Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations

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The organocatalytic amination of pyrazol‐5‐ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 %) and enantioselectivities (up to ee 97 %). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.