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

Research output: Contribution to journalArticle

5 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.
LanguageEnglish
Pages1386-1390
Number of pages5
JournalSynlett
Volume2008
Issue number9
DOIs
Publication statusPublished - 23 May 2008

Fingerprint

Ethers
Ketones
Carbon
Atoms
Deprotonation

Keywords

  • deprotonations
  • grignard reagents
  • ketones
  • magnesium
  • organometallic reagents

Cite this

@article{ae1fe76f7a4f45b79c2608379e4ee4fe,
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",
author = "Kerr, {William J.} and Watson, {Allan J. B.} and Douglas. Hayes",
note = "M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2008:781418(Journal)",
year = "2008",
month = "5",
day = "23",
doi = "10.1055/s-2008-1072739",
language = "English",
volume = "2008",
pages = "1386--1390",
journal = "Synlett",
issn = "0936-5214",
number = "9",

}

Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones. / Kerr, William J.; Watson, Allan J. B.; Hayes, Douglas.

In: Synlett, Vol. 2008, No. 9, 23.05.2008, p. 1386-1390.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

AU - Kerr, William J.

AU - Watson, Allan J. B.

AU - Hayes, Douglas.

N1 - M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2008:781418(Journal)

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

VL - 2008

SP - 1386

EP - 1390

JO - Synlett

T2 - Synlett

JF - Synlett

SN - 0936-5214

IS - 9

ER -