Abstract Mannich type reactions of a preformed aldimine with various carbonyl compounds were investigated with a series of functionalised indoline derivatives as catalysts: indoline-3- carboxylic acid, the diphenylcarbinol analogue and O-protected silyl ether analogues. All compounds were readily prepared in enantiopure form by using an enzymatic kinetic resolution as a key step (E≫ 100). The alcohol and ether catalysts failed to induce ...