4.6 Article

Syntheses of α-CF3-α-quaternary ketonesvia p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 24, Pages 4638-4644

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00951b

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New and successful results for the construction of new and structurally interesting compounds are reportedviaN-heterocyclic carbene (NHC)-catalyzed 1,6-conjugate additions of a variety of aldehydes to delta-CF3-delta-substitutedp-quinone methides generatedin situ, and the products are used for the 1,2-addition reactions of appropriate metal nucleophiles, enabling us to furnish highly diastereoselective products with a unique successive quaternary carbon-tertiary alcohol framework (up to dr = >99 : 1).

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