Synthesis of vinylogous esters, amides and related unsaturated compounds

Related: α,β-unsaturated compounds
(C-C Coupling)

Recent Literature

A zinc carbenoid-mediated chain extension of β-dicarbonyl compounds provides access to α,β-unsaturated-γ-keto esters and amides with complete E selectivity via an intermediate zinc enolate, which is treated sequentially with iodine and DBU.
M. D. Ronsheim, C. K Zercher, J. Org. Chem., 2003, 68, 4535-4538.

Among the reported examples of new reactivity of the hypervalent iodine reagent DMP (Dess-Martin periodinane) are the one-step oxidation of secondary amides to imides and N-acyl vinylogous carbamates or ureas and the direct oxidation of benzylic and related primary amines to the corresponding nitriles.
K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. Int. Ed., 2005, 44, 5992-5997.

A highly stereoselective synthesis of aromatic α,β-unsaturated amides was achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide. α,β-epoxyamides are easily prepared by the reaction of enolates derived from α-chloroamides with carbonyl compounds at -78°C.
J. M. Concellón, E. Bardales, J. Org. Chem., 2003, 5, 9492-9295.