Highly stereoselective synthesis of functionalized 1,3-dienes from a new allyl bromide

Abstract

New and highly functionalized 1,3-dienes 3 and 4 have been synthesized via two different pathways starting from allyl bromide 1. Firstly, the reaction of allyl bromide 1 with triethylphosphite leads to an allylphosphonate 2, which undergoes the Wittig-Horner reaction with a range of saturated and unsaturated aldehydes gives rise to the corresponding 1,3-dienes 3. Secondly, a highly stereoselective reaction between allyl bromide 1 and nitroalkane salts, offers the possibility to obtaining functionalized (E)-1,3-dienes 4.

New substituted indene derivatives from bicyclic Baylis-Hillman acetate

“…Conjugate addition of nitroalkane to functional allyl acetates has been the subject of intensive work by our group [43][44][45][46][47] . Based on the previous results achieved by our group and others 48 , we further investigated the reactivity of allyl acetates 2b with nitronate anion generated from primary and secondary nitroalkanes toward the formation of highly substituted ethyl 1-alkylidene-1H-indene-2-carboxylates 4.…”

New substituted indene derivatives from bicyclic Baylis-Hillman acetate

“…Continuing with our efforts toward the functionalization of the bicyclic Baylis-Hillman acetate 2, we report herein the reactivity of the bicyclic Baylis-Hillman adduct 2b with nitroalkanes salts as nucleophilic reagents. Conjugate addition of nitroalkane to functional allyl acetates has been the subject of intensive work by our group [43][44][45][46][47] . Based on the previous results achieved by our group and others 48 , we further investigated the reactivity of allyl acetates 2b with nitronate anion generated from primary and secondary nitroalkanes toward the formation of highly substituted ethyl 1-alkylidene-1H-indene-2carboxylates 4.…”