Selective Cross‐Metathesis of Highly Chelating Substrates in Aqueous Media,ChemistrySelect

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Selective Cross‐Metathesis of Highly Chelating Substrates in Aqueous Media
ChemistrySelect ( IF 1.9 ) Pub Date : 2020-06-26 , DOI: 10.1002/slct.202002220
Brian J. J. Timmer ₁ , Oleksandr Kravchenko ₁ , Olof Ramström _{1,

2,

3}

Affiliation

The role of non‐productive chelation in olefin metathesis has been investigated for a variety of highly functionalized substrates in aqueous environment. Using a morpholine‐substituted catalyst, the reactivity of oligoethylene glycols and oligopeptides was evaluated, either in self‐metathesis protocols, or in cross‐metathesis processes with allyl alcohol. The limited reactivity of the substrates in self‐metathesis reactions could be utilized to achieve selectivity in cross‐metathesis with more reactive alkenes. With 2.5 mol % catalyst loading, up to 62% conversion to cross‐metathesis products could be observed for the model systems within 5 h. Overall, this study opens up new potential avenues for olefin metathesis in the field of chemical biology where chelating substrates are omnipresent.

中文翻译：

水性介质中高度螯合基质的选择性交叉复分解

对于水性环境中各种高度官能化的底物，已经研究了非生产性螯合在烯烃复分解中的作用。使用吗啉取代的催化剂，可以在自我复分解方案中或在与烯丙醇的交叉复分解过程中评估寡乙二醇和寡肽的反应性。底物在自我复分解反应中受限制的反应性可用于实现与更多反应性烯烃的交叉复分解中的选择性。在催化剂负载量为2.5 mol％的情况下，模型系统在5小时内可以观察到高达62％的转化为复分解产物。总体而言，这项研究为在不存在螯合底物的化学生物学领域中烯烃复分解开辟了新的潜在途径。

更新日期：2020-06-26

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