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.
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