Pd(II)-Catalyzed Site-Selective [2 + 2 + 1] Spiroannulation of 2-Pyridone with Alkyne

Le résumé fourni par la source

Spiropiperidine, an important pharmacophore, is widely found in many drugs and bioactive molecules. Despite the progress these methods have made in the diversity-oriented synthesis of spiropiperidine, site-selective spiroannulation remains a significant challenge. Herein, we report a novel and previously unexplored Pd(II)-catalyzed spiroannulation that uses readily available 2-pyridone as a precursor for piperidine to react with alkyne, undergoing site-selective [2 + 2 + 1] spiroannulation through direct vinylic C-H activation and two metallization steps, efficiently producing 3-spiropiperidine derivatives. This protocol offers a broad substrate scope, strong atom economy, and notable site selectivity and will quickly provide a platform for the diversity-oriented synthesis of 3-spiropiperidine derivatives through the site-selective spiroannulation of conjugated diene.

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