Asymmetric synthesis of chiral cycloalkenone derivatives viapalladium catalysis

The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields gamma -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 buil...

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Veröffentlicht in:Chemical science (Cambridge) 2014-03, Vol.5 (4), p.1354-1360
Hauptverfasser: Trost, Barry M, Masters, James T, Lumb, Jean-Philip, Fateen, Dahlia
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Sprache:eng
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Zusammenfassung:The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields gamma -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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc53250j