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Issue 1, 2016
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Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

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Abstract

The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag2O and cinchona-derived amino phosphines applied to the synthesis of (−)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.

Graphical abstract: Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

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Publication details

The article was received on 22 Sep 2015, accepted on 19 Oct 2015 and first published on 29 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB02141C
Citation: Org. Biomol. Chem., 2016,14, 93-96
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    Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

    A. Franchino, P. Jakubec and D. J. Dixon, Org. Biomol. Chem., 2016, 14, 93
    DOI: 10.1039/C5OB02141C

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