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Catalysis

C&EN 中文版

光催化反应选择性翻转醛异构体

反应转化手性醛混合物为单一异构体

by Leigh Krietsch Boerner
March 3, 2022 | A version of this story appeared in Volume 100, Issue 9
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Scheme showing the isomerization of simple aldehydes to one single isomer.

请访问cenm.ag/chinese或关注ACS微信订阅号获取更多《化学与化工新闻》的中文内容.

在制药业，将分子的镜像形式或同分异构体的混合物转化为单一异构体是件重要的事，因为通常仅有一个异构体可被用做药品。但是当前该流程所选择的、名为“去消旋化”的方法复杂且烦琐。现在中国清华大学（Tsinghua University）的罗三中及其团队与物质绿色创造与制造海河实验室（Haihe Laboratory of Sustainable Chemical Transformations）的研究使之如同开灯一样简单。该研究团队用了一种铱化合物、烯胺和紫色光线将支链醛异构体的混合物转化为单一异构体(Science 2022, DOI: 10.1126/science.abl4922)。

该工作结合了两项广为人知的反应：双键光异构化反应和胺催化反应，后一反应获得了2021年诺贝尔化学奖。该团队的这一直接路径可用于多种手性醛类化合物的去消旋化。

该方法通过将目标分子的手性及不对称性转化至光控切换的手性催化剂。当光将该催化剂转化至所需异构体后，另一个反应将新的手性转回原始分子。罗三中及其同事首先混合等量的左旋/右旋醛（(分别为R-和 S-),然后添加仅能与S-醛发生反应的一种胺，从而形成一种烯胺异构体。

研究团队使用400nm光线照射该溶液，使烯胺异构体翻转至其相反的异构体。该烯胺异构体随后分解形成所需的R-醛。在R-醛与 S-醛之间的相互转换中，烯胺发挥了“摆渡”的作用， 罗三中说。为了证明这一点，研究团队合成了几种非甾体抗炎药物（ NSAID），其中包括布洛芬和洛索洛芬。 “ 对于一个重要且极富挑战的问题，这是一个雅致的解决方案，”美国麻省理工学院（the Massachusetts Institute of Technology）的催化反应化学家Alison Wendlandt在邮件中表示。“在我看来，这一方案毫无疑问也将为其他化学家所用，作者的方法将激发该领域的更多的进步。太酷了！”

本文原文（英文版本）发表于2022年3月3日，在此可查看。.

由YanYan为C&EN翻译为中文。原文（英文）点击此处。.

Chemical & Engineering News
ISSN 0009-2347
Copyright © 2024 American Chemical Society

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