The development of efficient processes for asymmetric synthesis is a great challenge in heterogeneous catalysis. An attractive approach is to modify a metal surface through the chemisorption of a chiral organic molecule. The modifier creates a chiral site on the surface where the prochiral substrate undergoes asymmetric induction. A lack of a detailed mechanistic understanding is a major stumbling block in the rational development of chirally modified heterogeneous catalysts. Nevertheless, great advances have been made in efforts to understand the enantioselective hydrogenation of alpha-ketoesters on cinchona modified platinum catalysts. We report a combined STM, RAIRS and computational study of  1:1 prochiral assemblies on chirally modified Pt(111). The study reveals the existence of chemisorption induced strong C-H to O=C intermolecular hydrogen bonding between co-adsorbed ketones and aromatics on Pt(111). It also shows how this interaction may be used to modulate both the chemical reactivity and selectivity in asymmetric heterogeneous catalytic systems.

Self-assembly with chiral chemical intent

243rd National Meeting (2012)

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