Fluorine-Containing Allenylpalladium Complexes. Synthesis of Optically Active Fluoroalkylated Allenes and Furan Derivatives

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Title:Fluorine-Containing Allenylpalladium Complexes. Synthesis of Optically Active Fluoroalkylated Allenes and Furan Derivatives
Creators:
Konno, Tsutomu
Tanikawa, Mitsuru
Ishihara, Takashi
Yamanaka, Hiroki
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 10, pp. 1421-1435
Uncontrolled Keywords:Allenes, Palladium catalysis, Propargyl esters, Fluorinated compounds, Alkynes, Cross-coupling reactions, Enantioselective synthesis, Furanes, Fluorine-containing allenylpalladium complexes

Abstract

The reaction of fluoroalkylated propargyl mesylates with various nucleophiles, such as zinc reagents and enolates derived from 1,3-dicarbonyl compounds, in the presence of a palladium catalyst was investigated in detail. Various zinc reagents participated in the coupling reaction to give the corresponding fluoroalkylated allenes in good yields. When chiral mesylates were employed, the corresponding optically active allenes were obtained without any loss of enantiomeric purity in the reaction. On the other hand, treatment of trifluoromethylated propargyl mesylate with stabilized carbanions derived from methyl acetoacetate, acetylacetone, and diethyl malonate afforded fluorine-containing furan derivatives in moderate to high yields. <p>

Title:Fluorine-Containing Allenylpalladium Complexes. Synthesis of Optically Active Fluoroalkylated Allenes and Furan Derivatives
Creators:
Konno, Tsutomu
Tanikawa, Mitsuru
Ishihara, Takashi
Yamanaka, Hiroki
Uncontrolled Keywords:Allenes, Palladium catalysis, Propargyl esters, Fluorinated compounds, Alkynes, Cross-coupling reactions, Enantioselective synthesis, Furanes, Fluorine-containing allenylpalladium complexes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:10
Page Range:pp. 1421-1435
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021421UNSPECIFIED
ID Code:2004
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Konno, Tsutomu; Tanikawa, Mitsuru; Ishihara, Takashi; Yamanaka, Hiroki (2002) Fluorine-Containing Allenylpalladium Complexes. Synthesis of Optically Active Fluoroalkylated Allenes and Furan Derivatives. Collection of Czechoslovak Chemical Communications, 67 (10). pp. 1421-1435. ISSN 0010-0765

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