title: Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine.
abstract: This paper reports on the generation and alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with ω,ω'-dihaloalkanes, followed by a novel ring-expansion protocol toward 2-CF3-pyrrolidines, 2-CF3-piperidines, and 3-CF3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains.
authors: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent (Belgium), Fax: (+32) 9-264-62-21.
authors: Jeroen
authors: J
authors: Dolfen
authors: Sara
authors: S
authors: Kenis
authors: Kristof
authors: K
authors: Van Hecke
authors: Norbert
authors: N
authors: De Kimpe
authors: Matthias
authors: M
authors: D'hooghe
mesh_terms: D000478:Alkylation; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001381:Azepines; D001388:Aziridines; D010880:Piperidines; D011759:Pyrrolidines; D005461:Fluorine; C033132:aziridine
keywords: azepanes; aziridines; aziridinyl anions; piperidines; pyrrolidines; trifluoromethyl