Xiaodan Yu, Arthur Desvals, Zong Chang, Vincent Orève, David J. Aitken, Thomas Boddaert
{"title":"Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes","authors":"Xiaodan Yu, Arthur Desvals, Zong Chang, Vincent Orève, David J. Aitken, Thomas Boddaert","doi":"10.1021/acs.orglett.4c03741","DOIUrl":null,"url":null,"abstract":"A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized <i>E</i>-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR is accomplished in a single protocol, comprising a tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer reaction followed by an acetal protection and an allylic substitution reaction. In parallel, a consecutive process has been established with distinct photochemical and nonradiative sequences. An intramolecular version of these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-12","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.4c03741","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
A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized E-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR is accomplished in a single protocol, comprising a tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer reaction followed by an acetal protection and an allylic substitution reaction. In parallel, a consecutive process has been established with distinct photochemical and nonradiative sequences. An intramolecular version of these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
