{"title":"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","authors":"Jinyi Qian, Wendi Shao, Qi Gao, Jiuling Li, Baomin Fan, Yafei Guo","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":"168 ","pages":"Article 134331"},"PeriodicalIF":2.1000,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles\",\"authors\":\"Jinyi Qian, Wendi Shao, Qi Gao, Jiuling Li, Baomin Fan, Yafei Guo\",\"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\":\"168 \",\"pages\":\"Article 134331\"},\"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}","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}
Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles
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.
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.