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<p>The low-cost and facile synthesis of chiral macrocyclic hosts that exhibit exceptional enantioselectivity in aqueous media remains a challenge. In this study, we successfully synthesize a pair of enantiopure water-soluble binaphthol macrocycles, namely <i>exo-R/S</i>-BINOL[2]-CAs, without requiring chiral separation. These macrocycles demonstrated enantioselective recognition towards water-soluble chiral ammonium salts, with an enantioselectivity (<i>K</i><sub><i>S</i></sub>/<i>K</i><sub><i>R</i></sub>) up to 14.4. Furthermore, the neutral forms of the macrocycles are effectively employed as a chiral stationary phase (CSP) in high performance liquid chromatography for chiral separation. This CSP effectively separates 26 racemic mixtures, including several commercial chiral drugs, demonstrating its excellent versatility in enantioseparation. The developed chiral macrocycles offer a compelling combination of economical streamlined synthesis, enantioselective recognition in aqueous media, and versatile chiral separation capabilities. They represent promising supramolecular tools for advancing modern chiral science and separation technologies.</p>

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Synthesis of chiral macrocyclic hosts for enantioselective recognition in water and versatile enantioseparation

  • 期刊论文

  • 发表日期：

    2026年2月27日

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  • Yuan Li,
  • Guang Sun,
  • Zhe Zheng,
  • Zhi-Yuan Zhang,
  • Xiaofei Ma,
  • Xue Zhang,
  • Yue-Yi Zhang,
  • Wen-Ting Wu,
  • Yao-Hua Liu,
  • Ming Dong,
  • Chunju Li,
  • Yin Xiao

摘要

The low-cost and facile synthesis of chiral macrocyclic hosts that exhibit exceptional enantioselectivity in aqueous media remains a challenge. In this study, we successfully synthesize a pair of enantiopure water-soluble binaphthol macrocycles, namely exo-R/S-BINOL[2]-CAs, without requiring chiral separation. These macrocycles demonstrated enantioselective recognition towards water-soluble chiral ammonium salts, with an enantioselectivity (KS/KR) up to 14.4. Furthermore, the neutral forms of the macrocycles are effectively employed as a chiral stationary phase (CSP) in high performance liquid chromatography for chiral separation. This CSP effectively separates 26 racemic mixtures, including several commercial chiral drugs, demonstrating its excellent versatility in enantioseparation. The developed chiral macrocycles offer a compelling combination of economical streamlined synthesis, enantioselective recognition in aqueous media, and versatile chiral separation capabilities. They represent promising supramolecular tools for advancing modern chiral science and separation technologies.