Sun Guang, Zhang Xue, Zheng Zhe, Zhang Zhi-Yuan, Dong Ming, Sessler Jonathan L, Li Chunju
Academy of Interdisciplinary Studies on Intelligent Molecules, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P.R. China.
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States.
J Am Chem Soc. 2024 Sep 25;146(38):26233-26242. doi: 10.1021/jacs.4c07924. Epub 2024 Sep 13.
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, /-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. /-BINOL[2] demonstrated enantioselective recognition toward chiral ammonium salts, with enantioselectivity (/) values reaching up to 13.2, although less favorable separations were seen for other substrates. /-BINOL[2] also displays blue circularly polarized luminescence with a || value of up to 2.2 × 10. The /-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.
高效合成具有高对映选择性识别能力的手性大环化合物仍然是一个挑战。我们通过合成一对手性大环化合物，即/-BINOL[2]，解决了这个问题，通过两步反应序列实现了高达62%的总分离产率。这些大环化合物很容易通过硅胶柱色谱纯化，无需手性分离，从而简化了整个合成过程。/-BINOL[2]对手性铵盐表现出对映选择性识别，对映选择性（/）值高达13.2，尽管对其他底物的分离效果不太理想。/-BINOL[2]还表现出蓝色圆偏振发光，||值高达2.2×10。本研究中的/-BINOL[2]大环化合物作为手性主体具有吸引力，因为它们既表现出对映选择性客体识别，又受益于简洁、高产率的合成。因此，它们可能在手性分离中发挥作用。
