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Issue 12, 2013
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One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

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Abstract

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Graphical abstract: One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

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Publication details

The article was received on 15 Aug 2013, accepted on 11 Sep 2013 and first published on 11 Sep 2013


Article type: Paper
DOI: 10.1039/C3GC41666F
Citation: Green Chem., 2013,15, 3318-3331
  • Open access: Creative Commons BY license
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    One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

    J. H. Schrittwieser, F. Coccia, S. Kara, B. Grischek, W. Kroutil, N. d'Alessandro and F. Hollmann, Green Chem., 2013, 15, 3318
    DOI: 10.1039/C3GC41666F

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