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Keywords:

  • allylic compounds;
  • aminopalladation;
  • oxidation;
  • palladium;
  • tetrahydrofurans
Thumbnail image of graphical abstract

Resolute in the face of elimination: Substituted 3-aminotetrahydrofurans were prepared in good yield and with modest to high diastereoselectivity by the Pd-catalyzed reaction shown in the scheme (Phth=phthaloyl). Mechanistic studies indicate a PdII/PdIV catalytic cycle involving cis aminopalladation and intramolecular C[BOND]O bond-forming reductive elimination with retention of configuration at the carbon atom.