Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
{"title":"Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles","authors":"","doi":"10.1016/j.tet.2024.134331","DOIUrl":null,"url":null,"abstract":"<div><div>The enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated <em>N</em>-acylindoles and <em>N</em>-acylpyrroles catalyzed by a commercial chiral oxazaborolidine is reported. This methodology tolerates a variety of substrates and diarylphosphine oxides, leading to high yields and enantioselectivities. Importantly, the resulting chiral products exhibit excellent transformation abilities to form corresponding acids, amides, and esters with high potential applications in the synthesis of chiral phosphine ligands.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040202400512X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

The enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles catalyzed by a commercial chiral oxazaborolidine is reported. This methodology tolerates a variety of substrates and diarylphosphine oxides, leading to high yields and enantioselectivities. Importantly, the resulting chiral products exhibit excellent transformation abilities to form corresponding acids, amides, and esters with high potential applications in the synthesis of chiral phosphine ligands.
噁唑硼烷催化二芳基膦氧化物与 α、β-不饱和 N-酰基吲哚和 N-酰基吡咯的不对称 1,4-加成反应
报告了在一种商用手性噁唑硼烷催化下,二芳基膦氧化物与 α、β-不饱和 N-酰基吲哚和 N-酰基吡咯的 1,4-对映体选择性加成。该方法可耐受多种底物和二元膦氧化物,从而获得高产率和高对映选择性。重要的是,所得到的手性产物具有极佳的转化能力,可以形成相应的酸、酰胺和酯,在手性膦配体的合成中具有极高的应用潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
×
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:481959085
Book学术官方微信