Chun Keng Thy , Yean Kee Lee , Iskandar Abdullah , Noorsaadah Abd Rahman , Chin Fei Chee
{"title":"Asymmetric Diels–Alder reaction of chalcone and isoprene mediated by titanium-based complexes","authors":"Chun Keng Thy , Yean Kee Lee , Iskandar Abdullah , Noorsaadah Abd Rahman , Chin Fei Chee","doi":"10.1080/00397911.2024.2324002","DOIUrl":null,"url":null,"abstract":"<div><p>The asymmetric Diels–Alder reaction of chalcone and isoprene has been accomplished by use of chiral titanium complexes. Notably, an enantiomeric excess as high as 61% and a regioselectivity of 95% have been achieved. The preparation of the chiral titanium complexes is simple and does not require the pre-installation of a chiral auxiliary. This study represents the first example of asymmetric Diels–Alder reaction between chalcone and isoprene.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 8","pages":"Pages 636-644"},"PeriodicalIF":1.8000,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000171","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/3/7 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The asymmetric Diels–Alder reaction of chalcone and isoprene has been accomplished by use of chiral titanium complexes. Notably, an enantiomeric excess as high as 61% and a regioselectivity of 95% have been achieved. The preparation of the chiral titanium complexes is simple and does not require the pre-installation of a chiral auxiliary. This study represents the first example of asymmetric Diels–Alder reaction between chalcone and isoprene.
期刊介绍：
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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