Memory of chirality in a room temperature flow electrochemical reactor.
Memory of chirality in a room temperature flow electrochemical reactor.
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DOI：
10.1038/s41598-020-73957-6
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发表时间：
2020-10-06
影响因子：
4.6
通讯作者：
Ahmed N
中科院分区：
文献类型：
--
作者：
Hardwick T;Cicala R;Wirth T;Ahmed N
手性化合物由于具有多种生物活性而引起了制药工业的极大兴趣。同时，“手性记忆”的概念已被证明是不对称合成中的有力工具，而流动化学作为一种新的使能技术已经开始崛起，以增加现代化学家可用的不断增加的技术库。在这里，我们采用了一种新的简单的电化学微反应器的设计，在室温下连续流中氧化的l-脯氨酸衍生物。与分批相比，通过微流反应器的有机电合成是有利的，因为它们允许更短的反应时间、优化和放大、更安全的工作环境和高选择性（例如减少过氧化）。流动电化学反应器还提供高的表面积与体积比，并且由于非常短的电极间距离而赋予排除支持电解质的可能性。通过对霍费尔型电化学氧化反应在室温下间歇和流动的比较，我们得出结论，连续流动电解是优于间歇，产生良好的产率（71%）和较高的对映体过量（64%）上级。这些结果表明，连续流动有可能作为一种新的使能技术的不对称合成，以取代传统的间歇电化学过程的某些方面。
Chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an l-proline derivative at room temperature in continuous flow. Compared to batch, organic electrosynthesis via microflow reactors are advantageous because they allow shorter reaction times, optimization and scale up, safer working environments, and high selectivities (e.g. reduce overoxidation). Flow electrochemical reactors also provide high surface-to-volume ratios and impart the possibility of excluding the supporting electrolyte due to a very short interelectrode distance. By the comparison of Hofer Moest type electrochemical oxidations at room temperature in batch and flow, we conclude that continuous flow electrolysis is superior to batch, producing a good yield (71%) and a higher enantiomeric excess (64%). These results show that continuous flow has the potential to act as a new enabling technology for asymmetric synthesis to replace some aspects of conventional batch electrochemical processes.
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