{"title":"Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis-2,3-Disubstituted Piperidines","authors":"Shaoyu Hao, Lin Tang, Chaoren Shen, Kaiwu Dong","doi":"10.1021/acs.orglett.4c04345","DOIUrl":null,"url":null,"abstract":"Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a (<i>Z</i>)/(<i>E</i>)-isomeric mixture of trisubstituted alkenes using the lactate-derived <i>C</i><sub>2</sub>-symmetric arylthiol catalyst was developed for the synthesis of <i>cis</i>-2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-16","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.4c04345","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
Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a (Z)/(E)-isomeric mixture of trisubstituted alkenes using the lactate-derived C2-symmetric arylthiol catalyst was developed for the synthesis of cis-2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.
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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