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

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

Research output: Contribution to journalArticle

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

Fingerprint

Benzoin
selectors
Enantiomers
Silica Gel
Hydrogen Bonding
Organic solvents
Hydrogen
Hydrogen bonds
High Pressure Liquid Chromatography
cavities
enantiomers
silica gel
hydrogen
hydrogen bonds

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

Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity. / Ema, Tadashi; Tanida, Daisuke; Sugita, Kyoko; Sakai, Takashi; Miyazawa, Ken Ichiro; Ohnishi, Atsushi.

In: Organic Letters, Vol. 10, No. 12, 2008, p. 2365-2368.

Research output: Contribution to journalArticle

Ema, T, Tanida, D, Sugita, K, Sakai, T, Miyazawa, KI & Ohnishi, A 2008, 'Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity', Organic Letters, vol. 10, no. 12, pp. 2365-2368. https://doi.org/10.1021/ol800940j
Ema, Tadashi ; Tanida, Daisuke ; Sugita, Kyoko ; Sakai, Takashi ; Miyazawa, Ken Ichiro ; Ohnishi, Atsushi. / Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity. In: Organic Letters. 2008 ; Vol. 10, No. 12. pp. 2365-2368.
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