Aza-quaternary centers are important structural motifs in natural products and pharmaceuticals. However, they can be challenging to synthesize. We demonstrate that installing a Brønsted basic auxiliary enables the dearomatizing amination of catechol derivatives. The amine nucleophile adds to a substituted aromatic carbon, resulting in an aza-quaternary center. We suggest that proton transfer to an auxiliary can offset unfavorable energetics associated with carbon-nitrogen bond formation.

Brønsted basic auxiliary enables synthesis of aza-quaternary centers

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