Reactions of dicarbanion equivalents generated from complexation of 1,3-dienes on Ti(II) moiety

Reactions of dicarbanion equivalents generated from complexation of 1,3-dienes on Ti(II) moiety

Conjugated dienes are able to react as 1,2- or 1,4-dicarbanions by coordination on Ti(II) moiety. These two possibilities are exemplified in this letter with isoprene, myrcene and several aldehydes to give 1,4- and 1,6-diols. When allowed to react with esters at room temperature, the titanium–diene...

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Veröffentlicht in:Tetrahedron letters 2006-11, Vol.47 (47), p.8319-8322
Hauptverfasser: Baraut, Johann, Perrier, Arnaud, Comte, Virginie, Richard, Philippe, Le Gendre, Pierre, Moïse, Claude
Format: Artikel
Sprache:eng
Schlagworte:
Allylic ketone
Chemical Sciences
Coordination chemistry
Cyclopentenol
Diene
Diol
Titanium
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Zusammenfassung:Conjugated dienes are able to react as 1,2- or 1,4-dicarbanions by coordination on Ti(II) moiety. These two possibilities are exemplified in this letter with isoprene, myrcene and several aldehydes to give 1,4- and 1,6-diols. When allowed to react with esters at room temperature, the titanium–diene complexes lead to cyclopentenol derivatives. Surprisingly, when this reaction is performed at lower temperature (−40 °C), allylic ketones are formed with high regio and diastereoselectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.09.077