Asymmetric Synthesis of Spirocyclic Oxindole δ‑Lactams via NHC-Catalyzed Formal [2+4] Annulation of Aliphatic Aldehydes with Oxindole-Derived α,β-Unsaturated Ketimines

An N-heterocyclic carbene (NHC)-catalyzed formal [2+4] annulation reaction of aliphatic aldehydes with oxindole-derived α,β-unsaturated ketimines under oxidative conditions is reported, affording spirocyclic oxindole δ-lactams with good yields, moderate diastereoselectivies, and good to excellent enantioselectivies. This reaction can be readily carried out on a gram scale, and the products could be further transformed to other synthetically useful compounds.