The synthesis of chiral annulet 1,4,7-triazacyclononanes

G. Argouarch, C.L. Gibson, G. Stones, D.C. Sherrington

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Novel and flexible routes for the synthesis of chiral ring annulet 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles are described. Efficient macrocyclisations were realised provided that chiral analogues of N,N-bis-[2-(toluene-sulfonyl-amino)ethyl]-toluene-4-sulfonamide were used as the nueleophilic components. Complexes prepared, in situ, from these 2,6-disubstituted 1,4,7-timethyl-1,4,7-triazamacrocycles and manganese(II) catalysed the asymmetric epoxidation of styrene with hydrogen peroxide.
LanguageEnglish
Pages3795-3798
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number21
DOIs
Publication statusPublished - 20 May 2002

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Toluene
Styrene
Epoxidation
Sulfonamides
Manganese
Hydrogen Peroxide
1,4,7-triazacyclononane

Keywords

  • asymmetric synthesis
  • epoxidation
  • polyamines

Cite this

Argouarch, G., Gibson, C. L., Stones, G., & Sherrington, D. C. (2002). The synthesis of chiral annulet 1,4,7-triazacyclononanes. Tetrahedron Letters, 43(21), 3795-3798. https://doi.org/10.1016/S0040-4039(02)00705-0
Argouarch, G. ; Gibson, C.L. ; Stones, G. ; Sherrington, D.C. / The synthesis of chiral annulet 1,4,7-triazacyclononanes. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 21. pp. 3795-3798.
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Argouarch, G, Gibson, CL, Stones, G & Sherrington, DC 2002, 'The synthesis of chiral annulet 1,4,7-triazacyclononanes' Tetrahedron Letters, vol. 43, no. 21, pp. 3795-3798. https://doi.org/10.1016/S0040-4039(02)00705-0

The synthesis of chiral annulet 1,4,7-triazacyclononanes. / Argouarch, G.; Gibson, C.L.; Stones, G.; Sherrington, D.C.

In: Tetrahedron Letters, Vol. 43, No. 21, 20.05.2002, p. 3795-3798.

Research output: Contribution to journalArticle

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N2 - Novel and flexible routes for the synthesis of chiral ring annulet 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles are described. Efficient macrocyclisations were realised provided that chiral analogues of N,N-bis-[2-(toluene-sulfonyl-amino)ethyl]-toluene-4-sulfonamide were used as the nueleophilic components. Complexes prepared, in situ, from these 2,6-disubstituted 1,4,7-timethyl-1,4,7-triazamacrocycles and manganese(II) catalysed the asymmetric epoxidation of styrene with hydrogen peroxide.

AB - Novel and flexible routes for the synthesis of chiral ring annulet 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles are described. Efficient macrocyclisations were realised provided that chiral analogues of N,N-bis-[2-(toluene-sulfonyl-amino)ethyl]-toluene-4-sulfonamide were used as the nueleophilic components. Complexes prepared, in situ, from these 2,6-disubstituted 1,4,7-timethyl-1,4,7-triazamacrocycles and manganese(II) catalysed the asymmetric epoxidation of styrene with hydrogen peroxide.

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KW - epoxidation

KW - polyamines

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Argouarch G, Gibson CL, Stones G, Sherrington DC. The synthesis of chiral annulet 1,4,7-triazacyclononanes. Tetrahedron Letters. 2002 May 20;43(21):3795-3798. https://doi.org/10.1016/S0040-4039(02)00705-0