Chengtan Li , Yuming Yang , Xiaolan Zheng , Cairong Zhang , Hui Cai , Weilong Lin
{"title":"Photocatalyzed sulfoximination/amidation of (Het)arylethenes tethered N-tosyl amide: a versatile entry to sulfoximidoyl β- and γ-lactams†","authors":"Chengtan Li , Yuming Yang , Xiaolan Zheng , Cairong Zhang , Hui Cai , Weilong Lin","doi":"10.1039/d4qo00631c","DOIUrl":null,"url":null,"abstract":"<div><div>Lactam and sulfoximine motifs are common in natural and biologically active molecules, and alkenes are important building blocks in synthetic chemistry. Through photoredox-mediated formation of cation intermediates, we have developed a highly versatile method for preparing various sulfoximidoyl lactams <em>via</em> C–N bond formation between CC and amide motifs. Mild reaction conditions, broad functional group tolerance and excellent <em>trans</em>-selectivity of this method would make it a general and efficient approach towards novel compounds containing valuable sulfoximine and lactam motifs for possible therapeutic use.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 16","pages":"Pages 4508-4515"},"PeriodicalIF":0.0000,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924004480","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Lactam and sulfoximine motifs are common in natural and biologically active molecules, and alkenes are important building blocks in synthetic chemistry. Through photoredox-mediated formation of cation intermediates, we have developed a highly versatile method for preparing various sulfoximidoyl lactams via C–N bond formation between CC and amide motifs. Mild reaction conditions, broad functional group tolerance and excellent trans-selectivity of this method would make it a general and efficient approach towards novel compounds containing valuable sulfoximine and lactam motifs for possible therapeutic use.