title: Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone.
abstract: An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, α-chlorination, hydride reduction and ring closure was developed. In addition, novel primary β-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF(3)-β-phenylethylamines upon treatment with lithium diphenylcuprate.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000, Ghent, Belgium.
authors.forename: Sara
authors.initials: S
authors.lastname: Kenis
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest
authors.forename: Vinh Duc
authors.initials: VD
authors.lastname: Nguyen
authors.forename: Tuyet Anh Dang
authors.initials: TA
authors.lastname: Thi
authors.forename: Tuyen Van
authors.initials: TV
authors.lastname: Nguyen
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry; D000478:Alkylation; D001388:Aziridines / Q000138:chemical synthesis*; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D008745:Methylation; D015394:Molecular Structure
chemical_list: D001388:Aziridines; D017611:Fluorine Compounds; D000096:Acetone