Yi Zhang, Jinqiang Kuang, Yongmin Ma, Lei Wang, Weiwei Fang
{"title":"通过 1,5-肼转移直接对哌啶进行 α,β-C-H-二官能化以构建 N,O-乙缩醛骨架。","authors":"Yi Zhang, Jinqiang Kuang, Yongmin Ma, Lei Wang, Weiwei Fang","doi":"10.1021/acs.joc.4c01539","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we describe an unprecedented Lewis acid-catalyzed annulation of phenols with <i>o</i>-aminobenzaldehydes via a cascade coupling/1,5-hydride transfer/cyclization sequence. The α- and β-positions of cyclic amines were functionalized utilizing enamines generated <i>in situ</i>. A series of complex <i>N</i>,<i>O</i>-acetal derivatives are synthesized in moderate to good yields in one step. The methodology features high atom and step economy, excellent diastereoselectivity, and water as the sole byproduct.</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\":\"Direct α,β-C-H Difunctionalization of Piperidines for the Construction of the <i>N</i>,<i>O</i>-Acetal Skeleton via 1,5-Hydride Transfer.\",\"authors\":\"Yi Zhang, Jinqiang Kuang, Yongmin Ma, Lei Wang, Weiwei Fang\",\"doi\":\"10.1021/acs.joc.4c01539\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Herein, we describe an unprecedented Lewis acid-catalyzed annulation of phenols with <i>o</i>-aminobenzaldehydes via a cascade coupling/1,5-hydride transfer/cyclization sequence. The α- and β-positions of cyclic amines were functionalized utilizing enamines generated <i>in situ</i>. A series of complex <i>N</i>,<i>O</i>-acetal derivatives are synthesized in moderate to good yields in one step. The methodology features high atom and step economy, excellent diastereoselectivity, and water as the sole byproduct.</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.4c01539\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/5 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.4c01539","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/5 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Direct α,β-C-H Difunctionalization of Piperidines for the Construction of the N,O-Acetal Skeleton via 1,5-Hydride Transfer.
Herein, we describe an unprecedented Lewis acid-catalyzed annulation of phenols with o-aminobenzaldehydes via a cascade coupling/1,5-hydride transfer/cyclization sequence. The α- and β-positions of cyclic amines were functionalized utilizing enamines generated in situ. A series of complex N,O-acetal derivatives are synthesized in moderate to good yields in one step. The methodology features high atom and step economy, excellent diastereoselectivity, and water as the sole byproduct.
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.