Anion reactions of 1,3-dithiane 1,3-dioxide with carbonyl compounds: high diastereoselectivity with aromatic aldehydes under conditions of equilibrium control

A study of the anion chemistry of 1,3-dithiane 1,3-dioxide with aldehydes and ketones shows that it undergoes selective addition reactions with aromatic aldehydes under equilibrium-controlled conditions. Li, Mg, Al, Ce and Ti exhibit reduced selectivity but Zn4 provided improved selectivity with aromatic aldehydes. The model developed to explain the disteroselectivity of aldehydes includes complexation of metal alkoxides with axial sulfoxide.