title: Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones.
abstract: Trans- and cis-2-aryl-3-(2-cyanoethyl)aziridines, prepared via alkylation of the corresponding 2-aryl-3-(tosyloxymethyl)aziridines with the sodium salt of trimethylsilylacetonitrile, were transformed into variable mixtures of 4-[aryl(alkylamino)methyl]butyrolactones and 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones via KOH-mediated hydrolysis of the cyano group, followed by ring expansion. In addition, next to this chemical approach, enzymatic hydrolysis of the former aziridinyl nitriles by means of a nitrilase was performed as well, interestingly providing a selective route towards the above-mentioned functionalized γ-lactams.
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Karen
authors.initials: K
authors.lastname: Mollet
authors.forename: Lena
authors.initials: L
authors.lastname: Decuyper
authors.forename: Saskia
authors.initials: S
authors.lastname: Vander Meeren
authors.forename: Nicola
authors.initials: N
authors.lastname: Piens
authors.forename: Karel
authors.initials: K
authors.lastname: De Winter
authors.forename: Tom
authors.initials: T
authors.lastname: Desmet
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
mesh_terms: D000619:Aminohydrolases / Q000737:chemistry / Q000378:metabolism*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D007769:Lactams; D007783:Lactones; D000619:Aminohydrolases; C021867:nitrilase