Bence S Nagy, Fegyverneki Dániel, Péter Szalai, András Kotschy, Márió Gyuris
{"title":"Direct catalytic synthesis of β-acylamino cyclobutanones <i>via</i> three-component Mannich reactions.","authors":"Bence S Nagy, Fegyverneki Dániel, Péter Szalai, András Kotschy, Márió Gyuris","doi":"10.1039/d4ob01543f","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, a versatile, robust, and solvent-free method is reported for the synthesis of novel β-acylamino cyclobutanone derivatives exploiting a Cu(OTf)<sub>2</sub>/TIPSCl-promoted Mannich-type three-component approach. The present work expands the utilization of a ring-strained ketone as well as various amide derivatives as amine equivalents, which has remained relatively underexplored due to their low reactivity profile. Following a rapid optimization of the reaction conditions, a relevant set of β-acylamino cyclobutanone derivatives has been designed and generated. Furthermore, the synthetic utility of our process has been demonstrated <i>via</i> a dual Au(I)/Ag(I)-catalyzed intramolecular hydroxygenation reaction to showcase a representative post-Mannich transformation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-06-12","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/d4ob01543f","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
Herein, a versatile, robust, and solvent-free method is reported for the synthesis of novel β-acylamino cyclobutanone derivatives exploiting a Cu(OTf)2/TIPSCl-promoted Mannich-type three-component approach. The present work expands the utilization of a ring-strained ketone as well as various amide derivatives as amine equivalents, which has remained relatively underexplored due to their low reactivity profile. Following a rapid optimization of the reaction conditions, a relevant set of β-acylamino cyclobutanone derivatives has been designed and generated. Furthermore, the synthetic utility of our process has been demonstrated via a dual Au(I)/Ag(I)-catalyzed intramolecular hydroxygenation reaction to showcase a representative post-Mannich transformation.
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.