Stereoselective Preparation of Precursors of α-C-(1→3)-Disaccharides

2005 ◽  
Vol 70 (9) ◽  
pp. 1411-1428 ◽  
Author(s):  
Petr Štěpánek ◽  
Ondřej Vích ◽  
Lukáš Werner ◽  
Ladislav Kniežo ◽  
Hana Dvořáková ◽  
...  
Keyword(s):  
Vinyl Ether ◽  
Vinyl Ethers ◽  
Chiral Catalyst ◽  
Substituted 1

The stereoselectivity of cycloaddition of sugar-containing substituted 1-(thiazol-2-yl)but-2-en-1-ones 1 and vinyl ethers was studied using the achiral vinyl ether/chiral catalyst as well as the chiral vinyl ether/achiral catalyst combinations. It has been shown that Eu(fod)3-catalyzed cycloaddition of oxadienes 1a-1e with the chiral vinyl ethers 9 and 10 affords stereoselectively almost pure cycloadducts 11a-11e and 12a-12e, respectively. The obtained cycloadducts are suitable precursors for the synthesis of α-C-(1→3)-disaccharides, containing 2-deoxy-arabino-hexopyranose moiety of D- or L-configuration.

scholarly journals Successive Activation of C–H and C–O Bonds of Vinyl Ethers by a Diphosphine and Hydrido-Bridged Diiridium Complex

Inorganics ◽  
2019 ◽  
Vol 7 (10) ◽  
pp. 121
Author(s):  
Takahashi ◽  
Shimbayashi ◽  
Fujita
Keyword(s):  
Vinyl Ether ◽  
Bond Activation ◽  
Ethyl Vinyl Ether ◽  
Vinyl Ethers ◽  
Ethyl Vinyl

The reaction of [(Cp*Ir)2(μ-dmpm)(μ-H)][OTf] (2) [Cp* = η5-C5Me5, dmpm = bis(dimethylphosphino)methane] with 2,3-dihydrofuran gives [(Cp*IrH)2(μ-dmpm){μ-(2,3-dihydrofuranyl)}][OTf] (3) in an isolated yield of 70% via the C–H bond activation at the 5-position of 2,3-dihydrofuran. Complex 3 is slowly converted into [(Cp*Ir)2(μ-dmpm)(μ-C=C(H)CH2CH2OH)][OTf] (4) quantitatively via the proton-mediated C–O bond activation. The reaction of 2 with ethyl vinyl ether gives [(Cp*Ir)2(μ-dmpm)(μ-CH=CH2)][OTf] (5) in the isolated yield of 64% via the successive activation of C–H and C–O bonds.

Investigation of quantitative structure–reactivity relationships in the aliphatic Claisen rearrangement of bis-vinyl ethers reveals a dipolar, dissociative mechanism

2014 ◽  
Vol 12 (8) ◽  
pp. 1292-1308 ◽  
Author(s):  
Natasha F. O'Rourke ◽  
Jeremy E. Wulff
Keyword(s):  
Vinyl Ether ◽  
Claisen Rearrangement ◽  
Substituent Effects ◽  
Quantitative Structure ◽  
Vinyl Ethers ◽  
Dissociative Mechanism ◽  
Mechanism Of Reaction ◽  
Kinetic Investigations

Kinetic investigations of substituent effects in the Claisen rearrangement of bis-vinyl ether substrates suggest a dissociative mechanism of reaction.

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