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Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions†
L. Peña Carrodeguas,À. Cristòfol,J. M. Fraile,J. A. Mayoral,V. Dorado,C. I. Herrerías
Green Chemistry Pub Date : 05/22/2017 00:00:00 , DOI:10.1039/C7GC01206C
Abstract

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 conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70–85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97 : 3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.

Graphical abstract: Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions
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