3 years ago

Inside Cover: Formation of δ-Lactones with anti-Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates (Chem. Eur. J. 30/2017)

Inside Cover: Formation of δ-Lactones with anti-Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates (Chem. Eur. J. 30/2017)
Irina Geibel, Anna Dierks, Thomas Müller, Jens Christoffers
δ-Lactones with anti-Baeyer–Villiger regiochemistry are formed by aerobic, cerium-catalyzed umpolung reactions. A mechanistic proposal involving an oxycarbenium ion intermediate is supported by kinetics of the reaction (Hammett plot). Furthermore, a conformational analysis obtained by DFT calculations explains the anti-Baeyer–Villiger regiochemistry of the rearrangement reaction by a primary stereoelectronic effect. More information can be found in the Full Paper by J. Christoffers, et al. on page 7245.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701039

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