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Stereoselective Synthesis of Dihydrofuranoindoles via the Friedel-Crafts Alkylation/Annulation Cascade Process.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-08-24 , DOI: 10.1021/acs.joc.0c00444
Xiaodi Dong 1 , Zhishun Tang 1 , Ling Ye 2 , Zhichuan Shi 1 , Zhigang Zhao 1 , Xuefeng Li 1
Affiliation  

A stereoselective annulation protocol was developed to construct dihydrofuranoindoles from readily available starting materials. In the presence of a bifunctional squaramide, the Friedel–Crafts alkylation/annulation cascade process occurred smoothly to provide dihydrofuranoindoles in 26–95% isolated yields exclusively as trans-diastereomers (38–99% ee). This catalytic protocol was compatible with a range of structurally distinct hydroxyindoles bearing the hydroxyl group at different positions, providing four kinds of dihydrofuranoindoles. Moreover, gram-scale synthesis and further synthetic manipulation of the product were also demonstrated.

中文翻译:

通过Friedel-Crafts烷基化/环流级联工艺立体选择性合成二氢呋喃吲哚。

开发了立体选择性环合方案以从容易获得的起始原料构建二氢呋喃吲哚。在存在双功能方酸酰胺的情况下,Friedel-Crafts烷基化/环化级联过程顺利进行,从而以反式-非对映体(38-99%ee)的形式提供了二氢呋喃吲哚,分离产率为26-95%。该催化方案与一系列结构不同的在不同位置带有羟基的羟基吲哚相容,提供了四种二氢呋喃吲哚。此外,还证明了克级合成和产物的进一步合成操作。
更新日期:2020-09-20
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