Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity

Tadashi Ema, Daisuke Tanida, Kyoko Sugita, Takashi Sakai, Ken Ichiro Miyazawa, Atsushi Ohnishi

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26 Citations (Scopus)

Abstract

(Chemical Equation Presented) Chiral macrocycles with the hydrogen bond donor/acceptor sites in the cavity were synthesized and covalently bonded to silica gel to give chiral stationary phases (CSPs), which showed excellent abilities to resolve various chiral compounds, such as benzoin and Co(acac) 3, in HPLC. Various organic solvents could be used as the mobile phase to optimize the resolution efficiency of CSPs, and in some cases, even MeCN, MeOH, and CO2 could be used for the complete resolution of enantiomers.

Original languageEnglish
Pages (from-to)2365-2368
Number of pages4
JournalOrganic Letters
Volume10
Issue number12
DOIs
Publication statusPublished - 2008

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Ema, T., Tanida, D., Sugita, K., Sakai, T., Miyazawa, K. I., & Ohnishi, A. (2008). Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity. Organic Letters, 10(12), 2365-2368. https://doi.org/10.1021/ol800940j