{"title":"Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes","authors":"Lianyi Cao, Shihai Yan, Fangzhi Hu, Fei Wang, Shuai-Shuai Li, Mengzhe Pan, Yingkun Yan, Xiao-Mei Zhang","doi":"10.1021/acs.orglett.5c00001","DOIUrl":null,"url":null,"abstract":"The TfOH-catalyzed dearomative [5 + 1] annulations were developed for the construction of chromane-fused spiroisoxazolines from readily available 5-amino-isoxazoles and <i>O</i>-alkyl <i>ortho</i>-oxybenzaldehydes. The “two-birds-with-one-stone” strategy featuring dearomatization of 5-amino-isoxazoles and α-C(sp<sup>3</sup>)–H bond functionalization of oxygen was disclosed via a cascade condensation/[1,5]-hydride transfer/dearomative spirocyclization process. In addition, the unprecedented direct dearomative spirocyclization of isoxazoles was achieved, which introduced a new family member of dearomative spirocyclization for dearomatization chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"16 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00001","RegionNum":1,"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
The TfOH-catalyzed dearomative [5 + 1] annulations were developed for the construction of chromane-fused spiroisoxazolines from readily available 5-amino-isoxazoles and O-alkyl ortho-oxybenzaldehydes. The “two-birds-with-one-stone” strategy featuring dearomatization of 5-amino-isoxazoles and α-C(sp3)–H bond functionalization of oxygen was disclosed via a cascade condensation/[1,5]-hydride transfer/dearomative spirocyclization process. In addition, the unprecedented direct dearomative spirocyclization of isoxazoles was achieved, which introduced a new family member of dearomative spirocyclization for dearomatization chemistry.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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