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Stereoselective Synthesis of New Ferrocene-Derived Amino Acid Building Blocks

✍ Scribed by Andrea Hunold; Ines Neundorf; Philippe James; Jörg Neudörfl; Hans-Günther Schmalz

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
458 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

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)

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