Sequential Synthesis of (<i>E</i>)-α,β-Unsaturated Primary Amides with Complete Stereoselectivity

A novel, efficient, and totally stereoselective synthesis of (<i>E</i>)-α,β-unsaturated primary amides is reported. This process is consistent with a SmI<sub>2</sub>-mediated sequential reaction of an unmasked samarium chloroacetamide enolate with an aldehyde, followed by a β-elimination to produce (<i>E</i>)-α,β-unsaturated primary amides in good yields.