American Chemical Society
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Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

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journal contribution
posted on 2010-10-01, 00:00 authored by Roberto Morán-Ramallal, Ramón Liz, Vicente Gotor
Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.