Enantioselective C–H bond oxidation using a bio-inspired chiral Fe-TAML catalyst

The development of the first chiral Fe-TAML catalyst, accessible in both (<i>R</i>,<i>R</i>)- and (<i>S</i>,<i>S</i>)-enantiomeric forms, that enables enantioselective oxidation of benzylic C-H bonds within spirocyclic oxindole substrates is reported. The catalyst delivers yields exceeding 90% with moderate to good enantioselectivity. Computational and structural analyses suggest that π-π interactions between the phenyl group of the catalyst and the aryl substituent on the oxoindole play a key role in chiral induction.