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Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides

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dc.contributor.authorArokianathar, Jude N.
dc.contributor.authorHartley, Will
dc.contributor.authorMcLaughlin, Calum
dc.contributor.authorGreenhalgh, Mark David
dc.contributor.authorStead, Darren
dc.contributor.authorNg, Sean
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2021-10-20T10:30:02Z
dc.date.available2021-10-20T10:30:02Z
dc.date.issued2021-10-20
dc.identifier276279349
dc.identifierf0fc5383-5d49-48cf-a0c1-31b374eb292c
dc.identifier85117896690
dc.identifier000723136400001
dc.identifier.citationArokianathar , J N , Hartley , W , McLaughlin , C , Greenhalgh , M D , Stead , D , Ng , S , Slawin , A M Z & Smith , A D 2021 , ' Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para -quinone methides ' , Molecules , vol. 26 , no. 21 , 6333 . https://doi.org/10.3390/molecules26216333en
dc.identifier.issn1420-3049
dc.identifier.otherORCID: /0000-0002-2104-7313/work/101958330
dc.identifier.otherORCID: /0000-0002-9527-6418/work/101958403
dc.identifier.urihttps://hdl.handle.net/10023/24172
dc.descriptionFunding: We thank the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013)/E.R.C. grant agreement n° 279850, AstraZeneca and EPSRC [EP/M506631/1 (J.N.A.)], Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis [CRITICAT, EP/L016419/1 (W.C.H.)], and EPSRC [EP/M508214/1 (C.M.)] for funding. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.en
dc.description.abstractThe isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides is reported. para-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, is proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products can be isolated, or derivatized in situ by addition of benzylamine to give amides, in up to 99% yield. Although low diastereocontrol is observed, the diastereoisomeric ester products are separable and formed with high enantiocontrol (up to 94:6 er).
dc.format.extent13
dc.format.extent3002056
dc.language.isoeng
dc.relation.ispartofMoleculesen
dc.subjectIsothioureaen
dc.subjectAmmonium enolateen
dc.subjectAyloxideen
dc.subjectQuinone methideen
dc.subjectEster functionalizationen
dc.subject1,6-conjugate additionen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleIsothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methidesen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.3390/molecules26216333
dc.description.statusPeer revieweden
dc.identifier.urlhttps://www.mdpi.com/1420-3049/26/21/6333en
dc.identifier.urlhttps://www.mdpi.com/journal/molecules/special_issues/Alexandra_Slawinen
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberWM140071en


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