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...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2018-01-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-018-19878-x |
| _version_ | 1818996564026195968 |
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| 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 |
| collection | DOAJ |
| 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%. |
| first_indexed | 2024-12-20T21:31:44Z |
| format | Article |
| id | doaj.art-c04e0dd87eb9419b8009fd40035080e4 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-12-20T21:31:44Z |
| publishDate | 2018-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-c04e0dd87eb9419b8009fd40035080e42022-12-21T19:26:02ZengNature PortfolioScientific Reports2045-23222018-01-01811810.1038/s41598-018-19878-xChirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidationKazuki Maruhashi0Yoichi Okayama1Ryo Inoue2Shiomi Ashida3Yuka Toyomori4Kentaro Okano5Atsunori Mori6Department of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityDepartment of Chemical Science and Engineering, Kobe UniversityAbstract 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%.https://doi.org/10.1038/s41598-018-19878-x |
| spellingShingle | 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 Scientific Reports |
| 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 |
| url | https://doi.org/10.1038/s41598-018-19878-x |
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