Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands

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 obta...

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Bibliographic Details
Published in:Tetrahedron 2011-06, Vol.67 (24), p.4352-4357
Main Authors: Petersen, Kimberly S., Stoltz, Brian M.
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Asymmetry
Baeyer–Villiger oxidation
Conversion
Lactones
Ligands
Oxidation
Palladium
Phosphinooxazoline ligands
Recrystallization
Tetrahedrons
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.04.046