1-ACETOXY AND 1-SILYLOXY-1,3-DIENES VIA REDUCTIVE HOMOLOGATION OF α,β-UNSATURATED ESTERS

Article abstract of DOI:10.1016/S0040-4039(00)95441-8

α,β-Unsaturated esters (1) are stereospecifically converted in a one-pot preparation into 1-oxygenated-E,E-dienes (4).This reductive homologation proceeds via lithium hydride reduction of the ene ynolate anion (2) to the dienolate anion 3, affording 1-acetoxy- or 1-silyloxy-1,3-dienes in yields of about 45-55percent.