ChemInform Abstract: Synthesis of 2‐Aryl‐3‐(2‐cyanoethyl)aziridines and Their Chemical and Enzymatic Hydrolysis Towards γ‐Lactams and γ‐Lactones.

Abstract

Synthesis of 2-Aryl-3-(2-cyanoethyl)aziridines and Their Chemical and Enzymatic Hydrolysis Towards-Lactams and -Lactones. -The title compounds (IV) are transformed into variable mixtures of 4-[aryl(alkylamino)methyl]butyrolactones and 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones by KOH-mediated hydrolysis of the cyano group, followed by ring expansion. The enzymatic hydrolysis of (IV) using nitrilase is performed as well and found to be a selective route to the functionalized -lactams (VI). -(MOLLET, K.; DECUYPER, L.; VANDER MEEREN, S.; PIENS, N.; DE WINTER, K.; DESMET, T.; D'HOOGHE*, M.; Org. Biomol. Chem. 13 (2015) 9, 2716-2725, http://dx.doi.org/10.1039/C4OB02615B ; Dep. Sustainable Org. Chem. Technol., Fac. Biosci. Eng., Univ. Gent, B-9000 Gent, Belg.; Eng.) -H. Toeppel