{"title":"异氰基烯烃加成-环化-脱羧级联反应","authors":"F. Fleming, John-Paul R Marrazzo, Tish Huynh","doi":"10.1055/s-0043-1774943","DOIUrl":null,"url":null,"abstract":"A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades\",\"authors\":\"F. Fleming, John-Paul R Marrazzo, Tish Huynh\",\"doi\":\"10.1055/s-0043-1774943\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.\",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-07-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/s-0043-1774943\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0043-1774943","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.
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