A general method for the α-acyloxylation of carbonyl compounds

Cory S. Beshara, Adrian Hall, Robert L. Jenkins, Kerri L. Jones, Teyrnon C. Jones, Niall M. Killeen, Paul H. Taylor, Stephen P. Thomas, Nicholas C. O. Tomkinson

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Abstract

A simple, one-pot method for the α-acyloxylation of carbonyl compds. that proceeded at room temp. in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provided the α-functionalized product in good isolated yield. The transformation was tolerant of a wide range of functional groups and, significantly, was regiospecific in the discrimination of secondary over primary centers in the case of nonsym. substrates.
Original languageUndefined/Unknown
Pages (from-to)5729-5732
Number of pages4
JournalOrganic Letters
Volume7
Issue number25
DOIs
Publication statusPublished - 2005

Keywords

  • α-acyloxylation
  • carbonyl compounds

Cite this

Beshara, C. S., Hall, A., Jenkins, R. L., Jones, K. L., Jones, T. C., Killeen, N. M., ... Tomkinson, N. C. O. (2005). A general method for the α-acyloxylation of carbonyl compounds. Organic Letters, 7(25), 5729-5732. https://doi.org/10.1021/ol052474e