Diastereoselective Metal-Catalyzed Synthesis of C-Aryl and C-Vinyl Glycosides

Cobalt, the catalyst of choice: The diastereoselective cobalt‐catalyzed cross‐coupling of 1‐bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N′‐tetramethylethylenediamine), gives full α selectiv...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-10, Vol.51 (44), p.11101-11104
Hauptverfasser:	Nicolas, Lionel, Angibaud, Patrick, Stansfield, Ian, Bonnet, Pascal, Meerpoel, Lieven, Reymond, Sébastien, Cossy, Janine
Format:	Artikel
Sprache:	eng
Schlagworte:	Aromatic compounds C-glycosides Catalysis Catalysts Cobalt Cobalt - chemistry cross-coupling diastereoselectivity Galactose Glucose Glycosides Glycosides - chemical synthesis Glycosides - chemistry Grignard reagent Iron - chemistry Mannose Molecular Structure Organometallic Compounds - chemistry Stereoisomerism Synthesis
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Beschreibung
Zusammenfassung:	Cobalt, the catalyst of choice: The diastereoselective cobalt‐catalyzed cross‐coupling of 1‐bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N′‐tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1–3:1.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201204786