Synthesis of 1-C-(tetra-O-acetyl-β-d-galactopyranosyl)-2,3-diiodo-1-propene and its reaction with primary amines

Iodination of 1-C-(tetra-O-acetyl-β-d-galactopyranosyl)allene affords an E/Z-mixture of 1-C-(tetra-O-acetyl-β-d-galactopyranosyl)-2,3-diiodo-1-propene. SN2 displacement of the allylic iodide with primary amines affords an E/Z-mixture of allylic amines under a variety of conditions. Due to its experimental simplicity and low cost of reagents, this procedure may find wide use in the laboratory for functionalization of sugar allenes.