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

Research output: Contribution to journalArticle

70 Citations (Scopus)

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
Beshara, Cory S. ; Hall, Adrian ; Jenkins, Robert L. ; Jones, Kerri L. ; Jones, Teyrnon C. ; Killeen, Niall M. ; Taylor, Paul H. ; Thomas, Stephen P. ; Tomkinson, Nicholas C. O. / A general method for the α-acyloxylation of carbonyl compounds. In: Organic Letters. 2005 ; Vol. 7, No. 25. pp. 5729-5732.
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Beshara, CS, Hall, A, Jenkins, RL, Jones, KL, Jones, TC, Killeen, NM, Taylor, PH, Thomas, SP & Tomkinson, NCO 2005, 'A general method for the α-acyloxylation of carbonyl compounds', Organic Letters, vol. 7, no. 25, pp. 5729-5732. https://doi.org/10.1021/ol052474e

A general method for the α-acyloxylation of carbonyl compounds. / Beshara, Cory S.; Hall, Adrian; Jenkins, Robert L.; Jones, Kerri L.; Jones, Teyrnon C.; Killeen, Niall M.; Taylor, Paul H.; Thomas, Stephen P.; Tomkinson, Nicholas C. O.

In: Organic Letters, Vol. 7, No. 25, 2005, p. 5729-5732.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A general method for the α-acyloxylation of carbonyl compounds

AU - Beshara, Cory S.

AU - Hall, Adrian

AU - Jenkins, Robert L.

AU - Jones, Kerri L.

AU - Jones, Teyrnon C.

AU - Killeen, Niall M.

AU - Taylor, Paul H.

AU - Thomas, Stephen P.

AU - Tomkinson, Nicholas C. O.

PY - 2005

Y1 - 2005

N2 - 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.

AB - 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.

KW - α-acyloxylation

KW - carbonyl compounds

U2 - 10.1021/ol052474e

DO - 10.1021/ol052474e

M3 - Article

VL - 7

SP - 5729

EP - 5732

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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Beshara CS, Hall A, Jenkins RL, Jones KL, Jones TC, Killeen NM et al. A general method for the α-acyloxylation of carbonyl compounds. Organic Letters. 2005;7(25):5729-5732. https://doi.org/10.1021/ol052474e