title: Nucleophile-directed selective transformation of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.
abstract: A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 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: Maaike
authors.initials: M
authors.lastname: Reybroeck
authors.forename: Tuyet Anh
authors.initials: TA
authors.lastname: Dang Thi
authors.forename: Chinh
authors.initials: C
authors.lastname: Pham The
authors.forename: Tham
authors.initials: T
authors.lastname: Thi Pham
authors.forename: Karl W
authors.initials: KW
authors.lastname: Törnroos
authors.forename: Nguyen
authors.initials: N
authors.lastname: Van Tuyen
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014270:Trifluoroethanol / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D001384:Azetidines; D001388:Aziridines; D004146:Dioxanes; D006571:Heterocyclic Compounds; D006845:Hydrocarbons, Fluorinated; D009025:Morpholines; D011807:Quinolizines; D013457:Sulfur Compounds; C585393:cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine; C438055:dithiane; D013455:Sulfur; D014270:Trifluoroethanol; D010100:Oxygen