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Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes.

Aimee K ClarkeJohn T R LiddonJames D CuthbertsonRichard J K TaylorWilliam P Unsworth
Published in: Organic & biomolecular chemistry (2018)
Two complementary dearomatising spirocyclisation protocols to generate spirocyclic dienones from anisole and phenol-tethered ynones are described, each proceeding via electrophilic alkyne activation. The first approach focuses on the spirocyclisation of para-substituted anisoles using either SnCl2·2H2O or Cu(OTf)2. The second approach, which enables the spirocyclisation of both ortho- and para-substituted phenols, uses silica-supported AgNO3 to generate similar scaffolds with much greater efficiency. Initial asymmetric studies are also outlined.
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