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Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis.

ABSTRACT: The palladium-catalyzed oxidative desymmetrization of meso dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3992253 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis.

Trost Barry M BM Masters James T JT Lumb Jean-Philip JP Fateen Dahlia D

Chemical science 20140401 4

The palladium-catalyzed oxidative desymmetrization of meso dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse ep ...[more]

PMID: 24761221

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