取代吲哚与氧烯丙基阳离子脱芳（3+2）环化反应的选择性规律

IF 3.7 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-04-08 Epub Date: 2025-03-18 DOI:10.1002/adsc.202401536

Dhiman Saha, Jimmy Wu

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引用次数: 0

摘要

我们报道了取代吲哚和氧烯丙基阳离子之间的脱芳（3+2）环反应的“选择性规则”的集合。这些规则的应用使我们能够以立体选择的方式合成四种不同的环化产物的区域异构体排列。研究表明，这些产物可以通过亲核分子拦截的贝克曼断裂（NuBFr）和贝克曼断裂（BFr）进一步转化为六氢和四氢咔唑。

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Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations

We report a collection of “selectivity rules” for the dearomative (3+2) annulation reaction between substituted indoles and oxyallyl cations. The application of these rules enables us to synthesize four different regioisomeric permutations of the annulation products in a stereoselective fashion. We demonstrated that these products could be further transformed into hexahydro- and tetrahydrocarbazoles by nucleophile-intercepted Beckmann fragmentation (NuBFr) and Beckmann fragmentation (BFr).

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.