Electrocyclization and Unexpected Reactions of Non-Stabilized α,β:γ,δ-Unsaturated Azomethine Ylides: Experimental and Theoretical Studies

Versatile, two-step syntheses of dihydrodibenzo[c,e]aze-pines, carbazole derivatives, and other alkaloid-type drug-like scaffolds by in situ generated azomethine ylide-induced intramolecular electro-cyclization reaction from commercially available materials are presented. The reaction mechanisms of transition-metal-free carbon-carbon bond formation and the role of the kinetic control, resulting in the good regioselectivity, were confirmed by theoretical calculations.

Automated summary

In this study, versatile and efficient syntheses of alkaloid-type drug-like scaffolds were achieved through an azomethine ylide-induced intramolecular electro-cyclization reaction. The reaction mechanisms and the role of kinetic control in achieving good regioselectivity were confirmed by theoretical calculations.