{"title":"烯醇-乌基反应中的酰胺衍生烯醇:拓宽拟肽支架合成的视野。","authors":"José Luis Ramiro, Ana G Neo, Carlos F Marcos","doi":"10.1039/d4ob01216j","DOIUrl":null,"url":null,"abstract":"<p><p>A highly efficient enol-Ugi reaction of β,β-diketoamides has been developed using a novel non-heterocyclic amide-stabilised enol. This approach enables a broad reaction scope, affording β-enaminoamide peptidomimetics with constrained conformations due to CH-π interaction and C(sp<sup>3</sup>)H⋯O hydrogen bonding. Notably, the use of a five-membered cyclic enol is crucial for achieving stable products in excellent yields. This work highlights the potential of the enol-Ugi reaction for constructing diverse peptidomimetic scaffolds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Amide-derived enols in enol-Ugi reactions: expanding horizons for peptidomimetic scaffold synthesis.\",\"authors\":\"José Luis Ramiro, Ana G Neo, Carlos F Marcos\",\"doi\":\"10.1039/d4ob01216j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A highly efficient enol-Ugi reaction of β,β-diketoamides has been developed using a novel non-heterocyclic amide-stabilised enol. This approach enables a broad reaction scope, affording β-enaminoamide peptidomimetics with constrained conformations due to CH-π interaction and C(sp<sup>3</sup>)H⋯O hydrogen bonding. Notably, the use of a five-membered cyclic enol is crucial for achieving stable products in excellent yields. This work highlights the potential of the enol-Ugi reaction for constructing diverse peptidomimetic scaffolds.</p>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-09-20\",\"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/d4ob01216j\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01216j","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Amide-derived enols in enol-Ugi reactions: expanding horizons for peptidomimetic scaffold synthesis.
A highly efficient enol-Ugi reaction of β,β-diketoamides has been developed using a novel non-heterocyclic amide-stabilised enol. This approach enables a broad reaction scope, affording β-enaminoamide peptidomimetics with constrained conformations due to CH-π interaction and C(sp3)H⋯O hydrogen bonding. Notably, the use of a five-membered cyclic enol is crucial for achieving stable products in excellent yields. This work highlights the potential of the enol-Ugi reaction for constructing diverse peptidomimetic scaffolds.