The acylation of lepidine

A number of ketones have been prepared in good to high yields by acylating the methyl group of lepidine (III) with a variety of esters using sodium diisopropylamide (II) as the condensing agent. Two ketones, ethyl and isopropyl lepidyl ketone, have been shown to exist in two forms, the keto form and the intermolecular, hydrogen bonded, enolic form.