Sequential oxidative dearomatization/asymmetric homologation: from simple naphthols to chiral benzocycloheptanes.

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 studies demonstrate the process of Lewis acid-promoted homologation, as well as the origin of stereoselectivity.

SUBMITTER: Zeng H 

PROVIDER: S-EPMC12557410 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature