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Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-12-07 , DOI: 10.3762/bjoc.16.249
Tereza Horáčková , Jan Budka , Vaclav Eigner , Wen-Sheng Chung , Petra Cuřínová , Pavel Lhoták

The introduction of chiral alkyl substituents into the lower rim of calix[4]arene immobilised in the 1,3-alternate conformation led to a system possessing a preorganised ureido cavity hemmed with chiral alkyl units in the near proximity. As shown by the 1H NMR titration experiments, these compounds can be used as receptors for chiral anions in DMSO-d6. The chiral recognition ability can be further strengthened by the introduction of another chiral moiety directly onto the urea N atoms. The systems with double chiral units being located around the binding ureido cavity showed better stereodiscrimination, with the highest selectivity factor being 3.33 (KL/KD) achieved for N-acetyl-ʟ-phenylalaninate. The structures of some receptors were confirmed by single crystal X-ray analysis.

中文翻译:

使用基于杯[4]芳烃的脲基受体以1,3-交替构型进行手性阴离子识别

将手性烷基取代基引入固定在1,3-交替构象的杯[4]芳烃的下边缘中,导致系统具有一个预先组织的脲基腔,该腔在近处具有手性烷基单元。如1 H NMR滴定实验所示,这些化合物可用作DMSO- d 6中手性阴离子的受体。通过将另一个手性部分直接引入到尿素N原子上,可以进一步增强手性识别能力。具有双手性单元的系统位于结合尿素腔周围,表现出更好的立体分辨,最高选择性因子为3.33(K L / K D)获得了N-乙酰基-ʟ-苯丙氨酸盐。通过单晶X射线分析确认了某些受体的结构。
更新日期:2020-12-07
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