Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids

Klaus Burger; Lothar Hennig; Annett Fuchs; Dieter Greif; Jan Spengler; Fernando Albericio

doi:10.1007/s00706-005-0366-z

Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids

Klaus Burger
, Lothar Hennig
, Annett Fuchs
, Dieter Greif
, Jan Spengler
, Fernando Albericio

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

16 Scopus citations

Abstract

A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.

Original language	English
Pages (from-to)	1763-1779
Number of pages	17
Journal	Monatshefte fur Chemie
Volume	136
Issue number	10
DOIs	https://doi.org/10.1007/s00706-005-0366-z
State	Published - Oct 2005
Externally published	Yes

Keywords

α-Trifluoromethyl-γ-keto acids
2-Fluoro-3-trifluoromethylfurans
2-Fluoro-3-trifluoromethylthiophenes
Domino reactions
Trifluoromethyl substituted butenolides

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10.1007/s00706-005-0366-z

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title = "Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids",

abstract = "A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.",

keywords = "α-Trifluoromethyl-γ-keto acids, 2-Fluoro-3-trifluoromethylfurans, 2-Fluoro-3-trifluoromethylthiophenes, Domino reactions, Trifluoromethyl substituted butenolides",

author = "Klaus Burger and Lothar Hennig and Annett Fuchs and Dieter Greif and Jan Spengler and Fernando Albericio",

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T1 - Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids

AU - Burger, Klaus

AU - Hennig, Lothar

AU - Fuchs, Annett

AU - Greif, Dieter

AU - Spengler, Jan

AU - Albericio, Fernando

PY - 2005/10

Y1 - 2005/10

N2 - A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.

AB - A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.

KW - α-Trifluoromethyl-γ-keto acids

KW - 2-Fluoro-3-trifluoromethylfurans

KW - 2-Fluoro-3-trifluoromethylthiophenes

KW - Domino reactions

KW - Trifluoromethyl substituted butenolides

UR - https://www.scopus.com/pages/publications/26244462689

U2 - 10.1007/s00706-005-0366-z

DO - 10.1007/s00706-005-0366-z

M3 - Artículo

AN - SCOPUS:26244462689

SN - 0026-9247

VL - 136

SP - 1763

EP - 1779

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 10

ER -

Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids

Abstract

Keywords

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