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Enantioselective parallel synthesis using polymer-supported chiral Co(salen) complexes.

S Peukert1, E N Jacobsen

  • 1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Organic Letters
|May 29, 2000
PubMed
Summary

This study introduces an enantioselective catalytic synthesis of parallel libraries using polymer-supported cobalt salen complexes. This method efficiently produces chiral 1-aryloxy-2-alcohols, valuable for drug discovery.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Chiral compounds are crucial in pharmaceuticals.
  • Efficient synthesis of enantiomerically pure molecules is a key challenge.
  • Parallel synthesis enables rapid exploration of chemical space.

Purpose of the Study:

  • To develop the first enantioselective catalytic synthesis of parallel libraries.
  • To utilize polymer-supported cobalt salen complexes for kinetic resolution of epoxides.
  • To provide access to pharmacologically active compounds.

Main Methods:

  • Kinetic resolution of epoxides with phenols.
  • Catalysis using a polymer-supported Cobalt(salen) complex.
  • Further elaboration with diversity elements.

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Main Results:

  • High yield, purity, and enantiomeric excess of 1-aryloxy-2-alcohols.
  • Successful application in parallel library synthesis.
  • Efficient access to important classes of pharmacologically active compounds.

Conclusions:

  • Polymer-supported Co(salen) catalyzed kinetic resolution is effective for enantioselective parallel library synthesis.
  • This approach provides a versatile route to chiral building blocks for drug discovery.
  • The methodology allows for rapid generation of diverse, biologically relevant molecules.