Bifurcated, modular syntheses of chiral annulet triazacyclononanes.
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.
Argouarch
Gilles
G
Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow, UK.
Stones
Graham
G
Gibson
Colin L
CL
Kennedy
Alan R
AR
Sherrington
David C
DC
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
D001372:Aza Compounds; D001388:Aziridines; D006573:Heterocyclic Compounds, 1-Ring