Organic Letters 2009-02-19

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

Hegui Gong, R Stephen Andrews, Joseph L Zuccarello, Stephen J Lee, Michel R Gagné

Index: Org. Lett. 11(4) , 879-82, (2009)

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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.