A room temperature Negishi cross-coupling approach to C-alkyl glycosides

Journal of the American Chemical Society

Volumn 129, Issue 7, 2007, Pages 1908-1909

  Gong, Hegui ^a   Sinisi, Riccardo ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CARBOHYDRATE; FUNCTIONAL GROUP; GLUCOSE; GLYCOSIDE; IMIDAZOLINE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; CROSS COUPLING REACTION; DIASTEREOISOMER; ELIMINATION REACTION; HYDROLYSIS; MOLECULAR INTERACTION; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE;

ALKYLATION; GLUCOSE; GLYCOSIDES; HYDROCARBONS, CHLORINATED; HYDROCARBONS, HALOGENATED; MONOSACCHARIDES; PYRIDINES; TEMPERATURE; ZINC;

EID: 33847301925     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068950t     Document Type: Article

References (39)

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36. In the course of the screening experiment, it was occasionally observed that β-H elimination can occur, but this product is absent in the indicated entries.
37. 3terpy, which significantly improves alkyl-alkyl Negishi cross-couplings (see ref 12a), did not yield the Cl-methyl product in DMA, though it was observed in THF (∼40% with high β-selectivity).
38. Preliminary experiments with aryl zinc reagents indicate that some Cl-aryl product can be obtained using the standard protocol (∼40%). Experiments to optimize the reaction conditions are underway and will be reported in due course. In contrast, preliminary experiments with BnZnBr did not give the C-glycoside.
39. 3Zn-Br a lower catalyst loading (5 mol %) was also tolerated with minimal diminution in yield and diastereoselectivity.