Datum
2024-06-06Schlagwort
540 Chemie CycloadditionPolycyclische heterocyclische VerbindungenKondensationsreaktionPhosphorMetadata
Zur Langanzeige
Aufsatz
Application of Primary Phosphine Oxides in Domino-Phospha- Aldol Reactions of Diketones
Zusammenfassung
An 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.
Zitierform
In: Advanced Synthesis & Catalysis Volume 366 / Issue 15 (2024-06-06) , S. 3354-3360 ; eissn:1615-4169Förderhinweis
Gefördert im Rahmen des Projekts DEALZitieren
@article{doi:10.17170/kobra-2024092010857,
author={Horký, Filip and Bruhn, Clemens and Kargin, Denis and Pietschnig, Rudolf},
title={Application of Primary Phosphine Oxides in Domino-Phospha- Aldol Reactions of Diketones},
journal={Advanced Synthesis & Catalysis},
year={2024}
}
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2024-09-27T13:21:03Z 2024-09-27T13:21:03Z 2024-06-06 doi:10.17170/kobra-2024092010857 http://hdl.handle.net/123456789/16064 Gefördert im Rahmen des Projekts DEAL eng Namensnennung 4.0 International http://creativecommons.org/licenses/by/4.0/ Phosphorus P−H activation condensation reaction heterocycles cycloaddition 540 Application of Primary Phosphine Oxides in Domino-Phospha- Aldol Reactions of Diketones Aufsatz An 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. open access Horký, Filip Bruhn, Clemens Kargin, Denis Pietschnig, Rudolf doi:10.1002/adsc.202400496 Cycloaddition Polycyclische heterocyclische Verbindungen Kondensationsreaktion Phosphor publishedVersion eissn:1615-4169 Issue 15 Advanced Synthesis & Catalysis 3354-3360 Volume 366 false
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