A Mild New Method for the C-Acylation of Ketone Enolates. A Convenient Synthesis of β-Keto Esters, -Thionoesters and Thioesters

Karl J. Hale, Milosz Grabski, Jakub T. Flasz

Research output: Contribution to journalLetter

10 Citations (Scopus)

Abstract

Abstract image.

A new method for ketone enolate C-acylation is described which utilizes alkyl pentafluorophenylcarbonates, thiocarbonates and thionocarbonates as the reactive acylating agents, and MgBr2.Et2O, DMAP and i-Pr2NEt as the reagents for enolization. A wide range of ketones have been observed to undergo clean C-acylation via this protocol.
Original languageEnglish
Pages (from-to)370-373
Number of pages4
JournalOrganic Letters
Volume15
Issue number2
Early online date31 Dec 2012
DOIs
Publication statusPublished - 2013

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acylation
Acylation
Ketones
ketones
esters
Esters
synthesis
reagents
magnesium bromide

Cite this

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title = "A Mild New Method for the C-Acylation of Ketone Enolates. A Convenient Synthesis of β-Keto Esters, -Thionoesters and Thioesters",
abstract = "Abstract image.A new method for ketone enolate C-acylation is described which utilizes alkyl pentafluorophenylcarbonates, thiocarbonates and thionocarbonates as the reactive acylating agents, and MgBr2.Et2O, DMAP and i-Pr2NEt as the reagents for enolization. A wide range of ketones have been observed to undergo clean C-acylation via this protocol.",
author = "Hale, {Karl J.} and Milosz Grabski and Flasz, {Jakub T.}",
year = "2013",
doi = "10.1021/ol303324a",
language = "English",
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pages = "370--373",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "2",

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A Mild New Method for the C-Acylation of Ketone Enolates. A Convenient Synthesis of β-Keto Esters, -Thionoesters and Thioesters. / Hale, Karl J.; Grabski, Milosz; Flasz, Jakub T.

In: Organic Letters, Vol. 15, No. 2, 2013, p. 370-373.

Research output: Contribution to journalLetter

TY - JOUR

T1 - A Mild New Method for the C-Acylation of Ketone Enolates. A Convenient Synthesis of β-Keto Esters, -Thionoesters and Thioesters

AU - Hale, Karl J.

AU - Grabski, Milosz

AU - Flasz, Jakub T.

PY - 2013

Y1 - 2013

N2 - Abstract image.A new method for ketone enolate C-acylation is described which utilizes alkyl pentafluorophenylcarbonates, thiocarbonates and thionocarbonates as the reactive acylating agents, and MgBr2.Et2O, DMAP and i-Pr2NEt as the reagents for enolization. A wide range of ketones have been observed to undergo clean C-acylation via this protocol.

AB - Abstract image.A new method for ketone enolate C-acylation is described which utilizes alkyl pentafluorophenylcarbonates, thiocarbonates and thionocarbonates as the reactive acylating agents, and MgBr2.Et2O, DMAP and i-Pr2NEt as the reagents for enolization. A wide range of ketones have been observed to undergo clean C-acylation via this protocol.

U2 - 10.1021/ol303324a

DO - 10.1021/ol303324a

M3 - Letter

VL - 15

SP - 370

EP - 373

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 2

ER -