Enantioselective cyclization of racemic supramolecular polymers

J Am Chem Soc. 2003 Jun 11;125(23):6860-1. doi: 10.1021/ja034273g.

Abstract

Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.

MeSH terms

  • Cyclization
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry*
  • Stereoisomerism

Substances

  • Polymers
  • Pyrimidinones