Emina Mehić, Robert Junior Kolman, Irena Dokli, Maja Majerić Elenkov
{"title":"Biocatalytically Generated Library of Chiral Building Blocks Containing a Quaternary Stereocenter","authors":"Emina Mehić, Robert Junior Kolman, Irena Dokli, Maja Majerić Elenkov","doi":"10.1021/acs.orglett.4c03399","DOIUrl":null,"url":null,"abstract":"A biocatalytic strategy for the preparation of a small library of compounds containing a quaternary chiral center is described. By applying halohydrin dehalogenases, four racemic 2,2-disubstituted epoxides were converted in the presence of four nucleophiles to 14 chiral products in yields of 21–47% with 74 to >99% <i>ee</i>. The obtained set of building blocks, which hold diverse functional groups, can be modified to form many high-value organic molecules for use in medicinal chemistry and other areas.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"67 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03399","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A biocatalytic strategy for the preparation of a small library of compounds containing a quaternary chiral center is described. By applying halohydrin dehalogenases, four racemic 2,2-disubstituted epoxides were converted in the presence of four nucleophiles to 14 chiral products in yields of 21–47% with 74 to >99% ee. The obtained set of building blocks, which hold diverse functional groups, can be modified to form many high-value organic molecules for use in medicinal chemistry and other areas.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.