Cu(OTf)2 and a novel axially chiral quinoline-arylphenol ligand partner enabled an enantioselective CH functionalization of indoles with vinylogous migratory carbene insertion of α-arylidene diazosuccinimides for stout preparation of chiral maleimides

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-05-22 DOI:10.1016/j.tetlet.2025.155662

Chun-Jun Zhu , Qian-Mao Zhang , Hao Fan , Xiao Fu , Chun-Chun Tang , Wen-Juan Wan , Fang Tian , Li-Xin Wang

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引用次数: 0

Abstract

An enantioselective vinylogous migratory carbene insertion for CH functionalization of indoles with α-arylidene diazo-succinimides has been disclosed in the presence of catalytic novel axially chiral quinoline-naphthanol ligand L1 and Cu(OTf)₂ partner. A wide range of chiral maleimides integrated with an indole scaffold were successfully obtained in moderate to good enantioselectivities (up to 91:9 er) with good to excellent yields (up to 91 %) after vinylogous isomerization, which represents a rare example of copper catalyzed enantioselective carbene migratory insertion reaction. Our protocol enables the effective construction of multifunctional chiral indole framework combined with a maleimide moiety, which are widely used as privileged pharmaceutical scaffolds while difficultly available by general synthetic means.

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Cu(OTf)2和一种新的轴向手性喹啉-芳基酚配体伙伴使吲哚的对映选择性CH功能化与α-芳基重氮琥珀酰亚胺的vinyous迁移碳插入，以制备手性马来酰亚胺

在新型轴向手性喹啉-萘乙醇配体L1和Cu(OTf) 2伴体的催化作用下，发现了一种对映选择性的枝性迁移碳插入物，用于吲哚与α-芳基重氮琥珀酰亚胺的CH功能化。在葡萄状异构化后，广泛的手性马来酰亚胺与吲哚支架结合，成功地获得了中等至良好的对映选择性（高达91:9 er）和良好至优异的产率（高达91%），这是铜催化的对映选择性卡宾迁移插入反应的罕见例子。我们的方案能够有效地构建与马来酰亚胺片段结合的多功能手性吲哚框架，这些框架被广泛用作特殊的药物支架，而一般合成方法难以获得。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.