Acetone Dimethyl Hydrazone: Useful Synthon+for the Synthesis of Pheromones with Keto and Spiro Ketal Functions

Abstract

Abstract The use of α-lithiated dimethyl hydrazones as an efficient enolate equivalent for the alkylation of ketones has been reported1,2,3. Due to the ragioselectivity exhibited by acetone dimethyl hydrazone (1) towards the formation of bis alkylated products, we have used the easily avaiLable (1) as a convenient synthon for achieving a short and simple synthesis of pheromones, 1,7-dioxaspiro (5,5) undecane4 (2) and Z-6-Heneicosen-11-one (2). The key step in both the syntheses is the regioselective bis alkylation of (1) using butyl lithium as a base, as shown in Scheme I.