Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement

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Abstract

A novel α-oxygenation reaction of carbonyl compounds was developed by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The reaction proceeds via the oxidation of enolates followed by the [1,2]-phospha-Brook rearrangement to afford α-oxygenated ester derivatives from easily accessible substrates having high functional group tolerance. In addition, the atom-economical tandem reaction of α-diethylphosphono ester derivatives with oxaziridines, which involves a carbon-carbon forming process in addition to α-oxygenation, was established under the low temperature conditions.

Original languageEnglish
Pages (from-to)801-805
Number of pages5
JournalOrganic Chemistry Frontiers
Volume2
Issue number7
DOIs
Publication statusPublished - 2015 Jul

ASJC Scopus subject areas

  • Organic Chemistry

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