Design of a new bifunctional asymmetric catalyst from carbohydrates: application to catalytic asymmetric cyanosilylation of aldehydes and acetophenone

A new active Lewis acid–Lewis base bifunctional asymmetric catalyst 7 was developed using carbohydrate as a scaffold and this catalyst was applied to the asymmetric cyanosilylation of aldehydes and acetophenone. The β-Ph group at the 6-position of 7 was found to be important for a high asymmetric induction (up to 80% ee) by bringing the Al and the phosphine oxide at optimum positions for a dual activation of carbonyl compounds and TMSCN.