Access to Chiral Oxindoles via Ir-Catalyzed Asymmetric Pudovik Addition/[1,2]-Phospha-Brook Rearrangement/Allylation Cascade

An asymmetric catalytic Pudovik addition/[1,2]-phospha-Brook rearrangement/allylation reaction of readily available isatins, phosphites, and vinyl ethylene carbonate enabled by a chiral iridium catalyst was developed in a one-pot fashion. A wide range of enantioenriched oxindole derivatives containing two adjacent stereocenters could be obtained in good to high yields with excellent diastereoselectivity and enantioselectivity (65-99% yield, 7:1 to >20:1 dr, and generally 99% ee). This cascade protocol owned the advantages of readily available starting materials, high regio-/diastereo-/enantioselectivity, and good substrate scope generality.