Tertiary Hydroxylamines as Bifunctional Single-Nitrogen Sources for De Novo Spirooxindole Synthesis.

We herein report a palladium-catalyzed cascade reaction that enables the de novo synthesis of spirooxindoles from simple ortho-iodoaniline derivatives, in which tertiary O-benzoyl hydroxylamines serve as bifunctional single-nitrogen sources through sequential C-H diamination and C-N activation. The reaction features a broad substrate scope and accommodates both diamination and triamination pathways. Preliminary asymmetric studies afford the desired product in up to 92% ee, providing a concise route to structurally diverse spirooxindoles.