Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals

A highly efficient and convenient C-glycosylation method was developed using ruthenium(III) chloride for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide and heterocycles such as thiophene...

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Veröffentlicht in:Carbohydrate research 2015-04, Vol.406, p.86-92
Hauptverfasser: Srinivas, Batthula, Reddy, Thurpu Raghavender, Kashyap, Sudhir
Format: Artikel
Sprache:eng
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Zusammenfassung:A highly efficient and convenient C-glycosylation method was developed using ruthenium(III) chloride for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide and heterocycles such as thiophene and furan reacted smoothly with glycals in the presence of catalytic amount of ruthenium trichloride under mild reaction conditions. [Display omitted] •A mild and efficient Ferrier C-glycosylation protocol was developed.•Stereoselective synthesis of C-glycosides was achieved by employing Ru-catalysis.•The scope of reaction was well illustrated with diverse range of substrates.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2015.01.009