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

A novel, efficient, and totally stereoselective synthesis of (E)-α,β-unsaturated primary amides is reported. This process is consistent with a SmI₂-mediated sequential reaction of an unmasked samarium chloroacetamide enolate with an aldehyde, followed by a β-elimination to produce (E)-α,β-unsaturated primary amides in good yields.