Open Access Article
This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported LicenceSequential oxidative dearomatization/asymmetric homologation: from simple naphthols to chiral benzocycloheptanes
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Hongkun Zeng , Shiyang Li , Lichao Ning , Tao Huang , Xiaoming Feng and Lili Lin
First published on 16th October 2025
Abstract
An oxidative dearomatization/asymmetric ring-expansion sequential approach is reported to synthesize chiral benzocycloheptanes from unfunctionalized simple β-naphthols under mild reaction conditions. This protocol integrates a copper-catalyzed oxidative dearomatization of β-naphthols, following a chiral N,N'-dioxide-Sc(III) complex-promoted enantioselective homologation with α-diazoesters in one pot, enriching the chemistry of naphthol dearomatization. Computational study demonstrates the process of Lewis acid-promoted homologation, as well as the origin of stereoselectivity.