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Asymmetric Dearomatization of Phenols via Ligand-Enabled Cooperative Gold Catalysis
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9 18 2023
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Source: Angew Chem Int Ed Engl. 62(38):e202309256
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Alternative Title:Angew Chem Int Ed Engl
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Description:By employing a chiral bifunctional phosphine ligand, a gold(I)-catalyzed efficient and highly enantioselective dearomatization of phenols is achieved via versatile metal-ligand cooperation. The reaction is proven to be remarkably general in scope, permitting substitutions at all four remaining benzene positions, accommodating electron-withdrawing groups including strongly deactivating nitro, and allowing carbon-based groups of varying steric bulk including tert-butyl at the alkyne terminus. Moreover, besides N-(o-hydroxyphenyl)alkynamides, the corresponding ynoates and ynones are all suitable substrates. Spirocyclohexadienone-pyrrol-2-ones, spirocyclohexadienone-butenolides, and spirocyclohexadenone-cyclopentenones are formed in yields up to 99 % and with ee up to 99 %.
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Pubmed ID:37506307
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Pubmed Central ID:PMC10528085
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