Palladium-catalyzed carbocyclization of allene-diene ...



Title Palladium-catalyzed carbocyclization of allene-diene derivatives. Exploring different nucleophiles
Author(s) Jeanne Lofstedt, K. Narhi, I. Dorange, J. E. Backvall
Journal The Journal of Organic Chemistry
Date 2003
Volume 68
Issue 19
Start page 7243
End page 7248
Abstract The palladium-catalyzed carbocyclization of allene-diene derivatives leading to the stereospecific formation of various 4-substituted [4.3.0] and [5.3.0] bicyclic systems is presented. Different functionalities were introduced at the C-4 position of the bicyclic systems by using a range of external nucleophiles such as carboxylic acids, alcohols, phenols, and thiophenols. In the previous protocol acetic acid was used as solvent and also served as nucleophile. In this new methodology, reactions were run in nonnucleophlic solvents such as CH(2)Cl(2) or acetone in the presence of the appropriate nucleophile, making this new protocol a more versatile tool in organic synthesis. It is noteworthy that the Pd(II)-catalyzed cyclization of cycloheptadiene-derivative 1b gave exclusively the trans-annulated bicycle 4. Depending on the nature of the nucleophile, the regioselectivity of the reaction could be tuned to afford exclusively 4b or 4c' (Scheme 1). The mechanistic pathway is discussed.
DOI 10.1021/jo034412c

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