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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 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%.

SUBMITTER: Maruhashi K 

PROVIDER: S-EPMC5786050 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Maruhashi Kazuki K   Okayama Yoichi Y   Inoue Ryo R   Ashida Shiomi S   Toyomori Yuka Y   Okano Kentaro K   Mori Atsunori A  

Scientific reports 20180126 1


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<sub>rel</sub> 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  ...[more]

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