Department of Chemistry, Georgetown University, 37th and O Streets, Washington, D.C. 20057, United States.
J Am Chem Soc. 2020 Mar 4;142(9):4121-4125. doi: 10.1021/jacs.9b13910. Epub 2020 Feb 21.
Quantitative chirality sensing of terpenes and terpenoids exhibiting a single double bond as the only functional group, such as α-pinene, β-pinene and camphene, or two alkene moieties like limonene, valencene, and β-caryophyllene is among the most difficult molecular recognition tasks. In this work, a fast chiroptical sensing method that accomplishes determination of the enantiomeric excess and overall amount of a large variety of terpenes and terpenoids using readily available phosphine derived late transition metal complexes is presented. The terpene coordination is complete within 10 min and coincides with spontaneous induction of strong CD signals at long wavelengths and distinct UV changes which together allow accurate and concentration quantification.
对仅具有一个双键作为官能团的萜类和类萜化合物（如α-蒎烯、β-蒎烯和莰烯），或具有两个烯烃部分的化合物（如柠檬烯、蒈烯和β-石竹烯）进行定量手性感应是最具挑战性的分子识别任务之一。在这项工作中，我们提出了一种快速手性感应方法，该方法使用易得的膦衍生的后过渡金属配合物来测定各种萜类和类萜化合物的对映体过量和总量。萜类化合物的配位在 10 分钟内完成，同时伴随着长波长处强圆二色性（CD）信号的自发诱导和明显的紫外变化，这些变化共同实现了准确的定量和浓度检测。
