Catalytic reaction of sylvan with alkyl diazoacetates as a method for the synthesis of stereoisomeric 4-acetyl-1,3-butadiene-1-carboxylic acids
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The reaction of alkyl diazoacetates with sylvan in the presence in rhodium, palladium and copper catalysts proceeds smoothly at from -20 to +60°C to give the Z, Z, E, Z and E,E isomers of the corresponding ester of 4-acetyl-l, 3-butadiene-l-carboxylic acid along with the alkyl ester of 3-methyl-2-oxabicyclo[3.1.0] hex-3-ene-6-carboxylic acid (in 62–94% total yield). The data obtained indicate the parallel formation of this bicyclic adduct and the corresponding isomeric ketodienes.
Optimal conditions were found for the stereoselective preparation of E, Z isomers of alkyl esters of 4-acety l-l,3-butadiene-l-carboxylic acid (up.to 70% yields), which hold interest as synthetic precursors for the preparation of beetle and weevil pheromones.
KeywordsCopper Ester Adduct Optimal Condition Palladium
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