{"title":"Catalytic Enantioselective Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones and Vinyl Selenides","authors":"Xinwen You, Quan Cai","doi":"10.1055/a-1990-5276","DOIUrl":null,"url":null,"abstract":"We report herein an asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of electron-deficient 2-pyrones with various phenyl vinyl selenides catalyzed by a chiral bis(oxazoline)/Cu(OTf)2 complex. Using a side arm-modified chiral bis(oxazoline)ligand, a variety of [2,2,2]-bicyclic lactones with phenyl selenide substituents were obtained with good to excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee) under mild conditions. Based on this strategy, enantioselective synthesis of Corey lactone was accomplished in a highly concise manner.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2022-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-1990-5276","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: 1
Abstract
We report herein an asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of electron-deficient 2-pyrones with various phenyl vinyl selenides catalyzed by a chiral bis(oxazoline)/Cu(OTf)2 complex. Using a side arm-modified chiral bis(oxazoline)ligand, a variety of [2,2,2]-bicyclic lactones with phenyl selenide substituents were obtained with good to excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee) under mild conditions. Based on this strategy, enantioselective synthesis of Corey lactone was accomplished in a highly concise manner.
期刊介绍:
SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.