{"title":"通过 Tf2O 介导的α-甲酰基氨基酮的一锅酰胺活化/正 式 [3 + 2]- 环加成法合成螺吡咯啉。","authors":"Khanh-Toan Ho, Joshua G Pierce","doi":"10.1021/acs.joc.4c01128","DOIUrl":null,"url":null,"abstract":"<p><p>An efficient method for the synthesis of spiropyrrolines from readily accessible α-formylamino ketones is reported. The method involves amide activation using Tf<sub>2</sub>O, followed by a formal [3 + 2]-cycloaddition of the resulting enolic nitrilium intermediate with Michael acceptors, ultimately affording spiropyrrolines. Mechanistic insights were gained through NMR studies, elucidating the precise role of the base additive and suggesting the formation of an enolic nitrilium intermediate.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Spiropyrrolines <i>via</i> One-Pot Tf<sub>2</sub>O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones.\",\"authors\":\"Khanh-Toan Ho, Joshua G Pierce\",\"doi\":\"10.1021/acs.joc.4c01128\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>An efficient method for the synthesis of spiropyrrolines from readily accessible α-formylamino ketones is reported. The method involves amide activation using Tf<sub>2</sub>O, followed by a formal [3 + 2]-cycloaddition of the resulting enolic nitrilium intermediate with Michael acceptors, ultimately affording spiropyrrolines. Mechanistic insights were gained through NMR studies, elucidating the precise role of the base additive and suggesting the formation of an enolic nitrilium intermediate.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c01128\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/4 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01128","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/4 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of Spiropyrrolines via One-Pot Tf2O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones.
An efficient method for the synthesis of spiropyrrolines from readily accessible α-formylamino ketones is reported. The method involves amide activation using Tf2O, followed by a formal [3 + 2]-cycloaddition of the resulting enolic nitrilium intermediate with Michael acceptors, ultimately affording spiropyrrolines. Mechanistic insights were gained through NMR studies, elucidating the precise role of the base additive and suggesting the formation of an enolic nitrilium intermediate.
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
