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Published on: October 27, 2018
Chiral Iminium Salt-Catalyzed Asymmetric Oxidative Dearomatization of Naphthols into ortho-Quinols
Tao Xu1, Yang Yin1, Yi-Fei Fu1
1Key Laboratory of Applied Chemistry of Chongqing Municipality and Chongqing Key Laboratory of Soft-Matter Material Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
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 (Na2CO3·1.5H2O2) as the oxidant. Moreover, the highly oxygenated epoxy ortho-quinols are synthesized by simply adjusting the dosage of sodium percarbonate and varying the reaction temperature.
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