The dearomative cyclization of linear
amides to complex spirocyclic
butyrolactams has been enabled by photoredox catalysis through a reductive
radical–polar crossover mechanism. This mechanism operates
with precision on unactivated aromatic substrates to give a wide range
of 1,4-hydroalkylation products. This method utilizes a simple organic
catalyst/reductant pair to deliver products in a highly flexible manner
with respect to substitution, and the products can be further functionalized
under simple conditions to afford a collection of motifs. The mechanistic
analysis performed here outlines the salient features of this strategy,
which were applied to prepare a collection of complex scaffolds including
the anticonvulsive agent gabapentin.
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