Direct synthesis of 4-fluoroisoxazoles through gold-catalyzed cascade cyclization-fluorination of 2-alkynone O-methyl oximes

Yunkyung Jeong, Bom I. Kim, Jae Kyun Lee, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

Original languageEnglish
Pages (from-to)6444-6455
Number of pages12
JournalJournal of Organic Chemistry
Volume79
Issue number14
DOIs
StatePublished - 18 Jul 2014

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