Peng Xu, Ming-Jun Li, Honglin Diao, Ning Shao, Zeng-Yang He, Shi-Zhu Fan, Ze Zhang and Hui Xu
{"title":"Chemodivergent and diastereoselective synthesis of syn- and anti-cyclopentenyl spiroisoxazolones under ball-milling conditions†","authors":"Peng Xu, Ming-Jun Li, Honglin Diao, Ning Shao, Zeng-Yang He, Shi-Zhu Fan, Ze Zhang and Hui Xu","doi":"10.1039/D4MR00125G","DOIUrl":null,"url":null,"abstract":"<p >A new cyclization pattern between arylidene isoxazolones and enamino esters has been demonstrated, efficiently affording various structurally novel cyclopentenyl spiroisoxazolones with high chemoselectivity in a ball mill. Interestingly, the diastereoselectivity of the spiro products is also controllable, with both <em>syn</em>- and <em>anti</em>-isomers generated selectively under different reaction conditions. The mechanochemical protocol features good chemo- and diastereoselectivity, high efficiency, mild reaction conditions and minimal solvent usage, providing rapid, environmentally benign and scalable access to spirocyclopentenes.</p>","PeriodicalId":101140,"journal":{"name":"RSC Mechanochemistry","volume":" 2","pages":" 317-321"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/mr/d4mr00125g?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"RSC Mechanochemistry","FirstCategoryId":"1085","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/mr/d4mr00125g","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A new cyclization pattern between arylidene isoxazolones and enamino esters has been demonstrated, efficiently affording various structurally novel cyclopentenyl spiroisoxazolones with high chemoselectivity in a ball mill. Interestingly, the diastereoselectivity of the spiro products is also controllable, with both syn- and anti-isomers generated selectively under different reaction conditions. The mechanochemical protocol features good chemo- and diastereoselectivity, high efficiency, mild reaction conditions and minimal solvent usage, providing rapid, environmentally benign and scalable access to spirocyclopentenes.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
