Barbier-type allylation of chiral α-Aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

Article abstract of DOI:10.1016/S0040-4020(97)00050-1

The chiral β-hydroxy-α-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in the Barbier reaction can be influenced by the choice of metal and 1 or allylic halide.