Solid-phase combinatorial synthesis of polyisoxazolines: A two-reaction iterative protocol

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

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Starting from a polymer-bound olefin, iterative application of nitrile oxide 1,3-dipolar cycloaddition and selenide oxidation/elimination steps were employed to deliver a polymer-bound triisoxazoline that can be liberated from the resin by transesterification. When four nitroseleno ethers (2-5) and four capping nitroalkanes (6-9) were employed, a triisoxazoline library (V) of 64 positional isomers was obtained by three iterative applications of these two reactions. The tactical flexibility of this strategy for preparing small polyfunctional oligomers is particularly attractive in that each subunit addition proceeds via a C-C bond-forming step.

Original languageEnglish (US)
Pages (from-to)8755-8761
Number of pages7
JournalJournal of Organic Chemistry
Volume61
Issue number25
DOIs
StatePublished - Dec 13 1996

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Polymers
Nitriles
Ethers
Cycloaddition
Transesterification
Alkenes
Oligomers
Isomers
Oxides
Resins
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Solid-phase combinatorial synthesis of polyisoxazolines : A two-reaction iterative protocol. / Kurth, Mark J.; Ahlberg Randall, Lisa A.; Takenouchi, Kazuya.

In: Journal of Organic Chemistry, Vol. 61, No. 25, 13.12.1996, p. 8755-8761.

Research output: Contribution to journalArticle

Kurth, Mark J. ; Ahlberg Randall, Lisa A. ; Takenouchi, Kazuya. / Solid-phase combinatorial synthesis of polyisoxazolines : A two-reaction iterative protocol. In: Journal of Organic Chemistry. 1996 ; Vol. 61, No. 25. pp. 8755-8761.
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