首页> 外文期刊>Chemistry: A European journal >One-pot organocatalytic tandem aldol/polycyclization reactions between 1,3-dicarbonyl compounds and α,β,γ,δ-unsaturated aldehydes for the straightforward assembly of cyclopenta[b]furan-type derivatives: New insight into the Knoevenagel reaction
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One-pot organocatalytic tandem aldol/polycyclization reactions between 1,3-dicarbonyl compounds and α,β,γ,δ-unsaturated aldehydes for the straightforward assembly of cyclopenta[b]furan-type derivatives: New insight into the Knoevenagel reaction

机译:1,3-二羰基化合物与α,β,γ,δ-不饱和醛之间的一锅式有机催化串联醇醛/多环化反应,用于直接组装环戊五[b]呋喃型衍生物:对Knoevenagel反应的新见解

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摘要

A new cascade pathway viable for Knoevenagel chemistry that involves the coupling between 1,3-dicarbonyl systems and α,β,γ,δ- unsaturated aldehydes has been developed. The process comprises the combination of a classic aldol-type condensation and a rare spontaneous metal-free cycloisomerization, representing a convergent and innovative approach for the stereoselective synthesis of cyclopenta[b]furan-type derivatives. The scope and limitations with respect to both reaction partners and mechanistic features were investigated. Meaningfully, our study provides valuable guidance concerning the structural and electronic effects controlling the reactivity of conjugated polyene carbonyl systems.
机译:已开发出一种适用于Knoevenagel化学的级联途径,该途径涉及1,3-二羰基体系与α,β,γ,δ-不饱和醛之间的偶联。该方法包括经典的醛醇型缩合反应和罕见的无自发的无金属环异构化反应的结合,代表了环戊并[b]呋喃型衍生物的立体选择性合成的融合和创新方法。研究了有关反应伙伴和机理特征的范围和局限性。有意义的是,我们的研究为控制共轭多烯羰基体系反应性的结构和电子效应提供了有价值的指导。

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