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Issue 15, 2017
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Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions

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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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Publication details

The article was received on 21 Apr 2017, accepted on 19 May 2017 and first published on 22 May 2017


Article type: Paper
DOI: 10.1039/C7GC01206C
Citation: Green Chem., 2017,19, 3535-3541
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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 and A. W. Kleij, Green Chem., 2017, 19, 3535
    DOI: 10.1039/C7GC01206C

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