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Keywords:

  • counteranion-directed catalysis;
  • hydrogen bonds;
  • natural products;
  • palladium;
  • tetrahydrofuran
Thumbnail image of graphical abstract

Hydrogen bonds can play a prominent role in organometallic catalysis, as shown for the title reaction, in which a counteranion directs the cyclization through the formation of hydrogen bonds that likely involve a proton of the π-allyl/palladium species itself. The reaction allows access to four out of the eight stereoisomers of 2,5-disubstitued 3-hydroxy-tetrahydrofurans and thus fragments of complex natural products.