Development of general methods for the synthesis of new substituted allyl bromides as promising alkenylating agents

Abstract

A general procedure has been developed for the synthesis of hitherto unknown substituted allyl bromides. The procedure includes preparation of the corresponding α,β-unsaturated carboxylic acid esters from accessible ketones according to the Horner-Emmons reaction, reduction of these esters with diisobutylaluminum hydride to allylic alcohols, and substitution of the hydroxy group by bromine by the action of PBr3. The E,Z isomer ratio of the synthesized unsaturated compounds ranges from 3: 1 to 4: 1.