Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions

Scott E. Denmark, Jeffrey M. Kallemeyn

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) A [3 + 2] cycloaddition reaction between alkynyldimethylsilyl ethers and aryl and alkyl nitrile oxides to produce isoxazolylsilanols has been developed. The cross-coupling reactions of these heterocyclic silanols with a variety of aryl iodides affords 3,4,5-trisubstituted isoxazoles. This sequential process allows for rapid variation of substituents at the 3, 4, and 5 positions of the isoxazole.

Original languageEnglish (US)
Pages (from-to)2839-2842
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number7
DOIs
StatePublished - Apr 1 2005

ASJC Scopus subject areas

  • Organic Chemistry

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