Desulfonylation with Mg−MeOH−NiBr2: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

Abstract

[reaction: see text] A catalytic amount of NiBr(2) with Mg-MeOH increases the efficiency of reductive desulfonylation of the beta-sulfonylated aminosugars. The Mg-MeOH-NiBr(2) system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44-75% with Mg-MeOH-NiBr(2).