Organocatalytic Dearomative Spirocyclization Reaction of Enone-Tethered α-and ß-Naphthols and Dearomatization Reaction of In Situ Generated Nitro-Olefin-Tethered α-Naphthols.

ABSTRACT

Herein, we report a catalytic dearomative spirocyclization reaction of new substrates having aryl/alkyl enone tethered α- and ß-naphthols and a dearomatization reaction of in situ generated nitro-olefin-tethered α-naphthols. The spirocarbocycles were obtained in moderate to good yields with high diastereoselectivities. A preliminary catalytic asymmetric variant was reported. A few applications such as hydrogenations and epoxidation reaction have also been demonstrated. Theoretical study has also been performed to understand high diastereoselectivity in the triethylamine catalyzed spirocyclization reaction.