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

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 k(rel) value up to ca. 35 affording the correspondi...

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Autores principales: Maruhashi, Kazuki, Okayama, Yoichi, Inoue, Ryo, Ashida, Shiomi, Toyomori, Yuka, Okano, Kentaro, Mori, Atsunori
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5786050/
https://www.ncbi.nlm.nih.gov/pubmed/29374202
http://dx.doi.org/10.1038/s41598-018-19878-x
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author Maruhashi, Kazuki
Okayama, Yoichi
Inoue, Ryo
Ashida, Shiomi
Toyomori, Yuka
Okano, Kentaro
Mori, Atsunori
author_facet Maruhashi, Kazuki
Okayama, Yoichi
Inoue, Ryo
Ashida, Shiomi
Toyomori, Yuka
Okano, Kentaro
Mori, Atsunori
author_sort Maruhashi, Kazuki
collection PubMed
description 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 k(rel) 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%.
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spelling pubmed-57860502018-02-07 Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation Maruhashi, Kazuki Okayama, Yoichi Inoue, Ryo Ashida, Shiomi Toyomori, Yuka Okano, Kentaro Mori, Atsunori Sci Rep Article 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 k(rel) 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%. Nature Publishing Group UK 2018-01-26 /pmc/articles/PMC5786050/ /pubmed/29374202 http://dx.doi.org/10.1038/s41598-018-19878-x Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Maruhashi, Kazuki
Okayama, Yoichi
Inoue, Ryo
Ashida, Shiomi
Toyomori, Yuka
Okano, Kentaro
Mori, Atsunori
Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
title 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_short 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5786050/
https://www.ncbi.nlm.nih.gov/pubmed/29374202
http://dx.doi.org/10.1038/s41598-018-19878-x
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