{"title":"Indium Mediated Reformatsky-Type Allylation of N-tert-Butanesulfinyl Iminoester with 1,3-Butadiene","authors":"Shuangjie Lin, Renxu Cao, Zhixian Wu, Yihe Zhu, Shaohua Zhang, Xuehan Qi, Qingyu Shi, Yizhe Mao, Yunhe Jin, Erjun Hao, Lei Shi","doi":"10.1021/acs.orglett.4c04086","DOIUrl":null,"url":null,"abstract":"This study presents the indium-mediated three-component radical Reformatsky-type allylation of <i>N</i>-<i>tert</i>-butanesulfinyl iminoester with 1,3-butadiene. This novel approach offers a rapid synthesis pathway to valuable homoallylic noncanonical amino acids, demonstrated with over 30 examples showing nice regio- and diastereoselectivity. Mechanism studies revealed that allylindium complexes served as key intermediates, formed through a single-electron reduction of allylic radicals by Indium species.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"61 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-20","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.4c04086","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
This study presents the indium-mediated three-component radical Reformatsky-type allylation of N-tert-butanesulfinyl iminoester with 1,3-butadiene. This novel approach offers a rapid synthesis pathway to valuable homoallylic noncanonical amino acids, demonstrated with over 30 examples showing nice regio- and diastereoselectivity. Mechanism studies revealed that allylindium complexes served as key intermediates, formed through a single-electron reduction of allylic radicals by Indium species.
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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