Efficient synthesis of allylamines from a novel (E)-2,3-difunctionalized allyl bromide

Abstract

We report a new procedure for highly stereoselective synthesis of difunctionalized allyl and vinyl bromides E-4 and E-5 via a tandem reaction of bromination-dehydrobromination of tetraethyl prop-2-ene-1,2-diyldiphosphonate in the presence of DBU in acetonitrile at room temperature. The coupling reaction of allyl bromide E-4 with various primary amines in methanol at 0 °C, followed by S N 2' reaction, provides a new family of tetraethyl 1-(alkylamino)prop-2-ene-1,2-diyldiphosphonates 6 in high yields.