Jialing Kang , Yifan Liu , Ronghai Cui , Jumei Shi , Jian Zhang , Huabin Wang , Qiang Huang
{"title":"银(I)催化和 DBU 促进丙炔醇与胺的异构化/加成,以获得 β-氨基酮","authors":"Jialing Kang , Yifan Liu , Ronghai Cui , Jumei Shi , Jian Zhang , Huabin Wang , Qiang Huang","doi":"10.1016/j.tetlet.2024.155163","DOIUrl":null,"url":null,"abstract":"<div><p>An alternative strategy for the synthesis of β-aminoketones have been achieved through silver(I)-catalyzed and DBU-promoted isomerization/addition of propargyl alcohols to amines. The mechanism likely involves an isomerization and sequential addition combined with the alkenyl radical process. This protocol features broad substrate scope, superior atom economy, operational simplicity, and good to excellent yields, and provides a new method for the synthesis of drug <em>Proroxan</em> on gram-scale, presenting a practical application for the construction of β-aminoketones.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Silver(I)-catalyzed and DBU-promoted isomerization/addition of propargyl alcohols to amines to access β-aminoketones\",\"authors\":\"Jialing Kang , Yifan Liu , Ronghai Cui , Jumei Shi , Jian Zhang , Huabin Wang , Qiang Huang\",\"doi\":\"10.1016/j.tetlet.2024.155163\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>An alternative strategy for the synthesis of β-aminoketones have been achieved through silver(I)-catalyzed and DBU-promoted isomerization/addition of propargyl alcohols to amines. The mechanism likely involves an isomerization and sequential addition combined with the alkenyl radical process. This protocol features broad substrate scope, superior atom economy, operational simplicity, and good to excellent yields, and provides a new method for the synthesis of drug <em>Proroxan</em> on gram-scale, presenting a practical application for the construction of β-aminoketones.</p></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-06-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924002582\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924002582","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Silver(I)-catalyzed and DBU-promoted isomerization/addition of propargyl alcohols to amines to access β-aminoketones
An alternative strategy for the synthesis of β-aminoketones have been achieved through silver(I)-catalyzed and DBU-promoted isomerization/addition of propargyl alcohols to amines. The mechanism likely involves an isomerization and sequential addition combined with the alkenyl radical process. This protocol features broad substrate scope, superior atom economy, operational simplicity, and good to excellent yields, and provides a new method for the synthesis of drug Proroxan on gram-scale, presenting a practical application for the construction of β-aminoketones.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.