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Keywords:

  • allylic esters;
  • anti-Markovnikov;
  • benzoquinone;
  • oxidation;
  • palladium
Thumbnail image of graphical abstract

An aldol alternative: The palladium(II)-catalyzed anti-Markovnikov oxidation of allylic esters to aldehydes at room temperature provides a viable alternative to valuable cross aldol products. High regioselectivity towards the aldehyde product was achieved using the ester protecting group for the allylic alcohol. Rapid isomerization and the much higher rate of oxidation of the branched isomer result in the same product forming from both linear and branched allylic esters.