Issue 24, 2003

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.

Graphical abstract: Bifurcated, modular syntheses of chiral annulet triazacyclononanes

Supplementary files

Article information

Article type
Paper
Submitted
01 Sep 2003
Accepted
13 Oct 2003
First published
06 Nov 2003

Org. Biomol. Chem., 2003,1, 4408-4417

Bifurcated, modular syntheses of chiral annulet triazacyclononanes

G. Argouarch, G. Stones, C. L. Gibson, A. R. Kennedy and D. C. Sherrington, Org. Biomol. Chem., 2003, 1, 4408 DOI: 10.1039/B310492C

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