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 SnCl·2HO or Cu(OTf). The second approach, which enables the spirocyclisation of both ortho- and para-substituted phenols, uses silica-supported AgNO to generate similar scaffolds with much greater efficiency. Initial asymmetric studies are also outlined.
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http://dx.doi.org/10.1039/c6ob02426b | DOI Listing |
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