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dc.contributor.authorZhao, Feng
dc.contributor.authorShu, Chang
dc.contributor.authorYoung, Claire M.
dc.contributor.authorCarpenter-Warren, Cameron
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2021-05-06T15:30:20Z
dc.date.available2021-05-06T15:30:20Z
dc.date.issued2021-05-11
dc.identifier.citationZhao , F , Shu , C , Young , C M , Carpenter-Warren , C , Slawin , A M Z & Smith , A D 2021 , ' Enantioselective synthesis of α-aryl-β 2 -amino-esters by cooperative isothiourea and Brønsted acid catalysis ' , Angewandte Chemie International Edition , vol. 60 , no. 21 , pp. 11892-11900 . https://doi.org/10.1002/anie.202016220en
dc.identifier.issn1433-7851
dc.identifier.otherPURE: 273137136
dc.identifier.otherPURE UUID: fce9e6c9-6839-42de-a339-1c5d76ed9666
dc.identifier.otherJisc: 14a4ec2a8f234bfd89eda12b9b4bc088
dc.identifier.otherJisc: 14a4ec2a8f234bfd89eda12b9b4bc088
dc.identifier.otherORCID: /0000-0002-2104-7313/work/91340759
dc.identifier.otherORCID: /0000-0002-9527-6418/work/91340854
dc.identifier.otherWOS: 000646714900001
dc.identifier.otherScopus: 85104658188
dc.identifier.urihttp://hdl.handle.net/10023/23120
dc.descriptionFunding: The research leading to these results has received funding from the Royal Society (Newton Fellowship Programme, F. Z.; C. S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe synthesis of α‐aryl‐β2 ‐amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Brønsted acid catalysis is demonstrated. The scope and limitations of this process are explored (25 examples, up to 94% yield and 96:4 er), with applications to the synthesis of (S)‐Venlafaxine·HCl and (S)‐Nakinadine B. Mechanistic studies are consistent with a C(1)‐ammonium enolate pathway being followed rather than an alternative dynamic kinetic resolution process. Control studies indicate that (i) a linear effect between catalyst and product er is observed; (ii) an acyl ammonium ion can be used as a precatalyst; (iii) reversible isothiourea addition to an in situ generated iminium ion leads to an off‐cycle intermediate that can be used as a productive precatalyst.
dc.format.extent10
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.rightsCopyright © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectIsothioureaen
dc.subjectCooperative catalysisen
dc.subjectMechanistic studyen
dc.subjectEnantioselective aminomethylationen
dc.subjectb2-amino aciden
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective synthesis of α-aryl-β2-amino-esters by cooperative isothiourea and Brønsted acid catalysisen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/anie.202016220
dc.description.statusPeer revieweden


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