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Palladium-catalyzed, asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones with PHOX ligands
Authors:Kimberly S PetersenBrian M Stoltz
Institution:Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, United States
Abstract:Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center.
Keywords:Baeyer-Villiger oxidation  Phosphinooxazoline ligands  Asymmetric catalysis  Palladium
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