Catalytic reaction of sylvan with alkyl diazoacetates as a method for the synthesis of stereoisomeric 4-acetyl-1,3-butadiene-1-carboxylic acids

  • O. M. Nefedov
  • L. E. Saltykova
  • A. E. Vasil'vitskii
  • V. M. Shostakovskii
Brief Communications
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Conclusions

  1. 1.

    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.

     
  2. 2.

    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.

     

Keywords

Copper Ester Adduct Optimal Condition Palladium 

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Literature cited

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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • O. M. Nefedov
    • 1
  • L. E. Saltykova
    • 1
  • A. E. Vasil'vitskii
    • 1
  • V. M. Shostakovskii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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