole bearing an olefin moiety takes place with Shi’s asymmetric epoxidation to observe krel value up to ca. 35 affording the corresponding epoxide. The reaction of a (±)-bithiophene derivative also recognized the chirality to give the corresponding epoxide with er of 96:4 at 39% conversion. Dynamic kinetic resolution is found to take place when unsymmetrical biaryl composed of benzoimidazole/thiophene is subjected to Shi’s epoxidation, whose conversion of the racemic substrate exceeds to 50%.
format	article
author	Kazuki Maruhashi Yoichi Okayama Ryo Inoue Shiomi Ashida Yuka Toyomori Kentaro Okano Atsunori Mori
author_facet	Kazuki Maruhashi Yoichi Okayama Ryo Inoue Shiomi Ashida Yuka Toyomori Kentaro Okano Atsunori Mori
author_sort	Kazuki Maruhashi
title	Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title_short	Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title_full	Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title_fullStr	Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title_full_unstemmed	Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title_sort	chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. kinetic and dynamic kinetic resolution by shi’s asymmetric epoxidation
publisher	Nature Portfolio
publishDate	2018
url	https://doaj.org/article/c04e0dd87eb9419b8009fd40035080e4
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Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation

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