A CONVENIENT SYNTHESIS OF ALLENES BY THE REACTION OF PROPARGYL ALCOHOLS WITH GRIGNARD REAGENTS USING 1-CHLORO-2-METHYL-N,N-TETRAMETHYLENEPROPENYLAMINE
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.
Fujisawa, Tamotsu,Iida, Sachio,Sato, Toshio
p. 4007 - 4010
(2007/10/02)
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