Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction Followed by Photoinduced Ring-Opening

The combination of a Lewis acid-catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction with a photoinduced ring-opening (PIRO) reaction in a domino process has been established as an efficient synthetic method to access medium-sized carbocycles. From readily available electron-rich and electron-poor phthalazines and enamines, respectively, as starting materials, various 9- and 11-membered carbocycles were prepared. This versatile transition-metal-free tool will be valuable for broadening the structural space in biologically active compounds and functional materials.

Automated summary

The combination of a Lewis acid-catalyzed inverse electron-demand Diels-Alder reaction with a photoinduced ring-opening reaction in a domino process is an efficient method to access medium-sized carbocycles. Various 9- and 11-membered carbocycles were successfully synthesized from readily available starting materials. This transition-metal-free tool has the potential to broaden the structural space in biologically active compounds and functional materials.