Semi-rigid N-para-ferrocenyl(benzoyl)amino-acid esters for biomaterials:: synthesis and characterization of Fc-C6H4CONHCH(R)CO2Me where Fc = (η5-C5H5)Fe(η5-C5H4) and R = H, CH3, CH2CH(CH3)2, CH2C6H5 and the X-ray crystal structures of Fc-C6H4CO2Me and the L-alanine derivative Fc-C6H4CONHCH(CH3)CO2Me

A series of N-para-(ferrocenyl)benzoyl amino-acid esters, para-Fc(C6H4)CONHCH(R)CO2CH3 {Fc = (eta(5)-C5H5)Fe(eta(5)-C5H4); R = H, CH3, CH2CH(CH3)(2), CH2C6H5}, 3-6 have been prepared by coupling para-(ferrocenyl)benzoic acid to the amino-acid esters (gly, L-Ala, L-Leu, L-Phe) using the standard 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The compounds were fully characterized by a range of spectroscopic techniques including FAB-MS. The X-ray crystal structures of the parent para-(ferrocenyl)benzoyl methyl ester, Fc-C6H4CO2Me, 1 and a chiral derivative N-{para-(ferrocenyl)benzoyl}-L-alanine methyl ester, FC-C6H4CONHCH(CH3)CO2Me, 4 have been determined. (C) 2002 Elsevier Science B.V. All rights reserved.