Synthesis of Secondary Allylic Amines

Abstract

Secondary allylic amines were synthesized from aldehydes and primary amines via successive conversion into aldimines, α-haloaldimines and α,β-unsaturated aldimines, the latter being selectively reduced by sodium borohydride at the imino function. This method allowed the synthesis of secondary allylic amines with high preponderance of the E-stereochemistry. A comparison was made with an alternative method involving the generation of α,β-unsaturated aldimines from α,β-unsaturated aldehydes and primary amines, and subsequent borohydride reduction.