Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis† †Electronic supplementary information (ESI) available: Detailed experimental procedures and copies of NMR spectra and HPLC chromatograms. See DOI: 10.1039/c3sc53250j Click here for additional data file.
نویسندگان
چکیده
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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Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights† †Electronic supplementary information (ESI) available: Detailed experimental procedures and characterization of all new compounds, including copies of NMR spectra and HPLC chromatograms traces, computational details and Cartesian coordinates of all stationary points. CCDC 1525188 (4l), 1525189 (6a) and 1525190 (9a). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00009j Click here for additional data file. Click here for additional data file.
Department of Organic Chemistry II, Unive P.O. Box 644, 48080 Bilbao, Spain Departamento de Śıntesis y Estructura de Bi y Catálisis Homogénea (ISQCH), Universida Servicio de Resonancia Magnética Nuclear, C (CEQMA), Universidad de Zaragoza, CSIC, † Electronic supplementary information procedures and characterization of all NMR spectra and HPLC chromatogram Cartesian coordinates of all stationary...
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