Chiral Macrocycles for Enantioselective Recognition

作者：Guang Sun, Xue Zhang, Zhe Zheng, Zhiyuan Zhang, Ming Dong, Jonathan L. Sessler, Chunju Li · 发表于：Journal of the American Chemical Society · 年份：2024 · DOI：10.1021/jacs.4c07924 · 被引用次数：88 · 研究领域：Analytical Chemistry and Chromatography、Crystallography and molecular interactions、Molecular Sensors and Ion Detection

The efficient synthesis of chiral macrocycles with highly enantioselective recognition remains a challenge. We have addressed this issue by synthesizing a pair of chiral macrocycles, namely, R / S -BINOL[2], achieving total isolated yields of up to 62% through a two-step reaction sequence. These macrocycles are readily purified by column chromatography over silica gel without the need for chiral separation, thus streamlining the overall synthesis. R / S -BINOL[2] demonstrated enantioselective recognition toward chiral ammonium salts, with enantioselectivity ( K S / K R ) values reaching up to 13.2, although less favorable separations were seen for other substrates. R / S -BINOL[2] also displays blue circularly polarized luminescence with a | g lum | value of up to 2.2 × 10 –3 . The R / S -BINOL[2] macrocycles of this study are attractive as chiral hosts in that they both display enantioselective guest recognition and benefit from a concise, high-yielding synthesis. As such, they may have a role to play in chiral separations.