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 [iPrCHO, tBuCHO, 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).
