Asymmetric synthesis of chiral cycloalkenone derivativesviapalladium catalysis.
The palladium-catalyzed oxidative desymmetrization ofmesodibenzoates 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.
Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.
Barry M
BM
Trost
Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.
James T
JT
Masters
Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.
Jean-Philip
JP
Lumb
Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.
Dahlia
D
Fateen