A CONVENIENT SYNTHESIS OF ALLENES BY THE REACTION OF PROPARGYL ALCOHOLS WITH GRIGNARD REAGENTS USING 1-CHLORO-2-METHYL-N,N-TETRAMETHYLENEPROPENYLAMINE

Article abstract of DOI:10.1016/0040-4039(84)80052-0

1-Chloro-2-methyl-N,N-tetramethylenepropenylamine was found to be an efficient condensation reagent for the regioselective coupling reaction of propargyl alcohols with Grignard reagents to give allenes in good yields with high chemo- and enantioselectivities.The utility of the reaction was demonstrated in the stereocontrolled synthesis of methyl (E)-2,4,5-tetradecatrienoate, the pheromone of the male dried bean beetle.