{"title":"Enantioselective Synthesis of 2-Azanorbornanes: Chiral Trisimidazoline-Catalyzed Desymmetrizing Transannular Bromoaminocyclization","authors":"Wan-Li Zhu, Hao He, Yong-Shuang Huang, Ya-Ting Wang, You-Gui Li, Xiang Wu","doi":"10.1021/acs.orglett.5c00478","DOIUrl":null,"url":null,"abstract":"An enantioselective desymmetrizing transannular bromoaminocyclization of cyclopentenylamines has been achieved by using <i>C</i><sub>3</sub>-symmetric trisimidazoline catalysis. This protocol could directly provide a range of chiral 2-azanorbornanes in excellent yields (up to 99%) and enantioselectivities (up to 97.5:2.5 enantiomeric ratio). The resulting enantioenriched 2-azanorbornanes are easily converted to synthetically useful building blocks. Further mechanistic investigations show that the presence of three imidazoline groups of the catalyst is crucial to the success of the enantioselective transformation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"89 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-21","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.5c00478","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
An enantioselective desymmetrizing transannular bromoaminocyclization of cyclopentenylamines has been achieved by using C3-symmetric trisimidazoline catalysis. This protocol could directly provide a range of chiral 2-azanorbornanes in excellent yields (up to 99%) and enantioselectivities (up to 97.5:2.5 enantiomeric ratio). The resulting enantioenriched 2-azanorbornanes are easily converted to synthetically useful building blocks. Further mechanistic investigations show that the presence of three imidazoline groups of the catalyst is crucial to the success of the enantioselective transformation.
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.
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