Stereoselective C-Glycoside Formation by a Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acetylated Enones Derived from Glycals

A new method for the formation of C-glycosides has been developed employing a cationic rhodium(I)-catalyzed 1,4-addition of arylboronic acids to enones derived from glycals. The reaction is stereoselective for the α-anomer and is highly dependent on the nature of the rhodium catalyst.

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Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2001-08, Vol.3 (16), p.2571-2573
Hauptverfasser:	Ramnauth, Jailall, Poulin, Odile, Bratovanov, Svetoslav S, Rakhit, Suman, Maddaford, Shawn P
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetylation Boronic Acids - chemistry Catalysis Glycosides - chemical synthesis Indicators and Reagents Magnetic Resonance Spectroscopy Rhodium - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	A new method for the formation of C-glycosides has been developed employing a cationic rhodium(I)-catalyzed 1,4-addition of arylboronic acids to enones derived from glycals. The reaction is stereoselective for the α-anomer and is highly dependent on the nature of the rhodium catalyst.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol016245d