Base-Catalyzed Domino Isomerization/Oxidant-Free Dehydrogenative Annulation of Allylic Alcohols: Scope, Mechanism, and Application,Advanced Synthesis & Catalysis

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Base-Catalyzed Domino Isomerization/Oxidant-Free Dehydrogenative Annulation of Allylic Alcohols: Scope, Mechanism, and Application
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-07-03 , DOI: 10.1002/adsc.202400465
Jia-Qi Li ₁ , Xiongyang Zhou ₂ , Xun Li ₂ , Cheng Le ₂

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A domino reaction comprising four consecutive steps based on the strategy of isomerization of allylic alcohols was developed. This base‐catalyzed protocol provided an approach for constructing polysubstituted quinolines without additional additives. A wide range of di‐ or trisubstituted γ‐aminoaryl allylic alcohols bearing alkyl or (hetero)aryl substituents were transformed to the structurally diverse quinolines. The utility of this transformation was demonstrated by the application in the concise synthesis of several polysubstituted quinoline derivatives, including natural products and pharmacological agents. Preliminary mechanistic experiments suggested that the isomerization of γ‐aminoaryl allylic alcohol underwent an intramolecular 1,3‐hydrogen shift and the aromatization of the dihydroquinoline intermediate went through two possible pathways simultaneously exist, acceptorless dehydrogenation and transfer hydrogenation process.

中文翻译：

烯丙醇的碱催化多米诺异构化/无氧化剂脱氢环化：范围、机制和应用

基于烯丙醇异构化策略，开发了包含四个连续步骤的多米诺骨牌反应。这种碱催化方案提供了一种无需额外添加剂即可构建多取代喹啉的方法。多种带有烷基或（杂）芳基取代基的二或三取代的γ-氨基芳基烯丙醇被转化为结构多样的喹啉。通过在几种多取代喹啉衍生物（包括天然产物和药物制剂）的简明合成中的应用，证明了这种转化的实用性。初步机理实验表明，γ-氨基芳基烯丙醇的异构化经历了分子内1,3-氢转移，二氢喹啉中间体的芳构化经历了两种可能的途径同时存在，即无受体脱氢和转移氢化过程。

更新日期：2024-07-03

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