The asymmetric synthesis and conformational analysis of new C2-symmetric macrocycles derived from head-to-head linked α-amino acids and benzene or pyridine

Patrick D. Bailey, S. R L Everitt, Keith M. Morgan, Andrew G. Brewster

Research output: Contribution to journalArticle

Abstract

The synthesis of several novel 15-18-membered macrocycles containing 1,3-disubstituted benzene or 2,6-disubstituted pyridine in a chiral environment is described. The syntheses used a series of di(Na-tosyl-L-alanylamido)alkanes, which could be prepared in good yield. The macrocyclisation reaction with 1,3-di(bromomethyl)benzene or 2,6-di(bromomethyl)pyridine was facilitated by the use of caesium carbonate as base, and NMR and molecular modelling were used to study the preferred conformations of the macrocycles. © 2001 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)1379-1386
Number of pages8
JournalTetrahedron
Volume57
Issue number7
DOIs
Publication statusPublished - 11 Feb 2001

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Benzene
Amino Acids
Alkanes
Molecular modeling
Conformations
Nuclear magnetic resonance
pyridine
cesium carbonate

Keywords

  • Amino acids and derivatives
  • Macrocycles
  • Molecular modelling/mechanics
  • Pyridines

Cite this

Bailey, Patrick D. ; Everitt, S. R L ; Morgan, Keith M. ; Brewster, Andrew G. / The asymmetric synthesis and conformational analysis of new C2-symmetric macrocycles derived from head-to-head linked α-amino acids and benzene or pyridine. In: Tetrahedron. 2001 ; Vol. 57, No. 7. pp. 1379-1386.
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The asymmetric synthesis and conformational analysis of new C2-symmetric macrocycles derived from head-to-head linked α-amino acids and benzene or pyridine. / Bailey, Patrick D.; Everitt, S. R L; Morgan, Keith M.; Brewster, Andrew G.

In: Tetrahedron, Vol. 57, No. 7, 11.02.2001, p. 1379-1386.

Research output: Contribution to journalArticle

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AB - The synthesis of several novel 15-18-membered macrocycles containing 1,3-disubstituted benzene or 2,6-disubstituted pyridine in a chiral environment is described. The syntheses used a series of di(Na-tosyl-L-alanylamido)alkanes, which could be prepared in good yield. The macrocyclisation reaction with 1,3-di(bromomethyl)benzene or 2,6-di(bromomethyl)pyridine was facilitated by the use of caesium carbonate as base, and NMR and molecular modelling were used to study the preferred conformations of the macrocycles. © 2001 Elsevier Science Ltd.

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