Silylated azolium salts and their applications in the synthesis of azolines and β-enaminoketones bearing allyl-, vinyl-, and acylsilane or α-silylketone units

Differently silylated 3- or 4-isoxazolines and 3-pyrazolines, bearing versatile vinyl- or allylsilane moieties in various positions of the heterocyclic system, have been synthesized starting from new silylazolium salts by reduction with metal complex hydrides or alkylation with organolithium reagent...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 28; pp. 5472 - 5483
Main Authors González-Nogal, Ana M., Calle, Mariola
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 11.07.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Silicon heterocycles
Silylisoxazolines
Silylpyrazolines
β-Enaminoacylsilanes
Silicon heterocycles
Silylisoxazolines
β-Enaminoacylsilanes
Silylpyrazolines
REGIOSPECIFIC SYNTHESIS
ENAMINONES
REGIOSELECTIVE SYNTHESIS
beta-Enaminoacylsilanes
PYRAZOLIUM SALTS
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Summary:Differently silylated 3- or 4-isoxazolines and 3-pyrazolines, bearing versatile vinyl- or allylsilane moieties in various positions of the heterocyclic system, have been synthesized starting from new silylazolium salts by reduction with metal complex hydrides or alkylation with organolithium reagents. On the other hand, the reductive ring-opening of silylated isoxazolium salts with lithium dimethylcuprate led to interesting β-enamino acylsilanes and α′-silylmethyl-β-enaminoketones. These polysynthetic equivalents are useful building blocks in organic synthesis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.01.114