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. 2009 Feb 19;11(4):879-82.
doi: 10.1021/ol8028737.

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

Hegui Gong  1 , R Stephen Andrews, Joseph L Zuccarello, Stephen J Lee, Michel R Gagné
Affiliations

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

Hegui Gong et al. Org Lett. .

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.

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