A new catalytic methodology for the direct dearomatization of substituted 2-naphthols via intermolecular condensation with allenamides is presented. PPhAuTFA (5 mol %) promotes the formal allylating dearomative protocol under mild conditions, large scope (24 examples), and high regioselectivity and stereoselectivity. The synergistic catalytic role played by the [PPhAu] (π-acid) and TFA (Lewis base) is highlighted.
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http://dx.doi.org/10.1021/acs.orglett.8b03018 | DOI Listing |
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