Access to Enantioenriched Spiro-ϵ-Lactam Oxindoles by an N-Heterocyclic Carbene-Catalyzed [4+3] Annulation of Flexible Oxotryptamines with Enals.

Oxotryptamines were firstly used as flexible four-atom synthons in an NHC-catalyzed formal [4+3] annulation, providing a novel enantioselective method to access structurally diverse spiro-ϵ-lactam oxindoles with excellent enantioselectivities. This metal-free reaction features a broad substrate scope, excellent functional-group tolerance and proceeds under mild reaction conditions. Importantly, enantiopure privileged hexahydropyrroloindoles could be easily constructed by a one-pot process from the resulting spiro-ϵ-lactam oxindoles.