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http://dx.doi.org/10.18419/opus-13736
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DC Element | Wert | Sprache |
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dc.contributor.author | Stöckl, Yannick | - |
dc.contributor.author | Tait, Ethan J. | - |
dc.contributor.author | Frey, Wolfgang | - |
dc.contributor.author | Wegner, Sascha | - |
dc.contributor.author | Claasen, Birgit | - |
dc.contributor.author | Zens, Anna | - |
dc.contributor.author | Laschat, Sabine | - |
dc.date.accessioned | 2023-11-09T08:29:51Z | - |
dc.date.available | 2023-11-09T08:29:51Z | - |
dc.date.issued | 2023 | de |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.issn | 1521-3765 | - |
dc.identifier.other | 1871022592 | - |
dc.identifier.uri | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-137557 | de |
dc.identifier.uri | http://elib.uni-stuttgart.de/handle/11682/13755 | - |
dc.identifier.uri | http://dx.doi.org/10.18419/opus-13736 | - |
dc.description.abstract | Molecules stereogenic only at tetrahedral boron atoms show great promise for applications, for example as chiroptical materials, but are scarcely investigated due to their synthetic challenge. Hence, this study reports a two-step synthesis of enantioenriched boron C,N-chelates. First, the diastereoselective complexation of alkyl/aryl borinates with chiral aminoalcohols furnished boron stereogenic heterocycles in up to 86 % yield and d.r. >98 : 2. Treatment of these O,N-complexes with chelate nucleophiles was surmised to transfer the stereoinformation via the ate-complex into the C,N-products. This chirality transfer succeeded by substitution of the O,N-chelates with lithiated phenyl pyridine to give boron stereogenic C,N-chelates in up to 84 % yield and e.r. up to 97 : 3. The chiral aminoalcohol ligands could be recovered after isolation of the C,N-chelates. The chirality transfer tolerated alkyl, alkynyl and (hetero-)aryl moieties at boron and could be further extended by post-modification: transformations such as catalytic hydrogenations or sequential deprotonation/electrophilic trapping were feasible while maintaining the stereochemical integrity of the C,N-chelates. Structural aspects of the boron chelates were studied by variable temperature NMR and X-ray diffraction. | en |
dc.description.sponsorship | Deutscher Akademischer Austauschdienst | de |
dc.description.sponsorship | Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg | de |
dc.description.sponsorship | Fonds der Chemischen Industrie | de |
dc.description.sponsorship | Deutsche Forschungsgemeinschaft | de |
dc.description.sponsorship | Erasmus+ | de |
dc.description.sponsorship | Projekt DEAL | de |
dc.language.iso | en | de |
dc.relation.uri | doi:10.1002/chem.202301324 | de |
dc.rights | info:eu-repo/semantics/openAccess | de |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | de |
dc.subject.ddc | 540 | de |
dc.title | Enantioenriched boron C,N‐chelates via chirality transfer | en |
dc.type | article | de |
dc.date.updated | 2023-10-10T22:17:16Z | - |
ubs.fakultaet | Chemie | de |
ubs.institut | Institut für Organische Chemie | de |
ubs.publikation.seiten | 9 | de |
ubs.publikation.source | Chemistry - a European journal 29 (2023), No. e202301324 | de |
ubs.publikation.typ | Zeitschriftenartikel | de |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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CHEM_CHEM202301324.pdf | 10,27 MB | Adobe PDF | Öffnen/Anzeigen |
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