Rate acceleration and diastereoselectivity in chelation-controlled indium-promoted Barbier allylation of pyridine-2- and quinoline-2-imines in aqueous solvents

The imines generated in situ from 2-pyridinecarboxaldehyde/2-quinolinecarboxaldehyde and aryl amines undergo indium-mediated Barbier allylation in aqueous media to provide homoallylic amines. Crotyl and cinnamyl bromides lead to diastereoselective allylation with d.r. up to 98:2.