A general method for the alpha-acyloxylation of carbonyl compounds

C S  Beshara; A  Hall; R L  Jenkins; K L  Jones; T C  Jones; N M  Killeen; P H  Taylor; S P  Thomas; N C O  Tomkinson

doi:10.1021/ol052474e

A general method for the alpha-acyloxylation of carbonyl compounds

C S Beshara, A Hall, R L Jenkins, K L Jones, T C Jones, N M Killeen, P H Taylor, S P Thomas, N C O Tomkinson

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Abstract

A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature 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 provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.

Original language	English
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 - 8 Dec 2005

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

abstract = "A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature 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 provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.",

author = "Beshara, {C S} and A Hall and Jenkins, {R L} and Jones, {K L} and Jones, {T C} and Killeen, {N M} and Taylor, {P H} and Thomas, {S P} and Tomkinson, {N C O}",

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doi = "10.1021/ol052474e",

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

AU - Beshara, C S

AU - Hall, A

AU - Jenkins, R L

AU - Jones, K L

AU - Jones, T C

AU - Killeen, N M

AU - Taylor, P H

AU - Thomas, S P

AU - Tomkinson, N C O

PY - 2005/12/8

Y1 - 2005/12/8

N2 - A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature 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 provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.

AB - A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature 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 provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.

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 -

A general method for the alpha-acyloxylation of carbonyl compounds

Abstract

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