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Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes.

Organic letters (2009-01-28)
Hegui Gong, R Stephen Andrews, Joseph L Zuccarello, Stephen J Lee, Michel R Gagné
ABSTRACT

A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,4-Dimethyl-3-pentanol, 99%

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