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

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

Schrittwieser, J.
Coccia, F.
Kara, S.
Grischek, B.
Kroutil, W.
d'Alessandro, N.
Hollmann, F.

Applied Sciences

Biotechnology

2013-09-11

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 10 possible using either method alone. Here we report the one-pot combination of alcohol dehydrogenasecatalysed 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 15 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 E-factor and solvent demand.

Gold for Gold
Open Access

http://resolver.tudelft.nl/uuid:3c69fe20-1986-4e6d-8067-2ab2f6ee3811

https://doi.org/10.1039/C3GC41666F

RSC Publishing

1463-9262

Green Chemistry, 2013

Institutional Repository

journal article

(c) 2013 RSC