Fatty Acid Based Biocarbonates: Al-Mediated Stereoselective Preparation of Mono-, Di- and Tricarbonates under Mild and Solvent-less Conditions

A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows to convert the fatty acid derived epoxides under comparatively mild reaction conditions (70‒85ºC, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios in the products of up to 97:3. Comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components shows that the presence of the Al-complex is crucial for retention of the original stereochemistry.