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Solid-Phase Combinatorial Synthesis of Polyisoxazolines: A Two-Reaction Iterative Protocol.

Mark J. Kurth1, Lisa A. Ahlberg Randall, Kazuya Takenouchi

  • 1Department of Chemistry, University of California, Davis, California 95616.

The Journal of Organic Chemistry
|December 13, 1996
PubMed
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A new method synthesizes diverse triisoxazoline libraries using iterative nitrile oxide cycloaddition and selenide elimination on polymer supports. This strategy offers flexible C-C bond formation for creating polyfunctional oligomers.

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Synthetic Methodology

Background:

  • Polymer-supported synthesis enables efficient purification and library generation.
  • Nitrile oxide cycloaddition is a versatile reaction for heterocycle synthesis.
  • Selenide chemistry offers unique functionalization and cleavage strategies.

Purpose of the Study:

  • To develop an iterative synthetic strategy for polymer-bound triisoxazolines.
  • To create a diverse library of triisoxazoline positional isomers.
  • To demonstrate the utility of C-C bond-forming steps in oligomer synthesis.

Main Methods:

  • Iterative 1,3-dipolar cycloaddition of nitrile oxides to polymer-bound olefins.
  • Selenide oxidation and elimination for sequential functionalization.

Related Experiment Videos

  • Transesterification for cleavage of the triisoxazoline from the resin.

    • Main Results:

    • A polymer-bound triisoxazoline was successfully synthesized and liberated.
    • A library of 64 positional isomers was generated using varied starting materials.
    • Each subunit addition proceeded via a carbon-carbon bond-forming step.

    Conclusions:

    • The developed strategy provides tactical flexibility for constructing polyfunctional oligomers.
    • This method is attractive for the rapid generation of diverse small molecule libraries.
    • The iterative C-C bond-forming approach enhances synthetic efficiency.