Palladium-catalyzed, asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones with PHOX ligands |
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Authors: | Kimberly S PetersenBrian M Stoltz |
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Institution: | Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, United States |
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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. |
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Keywords: | Baeyer-Villiger oxidation Phosphinooxazoline ligands Asymmetric catalysis Palladium |
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