{"title":"Efficient and Scalable Syntheses of 1,2-Thiaselenane-4-amine and 1,2-Thiaselenane-5-amine","authors":"Lukas Zeisel, M. Maier, O. Thorn-Seshold","doi":"10.1055/a-2022-1398","DOIUrl":null,"url":null,"abstract":"We develop the first regioselective syntheses of 1,2-thiaselenane-4-amine (TSA4) and 1,2-thiaselenane-5-amine (TSA5): redox-active motifs with high value in chemical biology, that until now were hindered by tedious synthesis. We leverage an aziridine intermediate and a kinetically controlled S-acylation for regioselective chalcogen installations. We optimise short, fast sequences with just one or two chromatographic steps that cheaply deliver these motifs on scale for high-throughput inhibitor screening, and provide a robust methodology for assembling other selenenylsulfides.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2022-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis-Stuttgart","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2022-1398","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 1
Abstract
We develop the first regioselective syntheses of 1,2-thiaselenane-4-amine (TSA4) and 1,2-thiaselenane-5-amine (TSA5): redox-active motifs with high value in chemical biology, that until now were hindered by tedious synthesis. We leverage an aziridine intermediate and a kinetically controlled S-acylation for regioselective chalcogen installations. We optimise short, fast sequences with just one or two chromatographic steps that cheaply deliver these motifs on scale for high-throughput inhibitor screening, and provide a robust methodology for assembling other selenenylsulfides.
期刊介绍:
SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.