Hao-Ran Wang , Wen-Guang Zhou , Li-Wen Zhan , Long-Long Xi , Ren-Rong Liu
{"title":"铑催化1,4-芳基硼酸加成烯酮手性七元环的对映选择性合成","authors":"Hao-Ran Wang , Wen-Guang Zhou , Li-Wen Zhan , Long-Long Xi , Ren-Rong Liu","doi":"10.1039/d5qo00444f","DOIUrl":null,"url":null,"abstract":"<div><div>A rhodium-catalyzed reaction between enones and arylboronic acids has been developed to construct chiral seven-membered rings through enantioselective 1,4-addition. This reaction offers outstanding functional group compatibility and excellent regio- and enantioselectivities using easily accessible arylboronic acids. Furthermore, to confirm the practicality of the reaction and understand its mechanism, we conducted in-depth studies on both product transformations and reaction pathways. This method demonstrates numerous advantages, including mild reaction conditions, readily available catalysts and ligands, a broad range of substrates, and the potential for synthesizing scaffolds similar to natural products.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 18","pages":"Pages 4963-4969"},"PeriodicalIF":0.0000,"publicationDate":"2025-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective synthesis of chiral seven-membered rings via Rh-catalyzed 1,4-addition of arylboronic acids to enones†\",\"authors\":\"Hao-Ran Wang , Wen-Guang Zhou , Li-Wen Zhan , Long-Long Xi , Ren-Rong Liu\",\"doi\":\"10.1039/d5qo00444f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A rhodium-catalyzed reaction between enones and arylboronic acids has been developed to construct chiral seven-membered rings through enantioselective 1,4-addition. This reaction offers outstanding functional group compatibility and excellent regio- and enantioselectivities using easily accessible arylboronic acids. Furthermore, to confirm the practicality of the reaction and understand its mechanism, we conducted in-depth studies on both product transformations and reaction pathways. This method demonstrates numerous advantages, including mild reaction conditions, readily available catalysts and ligands, a broad range of substrates, and the potential for synthesizing scaffolds similar to natural products.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 18\",\"pages\":\"Pages 4963-4969\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-04-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412925003171\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925003171","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Enantioselective synthesis of chiral seven-membered rings via Rh-catalyzed 1,4-addition of arylboronic acids to enones†
A rhodium-catalyzed reaction between enones and arylboronic acids has been developed to construct chiral seven-membered rings through enantioselective 1,4-addition. This reaction offers outstanding functional group compatibility and excellent regio- and enantioselectivities using easily accessible arylboronic acids. Furthermore, to confirm the practicality of the reaction and understand its mechanism, we conducted in-depth studies on both product transformations and reaction pathways. This method demonstrates numerous advantages, including mild reaction conditions, readily available catalysts and ligands, a broad range of substrates, and the potential for synthesizing scaffolds similar to natural products.