Synthesis and characterization of chiral iron carbonyl complexes from imine ligands with carbohydrates and amino acids as substituents

摘要

Imine ligands derived from 6-amino-6-desoxy-1,2,3-O-trimethyl-alpha-D-glucopyranose or from various amino acid esters react with Fe-2(CO)(9) to give chiral iron carbonyl complexes. Derivatives produced from benzaldehyde react via a C-H activation reaction in ortho-position with respect to the exocyclic imine substituent followed by an intramolecular hydrogen transfer reaction of the activated hydrogen towards the former imine carbon atom. The molecular structure of the diiron hexacarbonyl complexes of benzylide-neamino-L-phenylalanine ethyl ester and benzylideneamino-L-methionine methyl ester were characterized by means of X-ray structure determinations. Imines produced from cinnamaldehyde upon reaction with Fe-2(CO)(9) produce mononuclear iron tricarbonyl complexes with the imine ligand being coordinated in a eta(4)-fashion. (c) 2005 Elsevier Ltd. All rights reserved.