{"title":"Diastereoselective synthesis of (Z)-fluoroalkene dipeptide isosteres utilizing chiral auxiliaries†","authors":"Takuya Kobayakawa , Marisa Arioka , Kenichi Yamamoto , Kohei Tsuji , Hirokazu Tamamura","doi":"10.1039/d5ob00189g","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient method for diastereo-controlled synthesis of (<em>Z</em>)-fluoroalkene dipeptide isosteres (FADIs) was developed. Two chiral centers were constructed by applying our synthetic methodology for chloroalkene dipeptide isosteres (CADIs) using Ellman's imine for corresponding to the N-terminal amino acid residues and Oppolzer's sultam for corresponding to the C-terminal amino acid residues, affording dipeptidomimetic in a stereocontrolled manner with high diastereoselectivity.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 18","pages":"Pages 4333-4336"},"PeriodicalIF":2.7000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025002915","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/13 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient method for diastereo-controlled synthesis of (Z)-fluoroalkene dipeptide isosteres (FADIs) was developed. Two chiral centers were constructed by applying our synthetic methodology for chloroalkene dipeptide isosteres (CADIs) using Ellman's imine for corresponding to the N-terminal amino acid residues and Oppolzer's sultam for corresponding to the C-terminal amino acid residues, affording dipeptidomimetic in a stereocontrolled manner with high diastereoselectivity.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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