Abstract
The origin of rate and enantioselectivity enhancement by achiral amine addition in the asymmetric hydrogenation of alkenoic acid on chirally modified Pd has been a long-debated subject. We show by means of in situ attenuated total reflection infrared spectroscopy combined with modulation excitation spectroscopy that the rate enhancement in the presence of an amine originates from restructuring of surface acid–base type adducts dynamically involving the substrate, product, chiral modifier, and amine. Phase-sensitive detection provides insight into the surface dynamics at the solid–liquid chiral interface: the addition of the achiral amine changes the adsorption configuration of the chiral modifier on the Pd surface, leading to a better stereochemically controlled surface.
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