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

Abstract

The use of α-lithiated dimethyl hydrazones as an efficient enolate equivalent for the alkylation of ketones has been reported^1,2,3. 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.