{"title":"Organocatalytic modular synthesis of 2-functionalized 2,5-dihydrofurans from γ-hydroxy enals","authors":"Tie Lei , Jun Tan , Yifei Zhang , Dengke Ma","doi":"10.1039/d5ob01216c","DOIUrl":null,"url":null,"abstract":"<div><div>A convenient and modular method for the preparation of diverse 2-O/N/C-functionalized 2,5-dihydrofurans has been developed starting from readily available γ-hydroxy enals <em>via</em> organocatalysis. This reaction features broad substrate scope, excellent functional group tolerance, high efficiency, and green properties, with high atom economy and water as the sole byproduct. Its potential applications in organic synthesis and drug discovery are demonstrated through late-stage functionalization of natural products and drugs, as well as synthetic transformations. Detailed mechanistic studies provide valuable insights into the reaction pathway.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 36","pages":"Pages 8170-8175"},"PeriodicalIF":2.7000,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025006664","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A convenient and modular method for the preparation of diverse 2-O/N/C-functionalized 2,5-dihydrofurans has been developed starting from readily available γ-hydroxy enals via organocatalysis. This reaction features broad substrate scope, excellent functional group tolerance, high efficiency, and green properties, with high atom economy and water as the sole byproduct. Its potential applications in organic synthesis and drug discovery are demonstrated through late-stage functionalization of natural products and drugs, as well as synthetic transformations. Detailed mechanistic studies provide valuable insights into the reaction pathway.
以易获得的γ-羟基烯醛为原料,通过有机催化,建立了一种方便、模块化的制备多种2- o /N/ c功能化2,5-二氢呋喃的方法。该反应具有底物范围广、官能团耐受性好、效率高、绿色环保等特点,原子经济性高,副产品只有水。它在有机合成和药物发现方面的潜在应用是通过天然产物和药物的后期功能化以及合成转化来证明的。详细的机制研究为反应途径提供了有价值的见解。
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.