Rhodium-Catalyzed Regioselective Double Annulation of Enaminones with Propargyl Alcohols: Rapid Access to Arylnapthalene Lignan Derivatives

We present here a rhodium-catalyzed oxidative three-point double annulation of enaminones with propargylic alcohols via a C-H and a C-N bond activation to access arylnaphthalene-based lignan derivatives. The key step in the reaction is the regioselective insertion of propargylic alcohol into the rhoda-cycle, a result of hydroxyl rhodium coordination. Necessary control experiments and KIE studies were conducted to determine the mechanism.

Automated summary

This research presents a rhodium-catalyzed oxidative three-point double annulation of enaminones with propargylic alcohols to access arylnaphthalene-based lignan derivatives. The key step involves the regioselective insertion of propargylic alcohol into the rhoda-cycle due to hydroxyl rhodium coordination, with mechanism determined through control experiments and KIE studies.