Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

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

doi:10.1055/s-2008-1072739

Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

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

Pure And Applied Chemistry

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

7 Citations (Scopus)

Abstract

Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases.

Original language	English
Pages (from-to)	1386-1390
Number of pages	5
Journal	Synlett
Volume	2008
Issue number	9
DOIs	https://doi.org/10.1055/s-2008-1072739
Publication status	Published - 23 May 2008

Keywords

deprotonations
grignard reagents
ketones
magnesium
organometallic reagents

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10.1055/s-2008-1072739

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 = "Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones",

abstract = "Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases.",

keywords = "deprotonations, grignard reagents, ketones, magnesium, organometallic reagents",

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AU - Kerr, William J.

AU - Watson, Allan J. B.

AU - Hayes, Douglas.

PY - 2008/5/23

Y1 - 2008/5/23

N2 - Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases.

AB - Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases.

KW - deprotonations

KW - grignard reagents

KW - ketones

KW - magnesium

KW - organometallic reagents

U2 - 10.1055/s-2008-1072739

DO - 10.1055/s-2008-1072739

M3 - Article

SN - 0936-5214

VL - 2008

SP - 1386

EP - 1390

JO - Synlett

JF - Synlett

IS - 9

ER -

Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

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