Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: a convenient and stereoselective reaction

An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis–Hillman adducts in excellent yields with high Z-selectivity.