Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives

Article abstract of DOI:10.1016/S0040-4020(99)00610-9

The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [(i)PrCHO, (t)BuCHO, PhCHO, Me₂CO, Et₂CO, (CH₂)5CO, Ph₂CO, Me₃SiCl] in THF at different temperatures (-78, -30 or 0°C) leads, after hydrolysis with water to the corresponding allylated or benzylated products (2).