Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
Barry M Trost1, James T Masters1, Jean-Philip Lumb1
1Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.
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.
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