A bioinspired catalytic oxygenase cascade to generate complex oxindoles

Abstract

Catalytic, selective, and controlled oxidative functionalization of C-H bonds using molecular oxygen as an oxidant remains highly desirable and equally challenging in the development of synthetic methodologies. Presented herein is a one-pot oxygenase cascade reaction wherein a copper(I)-catalyzed oxygenase reaction transforms the allylic methyl group in 3-methylidene oxindoles into an aldehyde, which then undergoes an aldol-oxa-Michael addition sequence with β-ketoesters to yield dihydrofuran-bearing oxindoles.

Keywords: allylic compounds; bioinspired catalysis; copper; heterocycles; oxidation.