Phospholanes via Twofold C-H-Addition to Phospholes

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dc.date.accessioned2024-07-24T11:21:59Z
dc.date.available2024-07-24T11:21:59Z
dc.date.issued2024-05-23
dc.description.sponsorshipGefördert im Rahmen des Projekts DEAL ; DFG
dc.identifierdoi:10.17170/kobra-2024072410576
dc.identifier.urihttp://hdl.handle.net/123456789/15935
dc.language.isoeng
dc.relation.doidoi:10.1002/adsc.202400288
dc.relation.projectidDFG Grant Number: CRC 1319, ELCH
dc.rightsNamensnennung 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectaddition reactioneng
dc.subjectfused ring systemeng
dc.subjectphospholaneeng
dc.subjectphospholeeng
dc.subjectX-ray crystallographyeng
dc.subject.ddc540
dc.subject.swdRöntgenkristallographieger
dc.subject.swdPhospholaneger
dc.subject.swdAdditionsreaktionger
dc.titlePhospholanes via Twofold C-H-Addition to Phospholeseng
dc.typeAufsatz
dc.type.versionpublishedVersion
dcterms.abstractA synthetic route towards phospholanes via twofold C−H-addition of a DMSO molecule to β-H substituted phospholes is described. The resulting fused phospholane oxothiolane system in case of symmetric α-substitution possesses four stereogenic centers or rather six in case of asymmetric α-substitution. The reaction conditions are shown to be applicable for a variety of phospholes with different P- or α-substituents always leading to stereoselective formation of the fused heterocyclic ring system. All phospholane derivatives with one exception are sufficiently air stable for purification with column chromatography and are fully characterized by NMR and elemental analysis and mass spectrometry. With the help of X-ray crystallography, the different configurations of the isomers could be demonstrated. For one model system derivatization reactions are presented. When oxidizing or reducing the sulfoxide group only a single diastereomer is observed.eng
dcterms.accessRightsopen access
dcterms.creatorGetfert, Katharina
dcterms.creatorRoesler, Fabian
dcterms.creatorBruhn, Clemens
dcterms.creatorPietschnig, Rudolf
dcterms.source.identifiereissn:1615-4169
dcterms.source.issueIssue 12
dcterms.source.journalAdvanced Synthesis & Catalysiseng
dcterms.source.pageinfo2764-2774
dcterms.source.volumeVolume 366
kup.iskupfalse

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