Polymer-supported synthesis of cyclic ethers: Electrophilic cyclization of isoxazolines

Xenia Beebe, Neil E. Schore, Mark J. Kurth

Research output: Contribution to journalArticle

79 Scopus citations

Abstract

Polymer-supported synthesis of 2,5-disubstituted tetrahydrofurans via tandem 1,3-dipolar cycloaddition/electrophilic cyclization has been accomplished using a five-step reaction sequence to give 2-(cyanomethyl)-5-(iodomethyl)tetrahydrofuran (cis:trans ratio of 1:2) in 40% overall yield. The corresponding 2-(cyanomethyl)-6-(iodomethyl)tetrahydropyran was similarly formed in a 7% overall yield. The final electrophilic cyclization simultaneously releases the desired product and regenerates the initial polymer-bound functionality. In the process the desired cyclic ether is obtained exclusively; byproducts of the sequence are not cleaved from the polymer support. In addition the polymer support is sufficiently robust to be recovered and recycled through the reaction sequence.

Original languageEnglish (US)
Pages (from-to)4196-4203
Number of pages8
JournalJournal of Organic Chemistry
Volume60
Issue number13
StatePublished - 1995

ASJC Scopus subject areas

  • Organic Chemistry

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