Palladium-catalyzed stereoselective C-glycosidation of unprotected enones derived from d-glucal with trimethylsilyl cyanide

Acetylated and unprotected enones derived from d-glucal reacted with trimethylsilyl cyanide in the presence of a catalytic amount of a palladium compound in 1,4-addition fashion to afford the corresponding 3-keto-glycosyl cyanides in high yield and in high α-selectivity.

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 15; pp. 2591 - 2594
Main Authors Hayashi, Masahiko, Kawabata, Hirotoshi, Shimono, Satoshi, Kakehi, Akikazu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.04.2000
Elsevier
Subjects
C-glycosidation
Chemistry
Chemistry, Organic
enones
palladium and compounds
Physical Sciences
Science & Technology
C-glycosidation
palladium and compounds
enones
OXIDATION
GLYCOSYL CYANIDES
ORGANOCOPPER REAGENTS
ALLYLIC ALCOHOLS
GLYCALS
HEX-1-ENOPYRAN-3-ULOSES
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Summary:Acetylated and unprotected enones derived from d-glucal reacted with trimethylsilyl cyanide in the presence of a catalytic amount of a palladium compound in 1,4-addition fashion to afford the corresponding 3-keto-glycosyl cyanides in high yield and in high α-selectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00212-4