FigsharePub Date : 2016-05-06DOI: 10.1021/ja046115a.s001
J. Sivaguru (1720597), Thomas Poon (2448820), Roberto Franz (2682016), Steffen Jockusch (62236), Waldemar Adam (1392745), Nicholas J. Turro (62239)
{"title":"Stereocontrol within Confined Spaces: Enantioselective Photooxidation ofnEnecarbamates Inside Zeolite Supercages","authors":"J. Sivaguru (1720597), Thomas Poon (2448820), Roberto Franz (2682016), Steffen Jockusch (62236), Waldemar Adam (1392745), Nicholas J. Turro (62239)","doi":"10.1021/ja046115a.s001","DOIUrl":"https://doi.org/10.1021/ja046115a.s001","url":null,"abstract":"Dye-exchanged Y zeolite is shown to be an effective medium to control the stereoselectivity in the photooxygenation of chiral oxazolidinone-functionalized <i>Z/E</i>-<b>1</b> enecarbamates. An enantioselectivity (ee) as high as 80% was observed in the methyldesoxybenzoin (MDB) product, obtained in the methylene-blue-exchanged NaY zeolite at room temperature. The efficacy of the asymmetric induction in the MDB product depends on the <i>Z</i>/<i>E</i> geometry of the alkene, the <i>Z</i>-isomer being more effective than the corresponding <i>E</i>-isomer. The stereoselectivity is rationalized in terms of conformational effects through cationic interactions between the zeolite and the substrate.","PeriodicalId":522666,"journal":{"name":"Figshare","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2016-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147901417","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}