Lewis Acid Mediated Conjugate Addition of Isocyanides to β-Hydroxy-α-diazo Carbonyls: Synthesis of β-Carboxamido-α-diazo Carbonyl Compounds,Organic Letters

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Lewis Acid Mediated Conjugate Addition of Isocyanides to β-Hydroxy-α-diazo Carbonyls: Synthesis of β-Carboxamido-α-diazo Carbonyl Compounds
Organic Letters ( IF 4.9 ) Pub Date : 2022-12-22 , DOI: 10.1021/acs.orglett.2c04050
Yong-Xin Liang ₁ , Jie Wang ₁ , Xue-Cen Xu ₁ , Yue Gong ₁ , Yu-Long Zhao ₁

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A Lewis acid mediated conjugate addition of isocyanides to β-hydroxy-α-diazo carbonyls has been developed for the first time. The reaction realizes the efficient construction of quaternary carbon centers and provides a novel and efficient strategy for the synthesis of β-carboxamido-α-diazo carbonyls that would be otherwise difficult to form in a single step. Further applications, including synthesis of methylenecyclohexane, spiro-β-lactam, and nitrogen-bridged tricyclic β-lactam, demonstrated the tremendous potential of the coupling reaction.

中文翻译：

路易斯酸介导的异氰化物与 β-羟基-α-重氮羰基化合物的共轭加成：β-甲酰氨基-α-重氮羰基化合物的合成

首次开发了路易斯酸介导的异氰化物与 β-羟基-α-重氮羰基的共轭加成反应。该反应实现了季碳中心的高效构建，为难以一步合成的β-甲酰氨基-α-重氮羰基化合物提供了一种新颖高效的合成策略。进一步的应用，包括亚甲基环己烷、螺-β-内酰胺和氮桥三环 β-内酰胺的合成，证明了偶联反应的巨大潜力。

更新日期：2022-12-22

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