Catalyst-controlled regiodivergent Friedel-Crafts reactions of 1-naphthols with 2,3-dioxopyrrolidines: synthesis of polycyclic 2-pyrrolidinones.

In this study, we developed an organocatalyst-controlled site-selectivity switchable Friedel-Crafts reaction of 1-naphthols and 2,3-dioxopyrrolidines. The o -selective Friedel-Crafts reaction was achieved with chiral tertiary amines, while the p -selective Friedel-Crafts reaction was accomplished with Brønsted acids or Lewis acids. With this protocol, a range of functionalized polycyclic 2-pyrrolidinone derivatives were prepared. Moreover, theoretical mechanistic investigations provided insights into the site-selectivity reaction pathway and the origin of chiral induction for the o -selective Friedel-Crafts reaction.