Tandem SmI2-induced nitrone β-elimination/aldol-type reaction

Abstract

Upon treatment with SmI₂, the carbohydrate-derived nitrones 1a,b undergo a β-elimination of the benzyloxy group at C-1, forming original samarium(III) oxy-enamine intermediates. The latter can be reacted with carbonyl compounds to produce aldol-type adducts. The tandem process results in the transformation of a C–O bond into a C–C bond.