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

Abstract

In this study, we had 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 p-selective Friedel-Crafts reaction...

Asymmetric catalytic Friedel–Crafts alkylation with arenes and heteroarenes: construction of 3,3-disubstituted oxindoles

“…Alkenes with strong electron withdrawing groups can be used as acceptors to react with nucleophilic reagents. 2–7 Most of the strategies have concentrated on the asymmetric Friedel–Crafts alkylation of strong nucleophilic arenes such as indoles, 2 pyrroles, 3 naphthols 4 and anilines. 5 For example, the Fan group reported a rhodium-catalyzed asymmetric arylative ring-opening Friedel–Crafts alkylation of heterobicyclic alkenes with anilines in 2018 (Scheme 1a).…”

Achiral Counteranion-Induced Reversal of Enantioselectivity in Ni(II)-Catalyzed Friedel–Crafts Alkylation/Annulation of 2-Naphthols

“…In 2016, Kesavan and co-workers disclosed a proline-derived thiourea-catalyzed tandem Friedel–Crafts-type/hemiketalization of 2-naphthols with oxindole α-keto esters, delivering spirooxindole-naphthopyrans with excellent results . In 2023, Han and co-workers developed a hydroquinidine-derived thiourea-catalyzed Friedel–Crafts alkylation/annulation reaction of 1-naphthols with 2,3-dioxopyrrolidines to construct polycyclic 2-pyrrolidinones . However, the catalytic systems applied in these Friedel–Crafts alkylation/annulations are all organocatalysts, and there has been no report for this reaction on the reversal of enantioselectivity using a single chiral source-derived catalyst.…”