title: Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines.
abstract: 2-(Bromomethyl)-1-sulfonylaziridines were converted into novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines upon treatment with 2-aminothiophenol in THF in the presence of K2CO3. Starting from 3-substituted 2-(sulfonyloxymethyl)aziridines, a regio- and stereocontrolled synthesis of trans-2-phenyl- and trans-4-(phenyl or propyl)-3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines was developed in good yields via two different reaction pathways, depending on the nature of the sulfonyloxy group.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium.
authors.forename: Michinori
authors.initials: M
authors.lastname: Karikomi
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C106746:1,5-benzothiazepine; D001388:Aziridines; D013841:Thiazepines