Multicomponent Synthesis of Isoquinuclidines via Pd-Catalyzed Selective Dechlorination

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-17 DOI:10.1021/acs.orglett.5c03136

Qixin Zhou, , , Guocong Zhang, , , Yingqi Lan, , , Ting Long, , , Leixing Du, , , Tiancen Bian, , , Liejin Zhou*, , and , Zuxiao Zhang*,

引用次数: 0

Abstract

We report a visible-light palladium-catalyzed multicomponent reaction enabling efficient synthesis of 2-azabicyclo[2.2.2]octenes via a multicomponent coupling of cyclic 1,3-dienes, gem-dichloroalkanes, and amines. Mechanistic studies indicate a radical pathway with selective dechlorination and high 1,4-syn diastereoselectivity. This mild, efficient method provides sp³-rich bicyclic scaffolds amenable to further derivatization. Its utility is demonstrated in concise syntheses of bioactive alkaloids, including deethylibogamine and Rauwolfia analogues, highlighting its potential for complex molecule construction in medicinal chemistry.

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pd催化选择性脱氯多组分合成异喹啉。

我们报道了一种可见光钯催化的多组分反应，通过环1,3-二烯、双氯烷和胺的多组分偶联，可以高效合成2-氮杂环[2.2.2]辛烯。机理研究表明自由基途径具有选择性脱氯和高1,4-syn非对映选择性。这种温和、有效的方法提供了适于进一步衍生化的富含sp3的双环支架。它在生物活性生物碱的简明合成中得到了证明，包括去乙基脂gamine和Rauwolfia类似物，突出了它在药物化学中复杂分子构建的潜力。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.