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

Racine and Py have reported a novel tandem SmI₂-induced β-elimination / aldol-type reaction. Upon treatment with SmI₂ (0.1 mol/L in THF), a nitrone, bearing a benzyloxy group at the β position, underwent the beta-elimination of the benzyloxy group. The intermediate was reacted with cyclohexanecarboxaldehyde as an electrophile to produce an aldol-type adduct. The tandem process results in the transformation of a C–O bond into a C–C bond.