A room temperature Negishi cross-coupling approach to C-alkyl glycosides
H Gong, R Sinisi, MR Gagné - Journal of the American Chemical …, 2007 - ACS Publications
H Gong, R Sinisi, MR Gagné
Journal of the American Chemical Society, 2007•ACS PublicationsGlycosyl halides serve as effective alkyl halides for room temperature Negishi cross-
coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions
is in situ generated (PyBox) NiCl2. The functional group tolerance on the zinc reagent is
typically high, and both benzyl and ester protecting groups on the carbohydrate are
tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl
halides.
coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions
is in situ generated (PyBox) NiCl2. The functional group tolerance on the zinc reagent is
typically high, and both benzyl and ester protecting groups on the carbohydrate are
tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl
halides.
Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl halides.
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