Spatiotemporal Control of Pre-existing Alkene Geometry: A Bio-Inspired Route to 4-Trifluoromethyl-2H-chromenes,Organic Letters

当前位置： X-MOL 学术 › Org. Lett. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Spatiotemporal Control of Pre-existing Alkene Geometry: A Bio-Inspired Route to 4-Trifluoromethyl-2H-chromenes
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-16 00:00:00 , DOI: 10.1021/acs.orglett.7b03859
Svenja I. Faßbender ₁ , Jan B. Metternich ₁ , Ryan Gilmour ₁

Affiliation

Routes to prepare C4-trifluoromethyl analogues of the 2H-chromene scaffold are scarce: this is particularly striking given the importance of fluorine in pharmaceutical development. To address this limitation, a facile strategy has been developed that is reliant on catalytic, geometric isomerization of easily accessible allylic alcohols (up to >95:5) followed by intramolecular cyclization via Pd catalysis (up to 96%). This concise biomimetic approach emulates the photoisomerization/cyclization cascade inherent to phenylpropanoid biosynthesis.

中文翻译：

时空存在的烯烃几何结构的时空控制：一种生物启发的途径，以4-Trifluoromethyl-2 H -chromenes

制备2 H-亚甲基支架的C4-三氟甲基类似物的途径很少：鉴于氟在药物开发中的重要性，这一点尤其令人震惊。为了解决该限制，已经开发了一种容易的策略，该策略依赖于容易获得的烯丙醇的催化几何异构化（高达> 95：5），然后通过Pd催化进行分子内环化（高达96％）。这种简洁的仿生方法模拟了苯丙烷生物合成固有的光异构化/环化级联反应。

更新日期：2018-01-16

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11