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Construction of Spirolactams by Unexpected Oxidative Cyclization of Alkenyl Diynes via Copper Catalysis.

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A copper-catalyzed oxidative cyclization of alkenyl N-propargyl ynamides is described. This protocol enables the practical synthesis of diverse spirocyclic γ-lactams bearing an exocyclic double bond with generally high Z/E selectivity… Click to show full abstract

A copper-catalyzed oxidative cyclization of alkenyl N-propargyl ynamides is described. This protocol enables the practical synthesis of diverse spirocyclic γ-lactams bearing an exocyclic double bond with generally high Z/E selectivity in moderate to good yields. Importantly, this copper-catalyzed oxidative cyclization demonstrates a distinctive selectivity in comparison with the related gold catalysis.

Keywords: catalysis; copper; cyclization alkenyl; oxidative cyclization; cyclization

Journal Title: Organic letters
Year Published: 2023

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