Details
| Original language | English |
|---|---|
| Pages (from-to) | 3318-3331 |
| Number of pages | 14 |
| Journal | Green chemistry |
| Volume | 15 |
| Issue number | 12 |
| Publication status | Published - Dec 2013 |
| Externally published | Yes |
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.
ASJC Scopus subject areas
- Environmental Science(all)
- Environmental Chemistry
- Environmental Science(all)
- Pollution
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In: Green chemistry, Vol. 15, No. 12, 12.2013, p. 3318-3331.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols
AU - Schrittwieser, Joerg H.
AU - Coccia, Francesca
AU - Kara, Selin
AU - Grischek, Barbara
AU - Kroutil, Wolfgang
AU - D'Alessandro, Nicola
AU - Hollmann, Frank
PY - 2013/12
Y1 - 2013/12
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84888232250&partnerID=8YFLogxK
U2 - 10.1039/c3gc41666f
DO - 10.1039/c3gc41666f
M3 - Article
AN - SCOPUS:84888232250
VL - 15
SP - 3318
EP - 3331
JO - Green chemistry
JF - Green chemistry
SN - 1463-9262
IS - 12
ER -