Enantiopure trans-3-arylaziridine-2-carboxamides: preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D-α-amino acids.
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.
Morán-Ramallal
Roberto
R
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain.
Liz
Ramón
R
Gotor
Vicente
V
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D006868:Hydrolysis; D015394:Molecular Structure; D012240:Rhodococcus / Q000378:metabolism*; D013237:Stereoisomerism
D000596:Amino Acids; D001388:Aziridines; C518574:aziridine-2-carboxamide