Tetrahedron letters

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

J Baraut, A Perrier, V Comte, P Richard, P Le Gendre…

Index: Baraut, Johann; Perrier, Arnaud; Comte, Virginie; Richard, Philippe; Le Gendre, Pierre; Moise, Claude Tetrahedron Letters, 2006 , vol. 47, # 47 p. 8319 - 8322

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Citation Number: 4

Abstract

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 ...