Stereoselective Synthesis of New Ferrocene‐Derived Amino Acid Building Blocks

Abstract

Abstract As a contribution to bioorganometallic chemistry, a dia‐ and enantioselective synthesis of novel carbocyclic amino acid analogues with a 1,2‐ferroceno‐fused cyclopentene backbone has been developed. Using two related planar‐chiral intermediates, i.e. (1 S , E )‐ethyl‐3‐[2‐(phenylsulfonylacetyl)ferrocen‐1‐yl]acrylate, (1 S , E )‐ethyl‐3‐[2‐(methoxycarbonyl)ferrocen‐1‐yl]acrylate, stereoselective entries to different t Boc‐ or Fmoc‐protected ferroceno‐fused 1‐amino‐3‐carboxyalkyl‐2‐cyclopentenes were elaborated. These compounds were then used for the preparation of metal‐containing peptides by means of solid‐phase peptide synthesis (SPPS). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)