Dynamic Covalent Optical Chirality Sensing with a Sterically Encumbered Aminoborane
Dynamic Covalent Optical Chirality Sensing with a Sterically Encumbered Aminoborane
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利用空间位阻氨基硼烷进行动态共价光学手性传感
DOI：
10.1002/chem.202202028
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Wolf, Christian
中科院分区：
文献类型：
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作者：
De los Santos, Zeus A.;Lynch, Ciarán C.;Wolf, Christian
介绍了一种用于单醇、二醇和氨基醇定量立体化学分析的立体负载氨基硼烷传感器。小分子探针具有刚性的邻位取代芳烃支架，具有近似的硼结合位点和三芳胺圆二色性（CD）报告单元，这被证明对观察到的热带信号诱导至关重要。手性靶分子的配位产生强烈的棉花效应和紫外线变化，这些变化很容易与其绝对构型、对映体组成和浓度相关，从而在5%的绝对误差范围内实现全面的立体化学分析。该传感方法成功地应用于小于1毫克的粗不对称反应混合物的无色谱分析，并讨论了该方法与传统方法相比的优点，该方法适用于高通量实验设备和自动化。
A sterically encumbered aminoborane sensor is introduced and used for quantitative stereochemical analysis of monoalcohols, diols and amino alcohols. The small‐molecule probe exhibits a rigid ortho‐substituted arene scaffold with a proximate boron binding site and a triarylamine circular dichroism (CD) reporter unit which proved to be crucial for the observed chiroptical signal induction. Coordination of the chiral target molecule produces strong Cotton effects and UV changes that are readily correlated to its absolute configuration, enantiomeric composition and concentration to achieve comprehensive stereochemical analysis within a 5 % absolute error margin. The sensing method was successfully applied in the chromatography‐free analysis of less than one milligram of a crude asymmetric reaction mixture and the advantages of this chiroptical sensing approach, which is amenable to high‐throughput experimentation equipment and automation, over traditional methods is discussed.