{"title":"A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine","authors":"Archana Pareek, Sonam Tashi Khom, Pranjit Saikia, Nagendra Nath Yadav","doi":"10.1007/s00706-024-03187-3","DOIUrl":null,"url":null,"abstract":"<p>Ring expansion of 4-[(2<i>R</i>)-1-[(1<i>R</i>)-1-phenylethyl]aziridin-2-yl]butyl tosylate obtained from tosylation of 4-[(2<i>R</i>)-1-[(1<i>R</i>)-1-phenylethyl]aziridin-2-yl]butan-1-ol via formation of 1-azabicyclo[4.1.0]heptane tosylate gives substituted piperidine. The ring openings of azabicycloheptane tosylate with acetate nucleophiles proceeded in highly regio- and stereoselective manner with release of the ring-strain of the three-membered aziridine ring through the breakage of either C-N bond. This ring expansion streategy of aziridine provides a short route for asymmetric synthesis of biologically active natural alkaloid such as (<i>R</i>)-pipecolic acid.</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>","PeriodicalId":19011,"journal":{"name":"Monatshefte für Chemie / Chemical Monthly","volume":"48 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte für Chemie / Chemical Monthly","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1007/s00706-024-03187-3","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Ring expansion of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butyl tosylate obtained from tosylation of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butan-1-ol via formation of 1-azabicyclo[4.1.0]heptane tosylate gives substituted piperidine. The ring openings of azabicycloheptane tosylate with acetate nucleophiles proceeded in highly regio- and stereoselective manner with release of the ring-strain of the three-membered aziridine ring through the breakage of either C-N bond. This ring expansion streategy of aziridine provides a short route for asymmetric synthesis of biologically active natural alkaloid such as (R)-pipecolic acid.
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