Asymmetric Diels-Alder: Monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries

Article abstract of DOI:10.1016/0040-4039(96)01539-0

Lewis acid promoted Diels-Alder reactions of acrylate esters from monobenzylated isosorbide or isomannide and cyclopentadiene provided exclusively endo-adducts with good yields and high diastereoselectivities. The R/S selectivities are quasi total and opposed using either isosorbide or isomannide derivatives.