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

11 Citations (Scopus)

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

Keywords

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

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