Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction


Karadeniz L. , Astley S. T.

RESEARCH ON CHEMICAL INTERMEDIATES, vol.39, no.7, pp.3407-3415, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 39 Issue: 7
  • Publication Date: 2013
  • Doi Number: 10.1007/s11164-012-0853-x
  • Title of Journal : RESEARCH ON CHEMICAL INTERMEDIATES
  • Page Numbers: pp.3407-3415

Abstract

Several amino acids and their derivatives have been evaluated as organic catalysts for the nitroaldol reaction. It was found that when an unprotected amino group and an unprotected carboxylate group were present in the organocatalyst, both the nitroaldol reaction and subsequent elimination could occur to afford nitroalkenes from aromatic aldehydes and nitromethane. The best results were obtained by use of gamma-amino acids derived from l-glutamine. It is suggested that the amino group is important for intermediate Schiff base formation and that the free carboxylate group facilitates the elimination step.