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

doi:10.1021/ol052474e

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

84 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 language	Undefined/Unknown
Pages (from-to)	5729-5732
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	25
DOIs	https://doi.org/10.1021/ol052474e
Publication status	Published - 2005

Keywords

α-acyloxylation
carbonyl compounds

Access to Document

10.1021/ol052474e

Cite this

@article{dde2663091974694a792775bb7d99a1c,

title = "A general method for the α-acyloxylation of carbonyl compounds",

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. ",

keywords = "α-acyloxylation , carbonyl compounds",

author = "Beshara, \{Cory S.\} and Adrian Hall and Jenkins, \{Robert L.\} and Jones, \{Kerri L.\} and Jones, \{Teyrnon C.\} and Killeen, \{Niall M.\} and Taylor, \{Paul H.\} and Thomas, \{Stephen P.\} and Tomkinson, \{Nicholas C. O.\}",

year = "2005",

doi = "10.1021/ol052474e",

language = "Undefined/Unknown",

volume = "7",

pages = "5729--5732",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "25",

}

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

SN - 1523-7060

VL - 7

SP - 5729

EP - 5732

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -