A general method for the synthesis of 2-alkyl substituted 1,3-dienes starting from 2-(chloromethyl)-3-tosylpropene

Add time:07/18/2019    Source:sciencedirect.com

The alkylation of the monolithium derivative 5 of 2-(chloromethyl)-3-tosylpropene (1) with bromo- or iodo-methyltrimethylsilane affords the β-silyl sulfone 7, which after nucleophilic substitution of the chlorine atom followed by β-elimination of tosyltrimethylsilane, promoted by tetrabutylammonium fluoride (TBAF), gives 2-substituted conjugated dienes 6 and the outer-ring diene 14. Racemic ipsenol (10b), an aggregation pheromone of the bark beetle Ips paraconfusus Lanier, is prepared.

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