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A C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcohols

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dc.contributor.authorGreenhalgh, Mark D.
dc.contributor.authorSmith, Samuel M.
dc.contributor.authorWalden, Daniel M.
dc.contributor.authorTaylor, James E.
dc.contributor.authorBrice, Zamira
dc.contributor.authorRobinson, Emily R. T.
dc.contributor.authorFallan, Charlene
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorRichardson, H. Camille
dc.contributor.authorGrove, Markas A.
dc.contributor.authorCheong, Paul Ha-Yeon
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2019-02-19T00:33:29Z
dc.date.available2019-02-19T00:33:29Z
dc.date.issued2018-03-12
dc.identifier252045715
dc.identifierd1b5cdb2-e2b0-405b-b952-a05053a6d2c7
dc.identifier85042110491
dc.identifier000426759900035
dc.identifier.citationGreenhalgh , M D , Smith , S M , Walden , D M , Taylor , J E , Brice , Z , Robinson , E R T , Fallan , C , Cordes , D B , Slawin , A M Z , Richardson , H C , Grove , M A , Cheong , P H-Y & Smith , A D 2018 , ' A C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcohols ' , Angewandte Chemie International Edition , vol. 57 , no. 12 , pp. 3200-3206 . https://doi.org/10.1002/anie.201712456en
dc.identifier.issn1433-7851
dc.identifier.otherORCID: /0000-0002-2104-7313/work/42023858
dc.identifier.otherORCID: /0000-0002-5366-9168/work/42023872
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861440
dc.identifier.urihttps://hdl.handle.net/10023/17091
dc.descriptionThe research leading to these results has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013)/E.R.C. grant agreement n° 279850 and the EPSRC (EP/J500549/1). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. P.H.-Y.C. is the Bert and Emelyn Christensen Professor and gratefully acknowledges financial support from the Stone Family of OSU. Financial support from the National Science Foundation (NSF) (CHE-1352663) is acknowledged. D.M.W. acknowledges the Bruce Graham and Johnson Fellowships of OSU. D.M.W. and P.H.-Y.C. acknowledge computing infrastructure in part provided by the NSF Phase-2 CCI, Center for Sustainable Materials Chemistry (CHE-1102637).en
dc.description.abstractA combination of experimental and computational studies have identified a C=O•••isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to > 200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions
dc.format.extent7
dc.format.extent1591959
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.subjectAcylationen
dc.subjectKinetic resolutionen
dc.subjectLewis basesen
dc.subjectOrganocatalysisen
dc.subjectTertiary alcoholsen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectBDCen
dc.subjectR2Cen
dc.subject.lccQDen
dc.titleA C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcoholsen
dc.typeJournal articleen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doi10.1002/anie.201712456
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-02-19
dc.identifier.grantnumberWM140071en
dc.identifier.grantnumberN/Aen


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