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Issue 4, 2014
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Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid

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Abstract

Different optically active amido esters, mixed acid esters, amido acids, and diamides derived from trans-cyclopropane-1,2-dicarboxylic acid were prepared from the commercially available diethyl (±)-trans-cyclopropane-1,2-dicarboxylate. The key step was the Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis of the corresponding racemic amide. The amidase present in this microorganism showed moderate to high enantioselectivity towards these substrates. In addition a simple and efficient Curtius rearrangement of some of the enzymatically prepared cyclopropanecarboxylic acids allowed us to obtain optically active β-aminocyclopropanecarboxylic acid derivatives with high yields and enantiomeric excesses.

Graphical abstract: Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid

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Article information


Submitted
15 Oct 2013
Accepted
12 Nov 2013
First published
12 Nov 2013

Org. Biomol. Chem., 2014,12, 615-623
Article type
Paper

Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid

K. G. Hugentobler and F. Rebolledo, Org. Biomol. Chem., 2014, 12, 615
DOI: 10.1039/C3OB42066C

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