title: Bifurcated, modular syntheses of chiral annulet triazacyclononanes.
abstract: Three chiral 2,6-disubstituted tri-N-methyl azamacrocycles have been prepared by modular methods. These macrocycles were accessed from three chiral 1,4,7-triazaheptanes intermediates that were prepared by two independent routes. The first of these routes involved the benzylamine opening of chiral tosyl aziridines followed by debenzylation but was problematic on solubility grounds. A second, more effective, route was developed which avoided debenzylation by using ammonia in the nucleophilic opening of chiral tosyl aziridines.
authors.affiliation: Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow, UK.
authors.forename: Gilles
authors.initials: G
authors.lastname: Argouarch
authors.forename: Graham
authors.initials: G
authors.lastname: Stones
authors.forename: Colin L
authors.initials: CL
authors.lastname: Gibson
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.forename: David C
authors.initials: DC
authors.lastname: Sherrington
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D001388:Aziridines; D006573:Heterocyclic Compounds, 1-Ring