Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction
Articles > Article ยท 2012
Authors: Leman ALKAN, Stephen Thomas ASTLEY
RESEARCH ON CHEMICAL INTERMEDIATES, Journal Indexed in SCI Expanded, International, 2012, vol 39, pp 3407-3415
DOI: 10.1007/s11164-012-0853-x
Summary
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.