Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acidElectronic supplementary information (ESI) available: General procedures for the synthesis of racemic compounds involved in the determination of enantiomeric excesses, chiral HPLC and GC chromatograms, and NMR spectra for the new compounds. See DOI: 10.1039/c3ob42066c

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. Amidase from Rhodococcus rhodochrous enantioselectively catalyzes the hydrolysis of different racemic diamides ( rac - 10 ) and amido esters derived from trans -cyclopropane-1,2-dicarboxylic acid.