In one type of catalysis ion-pairing exists with a charged and chiral catalyst.
The first reported example of this type of catalysis is attributed to Dolling, Davis & Grabowski who in 1984 used a chiral cinchonidine based phase transfer catalyst in the synthesis of indacrinone.
The first reported example of asymmetric cation-binding catalysis originates from Cram and Sogah who in 1981 used a chiral crown ether in combination with a potassium base in an enantioselective Michael addition.
In 2000 Llewellyn, Adamson & Arndtsen used a chiral borate anion in olefin aziridination and cyclopropanation.
[4] Another regularly encountered scaffold is a chiral phosphate anion together with iminium, carbocationic or oxocarbenium counterions.