{"title":"Chemoselective epoxidation of electron-deficient olefins with molecular oxygen via conjugated olefins epoxidation and BHT hydroxylation","authors":"Jia Nie, Huanfeng Jiang, Chuanle Zhu","doi":"10.1007/s11426-024-2128-7","DOIUrl":null,"url":null,"abstract":"<div><p>The chemoselective epoxidation of electron-deficient olefins in the presence of electron-rich alkene moieties is reported. This chemoselective epoxidation strategy undergoes a conjugated olefin epoxidation and BHT hydroxylation process to give various useful oxiranes in high yields, especially for the 2-substituted 2-trifluoromethyloxiranes. Importantly, this protocol features mild conditions, is transition-metal free, operationally simple, and gram-scalable, and tolerates diverse functional groups. Drug candidate HSD-16 is synthesized smoothly by this protocol. Mechanism studies indicate molecular oxygen is the terminal oxidant and the <i>O</i>-source of the oxiranes.</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":772,"journal":{"name":"Science China Chemistry","volume":"67 9","pages":"3012 - 3018"},"PeriodicalIF":10.4000,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science China Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s11426-024-2128-7","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The chemoselective epoxidation of electron-deficient olefins in the presence of electron-rich alkene moieties is reported. This chemoselective epoxidation strategy undergoes a conjugated olefin epoxidation and BHT hydroxylation process to give various useful oxiranes in high yields, especially for the 2-substituted 2-trifluoromethyloxiranes. Importantly, this protocol features mild conditions, is transition-metal free, operationally simple, and gram-scalable, and tolerates diverse functional groups. Drug candidate HSD-16 is synthesized smoothly by this protocol. Mechanism studies indicate molecular oxygen is the terminal oxidant and the O-source of the oxiranes.
期刊介绍：
Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field.
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Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry.
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