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Application of Primary Phosphine Oxides in Domino-Phospha- Aldol Reactions of Diketones

dc.date.accessioned2024-09-27T13:21:03Z
dc.date.available2024-09-27T13:21:03Z
dc.date.issued2024-06-06
dc.identifierdoi:10.17170/kobra-2024092010857
dc.identifier.urihttp://hdl.handle.net/123456789/16064
dc.description.sponsorshipGefördert im Rahmen des Projekts DEAL
dc.language.isoeng
dc.rightsNamensnennung 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectPhosphoruseng
dc.subjectP−H activationeng
dc.subjectcondensation reactioneng
dc.subjectheterocycleseng
dc.subjectcycloadditioneng
dc.subject.ddc540
dc.titleApplication of Primary Phosphine Oxides in Domino-Phospha- Aldol Reactions of Diketoneseng
dc.typeAufsatz
dcterms.abstractAn approach for the preparation and stabilization of primary phosphine oxides is presented complementing previous methods of in situ generation. Specifically, RP(O)H₂ where R=benzyl (Bn), cyclohexyl (Cy), 2-naphthyl (2-Naph), phenyl (Ph), tert-butyl (t-Bu) was prepared by controlled oxidation of the corresponding primary phosphine in presence of ferrocene as stabilizing reagent. The primary phosphine oxides were characterized using NMR and MS and studied in twofold hydrophosphorylation of diketones. The domino-phospha-aldol reaction catalysed with 5 mol% of sodium methoxide yielded five-, six- and seven-membered heterocyclic tertiary phosphine oxides with a high degree of stereoselectivity, as confirmed by single X-ray diffraction.eng
dcterms.accessRightsopen access
dcterms.creatorHorký, Filip
dcterms.creatorBruhn, Clemens
dcterms.creatorKargin, Denis
dcterms.creatorPietschnig, Rudolf
dc.relation.doidoi:10.1002/adsc.202400496
dc.subject.swdCycloadditionger
dc.subject.swdPolycyclische heterocyclische Verbindungenger
dc.subject.swdKondensationsreaktionger
dc.subject.swdPhosphorger
dc.type.versionpublishedVersion
dcterms.source.identifiereissn:1615-4169
dcterms.source.issueIssue 15
dcterms.source.journalAdvanced Synthesis & Catalysiseng
dcterms.source.pageinfo3354-3360
dcterms.source.volumeVolume 366
kup.iskupfalse


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