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

Abstract

The development of the first chiral Fe-TAML catalyst, accessible in both (R,R)- and (S,S)-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.