Scientific Reports (Jan 2018)

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

  • Kazuki Maruhashi,
  • Yoichi Okayama,
  • Ryo Inoue,
  • Shiomi Ashida,
  • Yuka Toyomori,
  • Kentaro Okano,
  • Atsunori Mori

DOI
https://doi.org/10.1038/s41598-018-19878-x
Journal volume & issue
Vol. 8, no. 1
pp. 1 – 8

Abstract

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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%.