Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures
Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures
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DOI：
10.1038/s41467-018-07695-9
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发表时间：
2018-12
影响因子：
16.6
通讯作者：
F. Y. Thanzeel;Kaluvu Balaraman;C. Wolf
中科院分区：
文献类型：
--
作者：
F. Y. Thanzeel;Kaluvu Balaraman;C. Wolf
点击反应已经成为一种强大的合成工具，在健康和材料科学中有着独特的应用。尽管利用动态共价化学、金属配位或超分子组装原理的光学传感器取得了进展，但复杂混合物的定量分析仍然具有挑战性。在这里，我们报告了一种容易获得的香豆素共轭受体用于手性点击手性传感几个化合物类的绝对构型、浓度和对映体过量。该方法具有适用范围广、固定速度快、不产生副产物或在可逆的底物结合过程中经常遇到复杂的平衡、良好的溶剂兼容性、耐空气和水等特点。通过对非外消旋单胺样品和粗品不对称亚胺加氢混合物的综合分析，证明了该方法的坚固性和实用性。点击化学传感解决了越来越重要的时间效率、成本、劳动力和化学可持续性方面的问题，并简化了mg规模的不对称反应开发。
Click reactions have become powerful synthetic tools with unique applications in the health and materials sciences. Despite the progress with optical sensors that exploit the principles of dynamic covalent chemistry, metal coordination or supramolecular assemblies, quantitative analysis of complex mixtures remains challenging. Herein, we report the use of a readily available coumarin conjugate acceptor for chiroptical click chirality sensing of the absolute configuration, concentration and enantiomeric excess of several compound classes. This method has several attractive features, including wide scope, fast substrate fixation without by-product formation or complicate equilibria often encountered in reversible substrate binding, excellent solvent compatibility, and tolerance of air and water. The ruggedness and practicality of this approach are demonstrated by comprehensive analysis of nonracemic monoamine samples and crude asymmetric imine hydrogenation mixtures without work-up. Click chemosensing addresses increasingly important time efficiency, cost, labor and chemical sustainability aspects and streamlines asymmetric reaction development at the mg scale.