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Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1‑Naphthols: Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and Friedel–Crafts Alkylation of 1‑Naphthols at the C4 Position

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posted on 09.01.2018, 00:00 by Gongming Zhu, Yiping Li, Guangjun Bao, Wangsheng Sun, Liwu Huang, Liang Hong, Rui Wang
Switching the chemo- or regioselectivity from identical starting materials under readily tunable reaction conditions represents a great challenge in medicinal and synthetic organic chemistry. Herein, we report the asymmetric dearomatization/oxa-Michael reaction and Friedel–Crafts alkylation of 1-naphthols at the C4 position, wherein the chemoselectivity could be switched easily by using different reaction conditions without changing the catalyst and the substrates. The reactions feature asymmetric Friedel–Crafts alkylation of 1-naphthols at the C4 position and asymmetric dearomatization without using specific substrates or stepwise protocols.