Asymmetric Catalysis. 72.1Enantioselective Hydroarylation of Norbornene and Norbornadiene with Palladium(II) Acetate/Phosphine Catalysts

Authors:
  • HBH. Brunner
    H. Brunner
  • KKK. Kramler
    K. Kramler
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Abstract
The palladium(II) acetate catalyzed hydroarylation of norbornene and norbornadiene (bicyclo[2.2.1]hept-2-ene and bicyclo[2.2.1] hept-2,5-diene) with aryl iodides, triethylamine and formic acid was rendered enantioselective by using optically active phosphine ligands as co-catalysts. The screening of 5 aryl iodides and 19 optically active phosphine ligands gave the corresponding exo-2-arylbicyclo[2.2.1]heptanes and exo-5-arylbicyclo [2.2.1]hept-2-enes with enantioselectivities of up to 40.6% ee.