SmI2-promoted tandem desulfurization and reductive coupling reactions of aromatic lactams with carbonyl compounds

Treatment of sulfur-substituted aromatic lactams with carbonyl compounds in the presence of samarium(II) diiodide was found to undergo novel tandem desulfurization and reductive coupling reactions to generate α-hydroxyalkylated lactams in high yield. Stereochemistry of the coupling products was researched and the results that decreasing the steric bulkiness of the N-substituents as well as raising the reaction temperature leads to an increase of the erythro-selectivity were observed. The mechanistic origins of this stereoselectivity are also briefly documented.