title: Synthesis of new functionalized aziridine-2- and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications.
abstract: A short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. The aziridines are the kinetically favored cyclization products and could be transformed into 3-bromoazetidine-3-carboxylic acid derivatives via thermal isomerization. The new small-membered azaheterocyclic α- and β-amino acid derivatives contain a bromo-substituted carbon center as a useful moiety for functionalization. Transformation of these functionalized azaheterocycles via nucleophilic substitution with carbon, sulfur, oxygen, and nitrogen nucleophiles and via elaboration of the amino and carboxyl group provided a broad range of new conformationally constrained aziridine-2- and azetidine-3-carboxylic acid derivatives, which are of interest from a biological point-of-view as well as for applications in the field of foldamers.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
authors.forename: Asta
authors.initials: A
authors.lastname: Žukauskaitė
authors.forename: Sven
authors.initials: S
authors.lastname: Mangelinckx
authors.forename: Vida
authors.initials: V
authors.lastname: Buinauskaitė
authors.forename: Algirdas
authors.initials: A
authors.lastname: Šačkus
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides; D002244:Carbon / Q000737:chemistry; D002264:Carboxylic Acids; D003500:Cyclization; D054879:Halogenation; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry
chemical_list: D000596:Amino Acids; D001384:Azetidines; D001388:Aziridines; D001965:Bromides; D002264:Carboxylic Acids; C082735:azetidine; C073440:aziridine-2-carboxylic acid; D002244:Carbon; D009584:Nitrogen; D010100:Oxygen