Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland.
J Org Chem. 2020 Dec 4;85(23):15305-15313. doi: 10.1021/acs.joc.0c02135. Epub 2020 Nov 16.
The development of a multifunctional catalyst, which mimics the promiscuity of enzymes, that would catalyze more than one chemical transformation in a single reaction vessel is one of the key points of modern sustainable chemistry. The results of our experiments indicated that Grubbs-type catalysts possess such multitask activity, catalyzing the transvinylation reaction of carboxylic acids without losing their original metathetic activity. This new activity of Grubbs catalysts was evidenced on several examples. It allows us to design a transvinylation/ring-closing metathesis (RCM) cascade reaction leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot procedure. This unique ability of Grubbs catalyst to catalyze multiple mechanically distinct cascade reactions in a chemoselective way offers the new possibility for the synthesis of complex compounds from simple, easily accessible substrates.
开发一种多功能催化剂，模拟酶的混杂性，能够在单个反应容器中催化不止一种化学反应，这是现代可持续化学的关键点之一。我们的实验结果表明，Grubbs 型催化剂具有这种多任务活性，能够催化羧酸的反乙烯基化反应，而不会失去其原有的交换活性。Grubbs 催化剂的这种新活性在几个例子中得到了证明。这使我们能够设计一个反乙烯基化/环化交叉复分解（RCM）级联反应，从不饱和羧酸一锅法中形成内环烯醇内酯。Grubbs 催化剂以化学选择性方式催化多种机械上不同的级联反应的独特能力为从简单、容易获得的底物合成复杂化合物提供了新的可能性。
