Direct Conversion of Activated 5‐Hydroxymethylfurfural into δ‐Lactone‐Fused Cyclopentenones,ChemSusChem

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Direct Conversion of Activated 5‐Hydroxymethylfurfural into δ‐Lactone‐Fused Cyclopentenones
ChemSusChem ( IF 7.5 ) Pub Date : 2018-12-21 , DOI: 10.1002/cssc.201802537
Rafael F. A. Gomes ₁ , Jaime A. S. Coelho ₁ , Carlos A. M. Afonso ₁

Affiliation

Valorization of biomass derived feedstock (e.g., 5‐hydroxymethylfurfural platform) is a very active field of chemical research. In this study, 5‐hydroxymethylfurfural is converted into cyclopenten‐2‐ones by virtue of furfural's activation and Meldrum's acid's tendency to undergo decomposition/esterification. Experimental and computational studies suggest a domino rearrangement–lactonization reaction involving BINOL‐catalyzed lactonization as the rate‐determining step. The novel lactone‐fused cyclopenten‐2‐ones, which bear a quaternary carbon and resemble a didemnenone natural product structure, are converted into several derivatives with potential interest for the fields of synthetic and medicinal chemistry.

中文翻译：

将活化的5-羟基甲基糠醛直接转化为δ-内酯融合的环戊烯酮

生物质衍生原料（例如5-羟甲基糠醛平台）的估价是化学研究的一个非常活跃的领域。在这项研究中，由于糠醛的活化和梅德鲁姆酸的分解/酯化趋势，5-羟甲基糠醛被转化为环戊烯-2-酮。实验和计算研究表明，以BINOL催化的内酯化为速率确定步骤的多米诺骨牌重排-内酯化反应。新型的内酯融合的环戊二烯-2-酮具有季碳原子，类似于二甲烯酮的天然产物结构，已被转化为几种衍生物，在合成化学和药物化学领域具有潜在的兴趣。

更新日期：2018-12-21

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