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Amine-catalyzed coupling reactions of allenoate esters and α,β-unsaturated carbonyls lead to a diverse range of α,α′-disubstituted allenoates. With appropriately substituted monomers, intermolecular reactions can lead to pyrimidone products. Alternatively, with amine substituted allenoates, a 7-endo-dig cyclization can be carried out such that a divergent pathway is observed that leads to azepine scaffolds.