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Alpha-amino acids with metallocenyl side chains.

Harald Dialer1, Kurt Polborn, Walter Ponikwar

  • 1Department Chemie der Universität München, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 22, 2002
PubMed
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This study presents a new method for synthesizing enantiomerically pure bis(valine)metallocenes. These chiral compounds, derived from valine, can be further functionalized and show excellent diastereoselectivity in various reactions.

Area of Science:

  • Organometallic Chemistry
  • Asymmetric Synthesis
  • Coordination Chemistry

Background:

  • Chiral metallocenes are valuable in asymmetric catalysis and materials science.
  • Existing synthetic routes often lack efficiency or enantiomeric purity.
  • Development of versatile chiral ligands derived from amino acids is ongoing.

Purpose of the Study:

  • To develop a straightforward method for synthesizing enantiomerically pure bis(valine)metallocenes.
  • To explore the reactivity and coordination chemistry of these novel chiral ligands.
  • To demonstrate the utility of these compounds in forming diastereomerically pure metal complexes.

Main Methods:

  • Addition of chiral Schöllkopf reagents to 6,6-dimethylfulvene to form enantiomerically pure lithium cyclopentadienylvaline derivatives.

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  • Reaction of these derivatives with various metal halides (FeCl2, RuCl2(dmso)4, CoCl2, Re(CO)5Br, RhCl2(cod)2, Cp*MCl3) to synthesize diverse chiral metallocenes and complexes.
  • Hydrolysis and further functionalization of synthesized metallocenes, with structural confirmation by X-ray diffraction.

    • Main Results:

    • Successful synthesis of enantiomerically pure bis(valine)ferrocenes and ruthenocenes.
    • Formation of various chiral metallocenes and complexes with excellent diastereoselectivities using Co, Re, Rh, Ti, and Zr.
    • Demonstration of hydrolysis without racemization and further ligand modification, confirmed by X-ray crystallography for key compounds.

    Conclusions:

    • A versatile and efficient synthetic strategy for enantiomerically pure bis(valine)metallocenes has been established.
    • The synthesized chiral ligands exhibit broad applicability in coordination chemistry with various transition metals.
    • The method allows for the preparation of diastereomerically pure metal complexes, valuable for further applications.