Xiang Ji, Shengwen Yang, Zhifei Zhao and Shi-Wu Li
{"title":"Catalytic asymmetric synthesis of guaiazulene analogues†","authors":"Xiang Ji, Shengwen Yang, Zhifei Zhao and Shi-Wu Li","doi":"10.1039/D4NJ02771J","DOIUrl":null,"url":null,"abstract":"<p >The asymmetric Michael addition reaction of guaiazulene to α,β-unsaturated 2-acyl imidazoles was developed with a chiral-at-metal Rh(<small>III</small>) complex as the catalyst for the first time. The corresponding adducts were obtained in good yields (76–98%) with excellent enantioselectivities (up to 99%). The reaction could be conducted on a gram-scale with a low catalyst loading (0.05 mol%) without impacting its efficiency. DFT studies rationalize the enantioselectivity of the reaction.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02771j","RegionNum":3,"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
Abstract
The asymmetric Michael addition reaction of guaiazulene to α,β-unsaturated 2-acyl imidazoles was developed with a chiral-at-metal Rh(III) complex as the catalyst for the first time. The corresponding adducts were obtained in good yields (76–98%) with excellent enantioselectivities (up to 99%). The reaction could be conducted on a gram-scale with a low catalyst loading (0.05 mol%) without impacting its efficiency. DFT studies rationalize the enantioselectivity of the reaction.