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

doi:10.1021/ol303324a

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 journal › Letter › peer-review

13 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 language	English
Pages (from-to)	370-373
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	2
Early online date	31 Dec 2012
DOIs	https://doi.org/10.1021/ol303324a
Publication status	Published - 2013

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10.1021/ol303324a

http://pubs.acs.org/doi/abs/10.1021/ol303324a

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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",

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volume = "15",

pages = "370--373",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "2",

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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

SN - 1523-7060

VL - 15

SP - 370

EP - 373

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

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

Abstract

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