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Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldimines

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dc.contributor.authorSmith, Siobhan R.
dc.contributor.authorDouglas, James
dc.contributor.authorPrevet, Hugues
dc.contributor.authorShapland, Peter
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2015-02-05T00:01:38Z
dc.date.available2015-02-05T00:01:38Z
dc.date.issued2014-02-21
dc.identifier111957222
dc.identifier8146cf5a-4f59-40ed-b7b9-77b6790246c5
dc.identifier000331926900010
dc.identifier84894589142
dc.identifier000331926900010
dc.identifier.citationSmith , S R , Douglas , J , Prevet , H , Shapland , P , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N -sulfonylaldimines ' , The Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1626-1639 . https://doi.org/10.1021/jo402590men
dc.identifier.issn0022-3263
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567513
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861499
dc.identifier.urihttps://hdl.handle.net/10023/6072
dc.descriptionThis work is supported by a Royal Society for a University Research Fellowship and the EPSRC and GSK (Case Award) as well as by the European Research Council under the European Unionʼs Seventh Framework Programme (FP7/2007-2013) (ERC Grant Agreement No.279850)en
dc.description.abstractThe isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the β-lactam framework was possible without racemization by treatment with SmI2.
dc.format.extent14
dc.format.extent1740783
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.subjectHuman Cytomegalovirus Proteaseen
dc.subjectPromoted Bis-Cyclizationsen
dc.subjectAcyl Transfer Catalysten
dc.subjectPure Lithium Amidesen
dc.subjectEnantioselective Synthesisen
dc.subjectKinugasa Reactionen
dc.subjectAldol-Lactonizationen
dc.subjectStaudinger Reactionen
dc.subjectKinetic Resolutionen
dc.subjectDyotropic Rearrangementsen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleIsothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldiminesen
dc.typeJournal articleen
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.doi10.1021/jo402590m
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-02-05


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