In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

William J. Kerr; Allan J. B. Watson; Douglas. Hayes

doi:10.1039/b802082e

In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

William J. Kerr, Allan J. B. Watson, Douglas. Hayes

Pure And Applied Chemistry

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Abstract

Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.

Original language	English
Pages (from-to)	1238-1243
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	6
Issue number	7
Early online date	25 Feb 2008
DOIs	https://doi.org/10.1039/b802082e
Publication status	Published - 2008

Keywords

Mes2Mg
MesMgBr
silyl enol ethers
ketones

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10.1039/b802082e

In situ generationFinal published version, 176 KB

New Magnesium-based Enantioselective Deprotonation Methods; Greener General Base Strategies and the Development of a Catalytic Protocol x ref 040625
Kerr, W. (Principal Investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/09/05 → 31/01/09
Project: Research

Cite this

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title = "In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers",

abstract = "Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.",

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doi = "10.1039/b802082e",

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pages = "1238--1243",

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issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

AU - Kerr, William J.

AU - Watson, Allan J. B.

AU - Hayes, Douglas.

PY - 2008

Y1 - 2008

N2 - Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.

AB - Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.

KW - Mes2Mg

KW - MesMgBr

KW - silyl enol ethers

KW - ketones

U2 - 10.1039/b802082e

DO - 10.1039/b802082e

M3 - Article

SN - 1477-0520

VL - 6

SP - 1238

EP - 1243

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 7

ER -

In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

Abstract

Keywords

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Projects

New Magnesium-based Enantioselective Deprotonation Methods; Greener General Base Strategies and the Development of a Catalytic Protocol x ref 040625

Cite this