{"title":"通过 N-杂环羰基催化不对称合成 C3 功能化 2,1-苯并噻嗪 2,2-二氧化物","authors":"","doi":"10.1039/d4cc01754d","DOIUrl":null,"url":null,"abstract":"<div><p>We present herein an approach for the enantioselective C3-functionalization of 2,1-benzothiazine 2,2-dioxides using N-heterocyclic carbene (NHC) catalysis. Our method involves a sequence of [3+3] cycloaddition and ring-opening reactions with different <em>N</em>- and <em>O</em>-nucleophiles, followed by silylation. Overcoming the challenge of selectivity targeting the C3 position, this protocol demonstrates a broad substrate scope and high enantioselectivity. This marks a significant advancement in the field of NHC-catalyzed transformations.</p></div>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"60 56","pages":"Pages 7176-7179"},"PeriodicalIF":4.2000,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis†\",\"authors\":\"\",\"doi\":\"10.1039/d4cc01754d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>We present herein an approach for the enantioselective C3-functionalization of 2,1-benzothiazine 2,2-dioxides using N-heterocyclic carbene (NHC) catalysis. Our method involves a sequence of [3+3] cycloaddition and ring-opening reactions with different <em>N</em>- and <em>O</em>-nucleophiles, followed by silylation. Overcoming the challenge of selectivity targeting the C3 position, this protocol demonstrates a broad substrate scope and high enantioselectivity. This marks a significant advancement in the field of NHC-catalyzed transformations.</p></div>\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":\"60 56\",\"pages\":\"Pages 7176-7179\"},\"PeriodicalIF\":4.2000,\"publicationDate\":\"2024-07-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1359734524012060\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1359734524012060","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
我们在此介绍一种利用 N-杂环碳烯(NHC)催化对 2,1-苯并噻嗪 2,2- 二氧杂环进行对映选择性 C3 功能化的方法。我们的方法包括与不同的 N 型和 O 型亲核物进行一系列 [3+3] 环加成和开环反应,然后进行硅烷化。该方法克服了针对 C3 位的选择性难题,具有广泛的底物范围和高对映选择性。这标志着 NHC 催化转化领域的重大进展。
Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis†
We present herein an approach for the enantioselective C3-functionalization of 2,1-benzothiazine 2,2-dioxides using N-heterocyclic carbene (NHC) catalysis. Our method involves a sequence of [3+3] cycloaddition and ring-opening reactions with different N- and O-nucleophiles, followed by silylation. Overcoming the challenge of selectivity targeting the C3 position, this protocol demonstrates a broad substrate scope and high enantioselectivity. This marks a significant advancement in the field of NHC-catalyzed transformations.
期刊介绍:
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