Bifurcated, modular syntheses of chiral annulet triazacyclononanes

G. Argouarch, G. Stones, C.L. Gibson, A.R. Kennedy, D.C. Sherrington

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.
LanguageEnglish
Pages4408-4417
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number24
DOIs
Publication statusPublished - 2003

Fingerprint

Aziridines
routes
synthesis
Ammonia
Solubility
ammonia
solubility
triazacyclononane

Keywords

  • MANGANESE COMPLEXES
  • HYDROGEN-PEROXIDE
  • SUBSTITUTED 1
  • 4
  • 7-TRIAZACYCLONONANE
  • MEDIATED ADDITION
  • CRYSTAL-STRUCTURE
  • MODEL COMPLEXES
  • AZIRIDINES
  • LIGANDS
  • OXIDATION
  • ACID

Cite this

Argouarch, G. ; Stones, G. ; Gibson, C.L. ; Kennedy, A.R. ; Sherrington, D.C. / Bifurcated, modular syntheses of chiral annulet triazacyclononanes. In: Organic and Biomolecular Chemistry. 2003 ; Vol. 1, No. 24. pp. 4408-4417.
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Bifurcated, modular syntheses of chiral annulet triazacyclononanes. / Argouarch, G.; Stones, G.; Gibson, C.L.; Kennedy, A.R.; Sherrington, D.C.

In: Organic and Biomolecular Chemistry, Vol. 1, No. 24, 2003, p. 4408-4417.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bifurcated, modular syntheses of chiral annulet triazacyclononanes

AU - Argouarch, G.

AU - Stones, G.

AU - Gibson, C.L.

AU - Kennedy, A.R.

AU - Sherrington, D.C.

PY - 2003

Y1 - 2003

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AB - 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.

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KW - HYDROGEN-PEROXIDE

KW - SUBSTITUTED 1

KW - 4

KW - 7-TRIAZACYCLONONANE

KW - MEDIATED ADDITION

KW - CRYSTAL-STRUCTURE

KW - MODEL COMPLEXES

KW - AZIRIDINES

KW - LIGANDS

KW - OXIDATION

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