title: Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into δ-lactams and γ-lactones.
abstract: Treatment of 1-arylmethyl-2-(2-cyanoethyl)aziridines with a nitrile hydratase afforded the corresponding 2-(2-carbamoylethyl)aziridines, which underwent rearrangement into 5-hydroxypiperidin-2-ones upon heating under microwave irradiation. In addition, treatment of 2-(2-cyanoethyl)aziridines with a nitrilase selectively afforded 5-hydroxypiperidin-2-ones in good yields. On the other hand, chemical hydrolysis of 2-(2-cyanoethyl)aziridines using KOH in EtOH/H(2)O furnished the corresponding potassium 3-(aziridin-2-yl)propanoates, which, upon acidification with acetic acid, smoothly rearranged into 4-(aminomethyl)butyrolactones.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Karel
authors.initials: K
authors.lastname: Vervisch
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000619:Aminohydrolases / Q000378:metabolism*; D001388:Aziridines / Q000138:chemical synthesis* / Q000378:metabolism*; D006836:Hydro-Lyases / Q000378:metabolism*; D006868:Hydrolysis; D007769:Lactams / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure
chemical_list: D001388:Aziridines; D007769:Lactams; D007783:Lactones; D000619:Aminohydrolases; C021867:nitrilase; D006836:Hydro-Lyases; C048831:nitrile hydratase