Receptors functionalized with chiral aza‐crown ether rings. Attempted enantioselective catalysis of a Michael addition reaction

A series of receptors functionalized with chiral aza‐crown ether rings was synthesized. These compounds were studied as enantiopure catalysts for the addition of benzenethiols to cyclohex‐2‐en‐1‐one. Binding of 4‐hydroxybenzenethiol in these molecules allows for the orientation of the thiol with respect to an asymmetric catalytic site. This orientation was, however, found to be counterproductive for enantioselective catalysis.