Palladium-catalysed arylation of peracetylated glycals, III. Crystal structure of a by-product: mechanistic implications

Reinvestigation of the structure of (4,6-di-O-acetyl-2,3-dideoxy-α- D -erythro-hex-2-enopyranosyl)benzene, obtained by the title reaction, is described. The α anomeric configuration was clearly established by X-ray diffraction methods on the deacetylated compound. The sugar moiety exhibits a distort...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 68; no. 8; pp. 1364 - 1368
Main Authors Bellosta, Véronique, Czernecki, Stanislas, Avenel, Danièle, Bahij, Saïd El, Gillier-Pandraud, Hélène
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.08.1990
National Research Council of Canada
Subjects
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Arylation
Catalytic reaction
Anomer
Stereospecificity
Glycoside
X ray diffraction
Conformation
Circular dichroism
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Summary:Reinvestigation of the structure of (4,6-di-O-acetyl-2,3-dideoxy-α- D -erythro-hex-2-enopyranosyl)benzene, obtained by the title reaction, is described. The α anomeric configuration was clearly established by X-ray diffraction methods on the deacetylated compound. The sugar moiety exhibits a distorted half-chair 0 H 5 conformation. Circular dichroism data are included. These new data demonstrate the stereospecificity of intermediate arylpalladium syn addition on the α face of the glycal. The resulting adduct collapses in two different ways: syn elimination of acetatohydridopalladium leading to 3 , trans elimination of palladium acetate affording 5 . Keywords: C-glycosides, palladium, X-ray diffraction.
ISSN:0008-4042
1480-3291
DOI:10.1139/v90-209