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Bifurcated, modular syntheses of chiral annulet triazacyclononanes

Argouarch, G. and Stones, G. and Gibson, C.L. and Kennedy, A.R. and Sherrington, D.C. (2003) Bifurcated, modular syntheses of chiral annulet triazacyclononanes. Organic and Biomolecular Chemistry, 1 (24). pp. 4408-4417. ISSN 1477-0520

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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.