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

Abstract

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.