Chiral Iminium Salt-Catalyzed Asymmetric Oxidative Dearomatization of Naphthols into <i>ortho</i> -Quinols

Controlling the chemo-, regio-, and enantioselectivities of the asymmetric oxidative dearomatization of naphthols continues to pose a significant challenge in organic synthesis. Herein, we report an enantioselective oxidative dearomatization of both 1- and 2-naphthols utilizing a chiral iminium salt catalyst. This reaction employs inexpensive and stable sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the oxidant. Moreover, the highly oxygenated epoxy <i>ortho</i>-quinols are synthesized by simply adjusting the dosage of sodium percarbonate and varying the reaction temperature.

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Publication Details

Journal
Organic Letters
Published
2026-01-26
DOI
https://doi.org/10.1021/acs.orglett.5c05069
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Chiral Iminium Salt-Catalyzed Asymmetric Oxidative Dearomatization of Naphthols into ortho -Quinols

Wei Wen, Qi‐Xiang Guo, Yang Yin, Tao Xu et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Chiral Iminium Salt-Catalyzed Asymmetric Oxidative Dearomatization of Naphthols into ortho -Quinols

Wei Wen, Qi‐Xiang Guo, Yang Yin, Tao Xu, Yi-Fei Fu
article en

Abstract

Controlling the chemo-, regio-, and enantioselectivities of the asymmetric oxidative dearomatization of naphthols continues to pose a significant challenge in organic synthesis. Herein, we report an enantioselective oxidative dearomatization of both 1- and 2-naphthols utilizing a chiral iminium salt catalyst. This reaction employs inexpensive and stable sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the oxidant. Moreover, the highly oxygenated epoxy <i>ortho</i>-quinols are synthesized by simply adjusting the dosage of sodium percarbonate and varying the reaction temperature.

Organic LettersVol. 28(5)
Southwest University (CN), Smart Material (Germany) (DE)
Clean water and sanitation
Openalex Percentile: Top 79%
Catalytic C–H Functionalization Methods
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