An asymmetric method for the α-oxyacylation of carbonyl compounds.

Deborah A. Knowles, Christopher J. Matthews, Nicholas C. O. Tomkinson

Research output: Contribution to conferenceOther

Abstract

The development of metal-free processes in org. chem. has received much interest in recent years, following a drive to establish novel, selective transformations that are both cleaner and more efficient. We have recently reported a novel process for the α-oxygenation of carbonyl compds.; important synthetic building blocks more commonly accessed via air-sensitive metal intermediates. This process uses N-methyl-O-benzoyl hydroxylamine hydrochloride 1, the reaction proceeding via a [3,3]-sigmatropic rearrangement of an enamine intermadiate 2 (Figure 1). Reactions proceed in one practical step in the presence of moisture and air, giving the products in good to excellent yield. This talk will describe the development and optimization of an asym. variant of this important reaction through introduction of chirality at the nitrogen substituent of the reagent 3. [on SciFinder(R)]
LanguageEnglish
Publication statusPublished - 2008
EventAmerican Chemical Society , USA -
Duration: 31 Mar 2011 → …

Other

OtherAmerican Chemical Society , USA
Period31/03/11 → …

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Carbonyl compounds
Metalloids
Hydroxylamine
Oxygenation
Chirality
Air
Nitrogen
Moisture
Metals
O-benzoylhydroxylamine

Cite this

Knowles, D. A., Matthews, C. J., & Tomkinson, N. C. O. (2008). An asymmetric method for the α-oxyacylation of carbonyl compounds.. American Chemical Society , USA, .
Knowles, Deborah A. ; Matthews, Christopher J. ; Tomkinson, Nicholas C. O. / An asymmetric method for the α-oxyacylation of carbonyl compounds. American Chemical Society , USA, .
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title = "An asymmetric method for the α-oxyacylation of carbonyl compounds.",
abstract = "The development of metal-free processes in org. chem. has received much interest in recent years, following a drive to establish novel, selective transformations that are both cleaner and more efficient. We have recently reported a novel process for the α-oxygenation of carbonyl compds.; important synthetic building blocks more commonly accessed via air-sensitive metal intermediates. This process uses N-methyl-O-benzoyl hydroxylamine hydrochloride 1, the reaction proceeding via a [3,3]-sigmatropic rearrangement of an enamine intermadiate 2 (Figure 1). Reactions proceed in one practical step in the presence of moisture and air, giving the products in good to excellent yield. This talk will describe the development and optimization of an asym. variant of this important reaction through introduction of chirality at the nitrogen substituent of the reagent 3. [on SciFinder(R)]",
author = "Knowles, {Deborah A.} and Matthews, {Christopher J.} and Tomkinson, {Nicholas C. O.}",
note = "M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2008:954127(Conference; Meeting Abstract; Computer Optical Disk); American Chemical Society , USA ; Conference date: 31-03-2011",
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Knowles, DA, Matthews, CJ & Tomkinson, NCO 2008, 'An asymmetric method for the α-oxyacylation of carbonyl compounds.' American Chemical Society , USA, 31/03/11, .

An asymmetric method for the α-oxyacylation of carbonyl compounds. / Knowles, Deborah A.; Matthews, Christopher J.; Tomkinson, Nicholas C. O.

2008. American Chemical Society , USA, .

Research output: Contribution to conferenceOther

TY - CONF

T1 - An asymmetric method for the α-oxyacylation of carbonyl compounds.

AU - Knowles, Deborah A.

AU - Matthews, Christopher J.

AU - Tomkinson, Nicholas C. O.

N1 - M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2008:954127(Conference; Meeting Abstract; Computer Optical Disk)

PY - 2008

Y1 - 2008

N2 - The development of metal-free processes in org. chem. has received much interest in recent years, following a drive to establish novel, selective transformations that are both cleaner and more efficient. We have recently reported a novel process for the α-oxygenation of carbonyl compds.; important synthetic building blocks more commonly accessed via air-sensitive metal intermediates. This process uses N-methyl-O-benzoyl hydroxylamine hydrochloride 1, the reaction proceeding via a [3,3]-sigmatropic rearrangement of an enamine intermadiate 2 (Figure 1). Reactions proceed in one practical step in the presence of moisture and air, giving the products in good to excellent yield. This talk will describe the development and optimization of an asym. variant of this important reaction through introduction of chirality at the nitrogen substituent of the reagent 3. [on SciFinder(R)]

AB - The development of metal-free processes in org. chem. has received much interest in recent years, following a drive to establish novel, selective transformations that are both cleaner and more efficient. We have recently reported a novel process for the α-oxygenation of carbonyl compds.; important synthetic building blocks more commonly accessed via air-sensitive metal intermediates. This process uses N-methyl-O-benzoyl hydroxylamine hydrochloride 1, the reaction proceeding via a [3,3]-sigmatropic rearrangement of an enamine intermadiate 2 (Figure 1). Reactions proceed in one practical step in the presence of moisture and air, giving the products in good to excellent yield. This talk will describe the development and optimization of an asym. variant of this important reaction through introduction of chirality at the nitrogen substituent of the reagent 3. [on SciFinder(R)]

M3 - Other

ER -

Knowles DA, Matthews CJ, Tomkinson NCO. An asymmetric method for the α-oxyacylation of carbonyl compounds.. 2008. American Chemical Society , USA, .