ChemCatChem
ChemCatChem
4 years ago

Organocatalytic Synthesis of Lactones by the Oxidation of Alkenoic Acids

Organocatalytic Synthesis of Lactones by the Oxidation of Alkenoic Acids
Christoforos G. Kokotos, Marianna Raftopoulou, Anatoli Savvidou, Ierasia Triandafillidi
Along the lines of modern sustainable oxidation, a green and mild organocatalytic synthetic procedure for the synthesis of hydroxylactones from alkenoic acids is described. The reaction includes the activation of H2O2 by an organocatalyst (2,2,2-trifluoromethylacetophenone), the oxidation of an olefinic group to the corresponding epoxide, and intramolecular lactonization to afford a variety of substituted γ- or δ-lactones with multiple substitution patterns in good to high yields. The product can be obtained with high purity after simple extraction if the conversion is quantitative. Attempts to render the process asymmetric met with limited success. Metal-free: A green organocatalytic method for the activation of hydrogen peroxide and the oxidation of alkenoic acids to lactones is described.

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

DOI: 10.1002/cctc.201700837

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