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Keywords:

  • carbene ligands;
  • carbonyl ylides;
  • cycloaddition;
  • platinum;
  • ynones
Thumbnail image of graphical abstract

Two types of bicycles can be prepared selectively by the title reaction, depending on whether or not a substituent is present at the propargylic position of the ynone substrate (see scheme). The cycloaddition of carbonyl ylides derived from γ,δ-ynones with vinyl ethers (or styrene) gave intermediate bicyclic carbene complexes, which underwent a 1,2-hydrogen-atom shift or rearrangement to provide the products. R1=alkyl, Ph; R3=alkyl.