Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds

[Display omitted] •Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene. When α-alkyl substituted β-dicarbony...

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Veröffentlicht in:Tetrahedron letters 2025-01, Vol.154, p.155390, Article 155390
Hauptverfasser: Matsuda, Yuya, Mori, Shintaro, Tsuda, Susumu, Nishiyama, Yutaka
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Sprache:eng
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Zusammenfassung:[Display omitted] •Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene. When α-alkyl substituted β-dicarbonyl compounds were reacted with allylsilanes in the presence of a rhenium catalyst, the allylation of the benzylic carbon center proceeded through the elimination of the β-dicarbonyl unit to form the corresponding alkenes in moderate to good yields. Regarding the reaction with hydrosilane, the reduction of these compounds also proceeded through the elimination of the β-dicarbonyl unit to give the corresponding alkanes.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2024.155390