Bitte benutzen Sie diese Kennung, um auf die Ressource zu verweisen:
http://dx.doi.org/10.18419/opus-13982
Langanzeige der Metadaten
DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | Yu, Xin | - |
dc.contributor.author | Hu, Lingfei | - |
dc.contributor.author | Frey, Wolfgang | - |
dc.contributor.author | Lu, Gang | - |
dc.contributor.author | Peters, René | - |
dc.date.accessioned | 2024-03-01T14:55:36Z | - |
dc.date.available | 2024-03-01T14:55:36Z | - |
dc.date.issued | 2022 | de |
dc.identifier.issn | 1521-3773 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.other | 1882493648 | - |
dc.identifier.uri | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-140011 | de |
dc.identifier.uri | http://elib.uni-stuttgart.de/handle/11682/14001 | - |
dc.identifier.uri | http://dx.doi.org/10.18419/opus-13982 | - |
dc.description.abstract | The catalytic allylic substitution is one of the most important tools in asymmetric synthesis to form C-C bonds in an enantioselective way. While high efficiency was previously accomplished in terms of enantio‐ and regiocontrol using different catalyst types, a strong general limitation is a very pronounced preference for the formation of allylic substitution products with (E)-configured C=C double bonds. Herein, we report that with a planar chiral palladacycle catalyst a diastereospecific reaction outcome is achieved using isoxazolinones and allylic imidates as substrates, thus maintaining the C=C double bond geometry of the allylic substrates in the highly enantioenriched products. DFT calculations show that the reactions proceed via an SN2 mechanism and not via π‐allyl Pd complexes. Crucial for the high control is the stabilization of the allylic fragment in the SN2 transition state by π‐interactions with the phenyl substituents of the pentaphenylferrocenyl catalyst core. | en |
dc.description.sponsorship | Deutsche Forschungsgemeinschaft | de |
dc.description.sponsorship | China Scholarship Council | de |
dc.description.sponsorship | National Natural Science Foundation of China | de |
dc.description.sponsorship | Natural Science Foundation of Shandong Province | de |
dc.description.sponsorship | Taishan Scholar of Shandong Province | de |
dc.description.sponsorship | Qilu Young Scholar of Shandong University | de |
dc.description.sponsorship | Projekt DEAL | de |
dc.language.iso | en | de |
dc.relation.uri | doi:10.1002/anie.202210145 | de |
dc.rights | info:eu-repo/semantics/openAccess | de |
dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | de |
dc.subject.ddc | 540 | de |
dc.title | Stereoretentive regio‐ and enantioselective allylation of isoxazolinones by a planar chiral palladacycle catalyst | en |
dc.type | article | de |
dc.date.updated | 2023-11-14T00:09:20Z | - |
ubs.fakultaet | Chemie | de |
ubs.fakultaet | Fakultätsübergreifend / Sonstige Einrichtung | de |
ubs.institut | Institut für Organische Chemie | de |
ubs.institut | Fakultätsübergreifend / Sonstige Einrichtung | de |
ubs.publikation.seiten | 6 | de |
ubs.publikation.source | Angewandte Chemie international edition 61 (2022), No. e202210145 | de |
ubs.publikation.typ | Zeitschriftenartikel | de |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
---|---|---|---|---|
ANIE_ANIE202210145.pdf | 6,4 MB | Adobe PDF | Öffnen/Anzeigen |
Diese Ressource wurde unter folgender Copyright-Bestimmung veröffentlicht: Lizenz von Creative Commons