Hexafluoroacetone as protecting and activating reagent: Reactions of hexafluoroacetone with α-keto acids

Jan Spengler; Sergej N. Osipov; Elisabeth Heistracher; Alois Haas; Klaus Burger

doi:10.1016/j.jfluchem.2004.01.021

Hexafluoroacetone as protecting and activating reagent: Reactions of hexafluoroacetone with α-keto acids

Jan Spengler
, Sergej N. Osipov
, Elisabeth Heistracher
, Alois Haas
, Klaus Burger

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

6 Scopus citations

Abstract

Hexafluoroacetone and α-keto acids react to give 5,5-bis(trifluoromethyl) substituted 2(5H)-furanones and/or 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones depending upon the substituent pattern of the side chain of the acid. A fluoroanalogue of the natural product zymonic acid was obtained from ethyl 3,3,3-trifluoropyruvate and 2-oxosuccinic acid in one step.

Original language	English
Pages (from-to)	1019-1023
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	125
Issue number	6
DOIs	https://doi.org/10.1016/j.jfluchem.2004.01.021
State	Published - Jun 2004
Externally published	Yes

Keywords

α-Keto acids
2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-ones
5,5-Bis(trifluoromethyl)-2(5H)-furanones
5-Trifluoromethyl-2(5H)-furanones
Butenolides
Hexafluoroacetone
Zymonic acid

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10.1016/j.jfluchem.2004.01.021

Cite this

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title = "Hexafluoroacetone as protecting and activating reagent: Reactions of hexafluoroacetone with α-keto acids",

abstract = "Hexafluoroacetone and α-keto acids react to give 5,5-bis(trifluoromethyl) substituted 2(5H)-furanones and/or 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones depending upon the substituent pattern of the side chain of the acid. A fluoroanalogue of the natural product zymonic acid was obtained from ethyl 3,3,3-trifluoropyruvate and 2-oxosuccinic acid in one step.",

keywords = "α-Keto acids, 2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-ones, 5,5-Bis(trifluoromethyl)-2(5H)-furanones, 5-Trifluoromethyl-2(5H)-furanones, Butenolides, Hexafluoroacetone, Zymonic acid",

author = "Jan Spengler and Osipov, \{Sergej N.\} and Elisabeth Heistracher and Alois Haas and Klaus Burger",

year = "2004",

month = jun,

doi = "10.1016/j.jfluchem.2004.01.021",

language = "Ingl{\'e}s",

volume = "125",

pages = "1019--1023",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

number = "6",

}

TY - JOUR

T1 - Hexafluoroacetone as protecting and activating reagent

T2 - Reactions of hexafluoroacetone with α-keto acids

AU - Spengler, Jan

AU - Osipov, Sergej N.

AU - Heistracher, Elisabeth

AU - Haas, Alois

AU - Burger, Klaus

PY - 2004/6

Y1 - 2004/6

N2 - Hexafluoroacetone and α-keto acids react to give 5,5-bis(trifluoromethyl) substituted 2(5H)-furanones and/or 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones depending upon the substituent pattern of the side chain of the acid. A fluoroanalogue of the natural product zymonic acid was obtained from ethyl 3,3,3-trifluoropyruvate and 2-oxosuccinic acid in one step.

AB - Hexafluoroacetone and α-keto acids react to give 5,5-bis(trifluoromethyl) substituted 2(5H)-furanones and/or 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones depending upon the substituent pattern of the side chain of the acid. A fluoroanalogue of the natural product zymonic acid was obtained from ethyl 3,3,3-trifluoropyruvate and 2-oxosuccinic acid in one step.

KW - α-Keto acids

KW - 2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-ones

KW - 5,5-Bis(trifluoromethyl)-2(5H)-furanones

KW - 5-Trifluoromethyl-2(5H)-furanones

KW - Butenolides

KW - Hexafluoroacetone

KW - Zymonic acid

UR - https://www.scopus.com/pages/publications/3242777037

U2 - 10.1016/j.jfluchem.2004.01.021

DO - 10.1016/j.jfluchem.2004.01.021

M3 - Artículo

AN - SCOPUS:3242777037

SN - 0022-1139

VL - 125

SP - 1019

EP - 1023

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 6

ER -

Hexafluoroacetone as protecting and activating reagent: Reactions of hexafluoroacetone with α-keto acids

Abstract

Keywords

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