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Keywords:

  • asymmetric catalysis;
  • hydrogenation;
  • iridium;
  • isoquinoline;
  • 1,2,3,4-tetrahydroisoquinoline
Thumbnail image of graphical abstract

Reining in the outliers: An efficient approach for enantioselective hydrogenation of 3,4-disubstituted isoquinolines was successfully developed. When isoquinolines are treated with [Ir(cod)Cl]2/(R)-synphos in the presence of 1-bromo-3-chloro-5,5-dimethyl-hydantoin (BCDMH), the chiral 3,4-disubstituted tetrahydroisoquinoline derivatives are obtained with ee values as high as 96 % (see scheme; cod=1,5-cyclooctadiene).