Dynamic Control of Chiral Space in a Catalytic Asymmetric Reaction Using a Molecular Motor

Enzymes and synthetic chiral catalysts have found widespread application to produce single enantiomers, but in situ switching of the chiral preference of a catalytic system is very difficult to achieve. Here, we report on a light-driven molecular motor with integrated catalytic functions in which the stepwise change in configuration during a 360° unidirectional rotary cycle governs the catalyst performance both with respect to activity and absolute stereocontrol in an asymmetric transformation. During one full rotary cycle, catalysts are formed that provide either racemic (R,S) or preferentially the R or the S enantiomer of the chiral product of a conjugate addition reaction. This catalytic system demonstrates…