{"title":"通过手性氮丙啶的扩环，简短高效地正式合成(R)-联哌啶酸","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":"{\"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}","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}
A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine
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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