Double deprotonation of α-ketoamides generates dienediolates, which undergo regioselective α-alkylation to yield α-substituted-α-hydroxy-β,γ-unsaturated amides. 1,2-Disubstituted alkenes are generated exclusively as the E-isomer. 1,1-Disubstituted and 1,1,2-trisubstituted olefins can also be prepared. The amides can be readily converted to the corresponding acids.
ketoamides - alkylations - dianions - hydroxy acids - stereoselective olefin synthesis
