Catalytic enantioselective synthesis of hydroxyimino tetrahydrobenzofuranones bearing trifluoromethylated quaternary stereocenter via tandem Michael addition/interrupted Nef reactions
{"title":"Catalytic enantioselective synthesis of hydroxyimino tetrahydrobenzofuranones bearing trifluoromethylated quaternary stereocenter via tandem Michael addition/interrupted Nef reactions","authors":"","doi":"10.1016/j.tetlet.2024.155211","DOIUrl":null,"url":null,"abstract":"<div><p>Tetrahydrobenzofuran derivatives are widely distributed in biologically active molecules and natural products. Herein, we reported an asymmetric tandem Michael addition/interrupted Nef reaction triggered by nitromethane directly as Michael donor catalyzed by chiral 2-aminobenzimidazole bifunctional organocatalyst. A series of enantiomerically enriched trifluoromethylated hydroxyimino tetrahydrobenzofuranones were synthesized in moderate to good isolated yields (up to 97 %) and enantioselectivities (up to 80 % ee).</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040392400306X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Tetrahydrobenzofuran derivatives are widely distributed in biologically active molecules and natural products. Herein, we reported an asymmetric tandem Michael addition/interrupted Nef reaction triggered by nitromethane directly as Michael donor catalyzed by chiral 2-aminobenzimidazole bifunctional organocatalyst. A series of enantiomerically enriched trifluoromethylated hydroxyimino tetrahydrobenzofuranones were synthesized in moderate to good isolated yields (up to 97 %) and enantioselectivities (up to 80 % ee).
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.