通过铁催化从丙烯酰胺和二氧化硫制备手性 β-氨基砜

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Liping Luo, Xuemei Zhang, Chunxi Huang and Zhong Lian
{"title":"通过铁催化从丙烯酰胺和二氧化硫制备手性 β-氨基砜","authors":"Liping Luo, Xuemei Zhang, Chunxi Huang and Zhong Lian","doi":"10.1039/D3QO02004E","DOIUrl":null,"url":null,"abstract":"<p >A novel approach for the enantioselective synthesis of chiral β-azide sulfones utilizing sulfur dioxide (SO<small><sub>2</sub></small>) insertion under the catalysis of a cheap, abundant and readily available iron catalyst has been successfully developed for the first time. This four-component reaction could be performed under mild conditions and has a broad substrate scope, giving products with a chiral quaternary carbon center. The obtained compounds can be easily converted into chiral β-amino sulfones which have considerable application values in the pharmaceutical and agrochemical industries. Mechanism study suggests that a radical pathway may be involved in the transformation.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 6","pages":" 1678-1684"},"PeriodicalIF":4.7000,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis†\",\"authors\":\"Liping Luo, Xuemei Zhang, Chunxi Huang and Zhong Lian\",\"doi\":\"10.1039/D3QO02004E\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A novel approach for the enantioselective synthesis of chiral β-azide sulfones utilizing sulfur dioxide (SO<small><sub>2</sub></small>) insertion under the catalysis of a cheap, abundant and readily available iron catalyst has been successfully developed for the first time. This four-component reaction could be performed under mild conditions and has a broad substrate scope, giving products with a chiral quaternary carbon center. The obtained compounds can be easily converted into chiral β-amino sulfones which have considerable application values in the pharmaceutical and agrochemical industries. Mechanism study suggests that a radical pathway may be involved in the transformation.</p>\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\" 6\",\"pages\":\" 1678-1684\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2024-01-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d3qo02004e\",\"RegionNum\":1,\"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 Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d3qo02004e","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

在廉价、丰富且易于获得的铁催化剂的催化下,利用二氧化硫(SO2)插入法首次成功开发了一种对映体选择性合成手性β-叠氮砜的新方法。这种四组份反应可以在温和的条件下进行,并且具有广泛的底物范围,可以得到具有手性季碳中心的产物。得到的化合物可以很容易地转化为手性 β-氨基砜,在制药和农用化学品行业具有相当大的应用价值。机理研究表明,自由基途径可能参与了转化过程。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis†

Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis†

A novel approach for the enantioselective synthesis of chiral β-azide sulfones utilizing sulfur dioxide (SO2) insertion under the catalysis of a cheap, abundant and readily available iron catalyst has been successfully developed for the first time. This four-component reaction could be performed under mild conditions and has a broad substrate scope, giving products with a chiral quaternary carbon center. The obtained compounds can be easily converted into chiral β-amino sulfones which have considerable application values in the pharmaceutical and agrochemical industries. Mechanism study suggests that a radical pathway may be involved in the transformation.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信