{"title":"Diastereoselective thia-[3 + 2] cyclization of acetylpyranuloses and β-oxodithioesters.","authors":"Shihao Cheng, Xiao Ni, Guanyou Cui, Chenhu Dong, Yujie Ma, Jinlong Li, Xiaofeng Bao, Yu Zhao","doi":"10.1039/d5ob00022j","DOIUrl":null,"url":null,"abstract":"<p><p>Acetylpyranuloses and β-oxodithioesters, recognized as notable electrophiles and trinucleophiles, are frequently employed in intricate cyclization reactions. Nevertheless, there is a lack of literature documenting the cyclization products derived from these two reagents. This paper unveils a base-mediated sequential Michael addition and S<sub>N</sub>2-type cyclization reactions involving acetylpyranuloses and β-oxodithioesters. A total of 23 functionalized bicyclic molecules featuring a thieno[2,3-<i>b</i>] pyran scaffold have been obtained diastereoselectively in moderate to good yields. This novel method could aid in the development of new drugs and enrich the toolbox for synthesizing pharmaceuticals and natural products.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00022j","RegionNum":3,"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
Acetylpyranuloses and β-oxodithioesters, recognized as notable electrophiles and trinucleophiles, are frequently employed in intricate cyclization reactions. Nevertheless, there is a lack of literature documenting the cyclization products derived from these two reagents. This paper unveils a base-mediated sequential Michael addition and SN2-type cyclization reactions involving acetylpyranuloses and β-oxodithioesters. A total of 23 functionalized bicyclic molecules featuring a thieno[2,3-b] pyran scaffold have been obtained diastereoselectively in moderate to good yields. This novel method could aid in the development of new drugs and enrich the toolbox for synthesizing pharmaceuticals and natural products.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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
